Islamorada Resorts
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Find Hotels in Islamorada
Islamorada|1.05km from city center
Welcome to Cheeca Lodge & SpaTurquoise water. Towering palms. Calm breezes. Imagine yourself whisked away to a tropical paradise where you indulge in mind, body, and spirit, as you rediscover an oasis called Cheeca Lodge & Spa. Romantic, serene, and dynamic, our Florida Keys Islamorada resort is a standard of excellence achieved by few. Be swept away by the casual elegance emanating from every detail and settle into the laid-back lifestyle of Islamorada.Stay in the Sportfishing Capital of the WorldLocated in the Sportfishing Capital of the World, Cheeca Lodge is a premier destination for serious anglers. Charter a boat and find over 500 species of fish within minutes from shore. The casual fisherman can cast a line from the end of our 525-foot pier – the longest in the Keys. A host of other activities can be found at our Islamorada luxury resort, including snorkeling, sea kayaking, bicycling, and scuba diving. Between activities, enjoy first-class dining at one of our three restaurants: Atlantic’s Edge, Mia Cucina, or Nikai Sushi.
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FromHK$3,134
Latest Price
Islamorada|0.52km from city center
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 7 minutes by foot from Islamorada Brewery & Distillery. This beach hotel is 0.4 mi (0.7 km) from Matecumbe United Methodist Church and 0.7 mi (1.1 km) from Florida Keys Brewing Co..Spend the day on the private beach or dip into one of the 2 outdoor swimming pools. Additional features at this hotel include complimentary wireless internet access, concierge services, and gift shops/newsstands.Satisfy your appetite at Tides Beachside Bar, one of the hotel's 3 restaurants. Relax with a refreshing drink at the beach bar, the poolside bar, or one of 2 bars/lounges. Full breakfasts are available daily from 7:00 AM to 11:00 AM for a fee.Featured amenities include dry cleaning/laundry services, a 24-hour front desk, and multilingual staff. Event facilities at this hotel consist of a conference center and 13 meeting rooms. Free self parking is available onsite.Stay in one of 114 guestrooms featuring Smart televisions. Rooms have private lanais. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers.
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101 Reviews
8.9/10
FromHK$4,139
Latest Price
Islamorada|3.85km from city center
With a stay at Amara Cay Resort in Islamorada (Matecumbe), you'll be a 4-minute walk from Bud n' Mary's Dive Center and a 2-minute drive from Florida Keys Brewing Co.. This beach resort is 4.8 mi (7.6 km) from Windley Key Fossil Reef Geological State Park and 6.5 mi (10.4 km) from Anne's Beach.Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities including an outdoor pool and a fitness center. This resort also features gift shops/newsstands, wedding services, and a television in a common area.Grab a bite at ReelCatch, one of the resort's 2 restaurants, or stay in and take advantage of the room service (during limited hours). Relax with a refreshing drink from the poolside bar or one of the 3 bars/lounges. Cooked-to-order breakfasts are available daily from 6:00 AM to 11:00 AM for a fee.Featured amenities include a 24-hour front desk, multilingual staff, and luggage storage.Make yourself at home in one of the 110 air-conditioned rooms featuring flat-screen televisions. Your pillowtop bed comes with down comforters and Egyptian cotton sheets. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Conveniences include safes and desks, as well as phones with free local calls.
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101 Reviews
8.5/10
FromHK$2,400
Latest Price
Islamorada|0.23km from city center
With a stay at Sunset Inn in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 8 minutes by foot from Keys History & Discovery Center. This hotel is 0.5 mi (0.9 km) from Matecumbe United Methodist Church and 0.8 mi (1.3 km) from History of Diving Museum.Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional features at this hotel include complimentary wireless internet access, a picnic area, and barbecue grills.Featured amenities include luggage storage and a safe deposit box at the front desk. Free self parking is available onsite.Make yourself at home in one of the 30 air-conditioned rooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and bidets. Conveniences include laptop-compatible safes and blackout drapes/curtains, and housekeeping is provided daily.
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101 Reviews
8.7/10
FromHK$1,724
Latest Price
Islamorada|0.34km from city center
With a stay at Casa Morada in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 9 minutes by foot from Keys History & Discovery Center. This beach hotel is 0.6 mi (1 km) from Matecumbe United Methodist Church and 0.9 mi (1.4 km) from Florida Keys Brewing Co..Pamper yourself with onsite massages or enjoy recreation amenities such as an outdoor pool. Additional features at this hotel include complimentary wireless internet access and concierge services.Take advantage of the hotel's room service (during limited hours). A complimentary continental breakfast is served daily from 7 AM to 10:30 AM.Featured amenities include luggage storage and a safe deposit box at the front desk. Free self parking is available onsite.Make yourself at home in one of the 16 individually decorated guestrooms, featuring minibars and DVD players. Rooms have private balconies or patios. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Bathrooms have designer toiletries and hair dryers.
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83 Reviews
9.1/10
FromHK$2,452
Latest Price
Islamorada|0.12km from city center
With a stay at La Jolla Resort in Islamorada (Matecumbe), you'll be steps from Islamorada Brewery & Distillery and 10 minutes by foot from Keys History & Discovery Center. This hotel is 0.6 mi (1 km) from Matecumbe United Methodist Church and 0.7 mi (1.1 km) from History of Diving Museum.Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities, which include an outdoor pool. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and a picnic area.The front desk is staffed during limited hours. Limited parking is available onsite.Make yourself at home in one of the 20 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms with showers are provided. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.
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102 Reviews
8.8/10
FromHK$1,621
Latest Price
Islamorada|0.47km from city center
With a stay at Hadley Resort and Marina in Islamorada (Matecumbe), you'll be within a 10-minute walk of Islamorada Brewery & Distillery and History of Diving Museum. This beach hotel is 0.8 mi (1.3 km) from Keys History & Discovery Center and 1 mi (1.6 km) from Matecumbe United Methodist Church.Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities, which include an outdoor pool. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and gift shops/newsstands.A complimentary on-the-go breakfast is served daily from 8:00 AM to 10:30 AM.Featured amenities include express check-out, multilingual staff, and luggage storage. Free self parking is available onsite.Make yourself at home in one of the 37 air-conditioned rooms featuring refrigerators. Rooms have private furnished balconies or patios. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers.
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100 Reviews
7.8/10
FromHK$1,474
Latest Price
Islamorada|4.05km from city center
A stay at Fisher Inn Resort & Marina places you in the heart of Islamorada, just a 3-minute walk from Windley Key Fossil Reef Geological State Park and within a 5-minute drive of Rain Barrel Village. This beach motel is 1.9 mi (3.1 km) from History of Diving Museum and 2 mi (3.2 km) from Founders Park.Relax on the private beach or enjoy other recreational amenities such as an outdoor pool. Additional amenities at this Art Deco motel include complimentary wireless internet access, concierge services, and gift shops/newsstands.A complimentary on-the-go breakfast is served daily from 8:00 AM to 10:30 AM.Featured amenities include express check-out, luggage storage, and coffee/tea in a common area. Free self parking is available onsite.Make yourself at home in one of the 22 individually decorated guestrooms, featuring refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers. Conveniences include coffee/tea makers and irons/ironing boards, and housekeeping is provided on request.
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101 Reviews
7.3/10
FromHK$1,832
Latest Price
Islamorada|1.91km from city center
Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State Park. This beach hotel is 1.2 mi (2 km) from Islamorada Brewery & Distillery and 1.7 mi (2.8 km) from Keys History & Discovery Center.Spend the day on the private beach or dip into one of the 2 outdoor swimming pools. This hotel also features complimentary wireless internet access and concierge services.Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 6:00 AM to 10:00 AM.Featured amenities include a computer station, a 24-hour front desk, and multilingual staff.Make yourself at home in one of the 60 air-conditioned rooms featuring microwaves and flat-screen televisions. Your room comes with a pillowtop bed. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature showers, designer toiletries, and hair dryers.
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104 Reviews
8.8/10
FromHK$3,338
Latest Price
Islamorada|3.2km from city center
With a stay at Pines & Palms Resort in Islamorada (Matecumbe), you'll be a 5-minute walk from Indian Key Historic State Park and 12 minutes by foot from Bud n' Mary's Dive Center. This beach hotel is 1 mi (1.6 km) from Hurricane Monument and 1.2 mi (1.9 km) from Florida Keys Brewing Co..Relax on the private beach or enjoy other recreational amenities such as an outdoor pool and bicycles to rent. Additional features at this hotel include complimentary wireless internet access, concierge services, and wedding services.Take advantage of the hotel's room service. Need to unwind? Take a break at the bar/lounge, the beach bar, or the poolside bar for a tasty beverage.Featured amenities include limo/town car service, multilingual staff, and luggage storage. Free self parking is available onsite.Make yourself at home in one of the 26 individually decorated guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include separate sitting areas and microwaves, and housekeeping is provided daily.
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100 Reviews
9.0/10
FromHK$3,528
Latest Price
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Check other Islamorada hotels
Breakfast
Very Good101 Reviews
Islamorada|3.85km from city center
Ameracay is a very nice resort. It's not too far and easily accessible. It gas a nice tiki brand beach as well as a very nice courtyard with game areas and firepits.
The resort is in an area that has iguanas. These are harmless if left alone. Make sure yiu balcony door is shut so a curious iguana does not visit. You also should ve aware that in case of a cold snap, iguanas fall from trees. As long as they don't hit you in the head again they are harmless. Visited the outside bar fi a sandwich. Everything in the Keys cost more so prices are moderate. We shared a sandwich with no issues. The lobby area is very nice with suspended swinging chairs. Decorations are ”islandish” which is appropriate. There is a selfie wall which has keys mounted. There is also a wall mounted magnetic Scrapple game.
There are nice restaurants within walking distance. Both Midway and Lazy Boys were busy. If you go out for dinner, expect moderate wait.
Staff was exceptionally nice and helpful. The resort has a very snLl gift shop. Not much for men unless you need a bathing suit.
The only problem was the entire area was having water issues. There was no hot water in the room.
I would stay again. It's about half the cost of staying in Key West. There are places very close by if you want to plY in, on, or under the water. It may be possible to book a ride out to Alligator Reef Lighthouse via a service near by. Lots of places to hop on a fishing boat.
The water off Islamadora is a nationally protected coral reef. Make sure you know what you can and can't do on the reef.
The resort does not allow drone flying on property. You might be able to fly from a nearby bridge.
I will probably visit again.FromHK$2,400
101 Reviews
Islamorada|4.05km from city center
The reception staff were lovely, so welcoming and helpful. Little heated pool and nice sun loungers, just missing some umbrellas to make it perfect. The outside grill was great to use and clean. Room didn’t get cleaned during our two night stay though… 🤷🏼♀️FromHK$1,832
Very Good102 Reviews
Islamorada|3.29km from city center
The hotel was very comfortable and was very comfortable.FromHK$2,817
Very Good108 Reviews
Islamorada|1.05km from city center
Great trip! We enjoyed it a lot! Great service, we love our room (ocean front) the only issue that we had is that we didn’t have access to internet through wifiFromHK$3,134
Very Good101 Reviews
Islamorada|0.52km from city center
Nice hotel rooms that you can drive up to. Nice amount of space—although the bathroom is very small. Pool area is ok, not enough umbrellas. Didn’t get water everyday despite being told it was included with the resort fee. The access to the sea isn’t great. Yoga was fantastic.FromHK$4,139
Good100 Reviews
Islamorada|0.47km from city center
With a stay at Hadley Resort and Marina in Islamorada (Matecumbe), you'll be within a 10-minute walk of Islamorada Brewery & Distillery and History of Diving Museum. This beach hotel is 0.8 mi (1.3 km) from Keys History & Discovery Center and 1 mi (1.6 km) from Matecumbe United Methodist Church.Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities, which include an outdoor pool. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and gift shops/newsstands.A complimentary on-the-go breakfast is served daily from 8:00 AM to 10:30 AM.Featured amenities include express check-out, multilingual staff, and luggage storage. Free self parking is available onsite.Make yourself at home in one of the 37 air-conditioned rooms featuring refrigerators. Rooms have private furnished balconies or patios. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers.FromHK$1,474
Very Good104 Reviews
Islamorada|1.91km from city center
The place is beautiful and very clean. There were a couple of hiccups but the hotel was quick to fix it. The only part that is upsetting is using on the amenities: fish rod, it kept tangling up. But overall, we will be returning. The breakfast was like no other.FromHK$3,338
Great83 Reviews
Islamorada|0.34km from city center
With a stay at Casa Morada in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 9 minutes by foot from Keys History & Discovery Center. This beach hotel is 0.6 mi (1 km) from Matecumbe United Methodist Church and 0.9 mi (1.4 km) from Florida Keys Brewing Co..Pamper yourself with onsite massages or enjoy recreation amenities such as an outdoor pool. Additional features at this hotel include complimentary wireless internet access and concierge services.Take advantage of the hotel's room service (during limited hours). A complimentary continental breakfast is served daily from 7 AM to 10:30 AM.Featured amenities include luggage storage and a safe deposit box at the front desk. Free self parking is available onsite.Make yourself at home in one of the 16 individually decorated guestrooms, featuring minibars and DVD players. Rooms have private balconies or patios. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Bathrooms have designer toiletries and hair dryers.FromHK$2,452
Very Good102 Reviews
Islamorada|0.12km from city center
Bella struttura ristrutturata sapientemente, stanza ampia ed accogliente, zona esterna bella e suggestiva soprattutto al tramonto.FromHK$1,621
Very Good101 Reviews
Islamorada|0.23km from city center
Its decent but its not easy to find in the evening or night when its dark. Would help if it has a bright sign for the Inn.
It has a pool at the back and you can hear the noise if people are partying out there but it seems to quiet down fortunately for us for the day we were there.FromHK$1,724
Hot spring
Very Good100 Reviews
Islamorada|4.18km from city center
With a stay at Drop Anchor in Islamorada, you'll be on the waterfront, a 4-minute walk from Windley Key Fossil Reef Geological State Park and a 3-minute drive from Rain Barrel Village. This hotel is 1.9 mi (3 km) from Founders Park and 1.9 mi (3 km) from Islamorada County Park.Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities, which include an outdoor pool. This Art Deco hotel also features complimentary wireless internet access, wedding services, and a picnic area.Featured amenities include a business center, a safe deposit box at the front desk, and coffee/tea in a common area. Free self parking is available onsite.Make yourself at home in one of the 18 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and hair dryers. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.FromHK$1,119
Great100 Reviews
Islamorada|3.2km from city center
With a stay at Pines & Palms Resort in Islamorada (Matecumbe), you'll be a 5-minute walk from Indian Key Historic State Park and 12 minutes by foot from Bud n' Mary's Dive Center. This beach hotel is 1 mi (1.6 km) from Hurricane Monument and 1.2 mi (1.9 km) from Florida Keys Brewing Co..Relax on the private beach or enjoy other recreational amenities such as an outdoor pool and bicycles to rent. Additional features at this hotel include complimentary wireless internet access, concierge services, and wedding services.Take advantage of the hotel's room service. Need to unwind? Take a break at the bar/lounge, the beach bar, or the poolside bar for a tasty beverage.Featured amenities include limo/town car service, multilingual staff, and luggage storage. Free self parking is available onsite.Make yourself at home in one of the 26 individually decorated guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include separate sitting areas and microwaves, and housekeeping is provided daily.FromHK$3,528
Very Good69 Reviews
Islamorada|1.91km from city center
With a stay at Bayside Villas by Islander Resort, you'll be centrally located in Islamorada, just a 4-minute walk from Hurricane Monument and 7 minutes by foot from Florida Keys Brewing Co.. This beach hotel is 0.4 mi (0.7 km) from MoradaWay Arts & Cultural District and 0.5 mi (0.9 km) from Matecumbe United Methodist Church.Take advantage of recreation opportunities including an outdoor pool and bicycles to rent. Additional amenities at this hotel include complimentary wireless internet access, a picnic area, and barbecue grills. Getting to nearby attractions is a breeze with the complimentary area shuttle that operates within 1.5 miles.Satisfy your appetite at Tides Beachside Bar, one of the hotel's 3 restaurants. Quench your thirst with your favorite drink at the bar/lounge.The front desk is staffed during limited hours. Free self parking is available onsite.Make yourself at home in one of the 25 guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Your pillowtop bed comes with premium bedding, and all rooms are furnished with queen sofa beds. Rooms have private furnished balconies. 55-inch LCD televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected.FromHK$4,525
100 Reviews
Islamorada|3.84km from city center
With a stay at Coconut Cove Resort and Marina in Islamorada, you'll be on the waterfront, just steps from Windley Key Fossil Reef Geological State Park and a 3-minute drive from History of Diving Museum. This beach hotel is 2 mi (3.3 km) from Rain Barrel Village and 2.2 mi (3.5 km) from Founders Park.Enjoy recreational amenities such as an outdoor pool and a fitness center. Additional features at this hotel include complimentary wireless internet access, wedding services, and a picnic area.A complimentary continental breakfast is served daily from 9:00 AM to 11:00 AM.Featured amenities include a business center and coffee/tea in a common area. Free self parking is available onsite.Make yourself at home in one of the 20 guestrooms featuring refrigerators and microwaves. Rooms have private patios. 24-inch LCD televisions are provided, with cable programming available. Bathrooms have complimentary toiletries and hair dryers.FromHK$1,563
Amazing100 Reviews
Islamorada|6.56km from city center
My husband and I stayed a week at the Ragged Edge Resort & Marina. We were delighted with the spacious apartment especially the two bathrooms. Our apartment had a well equipped kitchen, a counter for eating and a comfortable living area with a sofa and chairs. From the kitchen/living room window we had a beautiful view of the pier and ocean. The pool and pier area provided lots of space and lounge chairs for swimming, fishing and enjoying the sun. In the evening we used the resort's bicycles to tour the neighborhood. The staff at Ragged Edge were wonderful. They made sure we had everything we needed. There were many restaurants nearby but our favorite was ”Lazy Days”. We also took a day trip to Key West which was about 70 miles south of the resort.FromHK$1,829
Very Good80 Reviews
Islamorada|3.71km from city center
Located in Islamorada (Matecumbe), Sands of Islamorada is within a 5-minute drive of Bud n' Mary's Dive Center and History of Diving Museum. This hotel is 4.7 mi (7.5 km) from Windley Key Fossil Reef Geological State Park and 6.6 mi (10.6 km) from Anne's Beach.Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. Additional features at this hotel include complimentary wireless internet access, a picnic area, and barbecue grills.Featured amenities include laundry facilities and a safe deposit box at the front desk. Free self parking is available onsite.Make yourself at home in one of the 9 individually decorated guestrooms, featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers. Conveniences include safes and microwaves, and housekeeping is provided daily.FromHK$1,613
0 Reviews
Islamorada|7.65km from city center
SOLD OUT
0 Reviews
Islamorada|7.92km from city center
Imagine waking up to warm ocean breezes, the gentle sway of palm trees, and the first golden light of the sun rising over the Atlantic. This is not just another day in paradise – this is your new way of living, breathing, and unwinding in the world-famous Florida Keys, known as the Sport Fishing Capital of the World. Whether your dream vacation includes world-class fishing excursions, snorkeling through coral reefs, paddling across turquoise waters, or simply relaxing in a private island oasis, your stay at our luxury resort-style 2-bedroom, 2-bath Seabreeze home promises an unforgettable experience. NO PETS ALLOWED.Perfect for Monthly Stays & Extended RetreatsThis property requires a minimum stay of 28 nights, making it perfect for:* Remote workers seeking serenity with high-speed internet* Retirees looking for extended winter escapes* Families wanting more than a vacation—those craving island living* Adventurers who want the Florida Keys lifestyle at their doorstepPet-friendly units are available upon request (please contact the resort for availability and approval).ABOUT THE HOMEThis 1,230 sq. ft. Seabreeze model has been intelligently designed to offer both privacy and connection, style and function, coastal elegance and home-like warmth. It’s not just a rental—it’s your very own island residence.Key Features:2 Bedrooms / 2 Full Bathrooms – One bedroom is located on the first floor (ideal for convenience), and the second is upstairs for ultimate privacy. Both living spaces offer sleeper sofas to accommodate the whole family.Loft Lounge & Wet Bar – The second-floor lounge features a sleeper sofa, wet bar, entertainment area, and opens to your private deck with spectacular Resort and Atlantic Ocean views.Fully Furnished, Coastal Inspired Décor – With a light, breezy tropical theme, each unit is individually decorated by its private owner, ensuring charm and uniqueness.Sleeps 6 Comfortably – Perfect for couples, families, or a group of friends.In-Unit Washer & Dryer – Convenience at your fingertips.Fully Equipped Kitchen – Stainless steel appliances, quartz countertops, farm sink, barn door pantry access, cookware, dishes, utensils, small appliances, and more.Private Balcony – Sip your morning coffee or evening cocktail while watching palm trees sway in the breeze and boats pass by on the horizon.Minimum stay: 28 nights. Boat slips may be booked for an additional fee. Disclaimer: Photos represent the general style and quality of our homes. Each unit is individually owned and decorated, so furnishings and décor may vary slightly. All meet resort standards for comfort and cleanliness.About pets:Pets allowed: dogs less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 2:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.SOLD OUT
0 Reviews
Islamorada|7.64km from city center
SOLD OUT
Family friendly
Very Good76 Reviews
Islamorada|2.88km from city center
The resort was very beautiful and well maintained. The cottage we stayed in was spacious and we really liked the decor and how soft the beds were. The food was good but a little pricey. We were not impressed with the cabana rental. The cabana was not ready when we arrived. We had to wait for it to be cleaned and set up. The cabana was not labeled and we were confused on which cabana was ours as there were 2 next to each other. We asked when service would start and we were told 10am, then we asked again at 10:45, then went to the front office at 11:30 and when 12pm rolled around with no service we decided to leave and get our money back on the cabana. At that point all we paid for was a chair and towel which did not meet our expectation when spending $250.00 on a cabana for the day. I would recommend several things for the cabana. 1. Number the cabanas so you can clearly see the number. Telling us Cabana 2 does not help when they are beside each other. 2. Stock the min fridge with water. 3. Clearly explain on the cabana rental that food/service will not start until a certain time. We expected to at least get something to drink while in the cabana. 4. Install a call button or app that you can be in contact with someone when you need something. There was a significant delay on getting our refund. And we do appreciate the Manager helping us on Friday get that resolved before we checked out on Saturday morning. All in all, the resort was great. We loved the vibe and updates made to the property. The rooms were comfortable and fresh, and we loved the beds as they were very comfortable, and the sheets were so soft. Everyone was friendly and pleasant. We most enjoyed fish like a local with Patrick. We found that the pool in the middle of the property was less used and felt more quiet and more private therefore we spent our time with a good book. I would give the stay at 4.5 out of 5. Highly recommend trying out Three Waters Resort.FromHK$4,162
Great40 Reviews
Islamorada|13.78km from city center
The Caloosa Cove Resort by CoolVacay provides a great place for travelers to relax after a busy day. The Caloosa Cove Resort by CoolVacay offers a pleasant stay in Islamorada for those traveling for business or leisure. This hotel is located near many of Islamorada's attractions including Anne's Beach, Channel 2 fishing spot and Caribsea Charters. In their spare time, guests can explore the hotel's surroundings. For those driving themselves, parking is provided on site. According to our trusted guests, the facilities at this hotel are first-rate. SOLD OUT
Outstanding0 Reviews
Islamorada|4.02km from city center
SOLD OUT
Amazing39 Reviews
Islamorada|0.66km from city center
With a stay at The Islands of Islamorada in Islamorada (Matecumbe), you'll be within a 10-minute walk of History of Diving Museum and Islamorada Brewery & Distillery. This beach villa is 0.8 mi (1.3 km) from Keys History & Discovery Center and 1.1 mi (1.8 km) from Matecumbe United Methodist Church.Dip into one of the 2 outdoor pools or enjoy other recreational amenities including a 24-hour fitness center and 2 outdoor pickleball courts. This villa also features complimentary wireless internet access, concierge services, and wedding services.Wrap up your day with a drink at the poolside bar. Cooked-to-order breakfasts are available daily from 9:00 AM to 11:00 AM for a fee.The front desk is staffed during limited hours. Free self parking is available onsite.Make yourself at home in one of the 30 individually decorated guestrooms, featuring microwaves and Smart televisions. Your pillowtop bed comes with premium bedding. Rooms have private furnished balconies or patios. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature showers with rainfall showerheads and designer toiletries.FromHK$5,709
0 Reviews
Islamorada|12.17km from city center
SOLD OUT
0 Reviews
Islamorada|10.22km from city center
With a stay at this villa in Tavernier, you'll be steps from Old Road Gallery and a 3-minute drive from Florida Keys Dive Center. This villa is 14.2 mi (22.9 km) from John Pennekamp Coral Reef State Park and 2 mi (3.2 km) from Islamorada County Park.Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.Make yourself comfortable in your villa.SOLD OUT
Amazing6 Reviews
Islamorada|0.69km from city center
A stay at The Caribbean Resort places you in the heart of Islamorada, within a 5-minute drive of Hurricane Monument and History of Diving Museum. This family-friendly hotel is 2.3 mi (3.7 km) from Bud n' Mary's Dive Center and 5.2 mi (8.4 km) from Founders Park.Don't miss out on recreational opportunities including an outdoor pool and a hot tub. Additional amenities at this hotel include wedding services, a picnic area, and barbecue grills.Featured amenities include laundry facilities and an elevator.Make yourself at home in one of the 14 individually decorated guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Rooms have private balconies or patios. LED televisions are provided for your entertainment. Conveniences include separate sitting areas and microwaves, and housekeeping is provided daily.SOLD OUT
Outstanding24 Reviews
Islamorada|9.41km from city center
Islamorada Rental License: VR - 065 *** SATURDAY TO SATURDAY RENTALS ONLY!If your preferred dates are not available, check our other home, The Last Resort Too - VRBO #4357870, MM 77, or contact us with an inquiry here, SPECIFYING The Last Resort TooCHECK OUT A FEW WORDS FROM THE OWNERS BELOW THE INITIAL INFORMATION...4 bed/5 bath beachfront on over 1 acre with a private beach, heated pool & dockSeparate upstairs Den area sleeps up to 6 kids.* 7 Day minimum rental - Saturday to Saturday *SORRY, NO WEDDINGS OR LARGE EVENTS ALLOWED Max 8 adults + 4 childrenYou must be 25 years+ to rent this home and must be staying for the duration of the rental.Our house is one of the most highly sought-after vacation homes in Islamorada that regularly books years in advance. The Last Resort is a firm favorite of multi-generational families and friends looking to create memorable moments that last a lifetime in a lush, private, and tropical setting.As owners, we have spent 24+ years providing the best possible Keys experience for guests. Michele handles the day-to-day operations of the property and ensures guests have everything they need for a stress-free vacation. We believe that guests should not have to worry about 'extra or hidden' charges, so our rates INCLUDE many of the things other vacation rentals charge for, such as pool heat, BBQ gas, kayaks, and baby equipment. Though the property is self-catering, we supply many household items so you don't have to worry about purchasing them, such as laundry detergent, dishwasher detergent, garbage bags, kitchen paper, cleaning fluids, etc.We also don't charge a security deposit or pet fee. We operate on an honor & integrity system, giving our guests an authentic Keys experience that keeps them returning year after year as repeat guests.From years of international travel with our kids, one of my pet peeves was the amount of equipment that I had to pack just to go on vacation. Another was arriving at houses that were sparsely stocked or having to rent additional equipment. Greg and I made the commitment to provide as many supplies and equipment for our guests, from all kitchen equipment to baby equipment, from hairdryers & straighteners to lifejackets and water shoes, all to alleviate the need for guests to stuff their suitcases and truly make it a 'pack your shorts, flip-flops & toothbrush' kind of house.The Last Resort is truly in a beautiful setting, and we look forward to the opportunity to host you, your family, and your friends someday.Michele & Greg.... AND NOW THE HOUSE...Built in 1922, this historic Conch Style oceanfront executive retreat boasts overwhelming views of the Atlantic, large open verandas, 165 feet of private sandy beach, a 15 x 30 seaside heated swimming pool, 37 ft. concrete protected dockage on the canal adjacent to the house, and a gated entrance. Quiet seclusion awaits you at this unique destination.This 4-bedroom, 5-bath home with 4,000 square feet of living area is situated on over an acre in a private, tropical setting. Located in an upscale neighborhood in famed Islamorada, this fine home offers you the ability to relax, entertain, and enjoy the many recreational activities found only in the Florida Keys! Recognized by international publications as a preferred location for resort and swimwear photo sessions, the interior is casually furnished, tropically decorated, and offers every imaginable convenience.* Ralph Lauren* Victoria's Secret* Abercrombie & Fitch* Michael Kors* Opening shot Bloodlines* Promo shot HGTV Dream Home* Variety of European magazinesYou'll find an abundance of great island shops, full-service marinas, and popular local restaurants nearby! Ideal home for extended families, as most of the living space is on the ground level. Also, wide-covered front and back porches are ideal for outdoor entertaining/relaxing. The rear veranda overlooks breathtaking ocean views, palm trees, and a private sand beach. The front veranda overlooks a beautiful, tropical landscaped yard. Our home also has a rooftop deck overlooking the palm-lined sand beach and brilliant shades of the tropical ocean.Amenities: Two-story home with front and back covered porches, a 15x30 heated in-ground pool, a 165-wide private sand beach, and beautiful landscaping. House includes phone, high-speed wireless Internet/DSL line, dual-zone central air conditioning, ceiling fans in all rooms, 3 cable/smart TVs (both Masters & Living room)(2 smart TVs in the kids' Den, DVD player, and Bluetooth speakerFull kitchen includes a microwave, dishwasher, refrigerator, beverage fridge, coffee maker & Keurig 2.0, toaster, cooking utensils, and linens provided. 2 washers, 2 dryers, and 2nd fridge in the Laundry room. Jacuzzi tub in the downstairs Master bath. Gas grill (BBQ). Pets are allowed with advanced permission. 37-foot concrete private dockage with mains water and direct ocean access is available on our canal lot adjacent to the oceanfront home, with plenty of room for a boat trailer.There is one exterior camera on the front porch pointing towards the driveway. and a 2nd camera on the exterior of the laundry room door. There are no other cameras anywhere on or on the property.Feel free to send us an inquiry for any further information before making a booking decision. We are always happy to help.MicheleAbout pets:Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total).Prior permission required..About children:Children allowed: ages 0-17.About customRules:Pro-rated refunds given in the event of a hurricane evacuation. For cancellations, refund given once replacement renter books property..IMPORTANT: Saturday to Saturday bookings ONLY..About smoking:Smoking is not permitted.About events:No events allowed.SOLD OUT
Amazing2 Reviews
Islamorada|0.82km from city center
Villa by the Bay – Your Islamorada Escape for Sunsets, Fishing & Island LivingBring your heart, your family, and your fishing gear to Villa by the Bay, a charming island retreat tucked inside the quaint gated community of Coral Cove in the heart of Islamorada. With just eight homes in the community, this peaceful getaway offers the perfect blend of privacy, comfort, and easy access to everything that makes the Florida Keys unforgettable.Whether you're planning a world-class fishing adventure, a relaxing family getaway, or a romantic escape, Villa by the Bay is your ideal home base. Breathtaking Bayfront SunsetsEnd every day the way island life was meant to be enjoyed—watching the sun melt into the bay from the dock area. Gentle ocean breezes and vibrant sunset colors create a relaxing atmosphere you’ll look forward to every evening. A Fisherman’s ParadiseIslamorada is known as the “Sport Fishing Capital of the World,” and Villa by the Bay puts you right where you want to be.Direct ocean accessPrivate dockage available (upon request and fee)Easy access to deep-sea fishing, backcountry fishing, and sandbarsPerfect for bringing your own boat or chartering a local guideSpend the day chasing sailfish, mahi, snapper, or tarpon, then return home to relax by the pool and relive the day’s best catches. Private Heated Saltwater Plunge PoolAfter a day on the water or exploring the Keys, unwind in your private heated saltwater plunge pool. The soothing waterfalls and tranquil sounds create a relaxing oasis perfect for evening cocktails, family time, or a quiet morning coffee. Community AmenitiesCoral Cove is a quiet gated enclave designed for peaceful island living. Guests enjoy access to:Community swimming poolCommunity dockGated privacyBeautiful bay views throughout the propertyWith only eight homes, the atmosphere remains calm, welcoming, and uncrowded. Walk to Islamorada’s Best Restaurants & BarsOne of the best parts of staying at Villa by the Bay is the central location. Many of Islamorada’s favorite spots are within walking distance.Enjoy fresh seafood, tropical cocktails, and live music at nearby local favorites. Whether you're craving sunset dining, casual tiki bars, or a lively night out, it’s all just steps away.No long drives—just pure island convenience. Relaxed Island LivingVilla by the Bay was designed for easy, comfortable stays where you can truly unwind.Wake up to warm tropical breezes.Spend afternoons fishing, boating, snorkeling, or paddleboarding.Return home for a refreshing swim in the plunge pool.Then end the day watching spectacular Florida Keys sunsets over the bay.This is the laid-back Keys lifestyle people come back for year after year. Thoughtful Guest AmenitiesTo help you settle in comfortably, we provide initial starter supplies, including:CoffeePaper towelsBasic toiletries for each guestFor longer stays, additional supplies can easily be purchased locally and are the responsibility of the guest. Optional Private DockageBringing your boat? Private dockage may be available upon request for an additional fee. Please inquire ahead of your stay to confirm availability and details. (Up to a 42 ft boat) Why Guests Love This Home✔ Private heated saltwater plunge pool with waterfalls✔ Beautiful sunset views from the dock area✔ Gated community with only 8 homes✔ Walkable location to restaurants and nightlife✔ Community pool and dock✔ Optional private dockage for boaters✔ Centrally located in Islamorada✔ Perfect for fishing trips, couples, or family vacations Your Keys Adventure Starts HereWhether you’re casting lines at sunrise, exploring the turquoise waters of the Keys, or enjoying sunset drinks on the balcony, Villa by the Bay delivers the authentic Islamorada experience.Relax. Fish. Explore. Repeat.Ready, set… book your unforgettable stay at Villa by the Bay today!License #26-0059About pets:Pets allowed: dogs less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 19.About events:No events allowed.SOLD OUT
0 Reviews
Islamorada|13.45km from city center
Incomparable villa directly on Tavernier Creek with immediate access to ocean and bay. Fully fenced and gated. Manatees and dolphins swim and play before your eyes. Managed professionally and housekeeping provided once a week, included in rate. Master bedroom with private balcony overlooking creek. Complete house stand by generator on property. Summer kitchen with ice maker, professional gas grill, and sink. Surround sound system in pool area. Grocery stores within one to eight miles. Islamorada shops and restaurants less than seven miles away. About pets:No pets allowed, service animals permitted.Must be potty trained and use pee and poop pads.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking allowed: in designated areas.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.SOLD OUT
5 star
Very Good20 Reviews
Islamorada|3.65km from city center
With a stay at The Ocean View Inn & Pub in Islamorada, you'll be steps from Windley Key Fossil Reef Geological State Park and a 2-minute drive from History of Diving Museum. This hotel is 2.1 mi (3.4 km) from Rain Barrel Village and 2.2 mi (3.6 km) from Founders Park.Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.Enjoy a satisfying meal at The Ocean View Pub serving guests of The Ocean View Inn & Pub. Need to unwind? Take a break with a tasty beverage at one of the 2 bars/lounges.The front desk is staffed during limited hours. Free self parking is available onsite.Make yourself at home in one of the 7 air-conditioned rooms featuring microwaves. Rooms have private patios. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and hair dryers.FromHK$1,234
Very Good100 Reviews
Islamorada|3.78km from city center
With a stay at Breezy Palms Resort in Islamorada (Matecumbe), you'll be within a 15-minute walk of Bud n' Mary's Dive Center and Indian Key Historic State Park. This beach aparthotel is 1.4 mi (2.3 km) from Hurricane Monument and 1.6 mi (2.6 km) from Florida Keys Brewing Co..Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace. This aparthotel also features complimentary wireless internet access, gift shops/newsstands, and tour/ticket assistance.Featured amenities include luggage storage, laundry facilities, and a safe deposit box at the front desk. Self parking (subject to charges) is available onsite.Make yourself at home in one of the 40 guestrooms, featuring kitchens with full-sized refrigerators/freezers and microwaves. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include separate sitting areas and coffee/tea makers, and housekeeping is provided weekly.FromHK$1,100
Great77 Reviews
Islamorada|6.67km from city center
With a stay at Treasure Harbor in Islamorada, you'll be within a 10-minute walk of Rain Barrel Village and Founders Park. This houseboat is 0.5 mi (0.8 km) from Islamorada County Park and 2 mi (3.2 km) from Windley Key Fossil Reef Geological State Park.Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and a vending machine.The front desk is staffed during limited hours. Free self parking is available onsite.Make yourself at home in one of the 6 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Bathrooms feature showers, complimentary toiletries, and hair dryers. Conveniences include separate sitting areas and coffee/tea makers, and housekeeping is provided once per stay.FromHK$1,265
Very Good108 Reviews
Islamorada|1.05km from city center
Great trip! We enjoyed it a lot! Great service, we love our room (ocean front) the only issue that we had is that we didn’t have access to internet through wifiFromHK$3,134
Very Good76 Reviews
Islamorada|2.88km from city center
The resort was very beautiful and well maintained. The cottage we stayed in was spacious and we really liked the decor and how soft the beds were. The food was good but a little pricey. We were not impressed with the cabana rental. The cabana was not ready when we arrived. We had to wait for it to be cleaned and set up. The cabana was not labeled and we were confused on which cabana was ours as there were 2 next to each other. We asked when service would start and we were told 10am, then we asked again at 10:45, then went to the front office at 11:30 and when 12pm rolled around with no service we decided to leave and get our money back on the cabana. At that point all we paid for was a chair and towel which did not meet our expectation when spending $250.00 on a cabana for the day. I would recommend several things for the cabana. 1. Number the cabanas so you can clearly see the number. Telling us Cabana 2 does not help when they are beside each other. 2. Stock the min fridge with water. 3. Clearly explain on the cabana rental that food/service will not start until a certain time. We expected to at least get something to drink while in the cabana. 4. Install a call button or app that you can be in contact with someone when you need something. There was a significant delay on getting our refund. And we do appreciate the Manager helping us on Friday get that resolved before we checked out on Saturday morning.
All in all, the resort was great. We loved the vibe and updates made to the property. The rooms were comfortable and fresh, and we loved the beds as they were very comfortable, and the sheets were so soft. Everyone was friendly and pleasant. We most enjoyed fish like a local with Patrick. We found that the pool in the middle of the property was less used and felt more quiet and more private therefore we spent our time with a good book. I would give the stay at 4.5 out of 5. Highly recommend trying out Three Waters Resort.FromHK$4,162
Very Good101 Reviews
Islamorada|3.85km from city center
Ameracay is a very nice resort. It's not too far and easily accessible. It gas a nice tiki brand beach as well as a very nice courtyard with game areas and firepits.
The resort is in an area that has iguanas. These are harmless if left alone. Make sure yiu balcony door is shut so a curious iguana does not visit. You also should ve aware that in case of a cold snap, iguanas fall from trees. As long as they don't hit you in the head again they are harmless. Visited the outside bar fi a sandwich. Everything in the Keys cost more so prices are moderate. We shared a sandwich with no issues. The lobby area is very nice with suspended swinging chairs. Decorations are ”islandish” which is appropriate. There is a selfie wall which has keys mounted. There is also a wall mounted magnetic Scrapple game.
There are nice restaurants within walking distance. Both Midway and Lazy Boys were busy. If you go out for dinner, expect moderate wait.
Staff was exceptionally nice and helpful. The resort has a very snLl gift shop. Not much for men unless you need a bathing suit.
The only problem was the entire area was having water issues. There was no hot water in the room.
I would stay again. It's about half the cost of staying in Key West. There are places very close by if you want to plY in, on, or under the water. It may be possible to book a ride out to Alligator Reef Lighthouse via a service near by. Lots of places to hop on a fishing boat.
The water off Islamadora is a nationally protected coral reef. Make sure you know what you can and can't do on the reef.
The resort does not allow drone flying on property. You might be able to fly from a nearby bridge.
I will probably visit again.FromHK$2,400
Very Good102 Reviews
Islamorada|3.29km from city center
The hotel was very comfortable and was very comfortable.FromHK$2,817
Very Good101 Reviews
Islamorada|0.52km from city center
Nice hotel rooms that you can drive up to. Nice amount of space—although the bathroom is very small. Pool area is ok, not enough umbrellas. Didn’t get water everyday despite being told it was included with the resort fee. The access to the sea isn’t great. Yoga was fantastic.FromHK$4,139
Amazing39 Reviews
Islamorada|0.66km from city center
With a stay at The Islands of Islamorada in Islamorada (Matecumbe), you'll be within a 10-minute walk of History of Diving Museum and Islamorada Brewery & Distillery. This beach villa is 0.8 mi (1.3 km) from Keys History & Discovery Center and 1.1 mi (1.8 km) from Matecumbe United Methodist Church.Dip into one of the 2 outdoor pools or enjoy other recreational amenities including a 24-hour fitness center and 2 outdoor pickleball courts. This villa also features complimentary wireless internet access, concierge services, and wedding services.Wrap up your day with a drink at the poolside bar. Cooked-to-order breakfasts are available daily from 9:00 AM to 11:00 AM for a fee.The front desk is staffed during limited hours. Free self parking is available onsite.Make yourself at home in one of the 30 individually decorated guestrooms, featuring microwaves and Smart televisions. Your pillowtop bed comes with premium bedding. Rooms have private furnished balconies or patios. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature showers with rainfall showerheads and designer toiletries.FromHK$5,709
101 Reviews
Islamorada|4.05km from city center
The reception staff were lovely, so welcoming and helpful. Little heated pool and nice sun loungers, just missing some umbrellas to make it perfect. The outside grill was great to use and clean. Room didn’t get cleaned during our two night stay though… 🤷🏼♀️FromHK$1,832
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Very Good
108 Reviews