This resort in Islamorada, Village of Islands, offers private beach access near coral reefs and is within 1 kilometre of Windley Key Fossil Reef Geological State Park, Lignumvitae Key Botanical State Park, the History of Diving Museum, and Theatre of the Sea. The "For The Whole Family! 3 Convenient Units, Pool" offer provides three separate hotel rooms, each 28 square metres, accommodating up to 12 guests with air conditioning, Wi-Fi, a heated outdoor swimming pool, and on-site parking, with pets welcome for an additional charge.
8.7 508 reviews
Islamorada, FL
04/08 – 09/08
479 €/nighttotal: 2395 € (5 )
Matecumbe Resort
2 5
resort , Islamorada, Village of Islands
The Matecumbe Resort is situated in Islamorada, a short distance from Sea Oats Beach, Upper Matecumbe Key, and Windley Key, offering a convenient base to explore the beautiful Florida Keys. This 2-star aparthotel consistently receives very good user ratings for its cleanliness, location, and overall experience. Each self-catering apartment comes equipped with a kitchen, including a fridge, microwave, and other essentials. Guests can enjoy a range of amenities, including a swimming pool, a terrace, a garden, free parking, and Wi-Fi, as well as access to a private beach.
9.3 3 reviews
Islamorada, FL
03/08 – 05/08
383 €/nighttotal: 766 € (2 )
2 Comfortable Units, Onsite Pool, Pets Allowed
2 5
resort , Islamorada, Village of Islands
This Islamorada apartment complex, situated on a private beach, offers easy walking access to the Theatre of the Sea and is close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks. Two 290 sq ft (approx. 27 sq m) units, each sleeping up to eight guests, feature two bedrooms, two bathrooms, a swimming pool, fitness centre, parking, and daily housekeeping, plus kayaks, paddleboards and bike rentals are available on-site.
8.8 954 reviews
Islamorada, FL
30/07 – 06/08
591 €/nighttotal: 4137 € (7 )
Bayside Villas By Islander Resort
1 2
resort , Islamorada, Village of Islands
Islander Bayside Villas & Boatslips is located in Islamorada, Florida, just a short walk from the beach and a short drive from Windley Key Fossil Reef Park. The resort has received very good ratings for user experience, location, and cleanliness. The villas offer a comfortable and convenient stay with fully equipped kitchens, flat-screen TVs, free WiFi, and laundry facilities. Guests can enjoy a refreshing dip in the outdoor pool, rent bicycles, and explore the nearby water sports activities.
Islamorada, FL
03/08 – 05/08
505 €/nighttotal: 1010 € (2 )
3 Relaxing Units, Free Parking, Breakfast, Pool
3 5
resort , Islamorada, Village of Islands
This Islamorada resort offers direct access to a private beach and is situated within 600 metres of the History of Diving Museum and the Theater of the Sea, with easy access to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. The "3 Relaxing Units, Free Parking, Breakfast, Pool" offer at this Islamorada accommodation provides 3 bedrooms and 3 bathrooms for up to 12 guests, featuring air conditioning, internet, a heated outdoor swimming pool, a garden, and allows pets for an additional charge.
9.2 2444 reviews
Islamorada, FL
26/06 – 30/06
455 €/nighttotal: 1820 € (4 )
Pines & Palms Resort
1 3
resort , Islamorada, Village of Islands
Pines & Palms Resort is located in Islamorada, close to Alligator Reef and less than a mile from Miss Islamorada Fishing Charters, with John Pennekamp Coral Reef State Park a short 30-minute drive away. This resort has very good user ratings, an excellent location rating and a very good cleanliness rating. The resort offers a range of apartments with full kitchens and ocean views. Guests can enjoy a private beach, an oceanfront pool, a Tiki Bar, kayak and bike rentals, private boat docks, a covered cabana with a barbecue grill, and premium sport fishing areas.
10 1 review
Islamorada, FL
07/08 – 23/08
1171 €/nighttotal: 18736 € (16 )
2 Bedroom Suite In Islamorada! Swimming Pool, Kitchenette, Pets Allowed!
2 4
resort , Islamorada, Village of Islands
This beachfront villa in Matecumbe, Islamorada, is situated a 15-minute walk from Indian Key Historic State Park and Bud n' Mary's Dive Centre, and under 2 km from the Hurricane Monument and Florida Keys Brewing Co. The 99 square metre property boasts two bedrooms, two bathrooms, sleeps eight guests, and includes a swimming pool, terrace, and fully equipped kitchen; concierge services are also available.
8.0 1 review
Islamorada, FL
09/10 – 12/10
988 €/nighttotal: 2964 € (3 )
Rare Find! 4 Pleasant Units! Free Breakfast
4 2
resort , Islamorada, Village of Islands
This Islamorada apartment rental, situated in the Village of Islands, offers private beach access within a pet-friendly resort, a short walk from the Theatre of the Sea and close to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. The 4-bedroom, 4-bathroom property boasts 290 sq ft units (approximately 27 sq m) with two queen beds each, sleeping up to 16 guests and including a heated pool, kayaks, paddleboards, bicycles, daily continental breakfast, and complimentary parking.
9.0 4007 reviews
Islamorada, FL
27/06 – 04/07
408 €/nighttotal: 2856 € (7 )
Islander Resort
1 2
resort , Islamorada, Village of Islands
Islander Resort is situated directly on the beach in Islamorada, offering easy access to the beautiful waters of the Florida Keys and the area's attractions. The resort has received very good ratings for its overall experience, with excellent marks for its location and cleanliness. The resort provides spacious rooms with private porches or lanais, perfect for enjoying the tropical ambiance. Guests can enjoy a range of amenities including swimming pools, a bar and restaurant, a spa, a fitness centre, and a concierge service.
Islamorada, FL
07/07 – 11/07
353 €/nighttotal: 1412 € (4 )
Islamorada Stay! Free Breakfast | Pool & Parking!
2 4
resort , Islamorada, Village of Islands
This Islamorada resort offers a prime location in the Village of Islands, approximately 160 kilometres south of Miami, known for its upscale, small-town atmosphere and natural beauty. The accommodation provides a 2-bedroom, 1-bathroom unit for up to 4 guests, featuring air conditioning, free Wi-Fi, a swimming pool, complimentary breakfast and parking, and welcomes pets for an additional nightly charge under the "Islamorada Stay! Free Breakfast | Pool & Parking!" offer.
8.0 1 review
Islamorada, FL
07/07 – 11/07
498 €/nighttotal: 1992 € (4 )
1 Bedroom Suite W/kitchenette, Pool View, Free Parking & Pet Friendly
1 4
resort , Islamorada, Village of Islands
This beachfront suite, ‘Beachside Retreat In Islamorada - Suite W/ Pool View Queen | Family Ready’, is situated in Matecumbe, Islamorada, within a 2.4km walk of Indian Key Historic State Park and Bud n' Mary's Dive Centre, and under 1.6km from the Hurricane Monument and Florida Keys Brewing Co. The 42 square metre self-catering apartment offers a queen-size bed, one bathroom, sleeps six, and includes a pool, terrace, and concierge service, providing easy access to Islamorada's attractions.
Islamorada, FL
03/08 – 05/08
1282 €/nighttotal: 2564 € (2 )
Two Bedroom Ocean Front Suite W/kitchenette, Pool, Free Parking & Pet Friendly
2 5
resort , Islamorada, Village of Islands
This pet-friendly oceanfront suite, part of a non-smoking resort in Islamorada's Matecumbe district, offers convenient access to beaches, parks, and attractions such as the Morada Way Arts & Cultural District and Indian Key Historic State Park (distances unspecified). The 'Two Bedroom Ocean Front Suite W/kitchenette, Pool, Free Parking & Pet Friendly' sleeps six, features a kitchenette, balcony access from each room, free Wi-Fi, and a shared pool; nearby water sports include jet skiing, kayaking, and scuba diving.
Best Islamorada, FL resorts with a jacuzzi
Among the 69 accommodations in Islamorada, FL, here are the 2 best resorts with a jacuzzi
9.1 3677 reviews
Islamorada, FL
09/10 – 12/10
593 €/nighttotal: 1779 € (3 )
Cheeca Lodge & Spa
1 2
resort , Islamorada, Village of Islands
Cheeca Lodge & Spa is situated on a 27-acre stretch of waterfront in Islamorada, just a 20-minute drive from downtown Key Largo and 13.7 miles from Long Key State Park. The resort has received very good user ratings, with excellent scores for location and cleanliness. The property features spacious rooms with balconies and resort views. Guests can enjoy a range of amenities, including a 9-hole golf course, spa, fishing pier, swimming pools, fitness centre, tennis courts, and watersports facilities.
9.0 2591 reviews
Islamorada, FL
10/07 – 15/07
1049 €/nighttotal: 5245 € (5 )
Chesapeake Beach Resort
2 6
resort , Islamorada, Village of Islands
Chesapeake Beach Resort is located in Islamorada, Florida, just two miles from Windley Key Fossil Reef Geological State Park and directly on the oceanfront, offering stunning ocean views and easy access to the beach. The resort has received very good ratings for location, cleanliness, and overall user experience. The resort offers a range of rooms and suites, all featuring a 37-inch flat-screen cable TV and a small refrigerator. Guests can enjoy an outdoor pool with ocean views, a Jacuzzi, a terrace or balcony, a garden, and a restaurant and bar on-site.
Best Islamorada, FL resorts with a pool
Among the 69 accommodations in Islamorada, FL, here are the 4 best resorts with a pool
8.0 4 reviews
Islamorada, FL
07/07 – 11/07
353 €/nighttotal: 1412 € (4 )
Ideal Location! Pets Allowed, Onsite Pool
2 4
resort , Islamorada, Village of Islands
This resort in Islamorada, Village of Islands, is located approximately 160 kilometres south of Miami, offering a prime spot for fishing, boating, and enjoying local cuisine with bay and ocean vistas. This pet-friendly hotel, offering the "Ideal Location! Pets Allowed, Onsite Pool" package, provides 2-bedroom accommodation for up to four guests, featuring air conditioning, internet, a swimming pool, and daily cleaning services within its 51.5 square metre rooms.
Islamorada, FL
03/08 – 05/08
337 €/nighttotal: 674 € (2 )
2 Pet-friendly Units, Free Breakfast, Pool
2 5
resort , Islamorada, Village of Islands
This resort offers two-bedroom, two-bathroom holiday accommodation for eight guests, situated on a private beach in Islamorada, Village of Islands, a short walk from the Theater of the Sea and near Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. Enjoy the "2 Pet-friendly Units, Free Breakfast, Pool" offer, which includes access to a heated outdoor swimming pool, complimentary toiletries, and on-site parking, with pet-friendly options available for an additional charge, whilst being close to coral reef snorkelling and scuba diving.
10 1 review
Islamorada, FL
09/10 – 12/10
314 €/nighttotal: 942 € (3 )
Large Unit W/ Private Beach Access! Free Breakfast
1 2
resort , Islamorada, Village of Islands
This Islamorada apartment, situated on a private beach within walking distance of the Theatre of the Sea and close to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park, offers convenient access to local attractions. The 37 square metre self-catering flat features two queen beds and a sofa bed, sleeping up to four guests, and includes a kitchenette, daily housekeeping, complimentary continental breakfast, and access to resort amenities such as a heated pool, kayaks, paddleboards, and bicycles.
9.7 6 reviews
Islamorada, FL
30/07 – 06/08
254 €/nighttotal: 1778 € (7 )
Perfect For Family Beach Vacation! Free Breakfast
1 2
resort , Islamorada, Village of Islands
This Islamorada apartment, situated on a private beach within a pet-friendly resort, is a short walk (less than 1km) from the Theatre of the Sea and close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks. The self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes a balcony, a swimming pool, fitness centre, free parking, and daily continental breakfast and housekeeping, plus access to kayaks, paddleboards and bikes.
Frequently asked questions about resorts in Islamorada, FL
What time of year is best to stay in a resort in Islamorada, FL?
The best time to visit Islamorada is during the spring (March - May) or autumn (September - November) when the weather is pleasant and there are fewer crowds. You can enjoy swimming, fishing, and other outdoor activities without the summer heat and humidity.
What are the best resorts with a swimming pool in Islamorada, FL?
A popular day trip is to Key West to explore the historic Old Town, visit the Hemingway House, or relax on the beaches. You can also take a boat trip to Dry Tortugas National Park, where you can see the Fort Jefferson and snorkel in the crystal-clear waters.
What are the best resorts with jacuzzi in Islamorada, FL?
What are the most romantic activities in and around Islamorada, FL?
For a romantic getaway, take a sunset cruise on a sailboat or catamaran. You can also enjoy a private dinner on the beach or have a picnic at Anne's Beach. Take a walk along the Islamorada Waterfront to watch the sunset over the ocean.
What are the best family friendly resorts in Islamorada, FL?
What are the nearest cities to explore when you are in Islamorada, FL?
The nearest major city is Miami, about a four-hour drive from Islamorada. You can also visit Key West, which is about an hour and a half drive from Islamorada, and Marathon, which is about 30 minutes away.
What are the best pet friendly resorts in Islamorada, FL?
What are the most requested amenities in resorts in Islamorada, FL?
Most resorts in Islamorada offer amenities like swimming pools, private beaches, and on-site restaurants. Many also have water sports activities like kayaking, paddleboarding, and fishing. Some resorts even have spas and fitness centres.
Destinations nearby
Best Islamorada, FL resorts with air conditioning
Islamorada, FL
03/08 – 05/08
505 €/nighttotal: 1010 € (2 )
Pleasant Stay! 3 Classy Units, Onsite Pool
3 5
resort , Islamorada, Village of Islands
The "Pleasant Stay! 3 Classy Units, Onsite Pool" resort offers direct access to a private beach in Islamorada, Village of Islands, placing guests within easy reach of coral reefs for diving, and just a short walk from the History of Diving Museum. This pet-friendly accommodation comprises three separate hotel rooms, each measuring 27.95 square meters, with a total capacity of 12 guests, and features an on-site heated outdoor swimming pool and complimentary parking.
Islamorada, FL
26/06 – 30/06
1108 €/nighttotal: 4432 € (4 )
One Bedroom Suite W/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly
2 3
resort , Islamorada, Village of Islands
This pet-friendly resort, offering the 'One Bedroom Suite W/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly' package, is located in Islamorada's Matecumbe district, directly on the beach and within easy reach of Indian Key Historic State Park and the Hurricane Monument. The self-catering suite features two bedrooms, two bathrooms, sleeps up to twelve guests, and includes a kitchenette, balcony, free Wi-Fi, and access to on-site and nearby water sports.
Islamorada, FL
07/07 – 11/07
822 €/nighttotal: 3288 € (4 )
2 Suites W/queen Beds, Kitchenette, Outdoor Pool, Free Parking & Pet Friendly
2 4
resort , Islamorada, Village of Islands
This pet-friendly resort, offering '2 Suites W/queen Beds, Kitchenette, Outdoor Pool, Free Parking & Pet Friendly', is located in Islamorada's Matecumbe district, close to recreational parks and beaches, with convenient access to Indian Key Historic State Park and the Hurricane Monument, though precise distances aren't specified. The two-suite property sleeps up to 12 guests, each suite featuring queen-size beds, a kitchenette, and a balcony; on-site or nearby activities include watersports such as jet skiing, kayaking, and scuba diving, plus cycling.
8.3 758 reviews
Islamorada, FL
10/07 – 15/07
938 €/nighttotal: 4690 € (5 )
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort
3 6
resort , Islamorada, Village of Islands
The Postcard Inn Beach Resort & Marina is located on an island in the Florida Keys, just 3 km from Windley Key Fossil Reef Geological Park and 34 km from Key Largo. The resort has received very good ratings for user experience, location, and cleanliness. The resort offers a range of amenities and activities, including a swimming pool, a terrace, a garden, a restaurant, a bar, and a marina. Guests can enjoy fresh seafood at the Raw Bar, charter fishing trips, or explore the surrounding area by jet ski.
Best Islamorada, FL resorts with a gym
8.7 83 reviews
Islamorada, FL
08/09 – 06/10
337 €/nighttotal: 9436 € (28 )
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort
1 2
resort , Islamorada, Village of Islands
Three Waters Resort And Marina, a Tribute Portfolio Resort, is located in Islamorada, Florida, offering fifteen waterfront acres with convenient access to the village's attractions and the renowned sport fishing opportunities of the area. This Islamorada resort boasts diverse lodging options, including rooms and cottages, a private beach lagoon at The Cove, nine restaurants ranging from casual to upscale dining (including the Kindler and Tiki Bar), a full-service marina, a fitness centre, and a swimming pool.