This Islamorada resort, offering a four-bedroom apartment, boasts private beach access and is 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. The 1160 sq ft property sleeps up to 16 guests, features four bathrooms, a private boat ramp (fee applies), daily housekeeping, a complimentary continental breakfast, and access to an on-site heated pool, kayaks, paddleboards, and bike rentals.
8.8 873 reviews
Islamorada, FL
23/07 – 26/07
401 €/nighttotal: 1203 € (3 )
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
28/06 – 01/07
604 €/nighttotal: 1812 € (3 )
Relaxing Stay! 3 Classy Units, Free Breakfast
3 5
resort , Islamorada, Village of Islands
This Islamorada resort apartment, offering private beach access, is located within walking distance of the Theatre of the Sea and close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks. The property comprises three separate 88-square-metre units, each sleeping four, with a total guest capacity of twelve, and includes on-site amenities such as a heated pool, kayaks, paddleboards, bike rentals, daily continental breakfast, and daily housekeeping.
Islamorada, FL
09/08 – 14/08
195 €/nighttotal: 975 € (5 )
Premium Suites W/ Kitchenette! Pets Allowed, Pool
1 2
resort , Islamorada, Village of Islands
This resort in Islamorada, Village of Islands, offers premium suites with kitchenettes and is situated on a private beach, within 500 meters of the Theater of the Sea and close to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. These pet-friendly lodgings provide 31 square meters of space for two guests, featuring air conditioning, internet, and access to a heated outdoor swimming pool and gardens, with complimentary parking available.
10 3 reviews
Islamorada, FL
09/08 – 14/08
174 €/nighttotal: 870 € (5 )
Luxury Beach Resort W/ Kayaking, Bike Rental, Pool
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 and Lignum Vitae Key Botanical State Parks, offers convenient access to local attractions. The 301 sq ft (28 sq m) self-catering flat features two queen beds, a balcony, and accommodates up to four guests, with amenities including a heated pool, kayaks, paddleboards, bike rentals, daily continental breakfast, and daily housekeeping.
Islamorada, FL
19/07 – 26/07
1035 €/nighttotal: 7245 € (7 )
2 Spacious Garden Suite W/ Kitchenette | Outdoor Pool + Beach Access
2 9
resort , Islamorada, Village of Islands
This beachfront property in Matecumbe, Islamorada, offers the '2 Spacious Garden Suites W/ Kitchenette | Outdoor Pool + Beach Access' option, situated 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 57 square metre suites, each sleeping up to 12 guests, feature two bedrooms, two bathrooms, a kitchenette, a terrace/balcony, and access to an outdoor pool, plus concierge services and on-site parking.
Islamorada, FL
03/07 – 05/07
389 €/nighttotal: 778 € (2 )
Large Unit Near Secret Beach! Free Breakfast
1 2
resort , Islamorada, Village of Islands
This Islamorada resort offers the "Large Unit Near Secret Beach! Free Breakfast" deal, situated on a private beach with direct access to coral reefs, just 700 meters from the History of Diving Museum and within walking distance of the Theater of the Sea, and a short drive to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. This pet-friendly accommodation, suitable for up to four guests, provides 33 square meters of living space, air conditioning, internet, a swimming pool, and complimentary parking, with cleaning services included and an additional charge for pets.
9.5 4 reviews
Islamorada, FL
16/10 – 18/10
879 €/nighttotal: 1758 € (2 )
Rare Gem! 4 Spacious Units, Free Parking, Pool
4 12
resort , Islamorada, Village of Islands
This Islamorada resort, offering four self-contained units, boasts private beach access with a boat ramp and is 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. Each 93 square metre (301 sq ft) unit features two queen-size beds, a balcony with partial ocean views, and the property includes a heated pool, kayaks, paddleboards, bicycles, barbecue facilities, and accommodates up to sixteen guests.
8.0 4 reviews
Islamorada, FL
21/06 – 26/06
371 €/nighttotal: 1855 € (5 )
Ideal Location! Pets Allowed, Onsite Pool
2 2
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.
10 1 review
Islamorada, FL
21/06 – 26/06
1327 €/nighttotal: 6635 € (5 )
3 Bedroom Suite W/kitchenette, Pool, Free Parking & Pet Friendly
3 2
resort , Islamorada, Village of Islands
This beachfront villa in Matecumbe, Islamorada, is situated a short 2.4km walk from 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. This three-bedroom, one-bathroom property offers 67 square metres of living space, sleeping up to eight guests and boasting a swimming pool, terrace, and concierge service, alongside convenient amenities such as Wi-Fi and parking.
Islamorada, FL
18/07 – 22/07
281 €/nighttotal: 1124 € (4 )
Convenient Stay, Superb Location, Free Breakfast
1 4
resort , Islamorada, Village of Islands
This Islamorada resort offers a "Convenient Stay, Superb Location, Free Breakfast" package, situated on a private beach just 200 metres from the History of Diving Museum and within easy reach of Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. This family-friendly accommodation, suitable for up to four guests, features air conditioning, Wi-Fi, an outdoor heated swimming pool, and allows pets for an additional fee, with complimentary parking available.
Islamorada, FL
28/06 – 01/07
1226 €/nighttotal: 3678 € (3 )
2 Separate Unites W/ 2 Bedrooms, Kitchenette, Pool, Free Parking & Pool
4 5
resort , Islamorada, Village of Islands
This four-bedroom, two-bathroom holiday property, offering '2 Separate Units W/ 2 Bedrooms, Kitchenette, Pool, Free Parking & Pool', is located in Islamorada's Matecumbe district, near Indian Key Historic State Park and the Hurricane Monument. The self-catering villa, sleeping up to 16 guests, boasts a pool, free Wi-Fi, and balconies with views, plus easy access to watersports such as jet skiing and kayaking in the nearby waters.
Best Islamorada, FL resorts with a jacuzzi
Among the 69 accommodations in Islamorada, FL, here are the 2 best resorts with a jacuzzi
9.0 2594 reviews
Islamorada, FL
24/07 – 26/07
406 €/nighttotal: 812 € (2 )
Chesapeake Beach Resort
1 2
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.
9.1 3678 reviews
Islamorada, FL
09/08 – 14/08
208 €/nighttotal: 1040 € (5 )
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.
Best Islamorada, FL resorts with a pool
Among the 69 accommodations in Islamorada, FL, here are the 4 best resorts with a pool
9.5 470 reviews
Islamorada, FL
02/07 – 05/07
675 €/nighttotal: 2025 € (3 )
Ragged Edge Resort & Marina
2 5
resort , Islamorada, Village of Islands
Ragged Edge Resort & Marina is located in Islamorada, just a short drive from Windley Key and Upper Matecumbe Key, offering easy access to the area's natural beauty. The resort has consistently received excellent ratings for location, cleanliness, and overall experience. The accommodation features a mix of rooms and suites, some with balconies offering sea views. Guests can enjoy amenities such as a swimming pool, terrace, free bikes, a communal grill, and free Wi-Fi.
This Islamorada apartment, situated on a private beach within walking distance of the Theatre of the Sea and close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks, offers convenient access to local attractions. This one-bedroom, one-bathroom flat sleeps four guests comfortably, boasting two queen-size beds, a private beach, on-site amenities including a heated pool, kayaks, paddleboards, bicycles, daily continental breakfast, daily housekeeping, and free parking.
Islamorada, FL
18/07 – 22/07
430 €/nighttotal: 1720 € (4 )
Best Place To Unwind! 2 Classy Units, Onsite Pool
2 4
resort , Islamorada, Village of Islands
This Islamorada apartment complex boasts private beach access and is within walking distance of the Theatre of the Sea, and close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks. Offering two separate 290 sq ft (approx. 27 sq m) units, each with two queen-size beds, this pet-friendly property sleeps eight, and includes a heated pool, kayaks, paddleboards, bike rentals, daily continental breakfast, and complimentary parking for one car.
9.2 2444 reviews
Islamorada, FL
03/07 – 10/07
869 €/nighttotal: 6083 € (7 )
Pines & Palms Resort
2 8
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.
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
01/07 – 08/07
1378 €/nighttotal: 9646 € (7 )
Two Bedroom Ocean Front Suite W/kitchenette, Pool, Free Parking & Pet Friendly
2 2
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.
8.3 758 reviews
Islamorada, FL
09/07 – 12/07
1087 €/nighttotal: 3261 € (3 )
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort
2 5
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.
10 2 reviews
Islamorada, FL
28/06 – 01/07
366 €/nighttotal: 1098 € (3 )
Proximity Ats Its Best! 2 Convenient Units, Pool
2 5
resort , Islamorada, Village of Islands
This Islamorada apartment rental is situated on a private beach, within walking distance of the Theatre of the Sea and close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks. The 606 sq ft property comprises two bedrooms, two bathrooms, sleeps eight guests, and offers amenities including a heated pool, kayaks, paddleboards, bicycles, and complimentary continental breakfast.
10 2 reviews
Islamorada, FL
28/06 – 01/07
706 €/nighttotal: 2118 € (3 )
2 Bedroom Suite W/ Kitchenette, Outdoor Pool, Free Parking & Pet Friendly!
2 5
resort , Islamorada, Village of Islands
This beachfront villa in Matecumbe, Islamorada, enjoys a central location, less than 2km from Hurricane Monument and the Florida Keys Brewing Company, and a 15-minute walk from Indian Key Historic State Park and Bud n' Mary's Dive Centre. The 125 square metre property offers two bedrooms, one bathroom, sleeps eight guests, and includes a swimming pool, terrace, and concierge service, alongside amenities such as Wi-Fi and parking.
Best Islamorada, FL resorts with a gym
8.7 83 reviews
Islamorada, FL
18/07 – 22/07
772 €/nighttotal: 3088 € (4 )
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort
2 4
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.
9.0 4004 reviews
Islamorada, FL
09/07 – 12/07
1111 €/nighttotal: 3333 € (3 )
Islander Resort
2 5
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.