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Islamorada, FL resorts
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69 Best resorts in Islamorada, FL

Best Islamorada, FL resorts with a jacuzzi

Among the 69 accommodations in Islamorada, FL, here are the 2 best resorts with a jacuzzi

Chesapeake Beach Resort - Islamorada, FL
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.
Cheeca Lodge & Spa - Islamorada, FL
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

Ragged Edge Resort & Marina - Islamorada, FL
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.
Florida Keys Tour! Private Beach Access W/ Marina! - Islamorada, FL
8.0 1 review
Islamorada, FL
30/07 – 06/08
233 €/nighttotal: 1631 € (7 )

Florida Keys Tour! Private Beach Access W/ Marina!

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. 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.
Best Place To Unwind! 2 Classy Units, Onsite Pool - Islamorada, FL
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.
Pines & Palms Resort - Islamorada, FL
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?

    Pines & Palms Resort, Cheeca Lodge & Spa and Chesapeake Beach Resort are among the best resorts with a swimming pool in Islamorada, FL.

  • What are the best daytrips from 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?

    The best family friendly resorts in Islamorada, FL are Pines & Palms Resort, Cheeca Lodge & Spa and Chesapeake Beach Resort.

  • 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?

    The best pet friendly resorts in Islamorada, FL are Pines & Palms Resort, Chesapeake Beach Resort and Islander Resort.

  • 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

Two Bedroom Ocean Front Suite W/kitchenette, Pool, Free Parking & Pet Friendly - Islamorada, FL
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.
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort - Islamorada, FL
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.
Proximity Ats Its Best! 2 Convenient Units, Pool - Islamorada, FL
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.
2 Bedroom Suite W/ Kitchenette, Outdoor Pool, Free Parking & Pet Friendly! - Islamorada, FL
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

Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort - Islamorada, FL
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.
Islander Resort - Islamorada, FL
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.
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