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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 2591 reviews
Islamorada, FL
28/06 – 01/07
SG$1098/nighttotal: SG$3294 (3 )

Chesapeake Beach Resort

1 5
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 3677 reviews
Islamorada, FL
01/07 – 05/07
SG$2919/nighttotal: SG$11676 (4 )

Cheeca Lodge & Spa

2 7
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

Rare Find! 4 Pleasant Units! Free Breakfast - Islamorada, FL
8.0 1 review
Islamorada, FL
09/10 – 12/10
SG$1469/nighttotal: SG$4407 (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.
Convenient Stay, Superb Location, Free Breakfast - Islamorada, FL
Islamorada, FL
30/07 – 06/08
SG$443/nighttotal: SG$3101 (7 )

Convenient Stay, Superb Location, Free Breakfast

1 2
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.
4 Pet-friendly Units! Onsite Pool, Free Breakfast - Islamorada, FL
Islamorada, FL
03/08 – 05/08
SG$1000/nighttotal: SG$2000 (2 )

4 Pet-friendly Units! Onsite Pool, Free Breakfast

4 5
resort , Islamorada, Village of Islands
This resort in Islamorada, Village of Islands, provides direct access to a private beach and is situated within 1 kilometre of Windley Key Fossil Reef Geological State Park, Lignumvitae Key Botanical State Park, the History of Diving Museum, and the Theater of the Sea.
The "4 Pet-friendly Units! Onsite Pool, Free Breakfast" package offers accommodation for up to 16 guests across four bedrooms and four bathrooms, featuring an outdoor heated swimming pool, air conditioning, internet, and complimentary parking, with pets permitted for an additional fee.
Ragged Edge Resort & Marina - Islamorada, FL
9.5 469 reviews
Islamorada, FL
28/06 – 01/07
SG$982/nighttotal: SG$2946 (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.

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 stay in a resort in Islamorada is during the shoulder seasons, from April to May and September to October. You'll have pleasant weather and fewer crowds. The summer months can be quite hot and humid, and the winter months can be a little cool, but it's still a great time to visit if you don't mind the crowds.
  • 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 most romantic activities in and around Islamorada, FL?

    For a romantic evening, you can take a sunset cruise on the water. You can also have a romantic dinner at one of the many waterfront restaurants in Islamorada. If you are looking for something more adventurous, you can go on a kayaking or paddleboarding tour through the mangroves.
  • What are the best resorts with jacuzzi in Islamorada, FL?

    Cheeca Lodge & Spa, Chesapeake Beach Resort and The Caribbean Resort are the best resorts with a jacuzzi in Islamorada, FL.

  • What are the nearest cities to explore when you are in Islamorada, FL?

    The nearest cities to Islamorada are Key West, Marathon, and Tavernier. Key West is about an hour and a half drive south, Marathon is about an hour drive north, and Tavernier is about 15 minutes north.
  • 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 most requested amenities in resorts in Islamorada, FL?

    The most requested amenities in resorts in Islamorada are swimming pools, private beaches, and restaurants. Many resorts also offer watersports activities, such as kayaking, paddleboarding, and fishing.
  • 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.

Destinations nearby

Best Islamorada, FL resorts with air conditioning

Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort - Islamorada, FL
8.3 758 reviews
Islamorada, FL
03/08 – 05/08
SG$1028/nighttotal: SG$2056 (2 )

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.
Rare Gem! Free Parking, Breakfast, Onsite Pool - Islamorada, FL
Islamorada, FL
30/07 – 06/08
SG$391/nighttotal: SG$2737 (7 )

Rare Gem! Free Parking, Breakfast, Onsite Pool

1 2
resort , Islamorada, Village of Islands
This Islamorada resort offers direct access to a private beach and is situated conveniently close to renowned coral reefs for snorkelling and diving, Windley Key Fossil Reef Geological State Park, Lignumvitae Key Botanical State Park, the History of Diving Museum, and the Theatre of the Sea.
The "Rare Gem! Free Parking, Breakfast, Onsite Pool" offer includes accommodation for two guests with one bathroom, featuring air conditioning, internet, a pet-friendly policy with additional charges, and an on-site outdoor heated swimming pool.
One Bedroom Suite W/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly - Islamorada, FL
Islamorada, FL
07/07 – 11/07
SG$1251/nighttotal: SG$5004 (4 )

One Bedroom Suite W/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly

2 4
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.
2 Bedroom Suite In Islamorada! Swimming Pool, Kitchenette, Pets Allowed! - Islamorada, FL
10 1 review
Islamorada, FL
26/06 – 30/06
SG$1917/nighttotal: SG$7668 (4 )

2 Bedroom Suite In Islamorada! Swimming Pool, Kitchenette, Pets Allowed!

2 3
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.

Best Islamorada, FL resorts with a gym

Islander Resort - Islamorada, FL
9.0 4007 reviews
Islamorada, FL
08/09 – 06/10
SG$384/nighttotal: SG$10752 (28 )

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.
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