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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 1 best resorts with a jacuzzi

Chesapeake Beach Resort - Islamorada, FL
9.0 2594 reviews
Islamorada, FL
08/09 – 06/10
A$402/nighttotal: A$11256 (28 )

Chesapeake Beach Resort

1 4
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

Premium Suites W/ Kitchenette! Pets Allowed, Pool - Islamorada, FL
Islamorada, FL
09/08 – 14/08
A$321/nighttotal: A$1605 (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.
Bayside Villas By Islander Resort - Islamorada, FL
8.8 873 reviews
Islamorada, FL
18/07 – 22/07
A$1430/nighttotal: A$5720 (4 )

Bayside Villas By Islander Resort

2 4
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.
4 Spacious Units! Free Parking, Pets Allowed - Islamorada, FL
Islamorada, FL
16/10 – 18/10
A$1515/nighttotal: A$3030 (2 )

4 Spacious Units! Free Parking, Pets Allowed

4 12
resort , Islamorada, Village of Islands
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.
Ideal Location! Pets Allowed, Onsite Pool - Islamorada, FL
8.0 4 reviews
Islamorada, FL
18/07 – 22/07
A$580/nighttotal: A$2320 (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.

Frequently asked questions about resorts in Islamorada, FL

  • How easy is it to get to Islamorada, FL?

    Getting to Islamorada is pretty straightforward. You can fly into Key West International Airport and then drive about an hour and a half, or you can drive down from Miami, which takes about four hours. If you're driving, you'll be on the famous Overseas Highway, which is a scenic drive over bridges and through islands.
  • What are the best resorts with a swimming pool in Islamorada, FL?

    Pines & Palms Resort, Chesapeake Beach Resort and Islander Resort are among the best resorts with a swimming pool 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 shoulder seasons, from April to May or September to October. The weather is still great, but the crowds are smaller and prices are usually lower. The summer months can get hot and humid, and hurricane season runs from June to November.
  • What are the best resorts with jacuzzi in Islamorada, FL?

  • What are the most romantic activities in and around Islamorada, FL?

    Islamorada is a perfect destination for a romantic getaway. You can take a sunset cruise on a sailboat, have a romantic dinner at one of the many waterfront restaurants, or spend a day exploring the Indian Key Historic State Park, which is a beautiful and secluded spot. There are also lots of opportunities for fishing, kayaking, and paddleboarding.
  • What are the best family friendly resorts in Islamorada, FL?

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

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

    The nearest city to Islamorada is Marathon, which is about 30 minutes away. You can also easily drive to Key West (about two hours), Miami (about four hours), and Fort Lauderdale (about four and a half hours).
  • 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?

    The most requested amenities in Islamorada resorts are private balconies or patios, swimming pools, and waterfront views. Many resorts also offer on-site restaurants, bars, and spa services.

Destinations nearby

Best Islamorada, FL resorts with air conditioning

2 Bedroom Suite In Islamorada! Swimming Pool, Kitchenette, Pets Allowed! - Islamorada, FL
10 1 review
Islamorada, FL
18/07 – 22/07
A$1989/nighttotal: A$7956 (4 )

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.
Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key - Islamorada, FL
Islamorada, FL
17/10 – 26/10
A$5897/nighttotal: A$53073 (9 )

Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key

6 6
resort , Islamorada, Village of Islands
This oceanfront villa in Islamorada, Florida, boasts private beach access and is located 2.1km from Sea Oats Beach, 9km from Upper Matecumbe Key, and 13km from the Theatre of the Sea.
This six-bedroom, four-bathroom property offers 303 square metres of living space, sleeps 20 guests, and features a heated pool, pickleball court, and well-equipped kitchen; massage treatments are available.
2 Bedroom Suite W/ Kitchenette, Outdoor Pool, Free Parking & Pet Friendly! - Islamorada, FL
10 2 reviews
Islamorada, FL
28/06 – 01/07
A$1160/nighttotal: A$3480 (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.
Islamorada Stay! Free Breakfast | Pool & Parking! - Islamorada, FL
Islamorada, FL
18/07 – 22/07
A$580/nighttotal: A$2320 (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.

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
24/12 – 02/01
A$1729/nighttotal: A$15561 (9 )

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.
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort - Islamorada, FL
8.3 758 reviews
Islamorada, FL
01/07 – 08/07
A$844/nighttotal: A$5908 (7 )

Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort

1 2
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.
Islander Resort - Islamorada, FL
9.0 4004 reviews
Islamorada, FL
20/06 – 27/06
A$1016/nighttotal: A$7112 (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.
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