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Hotels in Islamorada

Choose from 2220 Islamorada Hotel Deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
  • 8 min drive from Theater of the Sea
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,296 reviews)
They should have had a newsletter with activities.

Reviewed on Mar 23, 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
  • 22 min walk from Theater of the Sea
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,665 reviews)
Great location and beautiful beach

Reviewed on Mar 25, 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
  • 12 min drive from Theater of the Sea
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.8/10 Excellent! (1,263 reviews)
Here comes an AI response about “incorporating your feedback in our training”. I had a good time and the pool is best on the island. If you have no problem keeping your own room definitely stay (keys aren’t known for top service). However, staying in a suite for seven days and having to sweep, mop, ...

Reviewed on Mar 26, 2026

Amara Cay Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
  • 7 min drive from Theater of the Sea
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,000 reviews)
The AC was a split unit and didn't get cold even down at 62 degrees. The room was muggy. Also, the picture shows a normal bathroom, but the tropical double queen has no tub and a sink in the bedroom. You have to brush your teeth in the bedroom. Weird. Lastly, they removed the hot tub.

Reviewed on Mar 23, 2026

Islander Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
84001 Overseas Hwy Islamorada FL
  • 10 min walk from Theater of the Sea
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (176 reviews)
Very, very good architectural design and construction. And a well-maintained facility.

Reviewed on Mar 23, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
  • 11 min drive from Theater of the Sea
Book a stay at this beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious ...
8.6/10 Excellent! (1,000 reviews)
We had a enjoyable stay here and would come back again if we were ever in the area.

Reviewed on Mar 24, 2026

La Siesta Resort & Villas
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
  • 5 min walk from Theater of the Sea
Book a stay at this beach motel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
8.2/10 Very Good! (1,001 reviews)
Súper

Reviewed on Mar 24, 2026

Fisher Inn Resort & Marina
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
  • 5 min drive from Theater of the Sea
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
7.6/10 Good! (1,002 reviews)
Un lugar muy bonito y tranquilo, regresaré pronto

Reviewed on Mar 26, 2026

Hadley Resort and Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
  • 2 min walk from Theater of the Sea
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free parking, and a marina. Our guests praise the pool and the helpful staff in our reviews. ...
9/10 Wonderful! (224 reviews)
Do not b

Reviewed on Mar 22, 2026

Coconut Cove Resort and Marina
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy Islamorada FL
  • 6 min drive from Theater of the Sea
Stay at this hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the pool and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,001 reviews)
Needs maintenance. Staff was wonderful and very accommodating. Pool was nice.

Reviewed on Mar 25, 2026

Sunset Inn
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
  • 5 min drive from Theater of the Sea
Stay at this houseboat in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (147 reviews)
There is a really great Mexican place to walk to and a great bagel place that also serves breakfast and lunch. The boats have air conditioning, 2 large beds, bathroom and living area with a couch, small kitchen and table. It was very relaxing. We will definitely go back. Also has a beautiful pool ...

Reviewed on Mar 25, 2026

Treasure Harbor
Matecumbe Resort

Matecumbe Resort

2 out of 5
76261 Overseas Hwy Islamorada FL
  • 21 min drive from Theater of the Sea
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, free parking, and a private beach. Popular attractions Robbie’s of Islamorada and Indian Key ...
8.8/10 Excellent! (104 reviews)
Nice porch over looking the pool. Nice little beach.

Reviewed on Mar 23, 2026

Matecumbe Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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