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Choose from 2157 Islamorada Hotel Deals

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! (1,720 reviews)
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Reviewed on May 15, 2026

Chesapeake Beach Resort
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! (1,312 reviews)
I can't say enough good things about the Cheeka Lodge and Spa! The room was beautiful, the staff were amazing, amd the food was spectacular! Highly recommend!

Reviewed on May 15, 2026

Cheeca Lodge & Spa
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! (1,013 reviews)
Room was spacious but could use better lighting. Bathroom was very small and small vanity with extremely oversized vessel sink resulting nowhere to place anything. Outside shy s and landscaping extremely overgrown but they started trimming day we departed. A big plus was the pool area with plenty ...

Reviewed on May 15, 2026

Islander 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! (1,271 reviews)
Room was clean .some of the staff was really rude. The staff out by paddle board were never around. Better off staying at Three Waters resort . Staff much more accommodating . Nicer and it the sister resort to Amara Cay.

Reviewed on May 14, 2026

Amara Cay 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! (197 reviews)
Great vacation!! Room needed some work such as shower door panel missing and the door didn’t lock. Other than that is was beautiful place It also needs an onsite laundry facility. When you have fishermen you need that badly.

Reviewed on May 15, 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! (1,002 reviews)
Room was nice with balcony but not what I expected. Thought I was booking the room that was in the picture. All the pictures of my room at time of reservation appeared like the photos shown on the site, but this was not in fact the room we received. Overall the property is pretty nice with bikes, ...

Reviewed on May 14, 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! (1,005 reviews)
Needed some updating.

Reviewed on May 14, 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! (1,001 reviews)
There’s quite a bit of variety in the accommodation choices. Whether you are on a family vacation, a boater/jet skiier, or just want to gaze at the ocean or poolside, you’ll enjoy this hotel’s location.

Reviewed on May 11, 2026

Hadley Resort and Marina
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! (153 reviews)
This place is absolutely incredible. It offers a perfect harmony with nature—you immediately feel relaxed and at peace as soon as you arrive. The atmosphere is calm, quiet, and truly refreshing, making it the perfect escape from everyday stress. The fishing experience here is amazing. Whether you're ...

Reviewed on May 3, 2026

Treasure Harbor
Bayside Villas by Islander Resort

Bayside Villas by Islander Resort

3.5 out of 5
81450 Overseas Highway Islamorada FL
  • 9 min drive from Theater of the Sea
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 3 restaurants. Popular attractions Hurricane Monument and MoradaWay Arts & ...
8.8/10 Excellent! (429 reviews)
Really impressed with this property.

Reviewed on May 14, 2026

Bayside Villas by Islander Resort
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
  • 6 min drive from Theater of the Sea
Stay at this hotel in Islamorada. Enjoy free WiFi, a private beach, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (1,002 reviews)
Highly recommend La Jolla .. it is a gem of the Keys.

Reviewed on May 14, 2026

La Jolla Resort
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! (262 reviews)
The property is beautiful. The pool is amazing. It's a walk in pool that gradually gets deeper to a tall rock formation with a waterfall cascading down with cool refreshing water. You can relax in the pool with a picturesque ocean view. The property is owner operated, so much love goes into the care ...

Reviewed on May 12, 2026

Coconut Cove Resort and Marina
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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How many hotels are there in Islamorada?

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