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Choose from 2204 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! (1,702 reviews)
Super clean, we stayed in a 1 bdrm villa, ocean view. Recently updtd. Staff, anyone we ran into were so nice. April 18 - 25th, no crowds whatsoever there during our stay of 7 nights.

Reviewed on Apr 25, 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! (1,313 reviews)
Everything

Reviewed on Apr 24, 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! (1,004 reviews)
Perfect for a few days! In such a good location to be able to explore a lot of places outside of the resort property and tucked away from the main road.

Reviewed on Apr 24, 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! (1,266 reviews)
Nice quiet, relaxing property

Reviewed on Apr 24, 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! (190 reviews)
Clean updated room, great view and balcony! Loved the property and amenities.

Reviewed on Apr 25, 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! (1,001 reviews)
It was simply stunning. Beautiful location, great facilities, spacious apartment and for a family of 5 the door key card being on the wristband is genius. Thank you for a wonderful stay

Reviewed on Apr 21, 2026

La Siesta Resort & Villas
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)
Our room was very clean and we had a phenomenal view.

Reviewed on Apr 24, 2026

Hadley Resort and Marina
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! (1,004 reviews)
Room nice, with comfy beds and useful kitchenette area. Rest of property appears quite run down and needs a bit of TLC. There was a spilt breakfast porridge carton on stairwell that wasn’t cleaned up for the two days that we stayed which shows a bit of lack of care and attention.

Reviewed on Apr 25, 2026

Fisher Inn Resort & 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! (250 reviews)
Not a place I would recommend!!

Reviewed on Apr 24, 2026

Coconut Cove 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! (150 reviews)
Place was as described. Only thing i would recommend is a little more attention to detail during turnover cleaning as we found nail clippings and foot splatter on the wall. We loved the setting after our long days being able to be on the water, had manatees swim by us a couple times. Still recommend ...

Reviewed on Apr 16, 2026

Treasure Harbor
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)
Excellent stay, friendly staff and excellent location on the bayside of the Key. Great views and lots of chairs and recliners to take in the views.

Reviewed on Apr 22, 2026

La Jolla Resort
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
  • 8 min walk 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 helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (1,001 reviews)
The place over charges this is not a resort it’s more like a motel I payed over $1200 for two nights and I feel this place shouldn’t charge more than $250 a night. Also be aware there was a resort fee the kayaks weren’t working and the office was always closed. Will not be going back.

Reviewed on Apr 20, 2026

Drop Anchor
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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