Islamorada Beach Holidays

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Top Beach Islamorada Hotels

Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
  • 7 min drive from Theater of the Sea
Stay at this 4-star 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. ...
9/10 Wonderful! (1,003 reviews)
"I enjoyed the beach front property and all the activities available on the property. My family and I really enjoyed our stay."

Reviewed on 23 Aug. 2025

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
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,237 reviews)
"Not the best hotel in the Florida Keys, but it’s OK for cooling off for a couple of days. For me the pool by the ocean and the tiki bar were the stars of the show. Rooms were meh"

Reviewed on 22 Aug. 2025

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

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

3.5 out of 5
84001 Overseas Hwy, Islamorada, FL
  • 10 min walk from Theater of the Sea
Stay at this 3.5-star 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! (63 reviews)
"Super agradable"

Reviewed on 20 Aug. 2025

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.