Islamorada Luxury Holidays

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Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
  • 8 min drive from Theater of the Sea
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,155 reviews)
"Perfect experience from beginning to end. Greeted by friendly people at the gate that gave me excellent information on checking in and parking. The check in staff were very friendly and when asked if any upgrades to my room were avaliable she found me something nicer then I was able to. The room ..."

Reviewed on 23 Aug 2025

Cheeca Lodge & Spa
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! (1,235 reviews)
"Very clean also beautiful pool area"

Reviewed on 20 Aug 2025

Amara Cay 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 3-star hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (1,001 reviews)
"Liked the Atlantic bulkhead. Plenty of dock space and casting room. Tasteful atmosphere with clean grounds and pool. Boat launch looked safe and maintained. Outdoor lights gave a nice ambience. Room was clean and properly stocked. TV was outdated."

Reviewed on 22 Aug 2025

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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.