Islamorada Luxury Holidays

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Top Luxury Islamorada Hotels

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
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 ...
9.2/10 Wonderful! (1,287 reviews)
The rooms in those the lodge are in desperate need of new carpet it was so gross

Reviewed on 11 Jan 2026

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 beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...
8.8/10 Excellent! (1,260 reviews)
This resort exceed our expectations. Wonderful for families , very clean and amazing staff. We did a free fishing lesson with captain Patrick and he was wonderful-also great with kids. Loved the free water taxi to visit the sister resorts . We will definitely be back

Reviewed on 10 Jan 2026

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 hotel in Islamorada. Enjoy free Wi-Fi, free parking and free bicycles on-site. Our guests praise the helpful staff and the clean rooms in their ...
8.6/10 Excellent! (1,000 reviews)
The staff was personable, great location, having the bicycles and kayaks were a great touch

Reviewed on 1 Jan 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.