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Top Romantic Islamorada Hotels

Cheeca Lodge & Spa

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 ...

9/10 Wonderful! (1,276 reviews)

We stayed in the newest section of the Cheeca Lodge. It is so incredibly nice! We had other family staying in the lagoon area. We enjoyed all the activities on the property as well. My nephew especially loved the par3 golf course. I really loved the staff at Cheeca Lodge too. Shelia, Amber and David ...

Reviewed on 26 Nov 2025

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

22 min walk from Theater of the Sea

Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...

9.2/10 Wonderful! (1,587 reviews)

Excellent hotel

Reviewed on 26 Nov 2025

Amara Cay Resort

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! (1,268 reviews)

Loved the resort

Reviewed on 21 Nov 2025

See all 2,241 properties in Islamorada

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.