
Islamorada Luxury Holidays
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Top Luxury Islamorada Hotels

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
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! (1,222 reviews)
"I went there this weekend to celebrate my birthday. Great place, well kept, nice service, rooms are pretty and clean. The pools are nice. Loved the resort. Hope to come back soon. They had a room for me right away. Check in was very pleasant. The paddle boarding, and canoes are free with the stay. ..."
Reviewed on 12 Oct 2025

Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
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! (1,254 reviews)
"Room was spacious, clean with a great balcony."
Reviewed on 7 Oct 2025

Drop Anchor
84959 Overseas Highway, 222, Islamorada, FL
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! (1,000 reviews)
"Clean, comfortable room, friendly staff. Grounds clean and properly taken care of. Would stay here again."
Reviewed on 1 Oct 2025
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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