Islamorada Luxury Holidays
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Top Luxury Islamorada Hotels
Cheeca Lodge & Spa
81801 Overseas Highway, Mile 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 ...
9.2/10 Wonderful! (1,301 reviews)
This palce is awesome. Clean rooms. 2 large pools with a view. Covered garage spot.
Reviewed on 22 Jan 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
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! (1,276 reviews)
We enjoyed our stay and found the staff to be courteous and responsive. Our room was a generous size, clean and well appointed (as is often the case we wouldn’t have said no to a couple of more outlets lol). The beach and pool areas had plenty of seating and multiple things to do—ping pong, cornhole, ...
Reviewed on 26 Jan 2026
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
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! (1,007 reviews)
Great stay, better than I even expected from the pictures. Quiet, quaint little place right on the water. The edge is actually a dock, but it looks like it’s right on its own, private, wide beach! The internet was good - I had a half day of doing Zoom work calls and had no problems. It’s quiet, the ...
Reviewed on 21 Jan 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
