Islamorada Luxury Vacations

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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
Cheeca Lodge & Spa is a Islamorada luxury 5-star beach property where you can treat yourself to Champagne service, massage services, and more. The 2 poolside ...
9.2/10 Wonderful! (1,319 reviews)
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Reviewed on 2026/4/29

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
Amara Cay Resort is a Islamorada luxury 4-star beach property where you can treat yourself to pillowtop beds, Egyptian cotton sheets, and more. Notable amenities ...
8.8/10 Excellent! (1,270 reviews)
We had the most amazing stay at Amara Cay in Islamorada for our honeymoon! From the moment we arrived, everything felt effortless, relaxing, and truly special. The property is absolutely beautiful—clean, modern, and perfectly captures that laid-back luxury island vibe. The rooms were comfortable ...

Reviewed on 2026/4/29

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
Discover luxurious lodging at Drop Anchor, where you can enjoy amenities like plush bedding, premium channels, and more. Notable amenities include an outdoor ...
8.8/10 Excellent! (1,000 reviews)
Our room was comfortable and clean. The grounds and pool were really nice. The entire staff were awesome. It was really cool having the kayaks on the property. We had a great stay.

Reviewed on 2026/4/26

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.