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, 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 ...
9/10 Wonderful! (1,135 reviews)
"We absolutely loved our stay at cheeca, will not be our last!"

Reviewed on Jul 19, 2025

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! (1,237 reviews)
"Cool atmosphere. Lobby/lounge area was cute and the bar looked nice. We're here in the off season so the hours for the tiki bar werent super ideal, but it was still nice."

Reviewed on Jul 16, 2025

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 ...
8.6/10 Excellent! (1,000 reviews)
"Clean and convenient"

Reviewed on Jul 14, 2025

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.