Islamorada Luxury Vacations
Book a Luxury Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
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Top Luxury Islamorada Hotels
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
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! (1,300 reviews)
This palce is awesome. Clean rooms. 2 large pools with a view. Covered garage spot.
Reviewed on Jan 22, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
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! (1,267 reviews)
No issues
Reviewed on Jan 20, 2026
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
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! (1,004 reviews)
The room walked right out to water. Staff came around to ask if we needed anything. It was amazing!
Reviewed on Jan 19, 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.
