Islamorada Luxury Vacations
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- Better togetherSave up to ₩234,741 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! (1,288 reviews)
For a five star hotel, the grounds should be kept up better
Reviewed on Jan 14, 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! (1,263 reviews)
Amazing place to stay. Staff was great
Reviewed on Jan 16, 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! (1,000 reviews)
The staff was personable, great location, having the bicycles and kayaks were a great touch
Reviewed on Jan 1, 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.
