
Florida Keys Luxury Vacations
Book a Luxury Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ₩234,741 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Luxury Florida Keys Hotels

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Pamper yourself with a luxury stay at Oceans Edge Key West Resort, Hotel & Marina, where you can enjoy amenities like Egyptian cotton sheets, plush bedding, ...
8.8/10 Excellent! (1,718 reviews)
"Friendly staff, had a couple minor issues in our room but contacted front desk and things were taken care of immediately! Lots of activities located on property (kayaks, paddle boards, bicycles, & pools). This is located away from the hustle and bustle of Key West so it’s quiet. The shuttle is a ..."
Reviewed on Aug 15, 2025

The Marker Key West Harbor Resort
200 William Street, Key West, FL
Be treated to a grand stay at The Marker Key West Harbor Resort, where you'll find deep soaking bathtubs and premium bedding. The 3 outdoor pools, poolside bar, ...
9/10 Wonderful! (1,004 reviews)
"We liked the walkable access to old town and local dining options. We didn’t like that the room wasn’t made up until 5pm or so and several times had to postpone cleaning up at the end of a busy day doing things to allow housekeeping to make up the room. Also I think a hotel bar/restaurant should ..."
Reviewed on Aug 18, 2025

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, 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 ...
9/10 Wonderful! (1,149 reviews)
"Great place. Best way to relax and enjoy the keys."
Reviewed on Aug 17, 2025
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.