Key West Luxury Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to NZ$616 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 Key West Hotels
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Stay at this 4-star luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
8.8/10 Excellent! (1,716 reviews)
"I loved everything about this resort. So clean and easy to navigate our way around. Transportation offered worked well for us."
Reviewed on 18 Aug. 2025
The Marker Key West Harbor Resort
200 William Street, Key West, FL
Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our ...
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 18 Aug. 2025
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street, Key West, FL
Stay at this 4-star beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach ...
8.2/10 Very Good! (300 reviews)
"The staff and service is exemplary. Ask for Nicole and Marsha at the Dorada beach bar. Both are awesome bartenders and great people!!!"
Reviewed on 19 Aug. 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.