Florida Keys Luxury Holidays

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Top Luxury Florida Keys Hotels

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
  • 10 min drive from Duval Street
Stay at this luxury hotel in Key West. Enjoy free Wi-Fi, 6 outdoor pools and a marina. Our guests praise the pool and the restaurant in their reviews. Popular ...
8.8/10 Excellent! (1,799 reviews)
Very, very nice

Reviewed on 6 Feb 2026

Oceans Edge Key West Resort, Hotel & Marina
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
200 William Street Key West FL
  • 10 min walk from Duval Street
Stay at this business-friendly hotel in Key West. Enjoy free Wi-Fi, 3 outdoor pools and breakfast (surcharge). Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,000 reviews)
Incredible staff, especially at the pool bar. Property is in the best location, easily walkable to all Key West has to offer. The rooms are clean and comfortable with extremely cozy bed and pillows. As a repeat guest, we look forward to returning in February for another wonderful stay.

Reviewed on 27 Jan 2026

The Marker Key West Harbor Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
  • 3 hours drive from Duval Street
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,293 reviews)
Everything about this resort is wonderful. Lots to do for the whole family, great restaurants, and gorgeous areas. We will definitely be going back.

Reviewed on 4 Feb 2026

Cheeca Lodge & Spa
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.