Florida Keys Luxury Holidays

Book a Luxury Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to ₹43,962 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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 4-star 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. ...
8.8/10 Excellent! (1,684 reviews)
"Very nice property and staff. Really enjoyed our stay. Nice kayak trip with knowledgeable guide. Far from downtown and the drop off point for the shuttle is a hike, especially after sunset and a long stroll down Duval."

Reviewed on 16 Jul 2025

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 4-star eco-certified hotel in Key West. Enjoy free Wi-Fi, 3 outdoor pools and breakfast (surcharge). Our guests praise the pool and the bar in their ...
9/10 Wonderful! (1,023 reviews)
"We liked being so close to restaurants, shopping and boat tours! We enjoyed our stay and loved the on site restaurant and bar. Food and beverages were excellent. We love the pool area , it’s so clean including the restroom and awesome entertainment on the weekend. The employees go out of their way ..."

Reviewed on 17 Jul 2025

The Marker Key West Harbor Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, 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 ...
9/10 Wonderful! (1,139 reviews)
"This is a really great property."

Reviewed on 15 Jul 2025

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.