Explore top 2025 5 Star Hotels in Windley Key

Name: Waterfront House with Boat Dock
Rating: 6

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Top Windley Key 5 Star hotels

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL

Fully refundableReserve now, pay when you stay

$199 nightly

$224 total

Oct 26 - Oct 27

Total with taxes and fees

This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...

9/10 Wonderful! (1,236 reviews)

Nice room with everything you need.

Reviewed on Oct 20, 2025

Condo in the Keys

500 Burton Dr, 1313, Tavernier, FL

This luxury condo resort's private beach and full-service spa are among the highlights. There's fun for all ages with a playground and an arcade/game room, and ...

8.4/10 Very Good! (10 reviews)

Awesome!

This is going to be my go to whenever I go to the Key Largo area. Very comfortable accommodations. What amazed me is that the full kitchen not only jad appliances but dishes, silverware, pots and pans. Great pool area and on site cafe.

Reviewed on Jul 19, 2025

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Waterfront House with Boat Dock

213 Aberdeen Ct, Tavernier, FL

This villa features a picnic area, laundry facilities, and free self parking. Luggage storage and a virtual front desk are also provided.

6/10 (1 review)

Covered porch was nice for time outside. Inside was in need of work. Closets unfinished, no place to put any luggage, advertises a king bed and a queen bed, but only had a king and a full, no tp, or tissue products when we arrived. None of the above were deal breakers but just allot of small things ...

Reviewed on Feb 17, 2025

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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.

Windley Key Resorts & 5 Star Hotels

Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Windley Key to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Windley Key 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Windley Key before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.