Book a Windley Key Resort

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Resorts in Windley Key

Cheeca Lodge & Spa
Relax on the beach with lounge chairs, a shaded hut, and a long pier extending into the calm sea.

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1141)
"Great chill location. "
The price is ￥25,732
￥38,867 total
includes taxes & fees
Aug 21 - Aug 22
Cheeca Lodge & Spa
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Enjoy ocean views from the large window in this stylish living room, featuring a comfortable sofa and a potted plant.

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4.0 star property
8.6 out of 10, Excellent, (1002)
"The place was amazing. Food a little bit expensive but amazing place."
The price is ￥37,345
￥50,114 total
includes taxes & fees
Sep 1 - Sep 2
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort
Relax in a serene outdoor seating area with Adirondack chairs around a central fire pit, surrounded by palm trees and ocean views.

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1236)
"Great hotel a family room "
The price is ￥24,697
￥37,538 total
includes taxes & fees
Sep 1 - Sep 2
Amara Cay Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Relax by the oceanfront pool surrounded by palm trees and lounge chairs.

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 star property
9.0 out of 10, Wonderful, (56)
"Everyone was so nice. We had a great experience and will be back at Christmas. "
The price is ￥28,602
￥41,931 total
includes taxes & fees
Aug 27 - Aug 28
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Playa Largo Resort & Spa, Autograph Collection
Relax by the pool surrounded by palm trees and lounge chairs under a picturesque arched structure.

Playa Largo Resort & Spa, Autograph Collection

4.5 star property
9.0 out of 10, Wonderful, (1000)
"Beautiful place"
The price is ￥33,943
￥46,287 total
includes taxes & fees
Sep 1 - Sep 2
Playa Largo Resort & Spa, Autograph Collection
Lime Tree Bay Resort
Relax by the clear swimming pool surrounded by lounge chairs and umbrellas, with access to the beach and shallow waters.

Lime Tree Bay Resort

3.5 star property
9.2 out of 10, Wonderful, (1087)
"Great place, beautiful apartment! "
Lime Tree Bay Resort
La Siesta Resort & Villas
Relax by the uniquely shaped pool surrounded by palm trees and shaded by umbrellas.

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1003)
"Fantastic staff working there. Incredibly friendly and helpful. Very clean rooms and loved being able to take the water taxi to the 2 other resorts "
The price is ￥19,001
￥31,183 total
includes taxes & fees
Sep 7 - Sep 8
La Siesta Resort & Villas
Matecumbe Resort
Enjoy a serene beach experience with a tranquil sea and a picturesque pier.

Matecumbe Resort

2.0 star property
8.8 out of 10, Excellent, (65)
"Beautiful resort! All the amenities were great and it was centrally located."
The price is ￥19,705
￥22,167 total
includes taxes & fees
Aug 11 - Aug 12
Matecumbe Resort
2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL
Walk along the pier to the calm waters of the beach.

2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL

9.0 out of 10, Wonderful, (2)
"We enjoyed our stay here, although units are older and do need some sprucing up.It was nice to have a beach onsite, as well as a heated pool, the use of (older) bikes and kayaks. We were only a few miles from the action of Islamorada, including restaurants, tourist attractions, shopping, breweries"
2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL
Keys Villa
Stroll through lush gardens to a charming wooden retreat.

Keys Villa

10.0 out of 10, Exceptional, (7)
"Wonderful place to stay. It was quiet with a private beach. Just what we were looking for. "
Keys Villa
3-bedroom Townhome with Direct Ocean Views at resort in Islamorada
Marina

3-bedroom Townhome with Direct Ocean Views at resort in Islamorada

3-bedroom Townhome with Direct Ocean Views at resort in Islamorada
JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub
Relax in comfort under a shaded umbrella, surrounded by the soothing sounds of the ocean and the scenic views of the rocky shoreline.

JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub

JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub
On the water in Islamorada elevated detached unit!!!
Relax in a tropical oasis with modern, open spaces and lush surroundings.

On the water in Islamorada elevated detached unit!!!

On the water in Islamorada elevated detached unit!!!
Beautiful oceanfront resort located at mile marker 73.8
Relax by the ocean-view pool surrounded by lounge chairs and umbrellas.

Beautiful oceanfront resort located at mile marker 73.8

Beautiful oceanfront resort located at mile marker 73.8
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windley Key Hotel Reviews

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent
"Great resort, excellent staff and customer service, I'll definitely coming back "
Jose 2-night trip
Posted 1 day ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort