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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Resort 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, (1139)
"We absolutely loved our stay at cheeca, will not be our last!"
The price is NZ$581
includes taxes & fees
11 Aug - 12 Aug
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, (1008)
"The resort was beautiful and although it was sold out it never seemed med to crowded. "
The price is NZ$686
includes taxes & fees
14 Aug - 15 Aug
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, (1238)
"Amazing stay"
The price is NZ$423
includes taxes & fees
11 Aug - 12 Aug
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, (48)
"This place is a gem. It was beautiful and quiet. "
The price is NZ$447
includes taxes & fees
19 Aug - 20 Aug
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, (1005)
"really nice beach "
The price is NZ$619
includes taxes & fees
10 Aug - 11 Aug
Playa Largo Resort & Spa, Autograph Collection
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)
"Pool and bar area very nice and fun for our family "
The price is NZ$389
includes taxes & fees
3 Aug - 4 Aug
La Siesta Resort & Villas
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, (1086)
"Great resort! We loved the games and hammocks around the property. Loved how we could ride bikes and paddle board right from the resort. "
Lime Tree Bay Resort
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, (60)
"Beautiful resort! All the amenities were great and it was centrally located."
The price is NZ$270
includes taxes & fees
14 Aug - 15 Aug
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
2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay
Stroll along the boardwalk to the beach, where lush vegetation and a palm tree frame the path.

2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay

2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay
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
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
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.
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Top Windley Key Hotel Reviews

Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

10/10 Excellent
"Saw a palmetto roach outside our doorway and housekeeping never showed up. "
Enrique 2-night trip
Posted 13 hours ago
Hampton Inn Key Largo Manatee Bay