Search Resort Hotels in Windley Key from CA $173

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Windley Key resorts

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (308 reviews)
"Great place to stay!"
United States
Liosbel
The price is CA $290
CA $429 total
includes taxes & fees
Nov 29 - Nov 30
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A bathroom with a large bathtub, a view of the sea, and a pier with boats.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,508 reviews)
"Great place. Phenomenal food!"
United States
Brandon
The price is CA $254
CA $388 total
includes taxes & fees
Nov 19 - Nov 20
Cheeca Lodge & Spa
A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

3. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,329 reviews)
"Great location as well."
United States
Amir
The price is CA $229
CA $360 total
includes taxes & fees
Nov 15 - Nov 16
Amara Cay Resort
Terrace/patio

4. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,578 reviews)
"We truly enjoyed our stay at Lime Tree Bay. The room was nice and clean and I loved being able to relax in the chairs/hammocks close to the water."
United States
Jessica
The price is CA $174
CA $258 total
includes taxes & fees
Nov 17 - Nov 18
Lime Tree Bay Resort
An aerial view of a resort with a large pool, palm trees, and a beach.

5. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,003 reviews)
"Everything was amazing!!! Beautiful hotel and great location."
United States
Jorge
The price is CA $369
CA $492 total
includes taxes & fees
Nov 29 - Nov 30
Playa Largo Resort & Spa, Autograph Collection
A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
Key Largo
8.8 out of 10, Excellent, (1,200 reviews)
"Very relaxing the beach was nice and pretty from that side of the property clean rooms staff was nice and helpful they made the stay enjoyable"
United States
Damion
The price is CA $369
CA $492 total
includes taxes & fees
Nov 29 - Nov 30
Baker's Cay Resort Key Largo, Curio Collection by Hilton
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

7. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,000 reviews)
"Great place to stay!"
United States
Brianne
The price is CA $217
CA $346 total
includes taxes & fees
Nov 15 - Nov 16
La Siesta Resort & Villas
A compact kitchen with wooden cabinets, a refrigerator, and a window with curtains.

8. Matecumbe Resort

Matecumbe Resort
2.0 star property
Matecumbe
9.0 out of 10, Wonderful, (183 reviews)
"The room was very clean and had a park area that if traveling with little ones will enjoy."
United States
Adelangele
The price is CA $221
CA $248 total
includes taxes & fees
Nov 8 - Nov 9
Matecumbe Resort
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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Learn more about Windley Key

Check out the local area in Windley Key—home to attractions like Windley Key Fossil Reef Geological State Park and Hog Heaven.

See all hotels in Windley Key
A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Top reviews in Windley Key

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

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

10/10 Excellent

Beautiful place Great beds Lots of dining options
Canada
Eslita
Reviewed September 12, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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