A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Best Resorts in Windley Key

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Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

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, (291 reviews)
"Great place to stay!"
United States
Liosbel
$304 nightly
The price is $342
Nov 3 - Nov 4
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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.

2. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,321 reviews)
"Super clean resort."
United States
Danielle
$208 nightly
The price is $234
Oct 18 - Oct 19
Total with taxes and fees
Amara Cay Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

3. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,477 reviews)
$250 nightly
The price is $281
Oct 14 - Oct 15
Total with taxes and fees
Cheeca Lodge & Spa
Terrace/patio

4. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,539 reviews)
"We will definitely stay here again! Beautiful property that was always clean and peaceful."
United States
Katie
$179 nightly
The price is $201
Oct 14 - Oct 15
Total with taxes and fees
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, (1,004 reviews)
"Everything was amazing!!! Beautiful hotel and great location."
United States
Jorge
$312 nightly
The price is $351
Nov 1 - Nov 2
Total with taxes and fees
Playa Largo Resort & Spa, Autograph Collection
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

6. 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
$252 nightly
The price is $283
Nov 8 - Nov 9
Total with taxes and fees
La Siesta Resort & Villas
A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.

7. Matecumbe Resort

Matecumbe Resort
2.0 star property
Matecumbe
9.0 out of 10, Wonderful, (174 reviews)
"A very peaceful place."
United States
angel
$149 nightly
The price is $168
Oct 14 - Oct 15
Total with taxes and fees
Matecumbe Resort
A wooden deck with a view of the ocean and a palm tree.

8. 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
8.6 out of 10, Excellent, (1,185 reviews)
"We loved this place. Will definitely stay there again."
United States
Alan
$343 nightly
The price is $386
Oct 25 - Oct 26
Total with taxes and fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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

8/10 Good
"Private little beach area with tiki bar. It was awesome!"
Tera 1-night trip
Posted less than an hour ago
Hampton Inn Key Largo Manatee Bay

Find out more about Windley Key

Windley Key Resorts information

Number of reviews
5,340
Accommodation
11 Resorts
Lowest Price
$168
Highest Price
$386

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