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

Best Resorts in Windley Key

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4
In one month
Oct 16 - Oct 18
In two months
Nov 13 - Nov 15

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, (272 reviews)
"Beautiful place Great beds Lots of dining options"
Canada
Eslita
$264 nightly
The price is $297
Sep 23 - Sep 24
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,441 reviews)
"Excellent hotel to spend good time with friends and family, just amazing."
United States
RAIBEL
$186 nightly
The price is $209
Sep 29 - Sep 30
Total with taxes and fees
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, (1,310 reviews)
"Wonderful resort, very friendly staff, would definitely stay again!"
United States
Amy
$212 nightly
The price is $238
Sep 22 - Sep 23
Total with taxes and fees
Amara Cay Resort

4. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,498 reviews)
"Would stay again!"
United States
Chadwick
$172 nightly
The price is $194
Sep 20 - Sep 21
Total with taxes and fees
Lime Tree Bay Resort
A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.

5. Matecumbe Resort

Matecumbe Resort
2.0 star property
Matecumbe
9.0 out of 10, Wonderful, (162 reviews)
"Worth the money."
United States
paul
$143 nightly
The price is $161
Sep 20 - Sep 21
Total with taxes and fees
Matecumbe Resort
An aerial view of a resort with a large pool, palm trees, and a beach.

6. 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)
"Super good resorts"
United States
Danilo
$304 nightly
The price is $342
Sep 30 - Oct 1
Total with taxes and fees
Playa Largo Resort & Spa, Autograph Collection
A wooden deck with a view of the ocean and a palm tree.

7. 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, (1,183 reviews)
"Beautiful hotel"
United States
Milagros
$286 nightly
The price is $322
Sep 28 - Sep 29
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.
View all properties
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

Rock Reef Resort

Rock Reef Resort

10/10 Excellent
"Rustic Key Largo experience that was greatly enjoyed!"
Grace 2-night trip
Posted 3 hours ago
Rock Reef Resort

Find out more about Windley Key

Windley Key Resorts information

Number of reviews
2,935
Accommodation
12 Resorts
Lowest Price
$161
Highest Price
$342

Explore a world of travel with Expedia