Search Resorts in Windley Key

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 Feb

Our top choices for Windley Key resorts

Private beach, sun-loungers, beach towels, scuba diving
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
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (121)
"Beautiful chilled out hotel"
United Kingdom
Jacqueline
The price is Rp4.966.218
Rp6.698.264 total
includes taxes & fees
4 Jan - 5 Jan 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Exterior
Lime Tree Bay Resort

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1108)
"This place is the best kept secret "
United States
Kathleen
Lime Tree Bay Resort
Exterior
Amara Cay Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1267)
"Friendly staff and beautiful property !"
United States
ron
The price is Rp3.943.761
Rp5.547.999 total
includes taxes & fees
4 Jan - 5 Jan 2026
Amara Cay Resort
Outdoor pool, pool cabanas (surcharge), pool umbrellas
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
8.8 out of 10, Excellent, (1002)
"Beautiful location, great views, very clean property, room was great (great bed), friendly staff."
United States
Scott
The price is Rp5.742.163
Rp7.382.865 total
includes taxes & fees
19 Jan - 20 Jan 2026
Playa Largo Resort & Spa, Autograph Collection
Private beach, sun-loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1277)
"Fabulous waterfront, activities, and dining as well as the staff. "
Canada
David
The price is Rp5.005.559
Rp6.855.607 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cheeca Lodge & Spa
32-inch LCD TV with satellite channels, TV, iPod dock
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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, (1001)
"One of the nicest hotels we have stayed at. Amazing staff, food, activities and property "
United States
Sara
The price is Rp6.163.701
Rp7.857.094 total
includes taxes & fees
8 Jan - 9 Jan 2026
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Outdoor pool, pool loungers
La Siesta Resort & Villas

La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1001)
"Great accommodations, very peaceful setting "
United States
Susan
The price is Rp3.491.754
Rp5.039.491 total
includes taxes & fees
6 Jan - 7 Jan 2026
La Siesta Resort & Villas
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

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

10/10 Excellent
"Nice "
Sandra 1-night trip
Posted 2 days ago
The Pelican Key Largo Cottages

Find out more about Windley Key

Windley Key Resorts information

Number of reviews
6,775
Accommodation
8 Resorts
Lowest Price
Rp5.039.491
Highest Price
Rp7.857.094