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
Jan 9 - Jan 11
In two weeks
Jan 16 - Jan 18
In one month
Jan 30 - Feb 1
In two months
Feb 27 - Mar 1

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, (122)
"Beautiful chilled out hotel"
United Kingdom
Jacqueline
The price is NT$9,576
NT$12,856 total
includes taxes & fees
Jan 21 - 2026/1/22
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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, (1280)
"Fabulous waterfront, activities, and dining as well as the staff. "
Canada
David
The price is NT$9,383
NT$12,851 total
includes taxes & fees
Jan 4 - 2026/1/5
Cheeca Lodge & Spa
Outdoor 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, (1000)
"Beautiful location, great views, very clean property, room was great (great bed), friendly staff."
United States
Scott
The price is NT$13,274
NT$16,663 total
includes taxes & fees
Jan 14 - 2026/1/15
Playa Largo Resort & Spa, Autograph Collection
Exterior
Amara Cay Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1271)
"Friendly staff and beautiful property !"
United States
ron
The price is NT$7,393
NT$10,612 total
includes taxes & fees
Jan 4 - 2026/1/5
Amara Cay 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, (1117)
"This place is the best kept secret "
United States
Kathleen
Lime Tree Bay Resort
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, (1000)
"One of the nicest hotels we have stayed at. Amazing staff, food, activities and property "
United States
Sara
The price is NT$10,790
NT$13,870 total
includes taxes & fees
Jan 6 - 2026/1/7
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Outdoor pool, sun loungers
La Siesta Resort & Villas

La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1000)
"Great accommodations, very peaceful setting "
United States
Susan
The price is NT$6,545
NT$9,658 total
includes taxes & fees
Jan 6 - 2026/1/7
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Entire resort was clean and beautiful. Quiet location with beautiful rooms. We will return."
Julie 2-night trip
Posted 10 hours ago
Chesapeake Beach Resort

Find out more about Windley Key

Windley Key Resorts information

Number of reviews
6,784
Accommodation
8 Resorts
Lowest Price
NT$9,658
Highest Price
NT$16,663

Explore a world of travel with Expedia