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

Windley Key Vacation Rentals

  • 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

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Windley Key vacation rentals

25-inch flat-screen TV with digital channels, TV

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (161 reviews)
"Amazing stay!"
United States
Amanda
The price is P8,289
P17,947 total
includes taxes & fees
Jul 1 - Jul 2
Treasure Harbor
Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (704 reviews)
"Enjoyed this place."
United States
Christopher
The price is P6,409
P10,388 total
includes taxes & fees
Jul 6 - Jul 7
Breezy Palms Resort
Private beach, sun loungers

Kings Kamp

Kings Kamp
2.5 star property
Key Largo
8.6 out of 10, Excellent, (40 reviews)
"It was very nice!!"
United States
Michelle
The price is P12,236
P13,766 total
includes taxes & fees
Jul 5 - Jul 6
Kings Kamp
Private beach, sun loungers, beach umbrellas, beach towels

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (172 reviews)
"Very nice small resort."
United States
Dan
The price is P17,939
P20,181 total
includes taxes & fees
Jun 30 - Jul 1
Island Bay 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.
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
"This was a great find in Key Largo. Has private beach where you can swim and snorkel a bit and see some fish. Has kayaking as part of staying here and very close to State Park where you can take a Snorkeling boat trip and other things to do there. There are restaurants within walking distance, and all have great sunsets. We appreciated that there were plenty of towels and we had parking space and small table to sit outside. Overall awesome place to stay if you plan to visit Key Largo. The gentleman that checked us in as well as staff was very helpful and friendly. Would definitely stay extra days next time."
brian 2-night trip
Posted 1 hour ago
The Pelican Key Largo Cottages

Find out more about Windley Key

Search for holiday rentals in Windley Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Windley Key using one of the methods below:

  • View our selection of featured holiday rentals in Windley Key
  • Use the map to find apartments and other holiday homes in the Windley Key neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windley Key while they last

Look no further and take a look at our great range of rental properties in Windley Key!

Explore a world of travel with Expedia