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
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Windley Key holiday rentals

Private beach, sun-loungers

Kings Kamp

Kings Kamp
2.5 star property
Key Largo
8.6 out of 10, Excellent, (39 reviews)
"It was very nice!!"
United States
Michelle
The price is RM791
RM890 total
includes taxes & fees
4 Jun - 5 Jun
Kings Kamp
25-inch flat-screen TV with digital channels, TV

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (156 reviews)
"Beautiful accommodations. Friendly staff. Dallas made it feel like home. Great scenery! Daily viewing of dolphin and manatee! We will definitely be back !"
United States
Cheryl
The price is RM504
RM1,125 total
includes taxes & fees
14 Jun - 15 Jun
Treasure Harbor
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, (170 reviews)
"Very nice small resort."
United States
Dan
The price is RM1,160
RM1,305 total
includes taxes & fees
7 Jun - 8 Jun
Island Bay Resort
Exterior

Premium Floating Bungalow by Stay Ombi

Premium Floating Bungalow by Stay Ombi
3.5 star property
Key Largo
10.0 out of 10, Exceptional, (2 reviews)
The price is RM3,673
RM4,132 total
includes taxes & fees
8 Jun - 9 Jun
Premium Floating Bungalow by Stay Ombi
Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (687 reviews)
"Very clean, spacious, well located."
United Kingdom
Teresa
The price is RM498
RM623 total
includes taxes & fees
14 Jun - 15 Jun
Breezy Palms Resort
Balcony view

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (76 reviews)
"What a wonderful venue for our last 2 nights in the Keys. This place is a hidden gem. The entire staff, especially Edith, the bartender, were fantastic."
United States
Michael
The price is RM2,577
RM3,118 total
includes taxes & fees
10 Jun - 11 Jun
The Islands of Islamorada
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

Waterside Suites & Marina

Waterside Suites & Marina

8/10 Good
"The suite itself was clean, fresh, and exactly what you'd hope for when you arrive on vacation. The grounds, however, appeared to be participating in a week-long "I can't see you, you can't see me" competition with the groundskeepers, as the same litter remained in place for our entire stay. I'd read the reviews warning about the bar across the channel, so I came prepared for some noise. What I didn't anticipate was a boat docking directly outside our windows and turning into an unofficial floating nightclub. Our nautical neighbors kept the party going until about 3:00 am. This wasn't the hotel's fault, but I can confirm that standard earplugs were no match for these determined boat enthusiasts. The full bathroom featured a charming sliding barn door. Unfortunately, it created a unique open-concept shower experience. Even with the door closed, someone relaxing in bed could enjoy a front-row view of whoever was showering. Romantic for couples, perhaps; less ideal when traveling with children. The staff texted multiple times just to check on us. :-) GPS took us to the wrong Ocean Drive, so be aware before getting stuck in an hour of unnecessary traffic. Overall the hotel has a lot of potential. With a little landscaping and some outdoor cleanup, it could be a fantastic place to stay. Just remember to pack earplugs, a fan, a white-noise machine, or perhaps a tuba to compete with the surrounding soundscape. Or skip sleep altogether and join the party, you do you."
Jamie 4-night trip
Posted less than an hour ago
Waterside Suites & Marina

Find out more about Windley Key

Search for holiday rentals in Windley Key on Expedia.co.uk! 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!