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

Windley Key Holiday 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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Windley Key holiday rentals

A beach with palm trees, thatched-roof huts, and lounge chairs.

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (757 reviews)
"We loved our stay! Great location, clean rooms."
United States
Zack
The price is HK$641
HK$847 total
includes taxes & fees
4 Oct - 5 Oct
Breezy Palms Resort
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (175 reviews)
"Beautiful unique place"
United States
Laura
The price is HK$840
HK$2,048 total
includes taxes & fees
30 Sept - 1 Oct
Treasure Harbor
A beachside lounge with wooden lounge chairs and blue umbrellas, overlooking a calm sea and docked boats.

3. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
9.8 out of 10, Exceptional, (183 reviews)
"Amazing vacation spot!!"
United States
Katie Lyn
The price is HK$2,032
HK$2,286 total
includes taxes & fees
30 Sept - 1 Oct
Island Bay Resort
A beachfront hotel with two palm trees, a flag, and a pool area with lounge chairs.

4. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (39 reviews)
"Great place to stay down on the keys."
United States
GJ W.
The price is HK$679
HK$2,332 total
includes taxes & fees
4 Oct - 5 Oct
Florida Keys Getaway - Slps 4 - Ocean View
A beach with clear shallow waters, a row of blue lounge chairs, and palm trees.

5. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (170 reviews)
"Perfect spot to stay in the keys! Great for fishing. The condo had everything you need to make your stay amazing. We will be back! Check in and out was a breeze, guards at gate were super friendly!"
United States
Pam K.
The price is HK$981
HK$2,672 total
includes taxes & fees
1 Oct - 2 Oct
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
A beach with clear shallow waters, a row of blue lounge chairs, and palm trees.

6. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
"Everything was wonderful! We enjoyed our stay very much. "
United States
Colleen D.
The price is HK$1,020
HK$2,716 total
includes taxes & fees
28 Oct - 29 Oct
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, and a covered pavilion in the background.

7. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (52 reviews)
"Excellent accommodations. Unit was even nicer than it looked in pictures, everything was clean and in working order. Enjoyed our stay very much and would definitely stay here again!"
United States
Jerad E.
The price is HK$1,059
HK$2,584 total
includes taxes & fees
30 Sept - 1 Oct
Amazing Ocean view condo
A modern kitchen with white cabinets, a black refrigerator, and a dining area with a black table and two black chairs.

8. Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"Very clean with everything you could need for your time in the Florida keys! The host was very responsive and helpful. Perfect place for a weekend with our dog."
United States
Anonymous traveller
The price is HK$863
HK$2,319 total
includes taxes & fees
13 Oct - 14 Oct
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
A coastal area with clear water, a sandy beach, and a small island with buildings.

9. Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Key Largo
9.6 out of 10, Exceptional, (51 reviews)
"We had a nice stay"
United States
Kevin M.
The price is HK$769
HK$2,365 total
includes taxes & fees
10 Oct - 11 Oct
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
A laundry room with two stacked front-loading washing machines.

10. 4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Tavernier
9.8 out of 10, Exceptional, (48 reviews)
"We were two couples staying in this space with plenty of room. All the amenities on this property (pool, beach restaurant and bar)made this a terrific stay. "
United States
Donna B.
The price is HK$1,090
HK$3,904 total
includes taxes & fees
30 Sept - 1 Oct
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
A balcony with a view of the ocean, a chair, a sofa, and a decorative seahorse wall art.

11. Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Blain R.
The price is HK$1,174
HK$3,119 total
includes taxes & fees
30 Sept - 1 Oct
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
A waterfront property with a dock leading to a building with a blue roof.

12. Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (9 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
The price is HK$1,142
HK$3,082 total
includes taxes & fees
12 Oct - 13 Oct
Flamingo Flats Ocean Pointe 5306 2BR/2BA
Beach

13. Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is HK$1,142
HK$3,082 total
includes taxes & fees
30 Sept - 1 Oct
Aqua Vista Ocean Pointe 3307
A cozy RV interior with a sofa, a table with tea set, and a 'Welcome to the Beach' sign.

14. The place to go when you want to get away!

The place to go when you want to get away!
Key Largo
10.0 out of 10, Exceptional, (76 reviews)
"The pool was nice. Kayaks available. The park is quiet but close lots of good places."
United States
Steven H.
The price is HK$854
HK$2,442 total
includes taxes & fees
30 Sept - 1 Oct
The place to go when you want to get away!
A modern living room with a flat-screen TV, a black leather sofa, and a white ottoman.

15. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
10.0 out of 10, Exceptional, (41 reviews)
"Awesome house, convenient to everything we needed. Super clean and everything was pretty modern. I would definitely stay again and would definitely recommend this property"
United States
JOHN P.
The price is HK$1,130
HK$3,040 total
includes taxes & fees
1 Oct - 2 Oct
Charming Home in Key Largo
A kitchen with granite countertops, a dining area with a table and chairs, a balcony with a view, and a bedroom visible through an open door.

16. Reel Key Largo Escape Ocean Pointe 5209

Reel Key Largo Escape Ocean Pointe 5209
Tavernier
9.6 out of 10, Exceptional, (10 reviews)
"We had a great time and the property was the center-point of our stay. Thanks for making it easy!"
United States
Ty L.
The price is HK$1,174
HK$3,119 total
includes taxes & fees
30 Sept - 1 Oct
Reel Key Largo Escape Ocean Pointe 5209
A balcony with a view of the sea, a chair, and a table with a lamp.

17. Boho Chic Ocean Pointe 3214 King & Queen

Boho Chic Ocean Pointe 3214 King & Queen
Tavernier
9.8 out of 10, Exceptional, (15 reviews)
"The condo was nice and clean. The view from the balcony is very nice. The property is also nice with things to do but not too busy. The host was great and responsive. "
United States
Anthony F.
The price is HK$1,213
HK$3,173 total
includes taxes & fees
30 Sept - 1 Oct
Boho Chic Ocean Pointe 3214 King & Queen
A beach with a thatched-roof table and benches, surrounded by trees and a calm body of water.

18. RV by the Sea - Glamping in the Keys

RV by the Sea - Glamping in the Keys
Key Largo
9.0 out of 10, Wonderful, (32 reviews)
"It is a RV and served its purpose. The campground was nice. The pool was great. And the staff was pleasant while checking in."
United States
Andrea G.
The price is HK$554
HK$2,060 total
includes taxes & fees
1 Oct - 2 Oct
RV by the Sea - Glamping in the Keys
A beachside resort with a thatched umbrella, palm trees, and a dock.

19. Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (36 reviews)
"Loved the beach and pool."
United States
Haley P.
The price is HK$1,339
HK$3,337 total
includes taxes & fees
28 Oct - 29 Oct
Lazy Daze Double King Suite Ocean Pointe 2310
A beach with a wooden deck, palm trees, and a clear sky.

20. Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.8 out of 10, Exceptional, (77 reviews)
"The property was as described and very comfortable. I would definitely stay again."
United States
Eddie S.
The price is HK$953
HK$2,288 total
includes taxes & fees
30 Sept - 1 Oct
Paradise in Key Largo, FL
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

Islander Resort

Islander Resort

10/10 Excellent
"Amazing place would definitely recommend"
Steven 2-night trip
Posted 3 hours ago
Islander Resort

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