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

Search Vacation Homes in Windley Key

  • 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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Windley Key vacation homes

Two front-loading washing machines in a laundry room with a tiled floor and a vent on the wall.

1. Little Peace of Haven

Little Peace of Haven
Key Largo
10.0 out of 10, Exceptional, (5 reviews)
Little Peace of Haven
A modern living room with a flat-screen TV, a black leather sofa, and a white ottoman.

2. 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 ￥16,859
￥57,621 total
includes taxes & fees
Sep 28 - Sep 29
Charming Home in Key Largo
A wooden pier with a thatched roof, leading to a rocky beach area with clear blue water. Directional signs indicate nearby locations.

3. FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Key Largo
9.4 out of 10, Exceptional, (67 reviews)
"The pool was clean and enjoying "
United States
Aaron G.
The price is ￥43,524
￥101,076 total
includes taxes & fees
Oct 9 - Oct 10
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
A wooden deck with lounge chairs, a pool, and a dock with boats.

4. Waterfront Tiny House w Pool, Beach, and Boat Dock

Waterfront Tiny House w Pool, Beach, and Boat Dock
Key Largo
9.6 out of 10, Exceptional, (70 reviews)
"We were really impressed with the house - it had all the little things that made the stay so comfortable - reclining chairs in the living room, A/C in every room, a great outside deck complete with a big TV and clean, clean, clean."
United States
Ann
The price is ￥20,575
￥56,107 total
includes taxes & fees
Oct 1 - Oct 2
Waterfront Tiny House w Pool, Beach, and Boat Dock

5. Key Largo Villa, Kawama P6, 3/3

Key Largo Villa, Kawama P6, 3/3
Key Largo
9.8 out of 10, Exceptional, (150 reviews)
"Beautiful, clean home. Loved the property and the inlet with all the fish was amazing. Would stay again."
United States
Sandra C.
The price is ￥39,568
￥90,571 total
includes taxes & fees
Sep 26 - Sep 27
Key Largo Villa, Kawama P6, 3/3
A bedroom with a wooden headboard, a large bed, a bench, and a view of a swimming pool.

6. 1. Key Largo Waterfront Studio | Canal & Ocean

1. Key Largo Waterfront Studio | Canal & Ocean
Key Largo
9.4 out of 10, Exceptional, (13 reviews)
"Nice location. Enjoyed our stay. "
United States
David C.
1. Key Largo Waterfront Studio | Canal & Ocean

7. Kawama G12 Upscale OceansideVilla with Marina 2/2

Kawama G12 Upscale OceansideVilla with Marina 2/2
Key Largo
10.0 out of 10, Exceptional, (10 reviews)
"We had a wonderful stay, well stocked! Our host was not easy to get a hold of, but we would definitely stay again! "
United States
Brooke B.
The price is ￥37,505
￥80,999 total
includes taxes & fees
Sep 26 - Sep 27
Kawama G12 Upscale OceansideVilla with Marina 2/2
A bedroom with a wooden headboard, a bed with white bedding, a small round table, and a view of a swimming pool through a door.

8. 4. Cozy Key Largo Waterfront Studio | Dive

4. Cozy Key Largo Waterfront Studio | Dive
Key Largo
9.8 out of 10, Exceptional, (13 reviews)
"We loved our stay at the waterfront cabanas! The location is 10/10 with an awesome waterfront bar/restaurant and coffee truck within walking distance. We truly felt like keys locals staying here - highly recommend! "
United States
Brittany M.
The price is ￥29,486
￥58,772 total
includes taxes & fees
Sep 28 - Sep 29
4. Cozy Key Largo Waterfront Studio | Dive
A modern kitchen with a large island, wooden ceiling, and a view of the pool.

9. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (72 reviews)
"Great unit and wonderful host. We will be back!"
United States
Lauren S.
Sunrise Escape - Ocean Front Villa - Sleeps 10
A beach setting with white chairs arranged around a fire pit, a thatched-roof structure, and a view of the ocean.

10. Key Largo Kawama Villa L1, 3/3

Key Largo Kawama Villa L1, 3/3
Key Largo
9.4 out of 10, Exceptional, (230 reviews)
"Love the place , only problem with out a gulf car the beach and fishing area is too far away"
United States
Dayanis
Key Largo Kawama Villa L1, 3/3
A sunlit room with large windows, a wicker chair, a small table, and a view of a tree and water.

11. New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools

New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
Key Largo
9.2 out of 10, Wonderful, (23 reviews)
"The lagoon was beautiful and fun."
United States
Teresa H.
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
A marina with boats docked, thatched-roof structures, and a view of the water.

12. Key Largo Tiny House, Marina, Beach + Pool Access

Key Largo Tiny House, Marina, Beach + Pool Access
Key Largo
10.0 out of 10, Exceptional, (1 review)
"Everything was great, especially The Newman Hospitality Company who I dealt with. Great customer service!"
United States
Brittany C.
The price is ￥13,928
￥46,729 total
includes taxes & fees
Sep 30 - Oct 1
Key Largo Tiny House, Marina, Beach + Pool Access
A beach with white Adirondack chairs, a clear pool, and a building with blue and white exterior walls.

13. NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Key Largo
10.0 out of 10, Exceptional, (62 reviews)
"Especially enjoyed the private lagoon."
United States
Tom W.
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
A beach setting with white chairs arranged around a fire pit, overlooking the ocean.

14. Key Largo Villa, Kawama K5, 3/3

Key Largo Villa, Kawama K5, 3/3
Key Largo
10.0 out of 10, Exceptional, (68 reviews)
"Lovely location and nice kitchen."
United States
Susan S.
The price is ￥40,834
￥91,520 total
includes taxes & fees
Oct 7 - Oct 8
Key Largo Villa, Kawama K5, 3/3
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

15. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is ￥82,153
￥159,356 total
includes taxes & fees
Sep 28 - Sep 29
Oceanside Retreat w/Rooftop, Pool & Kayaks
A coastal area with clear water, a sandy beach, and a small island with buildings.

16. Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Key Largo
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay at this RV over July 4th weekend in Key Largo. The location was perfect exactly what we were looking for. Everything about the property made for a great family getaway.Communication was a little confusing at first — it seemed like a different number was reaching out initially, and when I replied to that one, I didn’t hear back. Once I was in touch with the host’s actual number, though, communication was reliable. By that point we’d already figured out the answers to our...
United States
Jennifer A.
The price is ￥10,921
￥43,980 total
includes taxes & fees
Sep 27 - Sep 28
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
A coastal area with clear water, a sandy beach, and a small island with buildings.

17. 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, (50 reviews)
"We had a nice stay"
United States
Kevin M.
The price is ￥9,338
￥42,041 total
includes taxes & fees
Sep 29 - Sep 30
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
A modern living room with a grey sofa, a patterned armchair, and a coffee table. Large windows offer a view of the sea and buildings.

18. Key Largo Oasis Oceanfront with Pool & Hot Tub

Key Largo Oasis Oceanfront with Pool & Hot Tub
Key Largo
9.8 out of 10, Exceptional, (6 reviews)
"Loved the location and views, house is amazing"
United States
Dan L.
Key Largo Oasis Oceanfront with Pool & Hot Tub
A bedroom with a large bed, a desk, and a mirror.

19. Sunset Bay View Bungalow at Largo Resort

Sunset Bay View Bungalow at Largo Resort
Key Largo
9.0 out of 10, Wonderful, (2 reviews)
"We got everything we need, a relaxing place, great service, easy to find, restaurants all over the place and most important of all very clean and beautiful. We loved."
United States
Ricardo M.
The price is ￥61,119
￥86,687 total
includes taxes & fees
Oct 26 - Oct 27
Sunset Bay View Bungalow at Largo Resort
A wooden deck with yellow chairs, a pool, and a building with a covered area.

20. Waterfront Tiny Home w/ Pool, Beach, Dock, Kayaks

Waterfront Tiny Home w/ Pool, Beach, Dock, Kayaks
Key Largo
9.6 out of 10, Exceptional, (88 reviews)
"Great little home to stay at!"
United States
Dave B.
The price is ￥20,479
￥56,099 total
includes taxes & fees
Oct 26 - Oct 27
Waterfront Tiny Home w/ Pool, Beach, Dock, Kayaks
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

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent
"Amando este lugar muchas gracias Yoli por toda la atención volveremos pronto"
isoruma 1-night trip
Posted 11 hours ago
Playa Largo Resort & Spa, Autograph Collection

Find out more about Windley Key

Windley Key Vacation Homes information

Number of reviews
827
Accommodation
599 Vacation Homes
Lowest Price
￥42,041
Highest Price
￥159,356

Explore a world of travel with Expedia