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

Holiday 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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Windley Key holiday homes

1. Little Peace of Haven

Little Peace of Haven
Key Largo
9.0 out of 10, Wonderful, (6 reviews)
"Lovely clean, quiet, perfect location for exploring the upper keys! An fantastic value!"
United States
Mitchel R.
The price is AU$574
includes taxes & fees
1 Dec - 2 Dec
Little Peace of Haven

2. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
10.0 out of 10, Exceptional, (41 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is AU$564
includes taxes & fees
9 Nov - 10 Nov
Charming Home in Key Largo

3. 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, (54 reviews)
"We had a nice stay"
United States
Kevin M.
The price is AU$438
includes taxes & fees
10 Nov - 11 Nov
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

4. Serenity Bungalow at Largo Resort

Serenity Bungalow at Largo Resort
Key Largo
10.0 out of 10, Exceptional, (2 reviews)
" We regret that we only booked for one night. We will definitely return for a longer stay. Everything about Key Largo Resort was perfect! The setting, the location, the accommodations, everything! Thank you for an amazing experience! We will be back! "
United States
Kimberly V.
The price is AU$592
includes taxes & fees
10 Nov - 11 Nov
Serenity Bungalow at Largo Resort

5. 4. Cozy Key Largo Waterfront Studio | Dive

4. Cozy Key Largo Waterfront Studio | Dive
Key Largo
9.8 out of 10, Exceptional, (13 reviews)
"Excellent stay, as always!"
United States
Monica G.
4. Cozy Key Largo Waterfront Studio | Dive

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

Key Largo Villa, Kawama P6, 3/3
Key Largo
9.8 out of 10, Exceptional, (152 reviews)
"The property was very nice, we recommend it."
United States
Gaby
The price is AU$859
includes taxes & fees
17 Nov - 18 Nov
Key Largo Villa, Kawama P6, 3/3

7. 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, (24 reviews)
"The lagoon was beautiful and fun."
United States
Teresa H.
The price is AU$613
includes taxes & fees
10 Nov - 11 Nov
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools

8. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (76 reviews)
"Great place!"
United States
Jessica S.
The price is AU$1,115
includes taxes & fees
11 Nov - 12 Nov
Sunrise Escape - Ocean Front Villa - Sleeps 10

9. Tranquility Bungalow at Largo Resort

Tranquility Bungalow at Largo Resort
Key Largo
9.4 out of 10, Exceptional, (9 reviews)
"Very Zen atmosphere. Alex and the rest of the staff very friendly and welcoming. "
United States
Becky M.
The price is AU$592
includes taxes & fees
9 Nov - 10 Nov
Tranquility Bungalow at Largo Resort

10. 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 AU$629
includes taxes & fees
9 Nov - 10 Nov
Sunset Bay View Bungalow at Largo Resort

11. 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 AU$843
includes taxes & fees
9 Nov - 10 Nov
Key Largo Villa, Kawama K5, 3/3

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 AU$497
includes taxes & fees
11 Nov - 12 Nov
Key Largo Tiny House, Marina, Beach + Pool Access

13. 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 AU$555
includes taxes & fees
17 Nov - 18 Nov
Waterfront Tiny House w Pool, Beach, and Boat Dock

14. Oceanside Kawama Villa R5

Oceanside Kawama Villa R5
Key Largo
9.2 out of 10, Wonderful, (184 reviews)
"Great place to stay"
United States
Eric B.
The price is AU$918
includes taxes & fees
15 Nov - 16 Nov
Oceanside Kawama Villa R5

15. 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, (63 reviews)
"Great house and even better location!"
United States
Sofia C.
The price is AU$870
includes taxes & fees
11 Nov - 12 Nov
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

16. New Tiny Home-Paddle Boards, Kayaks, Pool, Marina

New Tiny Home-Paddle Boards, Kayaks, Pool, Marina
Key Largo
8.8 out of 10, Excellent, (3 reviews)
"Tiny HomeThis tiny home was comfortable, clean, and fully stocked with all you need to vacation in the Keys! At first, I was hesitant on booking a tiny home coming from a 3,200sqft house but we found the layout functional and actually cozy with good amounts of space.I would recommend the place along with the property management team who ensured all communications were answered quickly and thoroughly!Would stay here again!"
United States
Christina R.
The price is AU$490
includes taxes & fees
11 Nov - 12 Nov
New Tiny Home-Paddle Boards, Kayaks, Pool, Marina

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

Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Key Largo
10.0 out of 10, Exceptional, (2 reviews)
"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 AU$465
includes taxes & fees
10 Nov - 11 Nov
Beachfront Retreat w Pool, Boat Ramp & Dock Rental

18. Keys Cottage with Beach and Dockage! Bayfront Property!

Keys Cottage with Beach and Dockage! Bayfront Property!
Key Largo
9.4 out of 10, Exceptional, (36 reviews)
"We had such a wonderful time here! The house was perfect and the grounds were beautiful! We will definitely come again! "
United States
Julia W.
Keys Cottage with Beach and Dockage! Bayfront Property!

19. 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.
The price is AU$1,771
includes taxes & fees
29 Nov - 30 Nov
Key Largo Oasis Oceanfront with Pool & Hot Tub

20. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is AU$1,353
includes taxes & fees
12 Nov - 13 Nov
Oceanside Retreat w/Rooftop, Pool & 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windley Key Hotel Reviews

Find out more about Windley Key

Windley Key Holiday Homes information

Number of reviews
810
Accommodation
608 Holiday Homes
Lowest Price
AU$438
Highest Price
AU$1,771

Explore a world of travel with Expedia