Holiday Homes in Windley Key

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Our top choices for Windley Key holiday homes

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, (45)
"We absolutely loved it! "
United States
Emily B.
The price is AU$513
includes taxes & fees
15 Dec - 16 Dec
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (28)
"It was clean and a very nice place to stay. Plenty of room and awesome amenities."
United States
Eric M.
The price is AU$721
includes taxes & fees
28 Dec - 29 Dec
Charming Home in Key Largo

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

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Key Largo
9.6 out of 10, Exceptional, (82)
"The place was clean and nice, no problems at all. Plenty of room for my family. Wish we could have stayed longer!"
United States
Brad W.
The price is AU$606
includes taxes & fees
15 Dec - 16 Dec
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Casa Largo

Casa Largo
Key Largo
9.0 out of 10, Wonderful, (129)
"We stayed in 2 vrbo properties while in Florida. This one met and exceeded our expectations. We would stay again without hesitation."
United States
Kelly M.
The price is AU$811
includes taxes & fees
12 Dec - 13 Dec
Casa Largo

NEW ! Marvelous 2-bedroom house with Marina in Key Largo

NEW ! Marvelous 2-bedroom house with Marina in Key Largo
2.0 star property
Key Largo
10.0 out of 10, Exceptional, (44)
"Good location. Lagoon and pool right outside door. "
United States
Debra C.
The price is AU$792
includes taxes & fees
15 Dec - 16 Dec
NEW ! Marvelous 2-bedroom house with Marina in Key Largo

Lovely Bungalow w/ Plenty Of Shade at Largo Resort

Lovely Bungalow w/ Plenty Of Shade at Largo Resort
Key Largo
10.0 out of 10, Exceptional, (17)
"Our bungalow was very clean and the beds were very comfortable! It was almost like we we're on our own private island and my 8 year old loved it! We hope to come back on our next visit!"
United States
Elizabeth M.
The price is AU$1,243
includes taxes & fees
24 Dec - 25 Dec
Lovely Bungalow w/ Plenty Of Shade at Largo Resort

Tranquil Bungalow at the Beautiful at Largo Resort

Tranquil Bungalow at the Beautiful at Largo Resort
Key Largo
9.6 out of 10, Exceptional, (7)
"10/10! This property itself is secluded and very safe. The pool and views were breathtaking. The complimentary paddle boards and bicycles were fun and just an extra service that bettered our experience. The employees were amazing, kind, and professional. The bungalow was so comfortable and smelt amazing when we entered. Beds were comfortable and the little kitchen was used! Plates, silverwear, & cups were provided thankfully. The host!!!! 100/10. Thank you!!!! She was able to provide a nice...
United States
Nancy H.
The price is AU$1,020
includes taxes & fees
11 Jan - 12 Jan 2026
Tranquil Bungalow at the Beautiful at Largo Resort

Ohana Cay 2brm/2bth - Book your getaway!

Ohana Cay 2brm/2bth - Book your getaway!
Rock Harbor
10.0 out of 10, Exceptional, (92)
"Perfect location and great community. Easy docking at the marina and nice amenities. "
United States
Gene Z.
The price is AU$1,219
includes taxes & fees
3 Jan - 4 Jan 2026
Ohana Cay 2brm/2bth - Book your getaway!

Beautiful Kawama Townhouse

Beautiful Kawama Townhouse
Key Largo
9.8 out of 10, Exceptional, (140)
"Great location, well stocked kitchen, bathrooms, etc. Excellent host, had a great time in a beautiful community. The lagoon is a great feature."
United States
jannet p.
The price is AU$924
includes taxes & fees
12 Dec - 13 Dec
Beautiful Kawama Townhouse

Key Largo Oasis Oceanfront with Pool & Hot Tub

Key Largo Oasis Oceanfront with Pool & Hot Tub
Key Largo
10.0 out of 10, Exceptional, (4)
"Loved the location and views, house is amazing"
United States
Dan L.
The price is AU$1,189
includes taxes & fees
14 Dec - 15 Dec
Key Largo Oasis Oceanfront with Pool & Hot Tub

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, (63)
"Great little place with awesome outdoor area. "
United States
James D.
The price is AU$621
includes taxes & fees
15 Dec - 16 Dec
Waterfront Tiny House w Pool, Beach, and Boat Dock

Oceanside Kawama Villa R5

Oceanside Kawama Villa R5
Key Largo
9.2 out of 10, Wonderful, (180)
"Very very nice villa in a superb location… Abcolutely loved the property!"
United States
Ricardo G.
Oceanside Kawama Villa R5

Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.

Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.
Key Largo Village
The price is AU$2,531
includes taxes & fees
24 Dec - 25 Dec
Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.

Waterfront Cottage - Beach and Dockage! Open Water Views!

Waterfront Cottage - Beach and Dockage! Open Water Views!
Key Largo
9.4 out of 10, Exceptional, (46)
"This was a very cute resort, with perfect views! We were able to stay with our family and even bring our puppies. We had an absolutely amazing time!!"
United States
Shane F.
Waterfront Cottage - Beach and Dockage! Open Water Views!

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Key Largo
9.6 out of 10, Exceptional, (123)
"Great stay!! Location was perfect view of the canal and close to the pool. Unit was very clean and would definitely stay again!!"
United States
Brad T.
The price is AU$661
includes taxes & fees
14 Dec - 15 Dec
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

The Grand Lodge Right On The Water at Largo Resort

The Grand Lodge Right On The Water at Largo Resort
Key Largo
9.6 out of 10, Exceptional, (4)
"would stay again"
United States
Jonathan G.
The price is AU$3,045
includes taxes & fees
15 Dec - 16 Dec
The Grand Lodge Right On The Water at Largo Resort

Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (66)
"This place was perfect for 9 people. Both the condo and the area had plenty to do "
United States
Ethan
The price is AU$1,540
includes taxes & fees
8 Jan - 9 Jan 2026
Sunrise Escape - Ocean Front Villa - Sleeps 10

Spacious Bungalow w/ Sunset Ocean View at Largo Resort

Spacious Bungalow w/ Sunset Ocean View at Largo Resort
Key Largo
9.0 out of 10, Wonderful, (2)
"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$1,151
includes taxes & fees
11 Jan - 12 Jan 2026
Spacious Bungalow w/ Sunset Ocean View at Largo Resort

Waterfront Pool, Beach, Dock, Kayaks

Waterfront Pool, Beach, Dock, Kayaks
Key Largo
9.8 out of 10, Exceptional, (80)
"Had a great time property was exactly as described. Would stay again."
United States
Michael S.
The price is AU$698
includes taxes & fees
15 Dec - 16 Dec
Waterfront Pool, Beach, Dock, Kayaks

Tropical House By The Shore at Largo Resort

Tropical House By The Shore at Largo Resort
Key Largo
Tropical House By The Shore at Largo 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.
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Top Windley Key Hotel Reviews

Find out more about Windley Key

Windley Key Holiday Homes information

Number of reviews
1,098
Accommodation
640 Holiday Homes
Lowest Price
AU$513
Highest Price
AU$3,045

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