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

Holiday Homes in Windley Key

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Windley Key holiday homes

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

1. Little Peace of Haven

Little Peace of Haven
Key Largo
10.0 out of 10, Exceptional, (5 reviews)
"Lovely clean, quiet, perfect location for exploring the upper keys! An fantastic value!"
United States
Mitchel R.
The price is NZ$731
includes taxes & fees
12 Oct - 13 Oct
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 NZ$657
includes taxes & fees
15 Oct - 16 Oct
Charming Home in Key Largo
A wooden deck with lounge chairs, a pool, and a dock with boats.

3. 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 NZ$592
includes taxes & fees
27 Oct - 28 Oct
Waterfront Tiny House w Pool, Beach, and Boat Dock
A bedroom with a large bed, a desk, and a chair, a mirror, and decorative wall art.

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.
Serenity Bungalow at Largo Resort
A beach with a wooden structure and a signpost indicating directions to various locations.

5. 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 NZ$1,093
includes taxes & fees
14 Oct - 15 Oct
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
A sunlit room with large windows, a wicker chair, a small table, and a view of a tree and water.

6. 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.
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
A bedroom with a large bed, a desk with a chair, a mirror, and a wall-mounted artwork.

7. Tranquility Bungalow at Largo Resort

Tranquility Bungalow at Largo Resort
Key Largo
9.6 out of 10, Exceptional, (8 reviews)
"Very Zen atmosphere. Alex and the rest of the staff very friendly and welcoming. "
United States
Becky M.
The price is NZ$641
includes taxes & fees
21 Oct - 22 Oct
Tranquility Bungalow at Largo Resort
A wooden deck with yellow chairs, a pool, and a building with a covered area.

8. 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.
Key Largo Tiny House, Marina, Beach + Pool Access
A modern indoor space with a pool, white wicker furniture, and a white crib.

9. El Encanto: private saltwater pool & tiki lounge

El Encanto: private saltwater pool & tiki lounge
Key Largo
The price is NZ$1,301
includes taxes & fees
18 Oct - 19 Oct
El Encanto: private saltwater pool & tiki lounge
A coastal area with clear water, a sandy beach, and a small island with buildings.

10. 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.
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
A beach setting with white chairs arranged around a fire pit, a thatched-roof structure, and a view of the ocean.

11. 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 coastal area with clear water, a sandy beach, and a small island with buildings.

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

New Tiny Home-Paddle Boards, Kayaks, Pool, Marina
Key Largo
9.0 out of 10, Wonderful, (2 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 NZ$545
includes taxes & fees
27 Oct - 28 Oct
New Tiny Home-Paddle Boards, Kayaks, Pool, Marina
A modern kitchen with a large island, wooden ceiling, and a view of the pool.

13. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (74 reviews)
"Great unit and wonderful host. We will be back!"
United States
Lauren S.
The price is NZ$1,469
includes taxes & fees
27 Oct - 28 Oct
Sunrise Escape - Ocean Front Villa - Sleeps 10
A bedroom with a large bed, a desk, and a mirror.

14. 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.
Sunset Bay View Bungalow at Largo Resort
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 NZ$1,410
includes taxes & fees
26 Oct - 27 Oct
Oceanside Retreat w/Rooftop, Pool & Kayaks
A beach with white Adirondack chairs, a clear pool, and a building with blue and white exterior walls.

16. 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)
"Great house and even better location!"
United States
Sofia C.
The price is NZ$1,094
includes taxes & fees
15 Oct - 16 Oct
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
A wooden deck with yellow chairs, a pool, and a building with a covered area.

17. 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 NZ$693
includes taxes & fees
26 Oct - 27 Oct
Waterfront Tiny Home w/ Pool, Beach, Dock, Kayaks
A modern kitchen with a large island, stainless steel appliances, and a view of the water.

18. New Oceanside Paradise with Pool and Waterfront Views!

New Oceanside Paradise with Pool and Waterfront Views!
Key Largo
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great "
United States
Ravone L.
The price is NZ$1,670
includes taxes & fees
19 Oct - 20 Oct
New Oceanside Paradise with Pool and Waterfront Views!
A coastal area with clear water, a sandy beach, and a small island with buildings.

19. Waterfront Tiny Home Pool Dock Kayaks Paddleboards

Waterfront Tiny Home Pool Dock Kayaks Paddleboards
Key Largo
9.6 out of 10, Exceptional, (131 reviews)
"We appreciated having our boat docked behind the house. The campground was well maintained."
United States
Barbara A K.
Waterfront Tiny Home Pool Dock Kayaks Paddleboards
A marina with boats, a thatched-roof building, and palm trees.

20. Waterfront Home 3/2.5,HotTub,2Sup,4Kayaks,Golf Car

Waterfront Home 3/2.5,HotTub,2Sup,4Kayaks,Golf Car
Key Largo
10.0 out of 10, Exceptional, (150 reviews)
"A very relaxing lace to stay. Enjoyed sitting under the tiki hut and watching the boats. We had fun taking the kayaks out and the use of the golf cart."
United States
Kay S.
The price is NZ$1,359
includes taxes & fees
11 Oct - 12 Oct
Waterfront Home 3/2.5,HotTub,2Sup,4Kayaks,Golf Car
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

Islander Resort

Islander Resort

10/10 Excellent
"Our room was very clean. Resort staff was super nice and accommodating. Amenities were nice. Pools were clean. Resort was very peaceful."
Grayson 5-night trip
Posted 16 hours ago
Islander Resort

Find out more about Windley Key

Windley Key Holiday Homes information

Number of reviews
1,010
Accommodation
610 Holiday Homes
Lowest Price
NZ$545
Highest Price
NZ$1,670

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