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

Windley Key Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Windley Key vacation 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 CA $214
CA $592 total
includes taxes & fees
Oct 29 - Oct 30
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 CA $158
CA $521 total
includes taxes & fees
Oct 29 - Oct 30
Charming Home in Key Largo
A coastal area with clear water, a sandy beach, and a small island with buildings.

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 CA $111
CA $413 total
includes taxes & fees
Oct 31 - Nov 1
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
A table with a glass of beverage, a mug, and a plate with food, overlooking a pool with boats and palm trees under a sunset sky.

4. 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 CA $279
CA $545 total
includes taxes & fees
Nov 9 - Nov 10
4. Cozy Key Largo Waterfront Studio | Dive
A modern kitchen with white cabinetry, a granite countertop, and a ceiling fan.

5. 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.
The price is CA $350
CA $743 total
includes taxes & fees
Nov 1 - Nov 2
Keys Cottage with Beach and Dockage! Bayfront Property!
Beach

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

Key Largo Villa, Kawama P6, 3/3
Key Largo
9.8 out of 10, Exceptional, (151 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 CA $351
CA $808 total
includes taxes & fees
Oct 29 - Oct 30
Key Largo Villa, Kawama P6, 3/3
A beach setting with white chairs arranged around a fire pit, a thatched-roof structure, and a view of the ocean.

7. Key Largo Kawama Villa L1, 3/3

Key Largo Kawama Villa L1, 3/3
Key Largo
9.4 out of 10, Exceptional, (231 reviews)
"Love the place , only problem with out a gulf car the beach and fishing area is too far away"
United States
Dayanis
The price is CA $369
CA $806 total
includes taxes & fees
Oct 29 - Oct 30
Key Largo Kawama Villa L1, 3/3
A bedroom with a large bed, a desk, and a chair, a mirror, and decorative wall art.

8. 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 CA $622
CA $894 total
includes taxes & fees
Nov 10 - Nov 11
Serenity Bungalow at Largo Resort
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, (76 reviews)
"Great unit and wonderful host. We will be back!"
United States
Lauren S.
The price is CA $349
CA $1,067 total
includes taxes & fees
Oct 29 - Oct 30
Sunrise Escape - Ocean Front Villa - Sleeps 10
A wooden deck with lounge chairs, a pool, and a dock with boats.

10. 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 CA $145
CA $455 total
includes taxes & fees
Oct 30 - Oct 31
Waterfront Tiny House w Pool, Beach, and Boat Dock
An aerial view of a resort with multiple buildings, a central pool area, and a beach.

11. 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 CA $378
CA $853 total
includes taxes & fees
Nov 2 - Nov 3
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
A bedroom with a large bed, a desk with a chair, a mirror, and a wall-mounted artwork.

12. 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 CA $558
CA $812 total
includes taxes & fees
Oct 29 - Oct 30
Tranquility Bungalow at Largo Resort
A coastal area with clear water, a sandy beach, and a small island with buildings.

13. 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 CA $121
CA $416 total
includes taxes & fees
Oct 29 - Oct 30
Key Largo Tiny House, Marina, Beach + Pool Access
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.
The price is CA $671
CA $956 total
includes taxes & fees
Nov 17 - Nov 18
Sunset Bay View Bungalow at Largo Resort
A modern kitchen with a dining area, large windows, and a ceiling fan.

15. 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 CA $205
CA $526 total
includes taxes & fees
Nov 18 - Nov 19
New Tiny Home-Paddle Boards, Kayaks, Pool, Marina
BBQ charcoal grills and tikies by the ocean

16. 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 CA $427
CA $872 total
includes taxes & fees
Nov 15 - Nov 16
Oceanside Kawama Villa R5
A beach setting with white chairs arranged around a fire pit, overlooking the ocean.

17. 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 CA $350
CA $806 total
includes taxes & fees
Oct 29 - Oct 30
Key Largo Villa, Kawama K5, 3/3
A sunlit room with large windows, a wicker chair, a small table, and a view of a tree and water.

18. 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 CA $356
CA $700 total
includes taxes & fees
Oct 29 - Oct 30
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

19. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is CA $525
CA $1,173 total
includes taxes & fees
Oct 29 - Oct 30
Oceanside Retreat w/Rooftop, Pool & Kayaks
A boat docked at a wooden pier with a thatched roof overhead, surrounded by palm trees and water.

20. 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.
The price is CA $212
CA $541 total
includes taxes & fees
Nov 1 - Nov 2
Waterfront Tiny Home Pool Dock Kayaks Paddleboards
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

Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

8/10 Good
"No elevator in the building"
Mark 1-night trip
Posted less than an hour ago
Hampton Inn Key Largo Manatee Bay

Find out more about Windley Key

Windley Key Vacation Homes information

Number of reviews
1,164
Accommodation
627 Vacation Homes
Lowest Price
CA $413
Highest Price
CA $1,173

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