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 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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 28 - Oct 29
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 $152
CA $514 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $139
CA $448 total
includes taxes & fees
Oct 26 - Oct 27
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.
The price is CA $423
CA $642 total
includes taxes & fees
Oct 26 - Oct 27
Serenity Bungalow at Largo Resort
A waterfront hotel with a pool, a covered walkway, and a view of the water.

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)
"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 $272
CA $541 total
includes taxes & fees
Nov 9 - Nov 10
4. Cozy Key Largo Waterfront Studio | Dive
A wooden deck with white railings overlooking a calm river, surrounded by trees and buildings.

6. 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.
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Living area

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 CA $331
CA $719 total
includes taxes & fees
Oct 26 - Oct 27
Kawama G12 Upscale OceansideVilla with Marina 2/2
A sunlit room with large windows, a wicker chair, a small table, and a view of a tree and water.

8. 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 $699 total
includes taxes & fees
Oct 26 - Oct 27
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
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, (75 reviews)
"Great unit and wonderful host. We will be back!"
United States
Lauren S.
The price is CA $361
CA $1,079 total
includes taxes & fees
Oct 28 - Oct 29
Sunrise Escape - Ocean Front Villa - Sleeps 10
A beachside wooden deck with Adirondack chairs, a thatched-roof gazebo, and a grill.

10. 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 $350
CA $806 total
includes taxes & fees
Oct 26 - Oct 27
Key Largo Villa, Kawama P6, 3/3
A wooden deck with yellow chairs, a pool, and a building with a covered area.

11. 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 $123
CA $418 total
includes taxes & fees
Oct 26 - Oct 27
Key Largo Tiny House, Marina, Beach + Pool Access
A wooden deck with yellow chairs, a pool, and a building with a covered area.

12. Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Key Largo
9.4 out of 10, Exceptional, (53 reviews)
"We had a nice stay"
United States
Kevin M.
The price is CA $111
CA $412 total
includes taxes & fees
Oct 31 - Nov 1
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
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)
"Great house and even better location!"
United States
Sofia C.
The price is CA $382
CA $857 total
includes taxes & fees
Nov 2 - Nov 3
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
A modern kitchen with white cabinetry, a dining area with white chairs, and a view of the outdoors through large windows.

14. 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 CA $178
CA $497 total
includes taxes & fees
Nov 17 - Nov 18
New Tiny Home-Paddle Boards, Kayaks, Pool, Marina
A bedroom with a large bed, a desk with a chair, a mirror, and a wall-mounted artwork.

15. 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 $423
CA $642 total
includes taxes & fees
Oct 26 - Oct 27
Tranquility Bungalow at Largo Resort
Open kitchen

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 $426
CA $880 total
includes taxes & fees
Oct 26 - Oct 27
Oceanside Kawama Villa R5
A two-story building with a pool, a boat dock, and a table set for dining.

17. Waterfront / Ocean Access Canal / Kamp Key / Homes

Waterfront / Ocean Access Canal / Kamp Key / Homes
Matecumbe
8.8 out of 10, Excellent, (5 reviews)
"Excellent house. Very clean. We had a little trouble with the check in code and we were immediately contacted and the code was changed and we were in within minutes. The maintenance guy stopped by to make sure we got in and everything was good. EXCELLENT Customer Service!!!!!House was very well stocked with pots and pans and misc things needed for a week stay! Right on a nice little canal with plenty of room for our boat."
United States
Mike H.
Waterfront / Ocean Access Canal / Kamp Key / Homes
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

18. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is CA $492
CA $1,129 total
includes taxes & fees
Oct 26 - Oct 27
Oceanside Retreat w/Rooftop, Pool & Kayaks
A modern kitchen with white cabinetry, a dining area with a white table and chairs, and a living room with a sofa and decorative pillows.

19. 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 CA $179
CA $499 total
includes taxes & fees
Oct 26 - Oct 27
Waterfront Tiny Home w/ Pool, Beach, Dock, Kayaks
A bedroom with a large bed, a desk, and a mirror.

20. 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 $452
CA $679 total
includes taxes & fees
Oct 26 - Oct 27
Sunset Bay View Bungalow 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

Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"Great location. Pool was extremely warm and a bit cloudy due to suntan lotion. Floor in the suite was also dirty as in your feet will be covered in minutes"
Richard 2-night trip
Posted 5 hours ago
Bayside Inn Key Largo

Find out more about Windley Key

Windley Key Vacation Homes information

Number of reviews
864
Accommodation
627 Vacation Homes
Lowest Price
CA $412
Highest Price
CA $1,129

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