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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Windley Key vacation rentals

A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

1. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (172 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
The price is ￥19,925
￥44,813 total
includes taxes & fees
Aug 30 - Aug 31
Treasure Harbor
A beach with palm trees, thatched-roof huts, and lounge chairs.

2. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (734 reviews)
"Good location"
United States
Orlando
The price is ￥16,045
￥20,590 total
includes taxes & fees
Sep 15 - Sep 16
Breezy Palms Resort
A beachside lounge with wooden lounge chairs and blue umbrellas, overlooking a calm sea and docked boats.

3. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (179 reviews)
"Very pleased with our stay"
United States
Vernon Micheal
The price is ￥40,781
￥45,878 total
includes taxes & fees
Aug 30 - Aug 31
Island Bay Resort
A beach with thatched umbrellas, lounge chairs, and a clear view of the ocean.

4. Kings Kamp

Kings Kamp
2.5 star property
Key Largo
8.6 out of 10, Excellent, (41 reviews)
"It was very nice!!"
United States
Michelle
The price is ￥32,108
￥36,121 total
includes taxes & fees
Aug 28 - Aug 29
Kings Kamp
A beach with rows of sun loungers, a wooden pier, and a thatched-roof structure.

5. Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Tavernier
9.8 out of 10, Exceptional, (25 reviews)
"The property was in a great location, close to several beach bars and restaurants, the condo was so cute and the host was accessible throughout the entire process before and after our stay."
United States
Alicia
The price is ￥36,057
￥82,054 total
includes taxes & fees
Aug 30 - Aug 31
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

6. 3212 Across from Pool * King & Queen/Twin Bunk Bed

3212 Across from Pool * King & Queen/Twin Bunk Bed
Tavernier
9.8 out of 10, Exceptional, (160 reviews)
"Perfect place for family to get away. Plenty of room"
United States
Aaron H.
The price is ￥28,613
￥74,065 total
includes taxes & fees
Aug 28 - Aug 29
3212 Across from Pool * King & Queen/Twin Bunk Bed
A floating house with a thatched roof, large sliding glass doors, and a wooden deck with a chair.

7. Premium Floating Bungalow by Stay Ombi

Premium Floating Bungalow by Stay Ombi
3.5 star property
Key Largo
9.6 out of 10, Exceptional, (4 reviews)
"Great experience ! Will do it again"
United States
Deivys
The price is ￥130,994
￥147,368 total
includes taxes & fees
Sep 3 - Sep 4
Premium Floating Bungalow by Stay Ombi
A beachfront hotel with clear waters, palm trees, and a sandy beach.

8. Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Tavernier
10.0 out of 10, Exceptional, (10 reviews)
"Such a beautiful condo! We loved our stay."
United States
Bethany B.
The price is ￥27,179
￥69,347 total
includes taxes & fees
Aug 30 - Aug 31
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
A waterfront property with a dock leading to a building with a blue roof, surrounded by palm trees and a clear sky.

9. Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (29 reviews)
"The space was family friendly and worked well for our stay. The pool area was very clean and the Island Grill on site was great for snacks and drinks while we swam."
United States
Miranda J.
The price is ￥27,179
￥68,392 total
includes taxes & fees
Aug 28 - Aug 29
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
A beach with palm trees, a thatched-roof hut, and beach chairs.

10. Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo

Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
Tavernier
9.6 out of 10, Exceptional, (232 reviews)
"Our stay was excellent. The home was immaculate and had everything we needed. We would definitely stay here again."
United States
Chris
The price is ￥25,642
￥62,892 total
includes taxes & fees
Sep 12 - Sep 13
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
A room with a large TV, a patterned armchair, a dining table, and a view of the ocean through a sliding door.

11. Sea View and Sunrise Ocean Pointe 2412 2BA/2BR

Sea View and Sunrise Ocean Pointe 2412 2BA/2BR
Tavernier
9.6 out of 10, Exceptional, (89 reviews)
"Good location"
United States
Dimitri O.
The price is ￥27,339
￥68,994 total
includes taxes & fees
Aug 28 - Aug 29
Sea View and Sunrise Ocean Pointe 2412 2BA/2BR
A canal with boats docked, surrounded by lush greenery and a clear sky.

12. Ocean View Overlooking Marina Ocean Pointe 5305

Ocean View Overlooking Marina Ocean Pointe 5305
Tavernier
10.0 out of 10, Exceptional, (27 reviews)
"Great place to stay and if you are fishing this is the building closest to the fish cleaning station."
United States
Justin C.
The price is ￥26,371
￥71,087 total
includes taxes & fees
Aug 29 - Aug 30
Ocean View Overlooking Marina Ocean Pointe 5305
A waterfront property with a dock, a boat, and a building with a blue roof.

13. Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor

Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor
Tavernier
9.6 out of 10, Exceptional, (33 reviews)
"The apartment was perfect, great location over looking the ocean, and nice and clean. They had everything we needed for our stay, The pool and the hot tub at the resort where clean and welcoming."
United States
Kimberly P.
The price is ￥23,880
￥80,714 total
includes taxes & fees
Aug 31 - Sep 1
Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor

14. Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (36 reviews)
"Loved the beach and pool."
United States
Haley P.
The price is ￥27,167
￥69,954 total
includes taxes & fees
Aug 30 - Aug 31
Lazy Daze Double King Suite Ocean Pointe 2310
A resort with multiple buildings, a swimming pool, tennis courts, and a view of the ocean.

15. Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (7 reviews)
"Super clean and neat location!"
United States
Christopher R.
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
A modern showerhead with multiple water streams, a tiled wall, and a pool area with blue chairs and a palm tree.

16. Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.6 out of 10, Excellent, (45 reviews)
"Wonderful stay! Beautiful view from the balcony"
United States
Katy T.
The price is ￥28,382
￥64,340 total
includes taxes & fees
Aug 30 - Aug 31
Ocean view condo with balcony/marina view
A balcony with a view of the sea, a chair, and a table with a lamp.

17. Boho Chic Ocean Pointe 3214 King & Queen

Boho Chic Ocean Pointe 3214 King & Queen
Tavernier
9.8 out of 10, Exceptional, (15 reviews)
"The condo was nice and clean. The view from the balcony is very nice. The property is also nice with things to do but not too busy. The host was great and responsive. "
United States
Anthony F.
The price is ￥24,631
￥66,025 total
includes taxes & fees
Aug 30 - Aug 31
Boho Chic Ocean Pointe 3214 King & Queen
A balcony with a table and chairs, a sofa, and a lamp.

18. Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Tavernier
9.8 out of 10, Exceptional, (9 reviews)
"An awesome place to stay, fish and relax!"
United States
robert d.
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

19. Coral Penthouse Key Largo Ocean Pointe 4216

Coral Penthouse Key Largo Ocean Pointe 4216
Tavernier
10.0 out of 10, Exceptional, (21 reviews)
"The ocean view was perfect. The property was nicely situated for all the activities and restaurants in the upper keys. Would definitely stay here again"
United States
David C.
The price is ￥26,065
￥70,583 total
includes taxes & fees
Aug 28 - Aug 29
Coral Penthouse Key Largo Ocean Pointe 4216
A spacious living room with a view of the sea, a ceiling fan, and a large mirror.

20. Ocean View Treehouse Double King Suite 3403

Ocean View Treehouse Double King Suite 3403
Tavernier
10.0 out of 10, Exceptional, (3 reviews)
"Great location and the condo was well done. Everything was great. We specifically choose this property because it had 2 king size beds. Everything was exactly as advertised."
United States
Mike P.
The price is ￥30,683
￥73,192 total
includes taxes & fees
Aug 30 - Aug 31
Ocean View Treehouse Double King Suite 3403
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

Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"We arrived one hour and twenty minutes before check in and were told there were no available rooms, although I am positive there were clean ready rooms. My husband and I went to the pool and enjoyed some music before checking into our room. Room was clean and comfortable. Continental breakfast served the next morning. The attendance were lovely and seemed happy to be at work. Check out soon after."
Cheryl 1-night trip
Posted 8 hours ago
Chesapeake Beach Resort

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