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

Windley Key Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Windley Key holiday rentals

25-inch flat-screen TV with digital channels, TV

1. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (169 reviews)
"The houseboat were a great experience not only for the kid's but the adults also. Seeing the manatees swim around the cove was awesome! It was a great place to meet your neighbors as the porches are very close. The swimming pool is a great addition to the property! If going back to the area, I would definitely go there again! We really enjoyed our visit there!"
United States
Kelly
The price is HK$911
HK$2,128 total
includes taxes & fees
16 Aug - 17 Aug
Treasure Harbor
Exterior

2. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (726 reviews)
"Great place to stay rooms were really nice nice boat ramp plenty of parking restaurants right down the street to eat at no complaints nice pool everybody was friendly room was ice cold from the air condition full kitchen nice balcony looking out over the ocean great stay"
United States
roger
The price is HK$805
HK$1,031 total
includes taxes & fees
1 Sept - 2 Sept
Breezy Palms Resort
Exterior

3. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (36 reviews)
"A comfortable little condo, conveniently located for exploring the Keys. There’s a nice pool and small beach area with a bar/restaurant that are well maintained."
United States
Stephen
The price is HK$644
HK$2,412 total
includes taxes & fees
2 Sept - 3 Sept
Florida Keys Getaway - Slps 4 - Ocean View
Pool

4. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (52 reviews)
"Excellent accommodations. Unit was even nicer than it looked in pictures, everything was clean and in working order. Enjoyed our stay very much and would definitely stay here again!"
United States
Jerad E.
The price is HK$1,059
HK$2,734 total
includes taxes & fees
16 Aug - 17 Aug
Amazing Ocean view condo
Interior

5. Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
10.0 out of 10, Exceptional, (4 reviews)
"Very clean with everything you could need for your time in the Florida keys! The host was very responsive and helpful. Perfect place for a weekend with our dog."
United States
Anonymous traveller
The price is HK$777
HK$2,325 total
includes taxes & fees
16 Aug - 17 Aug
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Private beach, sun-loungers, beach umbrellas, beach towels

6. 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 HK$2,009
HK$2,260 total
includes taxes & fees
24 Aug - 25 Aug
Island Bay Resort
On the beach

7. 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, (49 reviews)
"This was the perfect little home away from home! The house was perfectly clean and nice and cool! The AC in the bedroom was fantastic and kept the room a perfect temperature for sleeping. In addition the bed was super comfortable! We had a great time in the campground and were so excited about the kayaks available for our use. We have already recommended this house and the campground to our friends and family and can’t wait to come and stay again soon!"
United States
Carrie D.
The price is HK$557
HK$2,230 total
includes taxes & fees
1 Sept - 2 Sept
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Smart TV

8. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (39 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is HK$862
HK$2,888 total
includes taxes & fees
24 Aug - 25 Aug
Charming Home in Key Largo
Beach nearby

9. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
"Everything was wonderful! We enjoyed our stay very much. "
United States
Colleen D.
The price is HK$1,483
HK$3,473 total
includes taxes & fees
31 Aug - 1 Sept
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Marina

10. 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 HK$1,177
HK$3,978 total
includes taxes & fees
17 Aug - 18 Aug
Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor
Beach nearby

11. Marina to Ocean View Key Largo Ocean Pointe 5308

Marina to Ocean View Key Largo Ocean Pointe 5308
Tavernier
9.4 out of 10, Exceptional, (71 reviews)
"The host was quick to respond, condo was perfect, the view was exceptional!"
United States
Rosalie K.
The price is HK$1,261
HK$3,434 total
includes taxes & fees
13 Sept - 14 Sept
Marina to Ocean View Key Largo Ocean Pointe 5308
Beach nearby

12. RV by the Sea - Glamping in the Keys

RV by the Sea - Glamping in the Keys
Key Largo
9.0 out of 10, Wonderful, (32 reviews)
"Clean and in a good location to navigate key largo. "
United States
Emily M.
The price is HK$598
HK$2,204 total
includes taxes & fees
24 Aug - 25 Aug
RV by the Sea - Glamping in the Keys
Property grounds

13. Cozy place in Calusa Key Largo

Cozy place in Calusa Key Largo
Key Largo
9.0 out of 10, Wonderful, (18 reviews)
"Great location and perfect set up for our family of 5. We had everything we needed and more. The outside hang out area and grill were great. "
United States
Jordan and Lindsay G.
The price is HK$904
HK$2,570 total
includes taxes & fees
17 Aug - 18 Aug
Cozy place in Calusa Key Largo
Beach nearby

14. Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.8 out of 10, Exceptional, (76 reviews)
"Convenient, affordable, pet friendly, "
United States
mark e.
The price is HK$883
HK$2,311 total
includes taxes & fees
17 Aug - 18 Aug
Paradise in Key Largo, FL
Beach

15. 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.
The price is HK$1,261
HK$3,316 total
includes taxes & fees
16 Aug - 17 Aug
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Interior

16. Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315
Tavernier
9.8 out of 10, Exceptional, (17 reviews)
"The unit was clean. The bed was comfortable. Everything worked well."
United States
William G.
The price is HK$1,214
HK$3,253 total
includes taxes & fees
16 Aug - 17 Aug
Blue Haven Key Largo | Ocean Pointe 1315
Beach

17. Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is HK$1,135
HK$3,278 total
includes taxes & fees
18 Aug - 19 Aug
Aqua Vista Ocean Pointe 3307
Beach nearby

18. Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (9 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
The price is HK$1,143
HK$3,178 total
includes taxes & fees
16 Aug - 17 Aug
Flamingo Flats Ocean Pointe 5306 2BR/2BA
Smart TV, fireplace, DVD player, books

19. The place to go when you want to get away!

The place to go when you want to get away!
Key Largo
10.0 out of 10, Exceptional, (76 reviews)
"The pool was nice. Kayaks available. The park is quiet but close lots of good places."
United States
Steven H.
The price is HK$848
HK$2,568 total
includes taxes & fees
24 Aug - 25 Aug
The place to go when you want to get away!
Interior

20. 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.
Boho Chic Ocean Pointe 3214 King & Queen
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

Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Always a good time!"
Laura 2-night trip
Posted 5 hours ago
Amara Cay Resort

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