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

Windley Key condominium resorts to rent from $104

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31
No exact matches found, but these alternatives could be just right

Recommended hotels in Windley Key

A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

1. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,003 reviews)
"Great place. Friendly staff overall really wonderful."
United States
Siobhan
$208 nightly
The price is $234
Oct 7 - Oct 8
Total with taxes and fees
Fisher Inn Resort & Marina
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

2. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (295 reviews)
"Excellent stay! Love this place and will definitely be back!"
United States
Hailey Ritch and Patrick
$133 nightly
The price is $149
Oct 27 - Oct 28
Total with taxes and fees
Coconut Cove Resort and Marina
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

3. Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (288 reviews)
"Great place to stay!"
United States
Liosbel
$280 nightly
The price is $315
Oct 19 - Oct 20
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A beachside patio with white furniture, palm trees, and a thatched umbrella.

4. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.6 out of 10, Excellent, (1,001 reviews)
"Exceeded all my expectations, definitely going back. Highly recommend"
United States
Payman
$144 nightly
The price is $158
Oct 7 - Oct 8
Total with taxes and fees
Drop Anchor
A bedroom with a large bed, a sliding glass door to a balcony, a wooden cabinet, and a kitchen area with a microwave.

5. The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
Islamorada
9.2 out of 10, Wonderful, (32 reviews)
"Very friendly staff"
United States
Maria
$206 nightly
The price is $232
Nov 5 - Nov 6
Total with taxes and fees
The Ocean View Inn & Pub
A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

6. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,187 reviews)
"Absolutely lovely resort, we always have a wonderful stay ♥️"
United States
Tia
$93 nightly
The price is $104
Oct 8 - Oct 9
Total with taxes and fees
Rock Reef Resort
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

7. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,002 reviews)
"Nice hotel."
United States
Brett
$128 nightly
The price is $144
Oct 21 - Oct 22
Total with taxes and fees
La Jolla Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

8. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,474 reviews)
"Excellent hotel to spend good time with friends and family, just amazing."
United States
RAIBEL
$218 nightly
The price is $245
Oct 19 - Oct 20
Total with taxes and fees
Cheeca Lodge & Spa
A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.

9. Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,008 reviews)
"Excellent location"
United States
kelly
$102 nightly
The price is $115
Oct 21 - Oct 22
Total with taxes and fees
Drift Hotel
A beach with palm trees and lounge chairs.

10. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,797 reviews)
"Breakfast was excellent and the view and private beach was amazing"
United States
Leihla
$190 nightly
The price is $214
Oct 14 - Oct 15
Total with taxes and fees
Chesapeake Beach Resort
A beach with palm trees, lounge chairs, and a clear view of the ocean.

11. Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay
2.5 star property
Key Largo
8.8 out of 10, Excellent, (1,098 reviews)
"Place was great!! Can’t wait to go back!!"
United States
Cory
$130 nightly
The price is $147
Oct 13 - Oct 14
Total with taxes and fees
Hampton Inn Key Largo Manatee Bay
A beach with two thatched umbrellas, three sun loungers, and a view of the sea with boats.

12. Dolphin Point Villas

Dolphin Point Villas
3.5 star property
Key Largo
9.6 out of 10, Exceptional, (525 reviews)
"Wonderful location. Great staff."
United States
Ernest
$123 nightly
The price is $139
Oct 20 - Oct 21
Total with taxes and fees
Dolphin Point Villas
A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

13. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,325 reviews)
"Super clean resort."
United States
Danielle
$208 nightly
The price is $234
Oct 18 - Oct 19
Total with taxes and fees
Amara Cay Resort
A beachside lounge with two blue umbrellas, a hammock, and lounge chairs.

14. Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor
9.2 out of 10, Wonderful, (250 reviews)
"simple breakfast, older place but clean room, access to the beach - very convenient and nice!"
United States
ANDREW
$113 nightly
The price is $127
Oct 7 - Oct 8
Total with taxes and fees
Seafarer Key Largo
Terrace/patio

15. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,528 reviews)
"Beautiful location, great amenities, and comfortable rooms"
United States
Michael
$179 nightly
The price is $201
Oct 7 - Oct 8
Total with taxes and fees
Lime Tree Bay Resort
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.

16. Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
3.0 star property
Key Largo
7.8 out of 10, Good, (1,000 reviews)
"Volvería a venir gracias por su acogedora propiedad y por su buen servicio"
United States
Nextor
$126 nightly
The price is $142
Oct 14 - Oct 15
Total with taxes and fees
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.

17. Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
Key Largo
9.2 out of 10, Wonderful, (1,005 reviews)
"Very pleasant stay would recommend to anyone looking for a fun get away"
United States
Payton
$130 nightly
The price is $146
Oct 12 - Oct 13
Total with taxes and fees
Sunset Cove Beach Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

18. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,133 reviews)
"Amazing place would definitely recommend"
United States
Steven
$318 nightly
The price is $358
Oct 13 - Oct 14
Total with taxes and fees
Islander Resort
A balcony with a view of the sea, a table, and two chairs.

19. Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,501 reviews)
"i loved this place beautiful hotel full kitchen perfect for a little trip 100% recommend"
United States
Ysabella
$131 nightly
The price is $147
Oct 11 - Oct 12
Total with taxes and fees
Waterside Suites & Marina
A beach with palm trees, thatched-roof huts, and lounge chairs.

20. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (755 reviews)
"Such a great place to stay!!"
United States
Gavin
$107 nightly
The price is $120
Oct 7 - Oct 8
Total with taxes and fees
Breezy Palms 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

Sunset Cove Beach Resort

Sunset Cove Beach Resort

10/10 Excellent
"Very clean room with an amazing view of the water. Great food and drinks that you can walk to. Very happy with our stay!"
Brandon 1-night trip
Posted 2 hours ago
Sunset Cove Beach Resort

Find out more about Windley Key

Windley Key Condo Resorts information

Number of reviews
14,398
Accommodation
0 Condo Resorts
Lowest Price
$104
Highest Price
$358

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