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

Windley Key condominium resorts to rent from $103

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13
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, (1,010 reviews)
"We stay here once or twice a year, the staff is very friendly. The amenities are perfect and the location is right where you want to be."
United States
MARC
$148 nightly
The price is $167
Sep 20 - Sep 21
Total with taxes and fees
Fisher Inn Resort & Marina
A beachside patio with white furniture, palm trees, and a thatched umbrella.

2. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.6 out of 10, Excellent, (1,008 reviews)
"Great location,"
United States
Marianela
$161 nightly
The price is $177
Aug 24 - Aug 25
Total with taxes and fees
Drop Anchor
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, (253 reviews)
"Wonderful resort and friendly staff!"
United States
Ana
$272 nightly
The price is $306
Aug 30 - Aug 31
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

4. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (282 reviews)
"Amazing staff! Clancy is great! This place is so cute family oriented and friendly! I cant wait to stay here again!"
United States
Lisa C
$143 nightly
The price is $161
Aug 25 - Aug 26
Total with taxes and fees
Coconut Cove Resort and Marina
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
9.0 out of 10, Wonderful, (27 reviews)
"Staff was friendly and Inn was well maintained. My daughter loved the pool! It had a bar and restaurant attached to property so was nice being able to grab a drink for the pool area."
United States
Patrice
$186 nightly
The price is $210
Aug 24 - Aug 25
Total with taxes and fees
The Ocean View Inn & Pub
A beach with palm trees and lounge chairs.

6. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,761 reviews)
"Beautiful resort! Very tropical vibes! I would definitely stay here again!"
United States
Alisha
$197 nightly
The price is $221
Aug 25 - Aug 26
Total with taxes and fees
Chesapeake Beach Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

7. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,417 reviews)
"Wonderful stay! Friendly staff, clean rooms, highly recommend!"
United States
Jessica
$214 nightly
The price is $241
Sep 2 - Sep 3
Total with taxes and fees
Cheeca Lodge & Spa
A beach with rows of sun loungers and palm trees.

8. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (263 reviews)
"Great place. Highly recommended it"
United States
Katarzyna
$137 nightly
The price is $154
Sep 8 - Sep 9
Total with taxes and fees
Ragged Edge Resort & Marina
A balcony with a view of a beach, a pool, and a thatched-roof structure.

9. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,013 reviews)
"Nice pet friendly hotel, clean, nice staff, good continental breakfast."
United States
RAIBEL
$135 nightly
The price is $152
Sep 20 - Sep 21
Total with taxes and fees
Hadley Resort and Marina
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

10. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (171 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
$254 nightly
The price is $286
Aug 23 - Aug 24
Total with taxes and fees
Treasure Harbor
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

11. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,000 reviews)
"Good location and great staff"
United States
adrian
$134 nightly
The price is $151
Aug 27 - Aug 28
Total with taxes and fees
La Jolla Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

12. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,108 reviews)
"Staff and resort were amazing!"
United States
Chris
$304 nightly
The price is $342
Sep 22 - Sep 23
Total with taxes and fees
Islander Resort
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, (1,294 reviews)
"Best place to stay !!"
United States
David A
$224 nightly
The price is $252
Aug 24 - Aug 25
Total with taxes and fees
Amara Cay Resort
A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.

14. Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,008 reviews)
"Very nice and clean we really enjoyed the private beach as well"
United States
Sheily
$91 nightly
The price is $103
Aug 24 - Aug 25
Total with taxes and fees
Drift Hotel
A wooden dock extending over calm turquoise water, lined with white railings and palm trees.

15. Creekside Inn

Creekside Inn
2.5 star property
Tavernier
7.8 out of 10, Good, (1,015 reviews)
"Great place to stay!!!!"
United States
Cristy
$149 nightly
The price is $168
Aug 23 - Aug 24
Total with taxes and fees
Creekside Inn
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, (1,007 reviews)
"Very nice place"
United States
Mae L
$108 nightly
The price is $122
Sep 2 - Sep 3
Total with taxes and fees
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

17. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,169 reviews)
"Super nice place with family good parking area private beach"
United States
manuel
$97 nightly
The price is $109
Aug 25 - Aug 26
Total with taxes and fees
Rock Reef Resort
A beach with palm trees, thatched-roof huts, and lounge chairs.

18. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (729 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
$117 nightly
The price is $131
Sep 2 - Sep 3
Total with taxes and fees
Breezy Palms Resort
A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.

19. Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
2.5 star property
Rock Harbor
9.8 out of 10, Exceptional, (341 reviews)
"Very relaxing and low key spot with lots of fun outdoor amenities, staff got us into our room early and were super helpful and friendly. Would stay here again."
United States
Michelle
$99 nightly
The price is $111
Sep 9 - Sep 10
Total with taxes and fees
Kona Kai Resort and Gallery - Adults Only
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

20. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"I had an excellent stay at the resort. and look forward to returning!"
United States
Isabel
$224 nightly
The price is $252
Aug 30 - Aug 31
Total with taxes and fees
Pines & 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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Amazing breakfast, clean room and very friendly staff."
Oleksandr 5-night trip
Posted 11 hours ago
Chesapeake Beach Resort

Find out more about Windley Key

Windley Key Condo Resorts information

Number of reviews
12,280
Accommodation
0 Condo Resorts
Lowest Price
$103
Highest Price
$342

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