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

Find Cabins in Windley Key for Rent from CA $109

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27
No exact matches found, but these alternatives could be just right

Recommended hotels in Windley Key

Exterior

1. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,001 reviews)
"Amazing sunrise"
United States
James
The price is CA $175
CA $242 total
includes taxes & fees
Sep 21 - Sep 22
Fisher Inn Resort & Marina
View from property

2. 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, (262 reviews)
"Wonderful resort and friendly staff!"
United States
Ana
The price is CA $254
CA $386 total
includes taxes & fees
Sep 13 - Sep 14
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Exterior

3. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (286 reviews)
"Clean room, helpful staff, very friendly and welcoming"
United States
Jasmine
The price is CA $194
CA $218 total
includes taxes & fees
Sep 21 - Sep 22
Coconut Cove Resort and Marina
Room

4. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.6 out of 10, Excellent, (1,001 reviews)
"Great location,"
United States
Marianela
The price is CA $171
CA $241 total
includes taxes & fees
Sep 8 - Sep 9
Drop Anchor
Classic Room, Patio, Garden View

5. The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
Islamorada
9.0 out of 10, Wonderful, (28 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
The price is CA $258
CA $290 total
includes taxes & fees
Sep 7 - Sep 8
The Ocean View Inn & Pub
Water view

6. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,782 reviews)
"Excellent location, nice breakfast."
United States
Suresh
The price is CA $160
CA $258 total
includes taxes & fees
Sep 7 - Sep 8
Chesapeake Beach Resort
Basic Room

7. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (266 reviews)
"Great quaint stay on the water. Shower is awesome."
United States
Marianne
The price is CA $97
CA $109 total
includes taxes & fees
Sep 8 - Sep 9
Ragged Edge Resort & Marina
Exterior

8. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,118 reviews)
"Property is beautiful, staff is great and overall an amazing place to stay."
United States
Sonia
The price is CA $271
CA $398 total
includes taxes & fees
Sep 13 - Sep 14
Islander Resort
Reception

9. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,437 reviews)
"Excellent stay."
United States
Mian
The price is CA $202
CA $304 total
includes taxes & fees
Oct 4 - Oct 5
Cheeca Lodge & Spa
Exterior

10. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (740 reviews)
"Good location"
United States
Orlando
The price is CA $99
CA $133 total
includes taxes & fees
Sep 7 - Sep 8
Breezy Palms Resort
Exterior

11. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
"Good location and great staff"
United States
adrian
The price is CA $235
CA $303 total
includes taxes & fees
Sep 13 - Sep 14
La Jolla Resort
Front of property

12. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (173 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
The price is CA $186
CA $403 total
includes taxes & fees
Sep 7 - Sep 8
Treasure Harbor
Aerial view

13. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,311 reviews)
"Wonderful resort, very friendly staff, would definitely stay again!"
United States
Amy
The price is CA $197
CA $323 total
includes taxes & fees
Sep 20 - Sep 21
Amara Cay Resort
Exterior

14. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,000 reviews)
"Nice pet friendly hotel, clean, nice staff, good continental breakfast."
United States
RAIBEL
The price is CA $187
CA $256 total
includes taxes & fees
Sep 7 - Sep 8
Hadley Resort and Marina
Front of property

15. Creekside Inn

Creekside Inn
2.5 star property
Tavernier
7.8 out of 10, Good, (1,020 reviews)
"Great place to stay!!!!"
United States
Cristy
The price is CA $181
CA $204 total
includes taxes & fees
Sep 27 - Sep 28
Creekside Inn
Aerial view

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, (1,001 reviews)
"Nice location"
United States
WORTHINGTON
The price is CA $136
CA $197 total
includes taxes & fees
Sep 13 - Sep 14
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Front of property - evening/night

17. Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,007 reviews)
"Very nice and clean we really enjoyed the private beach as well"
United States
Sheily
The price is CA $118
CA $148 total
includes taxes & fees
Sep 7 - Sep 8
Drift Hotel
Exterior

18. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,178 reviews)
"Amazing property and staff"
United States
Tia
The price is CA $150
CA $169 total
includes taxes & fees
Sep 10 - Sep 11
Rock Reef Resort
Garden view

19. Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
3.5 star property
Tavernier
8.4 out of 10, Very good, (1,009 reviews)
"Great place"
United States
Felix
The price is CA $171
CA $223 total
includes taxes & fees
Oct 5 - Oct 6
Ocean Pointe Suites at Key Largo
Exterior

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
The price is CA $273
CA $383 total
includes taxes & fees
Sep 9 - Sep 10
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

Waterside Suites & Marina

Waterside Suites & Marina

8/10 Good
"Great suite. Very comfortable and inviting"
Laurence 1-night trip
Posted 5 hours ago
Waterside Suites & Marina

Find out more about Windley Key

Windley Key Cabin Rentals information

Number of reviews
10,467
Accommodation
2 Cabin Rentals
Lowest Price
CA $109
Highest Price
CA $403

Frequently asked questions

Are there cheap cabins in Windley Key?
Whether you'd prefer to stay next to the water or in the hills, we have a fantastic range of cheap cabins in Windley Key to suit your style and budget. Priced from CA $109 to CA $403 a night, your perfect cabin rental is waiting here.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why should I book a cabin in Windley Key?
For a vacation in the great outdoors at an impressive price, there's nothing better than a cabin. Imagine rising to the sounds of the wilderness and having breakfast on your deck surrounded by stunning views. Book a cabin in Windley Key and say "see ya" to the hustle and bustle of modern life. Whether they're riverside, beachside or in the mountains, cabins offer a relaxing, rustic experience for those in need of a break.

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