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

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22
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, (1,002 reviews)
"Was a very nice property, great location, great value."
United States
Gary
The price is P6,751
P9,604 total
includes taxes & fees
Aug 23 - Aug 24
Fisher Inn Resort & Marina
Premium bedding, in-room safe, laptop workspace, iron/ironing board

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, (241 reviews)
"Wonderful resort and friendly staff!"
United States
Ana
The price is P12,722
P18,803 total
includes taxes & fees
Aug 12 - Aug 13
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Exterior

3. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1,001 reviews)
"We really enjoyed the laid back vibe, matched with the amenities and the location. We had a great stay!"
United States
Noel
The price is P6,593
P9,572 total
includes taxes & fees
Aug 3 - Aug 4
Drop Anchor
Exterior

4. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (278 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
The price is P9,174
P10,321 total
includes taxes & fees
Aug 31 - Sep 1
Coconut Cove Resort and Marina
WiFi (free)

5. The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
Islamorada
9.0 out of 10, Wonderful, (26 reviews)
"Food was excellent and the staff was delightful. Very accommodating"
United States
Mark
The price is P11,439
P12,869 total
includes taxes & fees
Aug 12 - Aug 13
The Ocean View Inn & Pub
Balcony

6. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,746 reviews)
"Nice place 👌"
United States
Cristina
The price is P9,274
P13,888 total
includes taxes & fees
Aug 5 - Aug 6
Chesapeake Beach Resort
Balcony

7. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,353 reviews)
"I was an excellent vacation."
United States
Yuniel
The price is P10,405
P16,209 total
includes taxes & fees
Aug 12 - Aug 13
Cheeca Lodge & Spa
Premium bedding, in-room safe, desk, blackout drapes

8. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,080 reviews)
"Can't wait to stay there again!"
United States
Sarah
The price is P15,473
P21,551 total
includes taxes & fees
Aug 26 - Aug 27
Islander Resort
View from room

9. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,286 reviews)
"Beautiful hotel, amazing views , very friendly staff, I will definitely return to Amara cay"
United States
Estefani
The price is P10,348
P16,145 total
includes taxes & fees
Aug 11 - Aug 12
Amara Cay Resort
Exterior

10. Coconut Palm Inn

Coconut Palm Inn
3.0 star property
Tavernier
9.6 out of 10, Exceptional, (552 reviews)
"So happy with the stay, everything was clean and spacious. This is a little treasure nested in the keys. Can’t wait to be back"
United States
judith
The price is P11,581
P15,454 total
includes taxes & fees
Aug 2 - Aug 3
Coconut Palm Inn
Egyptian cotton sheets, premium bedding, in-room safe, blackout drapes

11. Creekside Inn

Creekside Inn
2.5 star property
Tavernier
7.8 out of 10, Good, (1,009 reviews)
"Great place to stay!!!!"
United States
Cristy
The price is P8,106
P9,119 total
includes taxes & fees
Aug 27 - Aug 28
Creekside Inn
Balcony view

12. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,001 reviews)
"Booked this on Expedia based on location alone- GREAT CHOICE. Lot of help from team (thanks Eric) very unique and ‘kitschy’ in a great location. Loved it here although we were one night only."
United States
Bill
The price is P7,275
P10,193 total
includes taxes & fees
Aug 30 - Aug 31
Hadley Resort and Marina
Lanai

13. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,002 reviews)
"Good location and great staff"
United States
adrian
The price is P7,702
P10,397 total
includes taxes & fees
Aug 3 - Aug 4
La Jolla Resort
Outdoor pool, sun loungers

14. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,000 reviews)
"Our families really enjoyed our stay there new favorite"
United States
Marc
The price is P9,517
P15,209 total
includes taxes & fees
Aug 12 - Aug 13
La Siesta Resort & Villas
Front of property

15. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (166 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 P7,702
P17,323 total
includes taxes & fees
Aug 2 - Aug 3
Treasure Harbor
Front of property - evening/night

16. Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,004 reviews)
"Very nice a cozy hotel . Location is perfect for boating . Our children enjoyed the kayak and the amenities . Five star"
United States
oscar
The price is P8,257
P9,981 total
includes taxes & fees
Aug 2 - Aug 3
Drift Hotel
Restaurant

17. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (454 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
United States
beata
The price is P14,812
P20,819 total
includes taxes & fees
Aug 12 - Aug 13
Bayside Villas by Islander Resort
Exterior

18. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,002 reviews)
"Lovely resort and very pet friendly which we loved!"
United States
Emily
The price is P14,715
P19,949 total
includes taxes & fees
Aug 31 - Sep 1
Playa Largo Resort & Spa, Autograph Collection
Aerial view

19. 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)
"Very nice place"
United States
Mae L
The price is P7,681
P10,589 total
includes taxes & fees
Aug 9 - Aug 10
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Fireplace

20. Reefhouse Resort & Marina

Reefhouse Resort & Marina
4.5 star property
Key Largo
9.4 out of 10, Exceptional, (1,490 reviews)
"Staff was friendly, very clean, great atmosphere, we would love to visit again!"
United States
Sabryna
The price is P13,447
P17,584 total
includes taxes & fees
Aug 5 - Aug 6
Reefhouse Resort & Marina
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

Islander Resort

Islander Resort

10/10 Excellent
"We love The Islander. We enjoyed our stay and can't wait to spend more time at this property."
Tish 1-night trip
Posted less than an hour ago
Islander Resort

Find out more about Windley Key

Windley Key Cottages information

Number of reviews
8,574
Accommodation
7 Cottages
Lowest Price
P9,119
Highest Price
P21,551

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