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

Search Condominium Resorts in Windley Key

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec
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, (1,010 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
The price is HK$793
HK$1,148 total
includes taxes & fees
20 Sept - 21 Sept
Fisher Inn Resort & Marina
Beach/ocean view

2. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.6 out of 10, Excellent, (1,008 reviews)
"Great location,"
United States
Marianela
The price is HK$957
HK$1,351 total
includes taxes & fees
24 Aug - 25 Aug
Drop Anchor
Room

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
The price is HK$1,624
HK$2,401 total
includes taxes & fees
7 Sept - 8 Sept
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Exterior

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
The price is HK$1,168
HK$1,314 total
includes taxes & fees
31 Aug - 1 Sept
Coconut Cove Resort and Marina
Room

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
The price is HK$1,461
HK$1,643 total
includes taxes & fees
3 Sept - 4 Sept
The Ocean View Inn & Pub
Beach

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
The price is HK$1,184
HK$1,773 total
includes taxes & fees
3 Sept - 4 Sept
Chesapeake Beach Resort
Balcony

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
The price is HK$1,169
HK$1,888 total
includes taxes & fees
2 Sept - 3 Sept
Cheeca Lodge & Spa
Exterior

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
The price is HK$993
HK$1,117 total
includes taxes & fees
8 Sept - 9 Sept
Ragged Edge Resort & Marina
Balcony view

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
The price is HK$860
HK$1,223 total
includes taxes & fees
21 Sept - 22 Sept
Hadley Resort and Marina
Living area

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
The price is HK$911
HK$2,127 total
includes taxes & fees
23 Aug - 24 Aug
Treasure Harbor
Lanai

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
The price is HK$935
HK$1,272 total
includes taxes & fees
27 Aug - 28 Aug
La Jolla Resort
Exterior

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
The price is HK$1,757
HK$2,506 total
includes taxes & fees
31 Aug - 1 Sept
Islander Resort
View from room

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
The price is HK$1,318
HK$2,056 total
includes taxes & fees
24 Aug - 25 Aug
Amara Cay Resort
Beach

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
The price is HK$700
HK$876 total
includes taxes & fees
24 Aug - 25 Aug
Drift Hotel
View from property

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
The price is HK$1,052
HK$1,183 total
includes taxes & fees
23 Aug - 24 Aug
Creekside Inn
Exterior

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
The price is HK$699
HK$1,034 total
includes taxes & fees
7 Sept - 8 Sept
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Sun deck

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
The price is HK$759
HK$853 total
includes taxes & fees
16 Sept - 17 Sept
Rock Reef Resort
Exterior

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
The price is HK$804
HK$1,030 total
includes taxes & fees
7 Sept - 8 Sept
Breezy Palms Resort
Terrace/patio

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
The price is HK$935
HK$1,272 total
includes taxes & fees
28 Aug - 29 Aug
Kona Kai Resort and Gallery - Adults Only
Room

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 HK$1,374
HK$1,977 total
includes taxes & fees
31 Aug - 1 Sept
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 5 hours ago
Chesapeake Beach Resort

Find out more about Windley Key

Windley Key Condominium Resorts information

Number of reviews
12,280
Accommodation
0 Condominium Resorts
Lowest Price
HK$853
Highest Price
HK$2,506

Explore a world of travel with Expedia