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

Search Vacation Homes 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
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8
No exact matches found, but these alternatives could be just right

Recommended hotels in Windley Key

Room, 1 King Bed, Balcony, Ocean View (Balcony) | Premium bedding, in-room safe, individually decorated

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, (228 reviews)
"Room was beautiful, just as pictured on the website. It is a lovely place."
United States
CATHY
The price is ₩393,676
₩552,497 total
includes taxes & fees
Aug 11 - Aug 12
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view

Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1,006 reviews)
"Great stay for boaters! right on the water and easy to launch. The rooms were clean and had the essentials. The staff was super friendly and helpful."
United States
Melissa
The price is ₩190,158
₩266,388 total
includes taxes & fees
Jul 14 - Jul 15
Drop Anchor
Exterior

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (274 reviews)
"Nice Relaxing family friendly spot!"
United States
Sean
The price is ₩283,285
₩318,696 total
includes taxes & fees
Jul 15 - Jul 16
Coconut Cove Resort and Marina
Exterior

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very Good, (1,006 reviews)
"clean and spacious room."
United States
omar
The price is ₩200,997
₩275,029 total
includes taxes & fees
Aug 9 - Aug 10
Fisher Inn Resort & Marina
Classic Room, Patio, Garden View | Free WiFi

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 ₩240,447
₩270,514 total
includes taxes & fees
Jul 15 - Jul 16
The Ocean View Inn & Pub
Private beach, sun loungers, beach towels, kayaking

Dolphin Point Villas

Dolphin Point Villas
3.5 star property
Key Largo
9.6 out of 10, Exceptional, (506 reviews)
"Wonderful place"
United States
Patrick
The price is ₩238,618
₩310,608 total
includes taxes & fees
Jul 16 - Jul 17
Dolphin Point Villas
3 restaurants; breakfast, lunch, and dinner served

Reefhouse Resort & Marina

Reefhouse Resort & Marina
4.5 star property
Key Largo
9.4 out of 10, Exceptional, (1,497 reviews)
"Nice place to stay!!!"
United States
Tula
The price is ₩313,262
₩412,381 total
includes taxes & fees
Jul 26 - Jul 27
Reefhouse Resort & Marina
Exterior

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,080 reviews)
"Beautiful rooms and resort."
United States
Neha
The price is ₩375,315
₩523,403 total
includes taxes & fees
Aug 9 - Aug 10
Islander Resort
Balcony

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,347 reviews)
"The room and property are clean and the staff is friendly and helpful."
United States
Brenna
The price is ₩298,273
₩445,169 total
includes taxes & fees
Aug 9 - Aug 10
Cheeca Lodge & Spa
Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1,385 reviews)
"Amazing we will be staying againn"
United States
JACLYN
The price is ₩195,414
₩287,290 total
includes taxes & fees
Jul 14 - Jul 15
Lime Tree Bay Resort
Beach/ocean view

Bay Harbor Lodge

Bay Harbor Lodge
3.0 star property
Rock Harbor
9.4 out of 10, Exceptional, (700 reviews)
"This property is very clean and well maintained. There is a small beach area with canoes. The best scones (thank you Peg!) and coffee in the morning. The location is great too as there are many restaurants within minutes. Will definitely be back soon."
United States
P
The price is ₩247,312
₩278,233 total
includes taxes & fees
Aug 3 - Aug 4
Bay Harbor Lodge
Private beach, white sand, sun loungers, beach towels

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,758 reviews)
"Love the place very clean and peaceful"
United States
Elizabeth
The price is ₩254,881
₩371,052 total
includes taxes & fees
Aug 3 - Aug 4
Chesapeake Beach Resort
Exterior

Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (447 reviews)
"The hotel was in the mist of redoing it's landscaping by adding gaint palm trees and some new boat docks, but it didn't interfere with the overall feel of the place. We enjoyed the free paddle boards and pool. Its also located on a beautiful part of the Keys"
United States
Lois
The price is ₩310,264
₩401,409 total
includes taxes & fees
Jul 26 - Jul 27
Casa Morada
Outdoor pool

Sunset Inn

Sunset Inn
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,005 reviews)
"Great location!"
United States
Jeanne
The price is ₩198,671
₩240,367 total
includes taxes & fees
Aug 5 - Aug 6
Sunset Inn
Aquamarina Deluxe Sea View Suite | Living area | 35-inch flat-screen TV with satellite channels, TV

Azul del Mar

Azul del Mar
3.5 star property
Key Largo
9.0 out of 10, Wonderful, (866 reviews)
"Location location location, friendly staff."
United States
Mark
The price is ₩130,701
₩147,038 total
includes taxes & fees
Jul 15 - Jul 16
Azul del Mar
Terrace/patio

Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,418 reviews)
"Very well situated to everything we needed to get to. Nice amenities."
United States
Elizabeth
The price is ₩183,685
₩248,795 total
includes taxes & fees
Jul 15 - Jul 16
Waterside Suites & Marina
Exterior

Coconut Palm Inn

Coconut Palm Inn
3.0 star property
Tavernier
9.4 out of 10, Exceptional, (547 reviews)
"Nice quiet family friendly place to stay"
United States
James
The price is ₩274,591
₩367,939 total
includes taxes & fees
Jul 20 - Jul 21
Coconut Palm Inn
Property grounds

Atlantic Bay Resort

Atlantic Bay Resort
3.0 star property
Tavernier
9.4 out of 10, Exceptional, (795 reviews)
"Our little Heaven in the Keys! S’Friendly staff. Quiet resort kept in pristine condition."
United States
Annie
The price is ₩283,824
₩349,279 total
includes taxes & fees
Jul 27 - Jul 28
Atlantic Bay Resort
Exterior

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,014 reviews)
"Great stay"
United States
Edgar
The price is ₩418,182
₩553,087 total
includes taxes & fees
Aug 10 - Aug 11
Playa Largo Resort & Spa, Autograph Collection
Sundeck

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,168 reviews)
"Good stay"
United States
Lisa
The price is ₩210,080
₩236,340 total
includes taxes & fees
Jul 19 - Jul 20
Rock Reef 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

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

10/10 Excellent
"Amazing place! Hope to come back"
xiomara 2-night trip
Posted less than an hour ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Find out more about Windley Key

Windley Key Vacation Homes information

Number of reviews
18,073
Accommodation
6 Vacation Homes
Lowest Price
₩147,038
Highest Price
₩553,087