Search Windley Key Villa Rentals from CA $642
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Browse Select Windley Key Villas

The Islands of Islamorada
The Islands of Islamorada
9.8 out of 10, Exceptional, (54)
The price is CA $828
CA $1,010 total
includes taxes & fees
Apr 6 - Apr 7

Sea Haven with Resort Privileges
Sea Haven with Resort Privileges
10.0 out of 10, Exceptional, (2)

Gull's Nest with Resort Privileges
Gull's Nest with Resort Privileges
9.4 out of 10, Exceptional, (20)

Endless Summer with Resort Privileges
Endless Summer with Resort Privileges
9.4 out of 10, Exceptional, (12)

Sandcastle Luxury Villa in Key Largo with Resort Privileges
Sandcastle Luxury Villa in Key Largo with Resort Privileges
10.0 out of 10, Exceptional, (2)

SPACIOUS 3/3.5 VILLA - INDOOR PICKLEBALL - MOST UPSCALE OCEANFRONT RESORT IN KL!
SPACIOUS 3/3.5 VILLA - INDOOR PICKLEBALL - MOST UPSCALE OCEANFRONT RESORT IN KL!
9.6 out of 10, Exceptional, (63)
The price is CA $642
CA $1,277 total
includes taxes & fees
Apr 17 - Apr 18

Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
10.0 out of 10, Exceptional, (109)

Twilight with Resort Privileges
Twilight with Resort Privileges
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Windley Key

OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards
10.0 out of 10, Exceptional, (175)

Breezy Palms Resort
Breezy Palms Resort
8.6 out of 10, Excellent, (435)
The price is CA $199
CA $298 total
includes taxes & fees
Apr 6 - Apr 7

The Islands of Islamorada
The Islands of Islamorada
9.8 out of 10, Exceptional, (54)
The price is CA $828
CA $1,010 total
includes taxes & fees
Apr 6 - Apr 7
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.
Find out more about Windley Key
Find out more about Windley Key
Windley Key Villas information
Number of reviews | 429 |
---|---|
Accommodation | 53 Villas |
Lowest Price | CA $642 |
Highest Price | CA $828 |
Recent Reviews in Windley Key
Recent Reviews in Windley Key

Baker's Cay Resort Key Largo, Curio Collection by Hilton
5/5 Excellent
"An oasis of calm, great location and amenities. Beautiful settings, hidden in hammocks, with perfect, clear turquoise water. "
A verified traveller stayed at Baker's Cay Resort Key Largo, Curio Collection by Hilton
Posted 13 hours ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
More Accommodation Types in Windley Key
- Vacation Homes in Windley Key
- Condo Rentals in Windley Key
- Apartments in Windley Key
- Cottages in Windley Key
- Houseboats in Windley Key
- Resorts in Windley Key
- RV Parks in Windley Key
- Aparthotels in Windley Key
- Motels in Windley Key
- Guest Houses in Windley Key
- Cabin Rentals in Windley Key
- Condo Resorts in Windley Key
- Lodges in Windley Key
- Hotels
All Accommodation Types
Be inspired: Top Villas destinations in 2025
- Niagara Falls Villas
- Toronto Villas
- Montreal Villas
- Vancouver Villas
- Ottawa Villas
- Calgary Villas
- Quebec Villas
- Edmonton Villas
- Whistler Villas
- Laurentians Villas
- Winnipeg Villas
- Kingston Villas
- The Blue Mountains Villas
- Saint Ferreol les Neiges Villas
- Saskatoon Villas
- Mississauga Villas
- Collingwood Villas
- Hamilton Villas
- Okanagan Valley Villas
- Vaughan Villas
More ways to book
Expedia's Latest Trends
Hotels
Flights
Cheap Flights from Athens (ATH) to Montreal (YUL)Cheap Flights from Ottawa (YOW) to Tokyo (NRT)Cheap Flights from Calgary (YYC) to Ontario (ONT)Cheap Flights from Montreal (YUL) to Delhi (DEL)Cheap Flights to Amelia IslandCheap Flights from Nanaimo (YCD) to London (LHR)Cheap Flights from Bangor (BGR) to Boston (BOS)Cheap Flights from Calgary (YYC) to London (LGW)Cheap Flights from Paris (CDG) to Split (SPU)Cheap Flights to HamiltonCheap Flights from Detroit (DTW) to Myrtle Beach (MYR)Cheap Flights from Calgary
Activities
Vacation Rentals