Windley Key Holiday Rentals

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Holiday Rentals in Windley Key

Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen

Islamorada
9.8 out of 10, Exceptional, (34)
"We had a great family trip! The house was perfect and so comfortable "
United States
Cheryl J.
Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen

NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

Islamorada
10.0 out of 10, Exceptional, (1)
"This property was amazing basically brand new definitely recommend "
United States
Isabella
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

Islamorada
10.0 out of 10, Exceptional, (185)
"Overall a good trip. A few items needed to be taken care of, but it didn't stop us from having a great time."
United States
Darrell P.
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

Treasure Harbor

3.0 star property
Islamorada
9.0 out of 10, Wonderful, (111)
"The houseboat was so cute! The staff was very friendly and helpful. We really enjoyed out stay. The pool was new and clean. We would definitely come back."
United States
Tracie
Treasure Harbor

Breezy Palms Resort

2.5 star property
Matecumbe
8.8 out of 10, Excellent, (568)
"Best hotel for the price"
United States
luzdari
The price is AU$205
includes taxes & fees
20 Nov - 21 Nov
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (68)
"Great for family vacation with kids. love it"
United States
Dixania
The price is AU$1,097
includes taxes & fees
19 Nov - 20 Nov
The Islands of Islamorada

Island Bay Resort

2.5 star property
Tavernier
10.0 out of 10, Exceptional, (136)
"Buutifull and cozy place "
United States
DILIA
The price is AU$427
includes taxes & fees
19 Nov - 20 Nov
Island Bay Resort

Key Largo Cottages

2.5 star property
Key Largo
9.6 out of 10, Exceptional, (26)
"Beautiful and peaceful place "
United States
Jacqueline
Key Largo Cottages

Kings Kamp

2.5 star property
Key Largo
8.8 out of 10, Excellent, (23)
"Kings Kamp was a charming stay. The owners were friendly and made the stay easy"
United States
Erica
Kings Kamp

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Key Largo
9.6 out of 10, Exceptional, (81)
"The place was clean and nice, no problems at all. Plenty of room for my family. Wish we could have stayed longer!"
United States
Brad W.
The price is AU$566
includes taxes & fees
19 Nov - 20 Nov
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball

Rock Harbor
10.0 out of 10, Exceptional, (134)
"Great place to stay!"
United States
Nicole P.
Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball

Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!

Tavernier
10.0 out of 10, Exceptional, (180)
"Great little condo! Lots of personal touches! "
United States
lee J.
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!

Condo with Pool and Beach Access

Tavernier
10.0 out of 10, Exceptional, (26)
"Our stay was perfect! Zach was great to work with and everything was what we were expecting, The pool was amazing! Would definitely come stay agin"
United States
Kristine K.
Condo with Pool and Beach Access

Paradise in Key Largo, FL

Key Largo
9.6 out of 10, Exceptional, (60)
"Beautiful property. We uh, I very much enjoyed our stay highly recommend we will stay here again"
United States
George D.
The price is AU$454
includes taxes & fees
19 Nov - 20 Nov
Paradise in Key Largo, FL

Paradise in Key Largo Florida 2

Key Largo
9.8 out of 10, Exceptional, (41)
"Ramses was great, communicates well and the rental was what we expected. Just booked again."
United States
eric k.
The price is AU$454
includes taxes & fees
19 Nov - 20 Nov
Paradise in Key Largo Florida 2

Charming Home in Key Largo

Key Largo
9.8 out of 10, Exceptional, (26)
"It was clean and a very nice place to stay. Plenty of room and awesome amenities."
United States
Eric M.
The price is AU$558
includes taxes & fees
19 Nov - 20 Nov
Charming Home in Key Largo

Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe

Tavernier
9.8 out of 10, Exceptional, (190)
"Condo was very clean and tidyHost was quick to respondWe really appreciated the beach chairs"
United States
Jennifer O.
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Tavernier
9.8 out of 10, Exceptional, (227)
"Great place to stay and relax. "
United States
Marianne P.
The price is AU$643
includes taxes & fees
30 Nov - 1 Dec
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Key Largo
9.6 out of 10, Exceptional, (123)
"Great stay!! Location was perfect view of the canal and close to the pool. Unit was very clean and would definitely stay again!!"
United States
Brad T.
The price is AU$620
includes taxes & fees
19 Nov - 20 Nov
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Waterfront Tiny House w Pool, Beach, and Boat Dock

Key Largo
9.6 out of 10, Exceptional, (62)
"Excelent place "
United States
Alexander D.
The price is AU$580
includes taxes & fees
9 Dec - 10 Dec
Waterfront Tiny House w Pool, Beach, and Boat Dock
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

Find out more about Windley Key

Everything you need to know about Windley Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windley Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windley Key holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windley Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windley Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windley Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windley Key holiday rentals we have selected for you start as low as AU$205 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windley Key rentals

At Expedia, we put the best Windley Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windley Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windley Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windley Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.