Windley Key Vacation Rentals

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Vacation Rentals in Windley Key

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 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

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
$251 nightly
The price is $283
Nov 23 - Nov 24
Total with taxes and fees
Treasure Harbor

Breezy Palms Resort

2.5 star property
Matecumbe
8.8 out of 10, Excellent, (572)
"Best hotel for the price"
United States
luzdari
$153 nightly
The price is $172
Dec 1 - Dec 2
Total with taxes and fees
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
$749 nightly
The price is $843
Nov 30 - Dec 1
Total with taxes and fees
The Islands of Islamorada

Island Bay Resort

2.5 star property
Tavernier
10.0 out of 10, Exceptional, (137)
"Buutifull and cozy place "
United States
DILIA
$239 nightly
The price is $269
Dec 15 - Dec 16
Total with taxes and fees
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
$199 nightly
The price is $224
Dec 12 - Dec 13
Total with taxes and fees
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.
$331 nightly
The price is $367
Dec 8 - Dec 9
Total with taxes and fees
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

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!

Welcome to Paradise!

Key Largo
9.6 out of 10, Exceptional, (73)
"The property was clean and well appointed. The outdoor pool was lovely. Next time we will stay there longer... "
United States
Melissa S.
Welcome to Paradise!

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.
$264 nightly
The price is $293
Nov 30 - Dec 1
Total with taxes and fees
Paradise in Key Largo Florida 2

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.
$372 nightly
The price is $413
Nov 30 - Dec 1
Total with taxes and fees
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

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.
$264 nightly
The price is $293
Nov 25 - Nov 26
Total with taxes and fees
Paradise in Key Largo, FL

Waterfront Tiny House w Pool, Beach, and Boat Dock

Key Largo
9.6 out of 10, Exceptional, (62)
"Great little place with awesome outdoor area. "
United States
James D.
$336 nightly
The price is $373
Dec 9 - Dec 10
Total with taxes and fees
Waterfront Tiny House w Pool, Beach, and Boat Dock

Condo with Pool and Beach Access

Tavernier
10.0 out of 10, Exceptional, (27)
"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

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.
$376 nightly
The price is $417
Dec 10 - Dec 11
Total with taxes and fees
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

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
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windley Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windley Key vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windley Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $172 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windley Key rentals

At Expedia, we put the best Windley Key vacation 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 vacation.

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.