Holiday Rentals in Windley Key

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Holiday Rentals in Windley Key

NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
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
Treasure Harbor
3.0 star property
8.8 out of 10, Excellent, (108)
"If you are looking for a laid back vibe with no hassle here is the place. Friendly staff. Aqualodge was cute and comfortable. Easily rented a boat for the day...found great snorkeling and beautiful views. "
United States
JoAnn
Treasure Harbor
Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (551)
"Nice place to stay for the wedding I went to "
United States
michael
The price is €109
includes taxes & fees
11 Nov - 12 Nov
Breezy Palms Resort
Island Bay Resort
2.5 star property
10.0 out of 10, Exceptional, (134)
"Buutifull and cozy place "
United States
DILIA
The price is €245
includes taxes & fees
30 Oct - 31 Oct
Island Bay Resort
The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (68)
"Great for family vacation with kids. love it"
United States
Dixania
The price is €578
includes taxes & fees
30 Oct - 31 Oct
The Islands of Islamorada
Key Largo Cottages
2.5 star property
9.6 out of 10, Exceptional, (25)
"Beautiful and peaceful place "
United States
Jacqueline
Key Largo Cottages
Kings Kamp
2.5 star property
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
Paradise in Key Largo, FL
9.6 out of 10, Exceptional, (58)
"Beautiful property. We uh, I very much enjoyed our stay highly recommend we will stay here again"
United States
George D.
The price is €256
includes taxes & fees
30 Oct - 31 Oct
Paradise in Key Largo, FL
Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball
10.0 out of 10, Exceptional, (133)
"Beautiful place and great amenities!"
United States
Lindsey S.
Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.
9.6 out of 10, Exceptional, (59)
"Awesome condo! "
United States
John M.
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
9.6 out of 10, Exceptional, (42)
"We had fun.we will be back next year."
United States
Thomas A.
The price is €258
includes taxes & fees
2 Nov - 3 Nov
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
9.4 out of 10, Exceptional, (79)
"Awesome experience specially whit Barbara"
United States
jorge l.
The price is €322
includes taxes & fees
30 Oct - 31 Oct
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
BEACHFRONT POOL HOME
9.6 out of 10, Exceptional, (106)
"Property was great. Everyone enjoyed their stay definitely would come back."
United States
Bradley P.
BEACHFRONT POOL HOME
Charming Home in 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 €375
includes taxes & fees
30 Oct - 31 Oct
Charming Home in Key Largo
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe
9.8 out of 10, Exceptional, (188)
"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
FALL '25 Deals! OCEANFRONT Lux 1350sf w/ Stunning Views & All Amenities of home!
9.6 out of 10, Exceptional, (291)
"The host was great to communicate .We really enjoyed our stay."
United States
Surama M.
FALL '25 Deals! OCEANFRONT Lux 1350sf w/ Stunning Views & All Amenities of home!
Mangrove Marina and Resort Aqualodge Houseboats
3.0 star property
9.4 out of 10, Exceptional, (331)
"Everything was good, cleaning, bar , pool and service was excellent "
United States
orampa
Mangrove Marina and Resort Aqualodge Houseboats
Condo with Pool and Beach Access
10.0 out of 10, Exceptional, (25)
"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
Key Largo Sunset Estate
10.0 out of 10, Exceptional, (58)
"Perfect house, beautiful sunsets, boat dock was convenient (kid's loved fishing off the dock), great location - loved it! Wonderful homes for a family vacation! We'll never forget it!"
United States
Iva T.
Key Largo Sunset Estate
5 Star Coastal Luxury: Key Largo 2BR Condo w/Lagoon, Golf Cart, Pools& Amenities
10.0 out of 10, Exceptional, (16)
"Great vacation spot , only thing missing is a good saltwater beach."
United States
Robert R S.
5 Star Coastal Luxury: Key Largo 2BR Condo w/Lagoon, Golf Cart, Pools& Amenities
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, apart-hotels, 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 favorite 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 depends 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 €109 per night. Entering your travel dates in the search wizard you might find 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.