Holiday Rentals in Windley Key

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Our top choices for Windley Key holiday rentals

9.8 out of 10, Exceptional, (34)
"Beautiful house in a great location. Wonderful attentive hosts. "
United States
Elizabeth M.
Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen

Houseboat in Islamorada

Treasure Harbor
3.0 star property
9.0 out of 10, Wonderful, (117)
"I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore."
United States
Mary
Treasure Harbor

Aparthotel in Matecumbe

Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (584)
"we stayed in the beach front cottage kitchen was stocked room was clean and the views were great friendly staff "
United States
Terry
The price is €133
includes taxes & fees
17 Dec - 18 Dec
Breezy Palms Resort

Aparthotel in Tavernier

Island Bay Resort
2.5 star property
10.0 out of 10, Exceptional, (140)
"Very quiet and the outdoor spaces are very nice. Staff was very friendly also."
United States
Jacob
The price is €243
includes taxes & fees
14 Dec - 15 Dec
Island Bay Resort

Villa in Matecumbe

The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (69)
"Great for family vacation with kids. love it"
United States
Dixania
The price is €621
includes taxes & fees
15 Dec - 16 Dec
The Islands of Islamorada

Aparthotel in Key Largo

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

Apartment in Key Largo

Key Largo Cottages
2.5 star property
9.6 out of 10, Exceptional, (26)
"Beautiful and peaceful place "
United States
Jacqueline
Key Largo Cottages
9.8 out of 10, Exceptional, (191)
"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
9.6 out of 10, Exceptional, (83)
"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 €355
includes taxes & fees
14 Dec - 15 Dec
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
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 €254
includes taxes & fees
14 Dec - 15 Dec
Paradise in Key Largo Florida 2
2.0 star property
10.0 out of 10, Exceptional, (1)
"Lovely, spotless RV. I would definitely recommend. "
United States
Apu Wasi Lodge
The price is €280
includes taxes & fees
15 Dec - 16 Dec
Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Condo in Key Largo

Welcome to Paradise!
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!
9.6 out of 10, Exceptional, (54)
"Great location, great pool, comfortable beds"
United States
Michael W.
Ohana Cay 4 bed & 4 bath Unit 906 @Mariners Club - Sleeps 10!!
2.0 star property
10.0 out of 10, Exceptional, (45)
"Good location. Lagoon and pool right outside door. "
United States
Debra C.
The price is €456
includes taxes & fees
15 Dec - 16 Dec
NEW ! Marvelous 2-bedroom house with Marina in Key Largo
9.8 out of 10, Exceptional, (228)
"Great place to stay and relax. "
United States
Marianne P.
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
10.0 out of 10, Exceptional, (87)
"Wonderful place to stay for families. We loved it. Rooms and bathrooms were fantastic. Michele was a great host that made sure our stay was perfect. "
United States
Kimber T.
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

Mobile Home in Key Largo

Cozy place in Calusa Key Largo
9.4 out of 10, Exceptional, (12)
"Perfect weekend getaway location."
United States
Tex H.
The price is €360
includes taxes & fees
13 Jan - 14 Jan 2026
Cozy place in Calusa Key Largo
9.6 out of 10, Exceptional, (32)
"Nice and convenient location. "
United States
Daniel D.
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Mobile Home in Key Largo

Paradise in Key Largo, FL
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 €254
includes taxes & fees
14 Dec - 15 Dec
Paradise in Key Largo, FL
10.0 out of 10, Exceptional, (180)
"The condo was beautifully decorated and just perfect for the 2 of us. The view was breathtaking. We’ll be back "
United States
Christine P.
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
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 €133 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.