Windley Key Vacation Rentals

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Our top choices for Windley Key vacation rentals

Houseboat in Islamorada

Treasure Harbor
3.0 star property
9.0 out of 10, Wonderful, (120)
"Great spot! Will be back someday hopefully. "
Canada
Diane
$294 nightly
The price is $331
Jan 5 - Jan 6, 2026
Total with taxes and fees
Treasure Harbor
3.5 star property
$1,259 nightly
The price is $1,417
Jan 1 - Jan 2, 2026
Total with taxes and fees
Premium Floating Bungalow by Stay Ombi

Aparthotel in Matecumbe

Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (600)
"Property was nice and easy to navigate, ocean view room was extra nice to have!"
United States
Lisa
$219 nightly
The price is $247
Jan 8 - Jan 9, 2026
Total with taxes and fees
Breezy Palms Resort
2.0 star property
10.0 out of 10, Exceptional, (3)
"Set up of RV was very nice. Great location and amenities at the campground."
United States
Cynthia C.
$283 nightly
The price is $315
Jan 7 - Jan 8, 2026
Total with taxes and fees
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
8.8 out of 10, Excellent, (19)
"Fun accommodation in Key Largo. Clean, good size, nice pool."
United States
James C.
$245 nightly
The price is $273
Jan 6 - Jan 7, 2026
Total with taxes and fees
RV by the Sea - Glamping in the Keys - Sleeps 6
9.8 out of 10, Exceptional, (41)
"The cleanliness, the availability, the comfort. Everything was perfect in fact. Vz are planning on contacting the owner and tomorrow maybe arrange another rental on that property. It was in the perfect spot walking distance to the pool. Everything was readily available. Everything that they advertised was actually above and beyond. Our expectations can't say enough. Good about it was a perfect vacation. Thank you"
United States
Steve V.
$269 nightly
The price is $300
Jan 7 - Jan 8, 2026
Total with taxes and fees
Paradise in Key Largo Florida 2

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.
$297 nightly
The price is $330
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy place in Calusa Key Largo

Aparthotel in Key Largo

Kings Kamp
2.5 star property
8.6 out of 10, Excellent, (24)
"Overall good. Location and safety wise very good. But bathroom didn’t have "
United States
Sivasankari
$302 nightly
The price is $340
Jan 4 - Jan 5, 2026
Total with taxes and fees
Kings Kamp

Condo in Tavernier

Amazing Ocean view condo
9.6 out of 10, Exceptional, (42)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
$342 nightly
The price is $380
Jan 19 - Jan 20, 2026
Total with taxes and fees
Amazing Ocean view condo

Vacation Home in Key Largo

Charming Home in Key Largo
9.8 out of 10, Exceptional, (29)
"It was clean and a very nice place to stay. Plenty of room and awesome amenities."
United States
Eric M.
$410 nightly
The price is $456
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming Home in Key Largo

Houseboat in Tavernier

Island Sanctuary Islamorada
9.8 out of 10, Exceptional, (13)
"It exceeded our expectations, and we are so glad we found this location!"
United States
Jenn H.
$361 nightly
The price is $402
Jan 1 - Jan 2, 2026
Total with taxes and fees
Island Sanctuary Islamorada
10.0 out of 10, Exceptional, (122)
"We enjoyed our stay!"
United States
Halley R.
$382 nightly
The price is $415
Jan 19 - Jan 20, 2026
Total with taxes and fees
Modern and Coastal Ocean Pointe 2307
9.6 out of 10, Exceptional, (19)
"Everything was just as described in the condo listing. We enjoyed the pool and hot tub. Wonderful location to explore the Keys. "
United States
Michele G.
$343 nightly
The price is $381
Jan 4 - Jan 5, 2026
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View
10.0 out of 10, Exceptional, (108)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
$417 nightly
The price is $464
Jan 5 - Jan 6, 2026
Total with taxes and fees
Serenity In The Sun Condo Fabulous Ocean View
9.6 out of 10, Exceptional, (31)
"Everything is as described. We brought our boat and used the marina. Our trailer fit on the property’s as well. "
United States
Jane O.
$372 nightly
The price is $413
Jan 11 - Jan 12, 2026
Total with taxes and fees
Where the sea, sun, and sand are just outside your door!
9.6 out of 10, Exceptional, (84)
"Very quiet and cozy "
United States
Stephanie T.
$384 nightly
The price is $427
Jan 7 - Jan 8, 2026
Total with taxes and fees
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
10.0 out of 10, Exceptional, (10)
"It was a lovely place, very clean and comfortable. Will be definitely be coming back. "
United States
Carol
$338 nightly
The price is $376
Jan 10 - Jan 11, 2026
Total with taxes and fees
Happy in the Keys Tiny Home-in Key Largo.
8.6 out of 10, Excellent, (88)
"It was very clean. Pet friendly. Everybody at the campground is wonderful."
United States
Tammie F.
$310 nightly
The price is $345
Jan 11 - Jan 12, 2026
Total with taxes and fees
2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental
9.6 out of 10, Exceptional, (15)
"This condo was everything we needed. Lots of space, bug comfy beds, hreat shower and the pool at the complex was great in the late afternoon after a day exploring the upper keys. There were works going on at the conplex when we were there which took the edge off things as 9am drilling on Monday morning wasnt welcome but I only knocked 1 star off - otherwise wouldnt hesitate to recommend!"
United Kingdom
Philippa
$397 nightly
The price is $431
Jan 21 - Jan 22, 2026
Total with taxes and fees
Blue Haven Key Largo | Ocean Pointe 1315

Apartment in Tavernier

Boho Chic Ocean Pointe 3214
10.0 out of 10, Exceptional, (12)
"It was clean, well organized and communication was great. Had a good time."
United States
Shirl
$428 nightly
The price is $466
Jan 27 - Jan 28, 2026
Total with taxes and fees
Boho Chic Ocean Pointe 3214
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 $247 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.