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Windley Key Vacation Rentals

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Our top choices for Windley Key vacation rentals

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (161 reviews)
"Amazing stay!"
United States
Amanda
$260 nightly
The price is $293
Jul 2 - Jul 3
Total with taxes and fees
Treasure Harbor

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (704 reviews)
"Enjoyed this place."
United States
Christopher
$154 nightly
The price is $173
Jul 7 - Jul 8
Total with taxes and fees
Breezy Palms Resort

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (33 reviews)
"A comfortable little condo, conveniently located for exploring the Keys. There’s a nice pool and small beach area with a bar/restaurant that are well maintained."
United States
Stephen
$287 nightly
The price is $318
Jul 7 - Jul 8
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View

Kings Kamp

Kings Kamp
2.5 star property
Key Largo
8.6 out of 10, Excellent, (40 reviews)
"It was very nice!!"
United States
Michelle
$195 nightly
The price is $220
Jul 5 - Jul 6
Total with taxes and fees
Kings Kamp

The place to go when you want to get away!

The place to go when you want to get away!
Key Largo
10.0 out of 10, Exceptional, (73 reviews)
"Perfect spot!"
United States
Jennifer A.
$322 nightly
The price is $358
Jul 6 - Jul 7
Total with taxes and fees
The place to go when you want to get away!

Waterfront Tiny Home Pool Dock Kayaks Paddleboards

Waterfront Tiny Home Pool Dock Kayaks Paddleboards
Key Largo
9.6 out of 10, Exceptional, (129 reviews)
"The view alone was worth the booking. It was exactly what we were looking for. A place to sit, have coffee and relax. The kitchen was fully stocked with cookware and utensils. I had forgotten there was a 1/2 bath so that was a very pleasant surprise when we got there. Communication with our host was excellent and timely. We would definitely book again! "
United States
Julia S.
$433 nightly
The price is $478
Jul 13 - Jul 14
Total with taxes and fees
Waterfront Tiny Home Pool Dock Kayaks Paddleboards

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (172 reviews)
"Very nice small resort."
United States
Dan
$308 nightly
The price is $347
Jul 2 - Jul 3
Total with taxes and fees
Island Bay Resort

Cozy place in Calusa Key Largo

Cozy place in Calusa Key Largo
Key Largo
9.0 out of 10, Wonderful, (18 reviews)
$295 nightly
The price is $328
Jul 6 - Jul 7
Total with taxes and fees
Cozy place in Calusa Key Largo

Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.8 out of 10, Exceptional, (75 reviews)
"Great place to stay everything was as stated. Everyone at campground was super friendly and pool was amazing. Would stay here again!!"
United States
Stacie B.
$293 nightly
The price is $326
Jul 21 - Jul 22
Total with taxes and fees
Paradise in Key Largo, FL

Beautiful Kawama Townhouse

Beautiful Kawama Townhouse
Key Largo
9.8 out of 10, Exceptional, (148 reviews)
"Relaxing time and great neighborhood "
United States
Randy M.
Beautiful Kawama Townhouse

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (38 reviews)
"The condo is extremely clean and has everything you need for your stay. "
United States
hillary w.
$371 nightly
The price is $412
Jul 7 - Jul 8
Total with taxes and fees
Charming Home in Key Largo

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
"Everything was wonderful! We enjoyed our stay very much. "
United States
Colleen D.
$394 nightly
The price is $438
Jul 5 - Jul 6
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Cozy 1-bedroom studio in tranquil Key Largo with AC

Cozy 1-bedroom studio in tranquil Key Largo with AC
key largo
$292 nightly
The price is $324
Jul 2 - Jul 3
Total with taxes and fees
Cozy 1-bedroom studio in tranquil Key Largo with AC

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Tavernier
9.8 out of 10, Exceptional, (219 reviews)
"Our stay was amazing, I highly recommend Heidi and this location!"
United States
Becky S.
$468 nightly
The price is $520
Jul 2 - Jul 3
Total with taxes and fees
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Modern and Coastal Ocean Pointe 2307

Modern and Coastal Ocean Pointe 2307
Tavernier
10.0 out of 10, Exceptional, (133 reviews)
"There’s plenty to do for families of all ages at Ocean Pointe, and the condo was an extremely comfortable place to do it from. The hosts made us feel welcome, and we appreciated their care. "
United States
Sherry G.
$422 nightly
The price is $458
Jul 15 - Jul 16
Total with taxes and fees
Modern and Coastal Ocean Pointe 2307

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
Key Largo
9.6 out of 10, Exceptional, (137 reviews)
"Had fun villa was in good condition."
United States
Michelle S.
$641 nightly
The price is $710
Jul 12 - Jul 13
Total with taxes and fees
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (50 reviews)
"Unit was really nice. The only complaint was the pillows were the worst we have ever used anywhere. We did find a pillow in the closet that was a little less lumpy but very stained. The pool does get very crowded. The beach area is really cute but smelled pretty bad. Overall a great place!"
United States
joleen s.
$355 nightly
The price is $394
Jul 6 - Jul 7
Total with taxes and fees
Amazing Ocean view condo

Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
Tavernier
9.0 out of 10, Wonderful, (99 reviews)
"Great stay with ocean views. "
United States
Timothy C.
$336 nightly
The price is $373
Jul 6 - Jul 7
Total with taxes and fees
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (169 reviews)
"Condo was beautiful would definitely stay here again."
United States
Dan M.
$417 nightly
The price is $463
Jul 8 - Jul 9
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (17 reviews)
"Great views and very nice condo. The hosts were welcoming and helpful. we truly enjoyed our stay."
United States
Beth H.
$450 nightly
The price is $490
Jul 16 - Jul 17
Total with taxes and fees
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
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 $173 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.

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