A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Windley Key Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Windley Key vacation rentals

25-inch flat-screen TV with digital channels, TV

1. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (171 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
$254 nightly
The price is $286
Aug 18 - Aug 19
Total with taxes and fees
Treasure Harbor
Exterior

2. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (727 reviews)
"Great place to stay rooms were really nice nice boat ramp plenty of parking restaurants right down the street to eat at no complaints nice pool everybody was friendly room was ice cold from the air condition full kitchen nice balcony looking out over the ocean great stay"
United States
roger
$117 nightly
The price is $131
Sep 8 - Sep 9
Total with taxes and fees
Breezy Palms Resort
Exterior

3. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (36 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
$276 nightly
The price is $306
Aug 18 - Aug 19
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View
Pool

4. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (52 reviews)
"Excellent accommodations. Unit was even nicer than it looked in pictures, everything was clean and in working order. Enjoyed our stay very much and would definitely stay here again!"
United States
Jerad E.
$315 nightly
The price is $349
Aug 23 - Aug 24
Total with taxes and fees
Amazing Ocean view condo
Interior

5. Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
10.0 out of 10, Exceptional, (4 reviews)
"Very clean with everything you could need for your time in the Florida keys! The host was very responsive and helpful. Perfect place for a weekend with our dog."
United States
Anonymous traveler
$268 nightly
The price is $297
Aug 18 - Aug 19
Total with taxes and fees
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Private beach, sun loungers, beach umbrellas, beach towels

6. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (179 reviews)
"Very pleased with our stay"
United States
Vernon Micheal
$256 nightly
The price is $288
Aug 23 - Aug 24
Total with taxes and fees
Island Bay Resort
On the beach

7. Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Key Largo
9.6 out of 10, Exceptional, (49 reviews)
"This was the perfect little home away from home! The house was perfectly clean and nice and cool! The AC in the bedroom was fantastic and kept the room a perfect temperature for sleeping. In addition the bed was super comfortable! We had a great time in the campground and were so excited about the kayaks available for our use. We have already recommended this house and the campground to our friends and family and can’t wait to come and stay again soon!"
United States
Carrie D.
$259 nightly
The price is $284
Sep 1 - Sep 2
Total with taxes and fees
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Smart TV

8. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (39 reviews)
"Very clean and nice location."
United States
Melinda V.
$332 nightly
The price is $368
Aug 24 - Aug 25
Total with taxes and fees
Charming Home in Key Largo
Beach nearby

9. 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.
$371 nightly
The price is $412
Sep 1 - Sep 2
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Marina

10. Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor

Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor
Tavernier
9.6 out of 10, Exceptional, (33 reviews)
"The apartment was perfect, great location over looking the ocean, and nice and clean. They had everything we needed for our stay, The pool and the hot tub at the resort where clean and welcoming."
United States
Kimberly P.
$457 nightly
The price is $507
Aug 24 - Aug 25
Total with taxes and fees
Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor
Beach nearby

11. Marina to Ocean View Key Largo Ocean Pointe 5308

Marina to Ocean View Key Largo Ocean Pointe 5308
Tavernier
9.4 out of 10, Exceptional, (71 reviews)
"The host was quick to respond, condo was perfect, the view was exceptional!"
United States
Rosalie K.
$406 nightly
The price is $440
Aug 18 - Aug 19
Total with taxes and fees
Marina to Ocean View Key Largo Ocean Pointe 5308
Beach nearby

12. RV by the Sea - Glamping in the Keys

RV by the Sea - Glamping in the Keys
Key Largo
9.0 out of 10, Wonderful, (32 reviews)
"Clean and in a good location to navigate key largo. "
United States
Emily M.
$249 nightly
The price is $277
Aug 24 - Aug 25
Total with taxes and fees
RV by the Sea - Glamping in the Keys
Property grounds

13. Cozy place in Calusa Key Largo

Cozy place in Calusa Key Largo
Key Largo
9.0 out of 10, Wonderful, (18 reviews)
"Great location and perfect set up for our family of 5. We had everything we needed and more. The outside hang out area and grill were great. "
United States
Jordan and Lindsay G.
$294 nightly
The price is $326
Aug 18 - Aug 19
Total with taxes and fees
Cozy place in Calusa Key Largo
Beach nearby

14. Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.8 out of 10, Exceptional, (76 reviews)
"Convenient, affordable, pet friendly, "
United States
mark e.
$265 nightly
The price is $294
Aug 18 - Aug 19
Total with taxes and fees
Paradise in Key Largo, FL
Beach

15. Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Tavernier
9.8 out of 10, Exceptional, (9 reviews)
"An awesome place to stay, fish and relax!"
United States
robert d.
$389 nightly
The price is $423
Aug 18 - Aug 19
Total with taxes and fees
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Interior

16. Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315
Tavernier
9.8 out of 10, Exceptional, (17 reviews)
"Loved this condo. Had all the amenities we needed and was super clean and tidy. Will definitely be staying here again. "
United States
Rodney B.
$381 nightly
The price is $415
Aug 18 - Aug 19
Total with taxes and fees
Blue Haven Key Largo | Ocean Pointe 1315
Beach

17. Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
$386 nightly
The price is $418
Aug 18 - Aug 19
Total with taxes and fees
Aqua Vista Ocean Pointe 3307
Beach nearby

18. Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (9 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
$373 nightly
The price is $405
Aug 18 - Aug 19
Total with taxes and fees
Flamingo Flats Ocean Pointe 5306 2BR/2BA
Smart TV, fireplace, DVD player, books

19. 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, (76 reviews)
"The pool was nice. Kayaks available. The park is quiet but close lots of good places."
United States
Steven H.
$295 nightly
The price is $327
Aug 24 - Aug 25
Total with taxes and fees
The place to go when you want to get away!
Interior

20. Boho Chic Ocean Pointe 3214 King & Queen

Boho Chic Ocean Pointe 3214 King & Queen
Tavernier
9.8 out of 10, Exceptional, (15 reviews)
"The condo was nice and clean. The view from the balcony is very nice. The property is also nice with things to do but not too busy. The host was great and responsive. "
United States
Anthony F.
$381 nightly
The price is $415
Aug 18 - Aug 19
Total with taxes and fees
Boho Chic Ocean Pointe 3214 King & Queen
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

Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"Great property friendly staff have no complaints @ all"
Carlos 2-night trip
Posted 7 hours ago
Bayside Inn Key Largo

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 $131 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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