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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Windley Key vacation rentals

A beach with palm trees, thatched-roof huts, and lounge chairs.

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (761 reviews)
"Such a great place to stay!!"
United States
Gavin
$107 nightly
The price is $120
Oct 8 - Oct 9
Total with taxes and fees
Breezy Palms Resort
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (177 reviews)
"Beautiful unique place"
United States
Laura
$244 nightly
The price is $275
Oct 8 - Oct 9
Total with taxes and fees
Treasure Harbor
A beachfront hotel with two palm trees, a flag, and a pool area with lounge chairs.

3. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (41 reviews)
"great stay and value! glad we went with this place for our trip, everyone loved it! beautiful, clean and the pool was great too!"
Canada
Nick
$301 nightly
The price is $335
Nov 3 - Nov 4
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View
A beach with clear shallow waters, a row of blue lounge chairs, and palm trees.

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (172 reviews)
"Perfect spot to stay in the keys! Great for fishing. The condo had everything you need to make your stay amazing. We will be back! Check in and out was a breeze, guards at gate were super friendly!"
United States
Pam K.
$324 nightly
The price is $360
Oct 13 - Oct 14
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
A beach with thatched umbrellas, lounge chairs, and a clear view of the ocean.

5. Kings Kamp

Kings Kamp
2.5 star property
Key Largo
8.6 out of 10, Excellent, (41 reviews)
"It was very nice!!"
United States
Michelle
$195 nightly
The price is $220
Oct 17 - Oct 18
Total with taxes and fees
Kings Kamp
A resort with multiple buildings, a swimming pool, tennis courts, and a view of the ocean.

6. Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (8 reviews)
"Super clean and neat location!"
United States
Christopher R.
$393 nightly
The price is $427
Oct 12 - Oct 13
Total with taxes and fees
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
A beach with clear shallow waters, a row of blue lounge chairs, and palm trees.

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
$342 nightly
The price is $379
Oct 11 - Oct 12
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
A laundry room with two stacked front-loading washing machines.

8. 4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Tavernier
9.8 out of 10, Exceptional, (48 reviews)
"We were two couples staying in this space with plenty of room. All the amenities on this property (pool, beach restaurant and bar)made this a terrific stay. "
United States
Donna B.
$478 nightly
The price is $525
Oct 12 - Oct 13
Total with taxes and fees
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Beach

9. 3212 Across from Pool * King & Queen/Twin Bunk Bed

3212 Across from Pool * King & Queen/Twin Bunk Bed
Tavernier
9.8 out of 10, Exceptional, (160 reviews)
"Perfect place for family to get away. Plenty of room"
United States
Aaron H.
$422 nightly
The price is $459
Oct 8 - Oct 9
Total with taxes and fees
3212 Across from Pool * King & Queen/Twin Bunk Bed
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, and a covered pavilion in the background.

10. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (53 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.
$310 nightly
The price is $344
Oct 9 - Oct 10
Total with taxes and fees
Amazing Ocean view condo
A pool area with a palm tree, a showerhead, and blue lounge chairs.

11. Ocean Pointe Ocean View w/heated pool beach marina

Ocean Pointe Ocean View w/heated pool beach marina
Tavernier
8.6 out of 10, Excellent, (13 reviews)
"Great location and host is great with communication!"
United States
Mary Katherine B.
$310 nightly
The price is $345
Oct 11 - Oct 12
Total with taxes and fees
Ocean Pointe Ocean View w/heated pool beach marina
A clear blue pool with lounge chairs and umbrellas, surrounded by palm trees and greenery.

12. Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (36 reviews)
"Loved the beach and pool."
United States
Haley P.
$412 nightly
The price is $447
Oct 9 - Oct 10
Total with taxes and fees
Lazy Daze Double King Suite Ocean Pointe 2310
Beach

13. 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
$381 nightly
The price is $413
Oct 15 - Oct 16
Total with taxes and fees
Aqua Vista Ocean Pointe 3307
A waterfront property with a dock, a house with a blue roof, and a marina with boats.

14. 2BR Oceanfront Suite w/ Beach & Marina Access

2BR Oceanfront Suite w/ Beach & Marina Access
Key Largo
10.0 out of 10, Exceptional, (1 review)
"This was a great place to stay. Incredibly clean and homey feel. I felt super safe walking the area after dinner at night"
United States
Alyssa H.
$218 nightly
The price is $242
Oct 13 - Oct 14
Total with taxes and fees
2BR Oceanfront Suite w/ Beach & Marina Access
A beach with rows of sun loungers, a wooden pier, and a thatched-roof structure.

15. Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Tavernier
9.8 out of 10, Exceptional, (25 reviews)
"The property was in a great location, close to several beach bars and restaurants, the condo was so cute and the host was accessible throughout the entire process before and after our stay."
United States
Alicia
$472 nightly
The price is $525
Oct 14 - Oct 15
Total with taxes and fees
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

16. Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (30 reviews)
"The space was family friendly and worked well for our stay. The pool area was very clean and the Island Grill on site was great for snacks and drinks while we swam."
United States
Miranda J.
$412 nightly
The price is $447
Oct 8 - Oct 9
Total with taxes and fees
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
A floating house with a thatched roof, large sliding glass doors, and a wooden deck with a chair.

17. Premium Floating Bungalow by Stay Ombi

Premium Floating Bungalow by Stay Ombi
3.5 star property
Key Largo
9.6 out of 10, Exceptional, (4 reviews)
"Great experience ! Will do it again"
United States
Deivys
$654 nightly
The price is $736
Oct 15 - Oct 16
Total with taxes and fees
Premium Floating Bungalow by Stay Ombi
A balcony with a view of the ocean, a chair, a sofa, and a decorative seahorse wall art.

18. Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (19 reviews)
"Great stay"
United States
Blain R.
$387 nightly
The price is $420
Oct 8 - Oct 9
Total with taxes and fees
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
A modern living room with a sofa, coffee table, and bar stools.

19. Captains Quarters Ocean Pointe 4405

Captains Quarters Ocean Pointe 4405
Tavernier
10.0 out of 10, Exceptional, (17 reviews)
"We love this place. Close to the pool and tennis courts. The space was clean and tidy. "
United States
Todd S.
$412 nightly
The price is $447
Oct 8 - Oct 9
Total with taxes and fees
Captains Quarters Ocean Pointe 4405
A compact kitchen with a dishwasher, a microwave, and a sink. There is a window with a view of the outdoors, and a ceiling fan.

20. 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, (220 reviews)
"Very cute cozy house boat. Well equipped and close to restaurant. Enjoyable weekend stay. Heidi the host is very welcoming."
United States
Michelle P.
$393 nightly
The price is $436
Oct 11 - Oct 12
Total with taxes and fees
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
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

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"Good stay"
Michael 1-night trip
Posted 15 hours ago
Fisher Inn Resort & Marina

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 $120 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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