Windley Key Holiday Rentals

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Our top choices for Windley Key holiday rentals

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (785 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is AU$213
includes taxes & fees
16 Nov - 17 Nov
Breezy Palms Resort

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (185 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
The price is AU$401
includes taxes & fees
16 Nov - 17 Nov
Treasure Harbor

3. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (43 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
The price is AU$465
includes taxes & fees
16 Nov - 17 Nov
Florida Keys Getaway - Slps 4 - Ocean View

4. 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.
The price is AU$486
includes taxes & fees
16 Nov - 17 Nov
Amazing Ocean view condo

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (172 reviews)
"Beautifully appointed, clean and comfortable. This place is worth it! We had a great stay. Location is also excellent. Would definitely stay here again. "
United States
Erica C.
The price is AU$590
includes taxes & fees
29 Nov - 30 Nov
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

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

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
9.8 out of 10, Exceptional, (6 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 traveller
The price is AU$437
includes taxes & fees
16 Nov - 17 Nov
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

7. Paradise Palms | 2 Balconies | Ocean Pointe 1206

Paradise Palms | 2 Balconies | Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (8 reviews)
"Super clean and neat location!"
United States
Christopher R.
The price is AU$651
includes taxes & fees
29 Nov - 30 Nov
Paradise Palms | 2 Balconies | Ocean Pointe 1206

8. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
10.0 out of 10, Exceptional, (41 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is AU$517
includes taxes & fees
16 Nov - 17 Nov
Charming Home in Key Largo

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (116 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is AU$532
includes taxes & fees
19 Nov - 20 Nov
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

10. Heavenly Hideaway | Ocean View | Ocean Pointe 3306

Heavenly Hideaway | Ocean View | Ocean Pointe 3306
Tavernier
10.0 out of 10, Exceptional, (4 reviews)
"Second time staying in this condo. Great view, clean, and really like the interior design. Looking forward to visiting again next year."
United States
Doug M.
The price is AU$693
includes taxes & fees
17 Nov - 18 Nov
Heavenly Hideaway | Ocean View | Ocean Pointe 3306

11. Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.6 out of 10, Excellent, (46 reviews)
"Wonderful stay! Beautiful view from the balcony"
United States
Katy T.
The price is AU$563
includes taxes & fees
16 Nov - 17 Nov
Ocean view condo with balcony/marina view

12. 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, (26 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
The price is AU$655
includes taxes & fees
16 Nov - 17 Nov
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

13. Piece of Paradise

Piece of Paradise
2.0 star property
Key largo
The price is AU$557
includes taxes & fees
1 Dec - 2 Dec
Piece of Paradise

14. 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.
The price is AU$501
includes taxes & fees
18 Nov - 19 Nov
Ocean Pointe Ocean View w/heated pool beach marina

15. 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)
"My host is amazing and the property was incredible. Highly recommended."
United States
Jean V.
The price is AU$681
includes taxes & fees
17 Nov - 18 Nov
Lazy Daze | Double King Suite | Ocean Pointe 2310

16. Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
9.8 out of 10, Exceptional, (45 reviews)
"Great stay, amazing pool and property, "
United States
Abbigail R.
The price is AU$572
includes taxes & fees
16 Nov - 17 Nov
Serene Oceanfront Keys Condo

17. 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, (54 reviews)
"We had a nice stay"
United States
Kevin M.
The price is AU$440
includes taxes & fees
16 Nov - 17 Nov
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

18. Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.8 out of 10, Exceptional, (78 reviews)
"This was a neat place to stay and the host was very helpful when I had questions!"
United States
Anonymous traveller
The price is AU$438
includes taxes & fees
18 Nov - 19 Nov
Paradise in Key Largo, FL

19. Cozy place in Calusa Key Largo

Cozy place in Calusa Key Largo
Key Largo
9.0 out of 10, Wonderful, (18 reviews)
"Great for a short stay! "
United States
Anonymous traveller
The price is AU$457
includes taxes & fees
16 Nov - 17 Nov
Cozy place in Calusa Key Largo

20. ARE YOU READY TO SPEND YOUR BEST HOLIDAYS AT SEA ???

ARE YOU READY TO SPEND YOUR BEST HOLIDAYS AT SEA ???
Key Largo
6.4 out of 10, (22 reviews)
"Nice boat, everything was in working order. Would stay here again. "
United States
Kevin J.
The price is AU$362
includes taxes & fees
16 Nov - 17 Nov
ARE YOU READY TO SPEND YOUR BEST HOLIDAYS AT SEA ???
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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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, 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 favourite 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 depend 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 chosen for you start as low as AU$213 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.

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