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Our top choices for Windley Key holiday rentals

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (158 reviews)
"Amazing stay!"
United States
Amanda
The price is £215
includes taxes & fees
21 Jun - 22 Jun
Treasure Harbor

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
The price is £248
includes taxes & fees
25 Jun - 26 Jun
Island Bay Resort

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
The price is £170
includes taxes & fees
5 Jul - 6 Jul
Kings Kamp

Premium Floating Bungalow by Stay Ombi

Premium Floating Bungalow by Stay Ombi
3.5 star property
Key Largo
10.0 out of 10, Exceptional, (2 reviews)
The price is £784
includes taxes & fees
25 Jun - 26 Jun
Premium Floating Bungalow by Stay Ombi

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.6 out of 10, Exceptional, (5 reviews)
"Easy check in if you come After business hours. Kayaks and sport equipment available. Has a small beach which is unique to the Keys. Pool pretty much vacant at all times. Great views. Highly recommend."
United States
Dana
The price is £165
includes taxes & fees
22 Jun - 23 Jun
Caloosa Cove Resort by CoolVacay

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (699 reviews)
"Enjoyed this place."
United States
Christopher
The price is £142
includes taxes & fees
1 Jul - 2 Jul
Breezy Palms Resort

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (76 reviews)
"What a wonderful venue for our last 2 nights in the Keys. This place is a hidden gem. The entire staff, especially Edith, the bartender, were fantastic."
United States
Michael
The price is £586
includes taxes & fees
6 Jul - 7 Jul
The Islands of Islamorada

Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (71 reviews)
"Host was very responsive, location safe and wuiet."
United States
Tracey C.
The price is £582
includes taxes & fees
23 Jun - 24 Jun
Sunrise Escape - Ocean Front Villa - Sleeps 10

Oceanside Kawama Villa R5

Oceanside Kawama Villa R5
Key Largo
9.2 out of 10, Wonderful, (181 reviews)
"Great place in Key Largo. Cool bonus a saltwater lagoon with fish to swim and snorkwl with. "
United States
Kenny C.
The price is £572
includes taxes & fees
12 Jul - 13 Jul
Oceanside Kawama Villa R5

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.
The price is £267
includes taxes & fees
1 Jul - 2 Jul
The place to go when you want to get away!

Key Largo Kawama villa K1, 3/3

Key Largo Kawama villa K1, 3/3
Key Largo
9.8 out of 10, Exceptional, (189 reviews)
"Great place, the lake outside was amazing. Would stay here again. "
United States
Spencer H.
The price is £561
includes taxes & fees
25 Jun - 26 Jun
Key Largo Kawama villa K1, 3/3

Key Largo Ocean Shore Villa 3 with pool & boat slip

Key Largo Ocean Shore Villa 3 with pool & boat slip
Key Largo
9.8 out of 10, Exceptional, (135 reviews)
"Beautiful, clean stay in Key Largo with views of the inlet, and kayaks on site to explore from! The unit had everything my family needed and we loved our 3 nights here."
United States
Heather W.
The price is £432
includes taxes & fees
21 Jun - 22 Jun
Key Largo Ocean Shore Villa 3 with pool & boat slip

Refined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests

Refined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests
Key Largo
9.8 out of 10, Exceptional, (122 reviews)
"Great stay "
United States
Gary N.
The price is £496
includes taxes & fees
21 Jun - 22 Jun
Refined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests

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.
The price is £331
includes taxes & fees
22 Jun - 23 Jun
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Bay Sunsets Free Kayaks/Paddleboard Jacuzzi

Bay Sunsets Free Kayaks/Paddleboard Jacuzzi
Key Largo
10.0 out of 10, Exceptional, (85 reviews)
"Great place to stay in a great location "
United States
Will H.
The price is £1,146
includes taxes & fees
29 Jun - 30 Jun
Bay Sunsets Free Kayaks/Paddleboard Jacuzzi

Where the sea, sun, and sand are just outside your door!

Where the sea, sun, and sand are just outside your door!
Key Largo
9.8 out of 10, Exceptional, (36 reviews)
"clean camper"
United States
Stacy B.
The price is £279
includes taxes & fees
22 Jun - 23 Jun
Where the sea, sun, and sand are just outside your door!

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.
The price is £335
includes taxes & fees
22 Jun - 23 Jun
Modern and Coastal Ocean Pointe 2307

Waterfront Home 3/2.5,HotTub,2Sup,4Kayaks,Golf Car

Waterfront Home 3/2.5,HotTub,2Sup,4Kayaks,Golf Car
Key Largo
10.0 out of 10, Exceptional, (147 reviews)
"Perfect location Nice outside area for sitting plus the kayaks "
United States
William V.
The price is £590
includes taxes & fees
5 Jul - 6 Jul
Waterfront Home 3/2.5,HotTub,2Sup,4Kayaks,Golf Car

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, (98 reviews)
"Right in the heart of Key Largo but just off the beaten path. Clean, comfortable and cozy. The property has a beach, pool and restaurant which was convenient after a long day of travel."
United States
jodi
The price is £249
includes taxes & fees
30 Jun - 1 Jul
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.6 out of 10, Excellent, (45 reviews)
"Rooms were spacious and a short drive to most of the attractions we wanted to do. Rooms and bathrooms were gorgeous!"
United States
Cindy
The price is £326
includes taxes & fees
22 Jun - 23 Jun
Ocean view condo with balcony/marina view
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 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, apart-hotels, 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 favorite 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 depends 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 selected for you start as low as £142 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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