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Our top choices for Windley Key holiday rentals

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (75 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 £538
includes taxes & fees
7 May - 8 May
The Islands of Islamorada

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (164 reviews)
"Very nice small resort."
United States
Dan
The price is £254
includes taxes & fees
2 Jun - 3 Jun
Island Bay Resort

Kings Kamp

Kings Kamp
2.5 star property
Key Largo
8.6 out of 10, Excellent, (39 reviews)
"It was very nice!!"
United States
Michelle
The price is £165
includes taxes & fees
5 May - 6 May
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 £853
includes taxes & fees
1 Jun - 2 Jun
Premium Floating Bungalow by Stay Ombi

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (153 reviews)
"Amazing stay!"
United States
Amanda
The price is £207
includes taxes & fees
7 May - 8 May
Treasure Harbor

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (669 reviews)
"Clean room, good staff and convenience location for a visit."
United States
Judbelth
The price is £111
includes taxes & fees
26 May - 27 May
Breezy Palms Resort

Oceanside Kawama Villa R5

Oceanside Kawama Villa R5
Key Largo
9.2 out of 10, Wonderful, (180 reviews)
"Very very nice villa in a superb location… Abcolutely loved the property!"
United States
Ricardo G.
The price is £452
includes taxes & fees
6 May - 7 May
Oceanside Kawama Villa R5

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Tavernier
9.8 out of 10, Exceptional, (240 reviews)
"Great place to stay"
United States
Llonda B.
The price is £303
includes taxes & fees
5 May - 6 May
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Key Largo
9.6 out of 10, Exceptional, (127 reviews)
"Great place, great view, great hosts. No complaints about a thing. Publix is 2 minutes away, the campground is peaceful, house was clean. There were 4 of us and we had plenty of room. Will do that again"
United States
Joe J.
The price is £374
includes taxes & fees
6 May - 7 May
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Key Largo
9.4 out of 10, Exceptional, (66 reviews)
"Nice location with 5 min walk to ocean view. "
United States
Trevor P.
The price is £420
includes taxes & fees
10 May - 11 May
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.8 out of 10, Excellent, (43 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 £316
includes taxes & fees
5 May - 6 May
Ocean view condo with balcony/marina view

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, (157 reviews)
"Really enjoyed the location and the unit. "
United States
Teresa L.
The price is £343
includes taxes & fees
5 May - 6 May
3212 Across from Pool * King & Queen/Twin Bunk Bed

Dazzling Ocean Pointe -OP-Main

Dazzling Ocean Pointe -OP-Main
Tavernier
9.0 out of 10, Wonderful, (94 reviews)
"Cleanliness, location, communication and the pool was just great! Thank you so very much!"
United States
Vicky W.
The price is £239
includes taxes & fees
5 May - 6 May
Dazzling Ocean Pointe -OP-Main

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.
Key Largo Ocean Shore Villa 3 with pool & boat slip

Beautiful Kawama Townhouse

Beautiful Kawama Townhouse
Key Largo
9.8 out of 10, Exceptional, (147 reviews)
"The host, house and amenities were perfect. all praises.."
United States
Pete S.
The price is £489
includes taxes & fees
17 May - 18 May
Beautiful Kawama Townhouse

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Key Largo
10.0 out of 10, Exceptional, (53 reviews)
"super nice and modern house, really lovely host, the kitchen is equipped with all you need for cookingall decoration is so nice fits to the beach feelingall rooms are modern and nice decoratedwe could just recommend ! if we will come back to Florida this will be again our choice!"
United States
Anonymous traveller
The price is £480
includes taxes & fees
18 May - 19 May
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

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)
"My family and I had a great time. The place was very comfortable. Location was great and we enjoyed all the amenities. Great experience over all."
United States
Raul e.
The price is £454
includes taxes & fees
5 May - 6 May
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (114 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is £332
includes taxes & fees
17 May - 18 May
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Key Largo Ocean Shore Villa 2 with pool & boat slip

Key Largo Ocean Shore Villa 2 with pool & boat slip
Key Largo
10.0 out of 10, Exceptional, (115 reviews)
"Just what we needed for two adult couples to spend a couple nights to attend a friends wedding. Love the marina location and proximity to some fun spots for food and drink."
United States
Mike L.
Key Largo Ocean Shore Villa 2 with pool & boat slip

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (165 reviews)
"Everything was as described and we truly enjoyed our stay. We traveled with small children and the home was fit for them. It’s a true vacation place. I highly recommend staying! "
United States
keli p.
The price is £327
includes taxes & fees
7 May - 8 May
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
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 £111 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.