Windley Key Holiday Rentals

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Our top choices for Windley Key holiday rentals

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 AU$314
includes taxes & fees
19 May - 20 May
Kings Kamp

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (169 reviews)
"Very nice small resort."
United States
Dan
The price is AU$451
includes taxes & fees
3 June - 4 June
Island Bay Resort

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 AU$1,538
includes taxes & fees
19 May - 20 May
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 AU$493
includes taxes & fees
1 June - 2 June
Treasure Harbor

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 AU$986
includes taxes & fees
20 May - 21 May
The Islands of Islamorada

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (677 reviews)
"Easy parking and great clean kitchen"
United States
JoAnn
The price is AU$186
includes taxes & fees
26 May - 27 May
Breezy Palms Resort

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, (241 reviews)
"Great place to stay"
United States
Llonda B.
The price is AU$696
includes taxes & fees
22 May - 23 May
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

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 AU$936
includes taxes & fees
1 June - 2 June
Oceanside Kawama Villa R5

La Fuentes

La Fuentes
Cross Key Waterways
The price is AU$1,137
includes taxes & fees
19 May - 20 May
La Fuentes

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 AU$915
includes taxes & fees
12 June - 13 June
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

Beautiful Kawama Townhouse

Beautiful Kawama Townhouse
Key Largo
9.8 out of 10, Exceptional, (148 reviews)
"The host, house and amenities were perfect. all praises.."
United States
Pete S.
The price is AU$902
includes taxes & fees
21 May - 22 May
Beautiful Kawama Townhouse

Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
10.0 out of 10, Exceptional, (37 reviews)
"We enjoyed our stay. It was very convenient to where we needed to be. The apartment was well stocked and had a nice view. The beds were very comfortable as well and the host was very responsive! Would recommend staying here if you’re in the area. "
United States
Mark F.
The price is AU$894
includes taxes & fees
22 May - 23 May
Serene Oceanfront Keys Condo

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 AU$600
includes taxes & fees
19 May - 20 May
Ocean view condo with balcony/marina view

Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.

Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.
Key Largo Village
10.0 out of 10, Exceptional, (1 review)
"This is by far the BEST experience I’ve ever had. Upon arrival, we were greeted by the boat driver, Captain Ryan. The ride over was easy and quick. We rode with 1 other couple and the captain helped everyone aboard, with a hand and carried our luggage aboard. He had a very friendly demeanor. He had knowledge of the wildlife in the area and told us to keep an eye out for manatee and dolphins, which we saw within a 1/2 hour of being dropped off. He brought dinner to us, which was still hot and he...
United States
Stacey P.
The price is AU$1,694
includes taxes & fees
19 May - 20 May
Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.

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, (96 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 AU$456
includes taxes & fees
20 May - 21 May
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

Key Largo Kawama Villa L1, 3/3

Key Largo Kawama Villa L1, 3/3
Key Largo
9.4 out of 10, Exceptional, (224 reviews)
"Perfect location, very nice and clean house"
United States
Golnar
The price is AU$887
includes taxes & fees
21 May - 22 May
Key Largo Kawama Villa L1, 3/3

the fountain

the fountain
Cross Key Waterways
6.6 out of 10, (4 reviews)
"We loved this home! It was perfect for our family. It was immaculate, with a Viking equipped gourmet kitchen perfect for cooking fresh catch from fishing earlier in the day. The home is on a quiet canal in a wonderful neighborhood. Great restaurants also nearby. Can’t wait for the pool to be completed in time for our next visit."
United States
Kate C.
The price is AU$1,936
includes taxes & fees
26 May - 27 May
the fountain

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 AU$612
includes taxes & fees
19 May - 20 May
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
Key Largo
9.8 out of 10, Exceptional, (199 reviews)
"The place is beautiful love having the golf cart also."
United States
Tina W.
The price is AU$1,254
includes taxes & fees
31 May - 1 June
NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views
4.0 star property
Long Key
The price is AU$1,462
includes taxes & fees
7 June - 8 June
Florida Keys Getaway w/ Stunning Ocean Views
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, 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 selected for you start as low as AU$186 per night. Entering your travel dates in the search wizard might find you 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.