Windley Key Holiday Rentals

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Holiday Rentals in Windley Key

OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

10.0 out of 10, Exceptional, (185)
"Lodgings first rate. Boat access to Mahi and Grouper catches."
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

10.0 out of 10, Exceptional, (195)
"We just got back from Islamorada and cannot stop talking about our trip. This property was clean and comfortable and the private development had everything we wanted. Everyone was very nice. I will definitely rent again if/when we return."
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

FALL SPECIALS! Islamorada Anglers Reef Oceanview: Private Beach, Pool, Marina

10.0 out of 10, Exceptional, (4)
"Our stay was nothing but amazing! The area/community is beautiful and Al was a wonderful host! Will definitely be staying here again next year!!"
FALL SPECIALS! Islamorada Anglers Reef Oceanview: Private Beach, Pool, Marina

NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

10.0 out of 10, Exceptional, (1)
"This property was amazing basically brand new definitely recommend "
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

Treasure Harbor

3.0 star property
8.8 out of 10, Excellent, (102)
"Unique House boat experience, friendly staff. "
The price is AU$370
includes taxes & fees
2 Sept - 3 Sept
Treasure Harbor

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (522)
"Best kept secret, love staying here,!"
The price is AU$201
includes taxes & fees
7 Sept - 8 Sept
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (66)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is AU$1,030
includes taxes & fees
4 Sept - 5 Sept
The Islands of Islamorada

Key Largo Cottages

2.5 star property
9.6 out of 10, Exceptional, (24)
"Beautiful and peaceful place "
Key Largo Cottages

Island Bay Resort

2.5 star property
10.0 out of 10, Exceptional, (130)
"Clean, friendly, has its own beach"
Island Bay Resort

Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe

9.8 out of 10, Exceptional, (186)
"Nice place, lots to do, great location, great views"
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe

Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!

10.0 out of 10, Exceptional, (173)
"The property was very clean and comfortable. The pool was beautiful. The condo fit all of our needs and we were glad yo have the opportunity to stay. We would love to come back!"
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!

Charming Home in Key Largo

9.8 out of 10, Exceptional, (25)
"loved it!!"
The price is AU$685
includes taxes & fees
2 Sept - 3 Sept
Charming Home in Key Largo

Premium Floating Bungalow by Stay Ombi

3.5 star property
The price is AU$1,375
includes taxes & fees
3 Sept - 4 Sept
Premium Floating Bungalow by Stay Ombi

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

9.8 out of 10, Exceptional, (221)
"Condo was clean and quiet. Loved the main suite in the back."
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

9.8 out of 10, Exceptional, (67)
"Such a neat complex. Very safe and quiet. The kayaks were nice for the lagoon. I loved all the fish and everyone was nice that was staying there. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

5 Star Coastal Luxury: Key Largo 2BR Condo w/Lagoon, Golf Cart, Pools& Amenities

10.0 out of 10, Exceptional, (13)
"Great vacation spot , only thing missing is a good saltwater beach."
5 Star Coastal Luxury: Key Largo 2BR Condo w/Lagoon, Golf Cart, Pools& Amenities

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

10.0 out of 10, Exceptional, (84)
"Enjoyed greatly!Fantastic host!!"
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

Oceanfront Key Largo Paradise with Private Beach~Pool~Tennis~Marina and more....

10.0 out of 10, Exceptional, (270)
"We enjoyed our stay! It was a great condo and was exactly as described in the listing. "
Oceanfront Key Largo Paradise with Private Beach~Pool~Tennis~Marina and more....

Amazing Ocean view at Ocean Pointe w/Heated Pool

9.6 out of 10, Exceptional, (38)
"We enjoyed our time at Ocean Point. "
Amazing Ocean view at Ocean Pointe w/Heated Pool

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

9.6 out of 10, Exceptional, (31)
"Nice property . Well kept. Good management "
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
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

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$201 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.