Windley Key Holiday Rentals

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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, (147 reviews)
"Staff was great, rooms clean, views excellent"
United States
Diane
The price is NZ$604
includes taxes & fees
13 Apr - 14 Apr
Treasure Harbor

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (153 reviews)
"Wonderful property and staff. Quite and beautiful!. "
United States
Ethan
The price is NZ$590
includes taxes & fees
13 Apr - 14 Apr
Island Bay Resort

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (645 reviews)
"Clean room, good staff and convenience location for a visit."
United States
Judbelth
The price is NZ$455
includes taxes & fees
30 Apr - 1 May
Breezy Palms Resort

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, (46 reviews)
"I really enjoyed our stay at the campsite. The home is right on the water with plenty of activities to do. Also the grocery store and places to eat are only a few minutes away. "
United States
Everett S.
The price is NZ$603
includes taxes & fees
29 Apr - 30 Apr
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.6 out of 10, Exceptional, (68 reviews)
"We really enjoyed our stay here .. the place was clean — had everything we needed… thanks for sharing your place.."
United States
brenda b.
The price is NZ$520
includes taxes & fees
13 Apr - 14 Apr
Paradise in Key Largo, FL

Kings Kamp

Kings Kamp
2.5 star property
Key Largo
8.6 out of 10, Excellent, (34 reviews)
"A hidden gem!!! Can’t wait to come back!!!"
United States
Jason
The price is NZ$537
includes taxes & fees
1 Apr - 2 Apr
Kings Kamp

2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental

2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental
Key Largo
8.6 out of 10, Excellent, (90 reviews)
"Great stay for the price"
United States
William B J.
The price is NZ$607
includes taxes & fees
21 Apr - 22 Apr
2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"Super clean and neat location!"
United States
Christopher R.
The price is NZ$740
includes taxes & fees
27 Apr - 28 Apr
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (113 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is NZ$842
includes taxes & fees
26 Apr - 27 Apr
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (33 reviews)
"Very nice place and definitely would stay there again! Very nice host and redponded on time."
United States
Amey P.
The price is NZ$734
includes taxes & fees
5 Apr - 6 Apr
Charming Home in Key Largo

Reel Key Largo Escape Ocean Pointe 5209

Reel Key Largo Escape Ocean Pointe 5209
Tavernier
9.6 out of 10, Exceptional, (8 reviews)
"Great area"
United States
Yesenia
The price is NZ$712
includes taxes & fees
29 Apr - 30 Apr
Reel Key Largo Escape Ocean Pointe 5209

Cozy place in Calusa Key Largo

Cozy place in Calusa Key Largo
Key Largo
9.0 out of 10, Wonderful, (16 reviews)
"Perfect weekend getaway location."
United States
Tex H.
The price is NZ$603
includes taxes & fees
13 Apr - 14 Apr
Cozy place in Calusa Key Largo

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (45 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is NZ$696
includes taxes & fees
13 Apr - 14 Apr
Amazing Ocean view condo

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.8 out of 10, Excellent, (42 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 NZ$788
includes taxes & fees
8 Apr - 9 Apr
Ocean view condo with balcony/marina view

OP-2 Ocean View w/heated pool beach marina

OP-2 Ocean View w/heated pool beach marina
Tavernier
8.4 out of 10, Very good, (11 reviews)
"Great location, thoughtful set-up. "
United States
Michelle J.
The price is NZ$569
includes taxes & fees
27 Apr - 28 Apr
OP-2 Ocean View w/heated pool beach marina

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Key Largo
10.0 out of 10, Exceptional, (10 reviews)
"Set up of RV was very nice. Great location and amenities at the campground."
United States
Cynthia C.
The price is NZ$695
includes taxes & fees
29 Apr - 30 Apr
Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Dazzling Ocean Pointe -OP-Main

Dazzling Ocean Pointe -OP-Main
Tavernier
9.0 out of 10, Wonderful, (92 reviews)
"Cleanliness, location, communication and the pool was just great! Thank you so very much!"
United States
Vicky W.
The price is NZ$569
includes taxes & fees
29 Apr - 30 Apr
Dazzling Ocean Pointe -OP-Main

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.6 out of 10, Exceptional, (23 reviews)
"Very good communication and everything was as advertised "
United States
Sam L.
The price is NZ$816
includes taxes & fees
7 Apr - 8 Apr
Florida Keys Getaway - Slps 4 - Ocean View

RV by the Sea - Glamping in the Keys

RV by the Sea - Glamping in the Keys
Key Largo
9.0 out of 10, Wonderful, (26 reviews)
"Good stay"
Netherlands
Anna d.
The price is NZ$502
includes taxes & fees
12 Apr - 13 Apr
RV by the Sea - Glamping in the Keys

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, (154 reviews)
"The condo was spotless and beautifully decorated. The hosts are exceptionally thoughtful, leaving clear instructions on how to use / where to find items, and a welcome guide with information on local attractions and restaurants. I loved the attention to detail, such as placing nightlights in the bathrooms and beach chairs. The balcony is not large, but comfortably seats two people and offers an expansive view of the ocean. Ocean Pointe is a beautiful complex with a nice pool and beach. I...
United States
Andrea
The price is NZ$855
includes taxes & fees
23 Apr - 24 Apr
3212 Across from Pool * King & Queen/Twin Bunk Bed
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 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 NZ$455 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.