Windley Key Vacation Rentals

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Our top choices for Windley Key vacation rentals

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (148 reviews)
"Staff was great, rooms clean, views excellent"
United States
Diane
The price is CA $259
CA $487 total
includes taxes & fees
Apr 16 - Apr 17
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 CA $467
CA $525 total
includes taxes & fees
Apr 6 - Apr 7
Island Bay Resort

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (649 reviews)
"Clean room, good staff and convenience location for a visit."
United States
Judbelth
The price is CA $238
CA $340 total
includes taxes & fees
May 3 - May 4
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 CA $198
CA $507 total
includes taxes & fees
Apr 29 - Apr 30
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 CA $156
CA $410 total
includes taxes & fees
Apr 7 - Apr 8
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 CA $356
CA $401 total
includes taxes & fees
Apr 6 - Apr 7
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 CA $195
CA $504 total
includes taxes & fees
May 3 - May 4
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 CA $213
CA $597 total
includes taxes & fees
May 4 - May 5
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 CA $285
CA $644 total
includes taxes & fees
May 3 - May 4
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.
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 CA $195
CA $573 total
includes taxes & fees
Apr 29 - Apr 30
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 CA $164
CA $471 total
includes taxes & fees
Apr 29 - Apr 30
Cozy place in Calusa Key Largo

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (46 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is CA $256
CA $573 total
includes taxes & fees
May 4 - May 5
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 CA $303
CA $631 total
includes taxes & fees
Apr 14 - Apr 15
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 CA $263
CA $458 total
includes taxes & fees
Apr 27 - Apr 28
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 CA $219
CA $526 total
includes taxes & fees
Apr 29 - Apr 30
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 CA $263
CA $458 total
includes taxes & fees
Apr 29 - Apr 30
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, (24 reviews)
"Very good communication and everything was as advertised "
United States
Sam L.
The price is CA $237
CA $582 total
includes taxes & fees
Apr 7 - Apr 8
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 CA $114
CA $402 total
includes taxes & fees
May 2 - May 3
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, (155 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 CA $267
CA $668 total
includes taxes & fees
Apr 23 - Apr 24
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windley Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.