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, (153 reviews)
"Amazing stay!"
United States
Amanda
The price is CA $184
CA $400 total
includes taxes & fees
May 21 - May 22
Treasure Harbor

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 CA $394
CA $443 total
includes taxes & fees
Jun 8 - Jun 9
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 CA $274
CA $308 total
includes taxes & fees
May 21 - May 22
Kings Kamp

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (678 reviews)
"Easy parking and great clean kitchen"
United States
JoAnn
The price is CA $157
CA $199 total
includes taxes & fees
May 26 - May 27
Breezy Palms Resort

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 CA $260
CA $608 total
includes taxes & fees
May 25 - May 26
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Cozy place in Calusa Key Largo

Cozy place in Calusa Key Largo
Key Largo
9.0 out of 10, Wonderful, (18 reviews)
"Great for a short stay! "
United States
Anonymous traveller
The price is CA $168
CA $458 total
includes taxes & fees
May 21 - May 22
Cozy place in Calusa Key Largo

Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.6 out of 10, Exceptional, (70 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 $155
CA $403 total
includes taxes & fees
Jun 1 - Jun 2
Paradise in Key Largo, FL

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (48 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 $237
CA $543 total
includes taxes & fees
May 21 - May 22
Amazing Ocean view condo

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (30 reviews)
"A comfortable little condo, conveniently located for exploring the Keys. There’s a nice pool and small beach area with a bar/restaurant that are well maintained."
United States
Stephen
The price is CA $200
CA $533 total
includes taxes & fees
May 30 - May 31
Florida Keys Getaway - Slps 4 - Ocean View

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Tavernier
10.0 out of 10, Exceptional, (8 reviews)
"Great location and clean"
United States
Matthew H.
The price is CA $231
CA $617 total
includes taxes & fees
Jun 3 - Jun 4
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

RV by the Sea - Glamping in the Keys

RV by the Sea - Glamping in the Keys
Key Largo
9.0 out of 10, Wonderful, (29 reviews)
"The host was very accommodating, the unit was clean & well furnished, close to market places, restaurants & amusements."
United States
JAMES B.
The price is CA $83
CA $355 total
includes taxes & fees
May 21 - May 22
RV by the Sea - Glamping in the Keys

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (37 reviews)
"Comfortable and well thought out space."
United States
Jessica E.
The price is CA $198
CA $565 total
includes taxes & fees
May 25 - May 26
Charming Home in Key Largo

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Tavernier
10.0 out of 10, Exceptional, (18 reviews)
"Perfect Stay."
United States
suhaela s.
The price is CA $246
CA $625 total
includes taxes & fees
May 28 - May 29
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

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 $268
CA $463 total
includes taxes & fees
Jun 15 - Jun 16
OP-2 Ocean View w/heated pool beach marina

Captains Quarters Ocean Pointe 4405

Captains Quarters Ocean Pointe 4405
Tavernier
10.0 out of 10, Exceptional, (14 reviews)
"We had a very pleasant weekend away with all the comforts of home, yet even better with the amazing view! Great communication with the host with quick pleasant responses. The property is conveniently located and easy to get around. "
United States
Debbie W.
The price is CA $228
CA $614 total
includes taxes & fees
Jun 2 - Jun 3
Captains Quarters Ocean Pointe 4405

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 CA $268
CA $463 total
includes taxes & fees
May 26 - May 27
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315
Tavernier
9.8 out of 10, Exceptional, (16 reviews)
"The unit was clean. The bed was comfortable. Everything worked well."
United States
William G.
The price is CA $238
CA $626 total
includes taxes & fees
Jun 9 - Jun 10
Blue Haven Key Largo | Ocean Pointe 1315

Paradise in Key Largo Florida 2

Paradise in Key Largo Florida 2
Key Largo
9.4 out of 10, Exceptional, (49 reviews)
"Upon arrival we could not get the key out of the lockbox. I contacted the owner with no response until the following morning. Luckily a neighbor was kind enough to help us get the key. The following morning we woke up to extremely cold temps due to the low temperatures but finally figured out the mini split. The beds were very comfortable and the pool and kiddie was perfect! My BIGGEST COMPLAINT was the bathroom lighting! The darkest bathroom u could ever imagine. Hopefully the owner can resolve...
United States
Kelly R.
The price is CA $155
CA $402 total
includes taxes & fees
May 21 - May 22
Paradise in Key Largo Florida 2

Salty Mermaid Ocean Pointe 4406

Salty Mermaid Ocean Pointe 4406
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"We had an amazing stay at the Salty Mermaid. We enjoyed gorgeous sunrises every morning! The condo was beautiful, comfortable, and clean. We would definitely stay here again."
United States
Nicole W.
The price is CA $234
CA $616 total
includes taxes & fees
May 21 - May 22
Salty Mermaid Ocean Pointe 4406

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 CA $286
CA $604 total
includes taxes & fees
May 21 - May 22
Ocean view condo with balcony/marina view
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.