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, (147 reviews)
"Staff was great, rooms clean, views excellent"
United States
Diane
The price is CA $246
CA $471 total
includes taxes & fees
Apr 2 - Apr 3
Treasure Harbor

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (643 reviews)
"Clean room, good staff and convenience location for a visit."
United States
Judbelth
The price is CA $261
CA $365 total
includes taxes & fees
Apr 12 - Apr 13
Breezy Palms Resort

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 $415
CA $467 total
includes taxes & fees
Apr 6 - Apr 7
Island Bay 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 $190
CA $489 total
includes taxes & fees
Apr 20 - Apr 21
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, (67 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 $168
CA $424 total
includes taxes & fees
Mar 31 - Apr 1
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
Kings Kamp

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 CA $243
CA $552 total
includes taxes & fees
Mar 30 - Mar 31
Amazing Ocean view condo

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 CA $217
CA $587 total
includes taxes & fees
Mar 29 - Mar 30
Charming Home in Key Largo

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 $311
CA $674 total
includes taxes & fees
Apr 26 - Apr 27
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

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 $235
CA $623 total
includes taxes & fees
Apr 20 - Apr 21
Reel Key Largo Escape Ocean Pointe 5209

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 $186
CA $487 total
includes taxes & fees
Apr 21 - Apr 22
2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (20 reviews)
"An amazing place to switch gears. Great host. Win/win."
United States
Alex Z.
The price is CA $365
CA $583 total
includes taxes & fees
Mar 29 - Mar 30
Island Sanctuary Islamorada

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 CA $255
CA $648 total
includes taxes & fees
Apr 23 - Apr 24
3212 Across from Pool * King & Queen/Twin Bunk Bed

Key Largo Kampground Brand New 2025 RV 2BR + 2 Lofts, 2BA Pool & Marina

Key Largo Kampground Brand New 2025 RV 2BR + 2 Lofts, 2BA Pool & Marina
Key Largo
10.0 out of 10, Exceptional, (11 reviews)
"This is a beautiful place to stay. Convenient and quiet. Exceptionally well run. "
United States
Joleen
Key Largo Kampground Brand New 2025 RV 2BR + 2 Lofts, 2BA Pool & Marina

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, (6 reviews)
"Clean, perfect place to stay for a couple nights. Being on the top floor was the best so we didn’t have to worry about people above us. "
United States
Natasha
The price is CA $281
CA $683 total
includes taxes & fees
Apr 15 - Apr 16
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

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 $189
CA $498 total
includes taxes & fees
Apr 21 - Apr 22
Cozy place in Calusa Key Largo

Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (7 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
The price is CA $288
CA $693 total
includes taxes & fees
Apr 20 - Apr 21
Flamingo Flats Ocean Pointe 5306 2BR/2BA

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (26 reviews)
"The place was clean, nicely decorated, and the kitchen was well equipped. No problems checking in. Pool was large and very nice."
United States
Dawn W.
The price is CA $254
CA $649 total
includes taxes & fees
Apr 20 - Apr 21
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

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, (16 reviews)
"Perfect Stay."
United States
suhaela s.
The price is CA $345
CA $752 total
includes taxes & fees
Apr 15 - Apr 16
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Paradise in Key Largo Florida 2

Paradise in Key Largo Florida 2
Key Largo
9.6 out of 10, Exceptional, (45 reviews)
"The cleanliness, the availability, the comfort. Everything was perfect in fact. Vz are planning on contacting the owner and tomorrow maybe arrange another rental on that property. It was in the perfect spot walking distance to the pool. Everything was readily available. Everything that they advertised was actually above and beyond. Our expectations can't say enough. Good about it was a perfect vacation. Thank you"
United States
Steve V.
The price is CA $186
CA $446 total
includes taxes & fees
Apr 15 - Apr 16
Paradise in Key Largo Florida 2
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.