Windley Key Vacation Rentals

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Our top choices for Windley Key vacation rentals

Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1,009 reviews)
"Clean room, beautiful view and loved being able to walk out to the beach. "
United States
Brian
The price is CA $304
CA $390 total
includes taxes & fees
Feb 11 - Feb 12
Drop Anchor

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (145 reviews)
"Great place"
United States
Kathryn
The price is CA $600
CA $766 total
includes taxes & fees
Feb 11 - Feb 12
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.4 out of 10, Very good, (1,004 reviews)
"Great little seaside place."
United States
Patience
The price is CA $288
CA $368 total
includes taxes & fees
Feb 11 - Feb 12
Fisher Inn Resort & Marina

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (183 reviews)
"Would stay again"
United States
Jordan
The price is CA $384
CA $433 total
includes taxes & fees
Feb 9 - Feb 10
Coconut Cove Resort and Marina

The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
Islamorada
8.8 out of 10, Excellent, (16 reviews)
"Great stay! Loved this property and staff. Clean and convenient. "
United States
Pamela
The price is CA $333
CA $374 total
includes taxes & fees
Mar 3 - Mar 4
The Ocean View Inn & Pub

Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (424 reviews)
"Friendly staff! Laid back place! We enjoyed our stay here! We will be back!"
United States
Neal
The price is CA $466
CA $604 total
includes taxes & fees
Feb 9 - Feb 10
Casa Morada

Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
2.5 star property
Rock Harbor
9.8 out of 10, Exceptional, (304 reviews)
"Very clean room and property staff very friendly and accommodating "
United States
Jeffrey
Kona Kai Resort and Gallery - Adults Only

Coconut Palm Inn

Coconut Palm Inn
3.0 star property
Tavernier
9.4 out of 10, Exceptional, (533 reviews)
"Wonderful, peaceful, charming place with very friendly and helpful staff. Highly recommend!"
United States
Peggy
The price is CA $380
CA $476 total
includes taxes & fees
Feb 9 - Feb 10
Coconut Palm Inn

Largo Resort

Largo Resort
3.0 star property
Key Largo
9.4 out of 10, Exceptional, (299 reviews)
"Alex was amazing and highly recommend for future stays. Bungalow serenity was so nice and spacious. Had some trouble with the getting the TV to work but the pool and views was stunning. A great place to get away from everyday stresses and relax. "
United States
Kevin
The price is CA $310
CA $440 total
includes taxes & fees
Feb 18 - Feb 19
Largo Resort

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,008 reviews)
"Rooms are clean, staff is friendly and the place is beautifull"
United States
James
The price is CA $533
CA $692 total
includes taxes & fees
Feb 9 - Feb 10
Islander Resort

Dolphin Point Villas

Dolphin Point Villas
3.5 star property
Key Largo
9.6 out of 10, Exceptional, (482 reviews)
"The rooms were very clean. Beautiful view"
United States
Linda
The price is CA $368
CA $452 total
includes taxes & fees
Feb 9 - Feb 10
Dolphin Point Villas

Azul del Mar

Azul del Mar
3.5 star property
Key Largo
9.0 out of 10, Wonderful, (818 reviews)
"The location, views and water access are all excellent! "
United States
Tom
Azul del Mar

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
Key Largo
8.6 out of 10, Excellent, (1,002 reviews)
"Great hotel "
United States
David Zion
The price is CA $711
CA $875 total
includes taxes & fees
Feb 9 - Feb 10
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Reefhouse Resort & Marina

Reefhouse Resort & Marina
3.5 star property
Key Largo
9.4 out of 10, Exceptional, (1,356 reviews)
"Would stay again"
United States
James
The price is CA $423
CA $530 total
includes taxes & fees
Feb 9 - Feb 10
Reefhouse Resort & Marina

Holiday Inn Key Largo by IHG

Holiday Inn Key Largo by IHG
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1,034 reviews)
"Good hotel in a convenient location to start exploring the Keys"
United Kingdom
Stephen
The price is CA $336
CA $378 total
includes taxes & fees
Feb 11 - Feb 12
Holiday Inn Key Largo by IHG

Courtyard by Marriott Key Largo

Courtyard by Marriott Key Largo
3.0 star property
Key Largo
8.0 out of 10, Very good, (1,005 reviews)
"It is a good hotel in a good location that makes getting to other places easy."
United States
Grant
The price is CA $368
CA $414 total
includes taxes & fees
Feb 11 - Feb 12
Courtyard by Marriott Key Largo

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
3.0 star property
Key Largo
7.6 out of 10, Good, (1,002 reviews)
"Nice place. Excellent location. "
United States
Carmen
The price is CA $313
CA $396 total
includes taxes & fees
Feb 9 - Feb 10
Dove Creek Resort & Marina, Trademark Collection by Wyndham

Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor
9.4 out of 10, Exceptional, (147 reviews)
"Clean room, friendly staff "
United States
Quaid
The price is CA $239
CA $289 total
includes taxes & fees
Feb 9 - Feb 10
Seafarer Key Largo

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
8.8 out of 10, Excellent, (408 reviews)
"Staff was very responsive. Great location "
United States
rebecca
The price is CA $480
CA $632 total
includes taxes & fees
Feb 11 - Feb 12
Bayside Villas by Islander Resort

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
8.8 out of 10, Excellent, (1,004 reviews)
"Everything was great. Very clean and excellent location"
United States
peter
The price is CA $732
CA $898 total
includes taxes & fees
Mar 1 - Mar 2
Playa Largo Resort & Spa, Autograph Collection
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.