Windward Isle

Cabin in Key West, Florida

Max 6 guests 2 bedrooms 1 bath Dog-friendly 
4.15
47 reviews
What our guests are saying...
Diamond AI-summarized from guest reviews for this property
Windward Isle is described as a cozy, charming, and great-value cottage with authentic Key West character that felt perfect, welcoming, and ideal for a relaxing stay. Guests consistently found the home comfortable, with comfy beds, spacious bedrooms, effective air conditioning, and inviting indoor and outdoor spaces including a lovely front porch, private backyard, and shaded patio area. Cleanliness stood out throughout the reviews, with guests frequently calling Windward Isle clean, spotless, well kept, and nicely maintained. The property’s location was a standout, with easy walking or biking access to shops, restaurants, bars, attractions, and the heart of Key West while still feeling tucked away. Guests also appreciated the well-equipped kitchen, beach towels, convenient parking, and the hot tub as enjoyable features that added to the overall experience. Overall, Windward Isle left guests very happy and eager to return. Read more

OVERVIEW

Dog-Friendly Cottage with Private Hot Tub & Garden - Great Downtown Location

Dreaming about a tropical vacation? This two-bedroom, one-bathroom cottage in Key West is the perfect destination - a private hot tub, garden, and a great location downtown will make this your best vacation yet!

Located only half a block from the restaurants and bars on Duval Street, you'll have plenty to do within walking or biking distance of this rental, so leave your car in the private parking space provided. Check out the Ernest Hemingway Home and Museum, Fort Zachary Taylor Historic State Park, or say goodbye to land for a while and hop on a sailboat for a romantic cruise into the sunset.

When you need to rest and freshen up, you'll be glad to have a private garden and hot tub in the backyard, a fully equipped kitchen for cooking meals, several flatscreen cable TV's, and free WiFi to browse and upload photos. There's patio furniture out back, as well as a grill to have your own island barbecue. The family dog is also welcome to come along for an additional nightly fee.

You deserve the privacy and comfort of home when you're on vacation, and this charming cottage is the key!

Permit info: 25230-140087

You must be 25 years or older to rent this property.

AMENITIES

 Hot tub

 Internet

 Cable

Heating & cooling

Central AC

Partial AC

House rules

Dog-friendly

Kitchen & dining

Fridge

Microwave

Stove

Media

Internet

TV

Cable

On-site activities

Hot tub

Outdoor

Gas grill

Location

Key West, Florida, USA

(Exact address will be provided after booking)
Map showing the location of the Unit

Rating

4.15
What our guests are saying...
Windward Isle is described as a cozy, charming, and great-value cottage with authentic Key West character that felt perfect, welcoming, and ideal for a relaxing stay. Guests consistently found the home comfortable, with comfy beds, spacious bedrooms, effective air conditioning, and inviting indoor and outdoor spaces including a lovely front porch, private backyard, and shaded patio area. Cleanliness stood out throughout the reviews, with guests frequently calling Windward Isle clean, spotless, well kept, and nicely maintained. The property’s location was a standout, with easy walking or biking access to shops, restaurants, bars, attractions, and the heart of Key West while still feeling tucked away. Guests also appreciated the well-equipped kitchen, beach towels, convenient parking, and the hot tub as enjoyable features that added to the overall experience. Overall, Windward Isle left guests very happy and eager to return. Read more
Diamond AI-generated from guest reviews for this property

47 reviews

24 hour cancellation*
Get a full refund if you cancel within 24 hours of booking
Local expertise
Count on care—just a call, text, or email away
Lowest price
Book directly for the lowest rates

*Some exceptions may apply. Review the unit cancellation terms before payment.

Similar Homes

Based on your search you might also like these properties

Home USA Southeast Florida Florida Key West