Cabin in Key West, Florida

Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK

Cabin in Key West, Florida

6 Guests

2 Bedrooms

1 Bathroom

Pets allowed

Locally Owned & Operated

Florida Keys

Casago Franchise Owner

4.45

Leeward Isle is described as a charming, spacious, and comfortable cottage that feels welcoming and well suited for relaxing stays with family, friends, or couples. Guests consistently praised the comfortable beds, roomy layout, bright bathroom, and inviting indoor and outdoor living areas, including the front porch, back patio, and private backyard. The property was frequently noted as very clean, fresh, and well maintained, with plenty of towels and a pleasant overall atmosphere. Its location is a standout feature, with easy walking access to shops, restaurants, attractions, and the heart of Old Town while still offering a sense of privacy. Guests also appreciated amenities such as off street parking, the hot tub, outdoor shower, air conditioning, televisions, and a kitchen with the basics for a convenient stay. The historic character, tropical setting, and cozy Key West charm made Leeward Isle a memorable place that many guests said they would gladly book again.

Overview

Bask in the peaceful sunshine of Key West and feel all your stress melt away when you stay at this cozy dog-friendly cottage right in town. With a private hot tub in the garden area out back plus all the conveniences of home, what's not to love?

Sitting only half a block from all the fun and excitement of Duval Street, park your car in the private space and forget about it - you'll be able to walk or bicycle everywhere you want to go. Head to the Southernmost Point and check out the Key West Butterfly and Nature Conservatory while you're at it, then head north to check out Mallory Square and other historical landmarks along the way.

Spend quiet mornings in the garden, sipping coffee and eating a delicious breakfast prepared in your fully equipped kitchen. After a full day of exploring, come back for a relaxing soak in the hot tub, watch a show on the flatscreen cable TV, and surf the free WiFi to find activities for tomorrow. A dog is welcome for a small nightly fee.

Make sure your Florida vacation is exactly how you imagine - book this charming cottage today!

Permit number: LIC2025-000249

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

Amenities

Central AC

Internet

Cable

Microwave

Fridge

Stove

Gas grill

Hot tub

Dog-friendly

Sleeping Arrangements

Bedroom 1

sleeps 2

1 king bed

Bedroom 2

sleeps 2

1 king bed

Location

Key West, Florida, Home

(Exact address will be provided after booking)

5 Star

62%

4 Star

27%

3 Star

2 Star

1 Star

Sort by:

carole m2026-03-11

location is great but, in the mornings, noisy so don't expect to sleep in. :)

henry N2026-02-17

This was a perfect spot for us to stay and I would recommend it for 1-2 couples. More would be crowded and you would need to use the sofa sleeper. Location, location, location. Close enough to walk everywhere. (We did!) but far enough away to be mostly quiet at night. And the hot tub was the icing on the cake. 5+Stars. Well done.

debra k2026-02-16

Great location, comfortable beds and easy walk to duval and the marina

Susan K2026-01-19

Beds were good

Valerie H2025-12-28

This house was a perfect size for my family of three plus a dog:) Beautiful wood floors. Comfy beds. Hot tub was perfect. Great private place to park! Wonderful front porch with SUPER friendly neighbors. Not any grass for a dog to go potty however there’s not much grass in the Keys:/

Lisa D2025-12-23

Great location!

Dates

Guests

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Leeward Isle

Cabin in Key West, Florida

Locally Owned & Operated

What our guests are saying...

Overview

Amenities

Sleeping Arrangements

Bedroom 1

Bedroom 2

Location

Key West, Florida, Home

Rating