Cabin in Key West, Florida

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

Cabin in Key West, Florida

6 Guests

2 Bedrooms

1 Bathroom

Pets allowed

Locally Owned & Operated

Florida Keys

Casago Franchise Owner

4.12

Windward Isle is described as a great value and a perfect fit for a Key West stay, with charming cottage style, authentic character, and a cozy, welcoming feel. Guests consistently praise the comfortable beds, spacious bedrooms, pleasant living spaces, and effective air conditioning that keeps the home relaxing after a day out. The property is repeatedly noted as very clean, spotless, well kept, and well equipped for an enjoyable stay. Windward Isle stands out for its excellent walkable location near shops, restaurants, attractions, and the historic district, while still feeling tucked away and convenient for exploring. Guests also highlight the inviting front porch, private backyard, shaded patio, outdoor sitting areas, off street parking, and pet friendly appeal.

Overview

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 number: 25230-140087

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

44%

4 Star

33%

3 Star

17%

2 Star

1 Star

Sort by:

Victoria E2026-03-29

I wish I read the reviews closer, this place is a great location but the place is very out dated and kind of dingy. There’s no washer and dryer as advertised. The shower is kind of falling apart and if you are tall you have to duck to have the shower head on you. All the fans and fixtures had a lot of dust on them. I also didn’t like that there was no window shade on the large window on the front door so not alot of privacy from the street

Tammy S2026-02-19

Great location. House needs some attention and updates.

neil M2025-12-10

Excellent location, walkable to great coffee restaurants and bars, but away from the noise. Parking spot was tight but super important. Clean well maintained hot tub was a great extra

Lisa H2025-03-16

Very expensive for what we got

Lee Waldon W2025-03-11

Nothing but the off street parking in back of the home. Interior was sub standard and the owner representative said that it was going to be completely updated soon which didn't affect us.

David B2025-02-21

Great location,nice house and very clean!

Dates

Guests

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Windward 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