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

4.15

KW33B - Windward Isle is described as a cozy, charming, and welcoming cottage that offers great value and a comfortable stay. Guests frequently praised the comfortable beds, spacious bedrooms, inviting decor, and relaxing indoor and outdoor spaces, including a lovely porch, private backyard, and shaded patio. Cleanliness was consistently appreciated, with many guests noting the home was clean, spotless, well kept, and well equipped for a pleasant visit. The property stands out for its excellent walkable location near shops, restaurants, bars, and local attractions while still offering a peaceful setting at night. Guests also appreciated the convenience of parking and the authentic Key West character that made the stay feel special. Overall, guests found KW33B - Windward Isle to be a delightful and highly recommended place to stay.

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!

This home is managed by Seven Keys Vacations by Casago.

• County: Monroe County BTR | #25230-140087

• City/town: Key West Medallion | #LIC2025-000251

• City/town: Key West BTR | #LIC2025-000250

• State/province: DBPR | #DWE540402

Permit info: 25230-140087

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

Amenities

Air conditioning

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

45%

4 Star

34%

3 Star

15%

2 Star

1 Star

Sort by:

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 H2025-03-17

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 B2025-02-22

Great location,nice house and very clean!

Tony A2025-01-21

The location of this property was great, but there were many concerns with the stay. One of the two bedrooms was unusable because of terrible musty odor in the room that burned my clients' eyes. My client called the number given to them to report any problems and a woman said they would send someone out the next day to fix the smell. No one ever came. The unit said it came with a washer and dryer, but there wasn't a washer or dryer. The couch was so filthy they put the extra sheet on it to sit. Floors were filthy and gritty with sand. They had to wear shoes during the stay. Toaster didn't work and was a fire hazard. There were several broken wires inside it when they looked inside. The outlet by the stove didn't work. The hot tub was very dirty so they did not use it. The only good thing about the stay was the fact that it was easy to get into upon arrival. Would not recommend this property.

Dates

Guests

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Arrive at a completely cleaned and inspected home.

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KW33B - 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