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Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4

Photo gallery for Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4

A white building with a porch, a pool, and tropical plants. - Historic Old Town  Key West Cigarmaker's Cottage - Cigar House, Sleeps 4 (Key West)
A kitchen with wooden cabinets, a white countertop, and a gas stove. - Historic Old Town  Key West Cigarmaker's Cottage - Cigar House, Sleeps 4 (Key West)
A spacious room with wooden flooring, a large window with a view of greenery, a television, and a wooden bench. - Historic Old Town  Key West Cigarmaker's Cottage - Cigar House, Sleeps 4 (Key West)
A porch with white railings, a door, and two windows with shutters. - Historic Old Town  Key West Cigarmaker's Cottage - Cigar House, Sleeps 4 (Key West)
A spacious living room with a wooden staircase, a large fish decoration, and a tropical chair. - Historic Old Town  Key West Cigarmaker's Cottage - Cigar House, Sleeps 4 (Key West)
Near Duval Street and Mallory Square, Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4 provides a garden, laundry facilities and a hot tub. Guests can connect to free in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

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About this property

Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4

  • OVERVIEW
    The Cigar House is a 100+ year old “Cigar maker’s house”. The recently completely renovated house is charming, spacious, secluded and private. The cottage has a raised vaulted wood ceiling, creating a rustic, Caribbean ambiance. The downstairs floor is the original Dade County Pine. All window, door, and floor trim is turn of the century style, and all windows are 6/6 double-hung sash. All linens and towels are furnished.

    The house has a Starlink secured high speed wi-fi network, streaming internet TV, and two (2) 32" Samsung SMART HDTVs. The house has central air conditioning, a ceiling fan, and a stacked LP washing machine and dryer. There is a Weber propane barbecue located on the pool deck.

    The cottage can comfortably accommodate a maximum of four (4) guests – who are comfortable sharing an open social living environment.

    FIRST FLOOR
    The kitchen, living, dining, sitting, and bathroom and a small bedroom are located on the ground floor. The living room has a queen sleeper sofa/ day bed and a 32" Samsung SMART HDTV. The bathroom, located off the living room, has been recently completely renovated and has a vaulted ceiling and a new full size marble walk-in shower. There is a full bed in the small bedroom at the end of the living room.

    KITCHEN
    The kitchen is new and contemporary with mahogany cabinets, white Corian worktops, and integrated Corian sink, and serve thru access to the dining room. The ceiling is vaulted with architectural beams and LED lighting. The kitchen has a pantry, refrigerator, electric range, rubbish disposal, microwave, and Braun coffee maker, Krupps toaster, dishes, flatware, glasses (service for 6), pots, pans, and all the basic cooking utensils. There is a French door providing access to the rear deck where the washing machine and dryer are located.

    LOFT SLEEPING AREA
    A ship's ladder is used to access the loft sleeping area. The loft has a queen bed, and a 32" Samsung SMART HDTV.

    COMMON ELEMENTS
    The five (5) house compound is private and secure with a 25' x 10' heated pool including a 5' x 10' heated Jacuzzi. In addition, there is a 10' x 8' heated Jacuzzi. There are brick walkways, and a 40' x 10' sun deck, including a stainless steel propane barbecue, chaise lounges for sunbathing and relaxing; and tables and chairs for dining. Throughout the property there is secured wireless internet access, and CCTV security monitoring. The design of the property lends itself perfectly for small gatherings with friends and family.

    LANDSCAPING
    The landscaping is lush including various palm species, Poinciana, Spanish limes, avocado, bananas, hibiscus, bougainvillea, halliconias, bromeliads, and orchids, brick walkways.

    EXCELLENT LOCATION
    The house is located in Old Town Key West at the corner of Thomas and Angela Streets - (2) blocks west of the centre of Duval Street in one of the oldest sections of Key West; (4) blocks east of Fort Zachary Taylor State Park/Beach, the best beach and picnic area in Key West. The gated compound is within easy walking or biking distance to everything in Old Town Key West, Duval Street, and the best entertainment and dining on the island.

    CHICKENS & ROOSTERS
    The City of Key West protects chickens and cockerels, and considers them as part of the history and charm of Key West. As a result, Key West and many of the islands throughout the Florida Keys have free-range chickens and cockerels. You will definitely see and hear chickens and cockerels during your stay in Key West. Some visitors to Key West love them, and some visitors hate them - personally, I enjoy them best roasted, with plantains, and black beans and rice!

    CRITTERS
    Also, please remember that you are in the tropics and most life forms typically thrive in the tropics. Please don' t be surprised or alarmed if you see a lizard, or an insect.

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About the area

Located by the sea, this holiday home is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. USCGC Ingham Maritime Museum and Florida Keys Eco - Discovery Center are also worth visiting. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby. Visit our Key West travel guide
View more Holiday homes in Key West
Map
Key West, FL

What's nearby

  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    4 min walk - 0.4 km
  • A military jet flying low over a concrete path surrounded by vegetation.
    Key West Naval Station
    5 min walk - 0.4 km
  • A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.
    Ernest Hemingway Home and Museum
    6 min walk - 0.6 km
  • A coastal fortification with a staircase leading to a higher platform, overlooking the sea.
    Fort Zachary Taylor Historic State Park
    9 min walk - 0.8 km
  • A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.
    Mallory Square
    12 min walk - 1.1 km

Getting around

  • Key West, FL (EYW-Key West Intl.)
    14 min drive

Restaurants

  • Green Parrot Bar
    4 min walk
  • Blue Heaven
    4 min walk
  • Moondog Cafe & Bakery
    4 min walk
  • 801 Bourbon Bar
    5 min walk
  • Bourbon Street Pub
    5 min walk

Frequently asked questions

Does Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4 have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4 pet-friendly?

No, pets are not allowed at this property.

How much is parking at Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4?

On-site parking is available at the property.

What time is check-in at Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4?

Check-in begins at 4:00 PM.

What time is check-out at Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4?

Checkout is at 10:00 AM.

Where is Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4 located?

Located in Old Town Key West, this holiday home is within a 5-minute walk of We Cycle Key West, Duval Street and Ernest Hemingway Home and Museum. Florida Keys Beaches and Mallory Square are also within 15 minutes.

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Reviews

Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4 Reviews

10

Exceptional

10

Cleanliness

9.8

Location
Rating 10 - Excellent. 37 out of 41 reviews
Rating 8 - Good. 4 out of 41 reviews
Rating 6 - Okay. 0 out of 41 reviews
Rating 4 - Poor. 0 out of 41 reviews
Rating 2 - Terrible. 0 out of 41 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful getaway

Super cute place in excellent location. Really loved it.
Stayed 4 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location

Right across the street from blue Heaven and many places you want to visit while you were in Key West. Perfect location and perfect size unit.
Stayed 4 nights in Aug 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

cute house

private, well maintained… perfect for relaxing and enjoying downtown Key West
Stayed 5 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Everything I hoped

There's nothing that could have made this trip any better. The location is ideal. All the amenities are perfect. Cant wait to come back!!
Stayed 7 nights in Feb 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cigar house

Great location…. Owner was always available when we needed him…. P.S we did not need him much.
Stayed 7 nights in Feb 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Everything they said it was

All the reviews were spot on!!! The location is perfect, yet while so centrally located the property is quiet & peaceful. The boys loved the pool & hot tub. My husband & I slept downstairs- bed was plenty big enough, I kid took upstairs (even they both could’ve) & the other crashed on the couch. Just one bathroom can get tricky, but doable.
Stayed 5 nights in Mar 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Location..location…location

If you want a place that is centrally located and you can essentially walk where ever you want in less than 15 minutes, look no further. A few minutes off ducal, 10-15 minute walk to Mallory and southernmost buoy. Only issue, the address is not easily found, as the cottage is behind other cottages. I would suggest adding this to the welcome communication, I had to search for the cottage as the street number on the cottage is not visible to the street. The space is tight, but functional. I would recommend to family and friends.
Stayed 4 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location! Had an excellent visit to Key West.
Stayed 4 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Mother/Daughter Spring Break

Great vibe, relaxing and close to all that Key West offers.
Stayed 5 nights in Feb 2023
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location
Stayed 4 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage, pool, hotub, and gardens were delightful. Felt very secluded right in the middle of Old Town. So convenient to walk to so many places. The cottage decor is decidedly Key West and so much fun. We had a great week celebrating our 40th anniversary - it was perfect.
Stayed 7 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key West getaway

We had a great time on a 3 night stay. Steven’s property is close to Fort Zach, Truman Annex and Duvall St. great location. Property was phenomenal, even though there are other guest houses you feel alone.
Stayed 3 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Location

We had a great stay! Did so much and most was within walking distance of house. House was cute and suited our family of 4 perfectly. Missing the roosters already:)
Stayed 5 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Keys rental

Great little house very good location. Was able to was able to walk to everywhere. Property was super clean and quite. Would definitely recommend and will be back.
Stayed 4 nights in Jan 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic Location

The stay was great. House is very pretty and just enough off of Duval. The only warning we have if you are a light sleeper be prepared to wake up with the roosters at 5 am. Thanks for a great stay.
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay and the owner was so accommodating! Our flight was cancelled on the way down, arriving us a day late. He offered to extend our stay by a day at no charge, so that we were able to have the full 5 days that we booked. The location was perfect and within walking distance to everything. It was our first trip to key west, definitely would recommend!!!
Stayed 5 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cigar House

We really enjoyed our time in Key West. The property is beautiful and private. The pool and jacuzzi were wonderful and we made use of both most days. The location was perfect for us and the use of the bikes made getting to Fort Zachary really easy. Short walk to Moondog Cafe and Blue Heaven for breakfast/lunch/dinner were great!
Stayed 4 nights in Apr 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very Happy

The location was small, but more than enough for the two of us. The pool was warm and the hot tub hot! Plantings gave us a lot of privacy and we were within walking distance to wherever we wanted to go. Would definitely book again.
Stayed 10 nights in Feb 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Location, location, location

Cigar house was the perfect location for exploring Key West. The house was quaint, clean, and cozy. The loft and queen bed require climbing a ladder, which is best for a young couple or children. The pool and hot tub were also a nice addition, and the porch was a nice place to sit and relax in the evening. Stephen was great with communication and the check in/ check out process was seemless. We'd definitely stay again.
Stayed 4 nights in Feb 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

In the middle of everything

Rented with my two boys, ages 16 and 10. The loft was great for them but it’s a low ceiling so may not be for everyone. Place was clean, pool was great, hot tub super hot, and you’re a half block to Blue Heaven for some of the best food. And you can walk to Hemingway’s house, lighthouse, duval, little White House and nearly anything else you want to see or do.
Stayed 6 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Charming cottage in great location

The Cigar House is part of a small compound of houses with lovely shared grounds, a pool, and jacuzzi. The house itself is cozy and cute. The main bedroom is a loft (with very low ceiling height) but there is another queen bed on the first floor (and a pull out couch). We didn’t cook but the kitchen has everything you need for prepping meals if desired. Location is great - a block from a number of good restaurants and not far from Fort Zachary Taylor (and a lovely beach). You will hear roosters in the night, but that’s part of the charm of Key West. We enjoyed our stay.
Stayed 4 nights in Dec 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect little house

We loved this little place. It’s clean, comfortable, perfectly located and well appointed. There is only 1 bathroom and very little privacy for the bedrooms, but it was perfect for my family of 4 for a long weekend.
Stayed 3 nights in Sep 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice place, owner very accommodating

Great experience, first time in Keys
Stayed 5 nights in May 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spring Break @ The Cigar House

The provided description, photos, and previous reviews were spot on and super helpful. Perfect amount of space for a family of 3 on spring break. The bathroom no longer has a claw foot tub shower as pictured. It is now just a large shower. The properties that border the rental community have resident chickens and roosters. Expect to hear them. Starting ~3-4am. Hens and chicks were often about the property. There is no closet space for hanging clothing/coats. Very limited floor space for living out of luggage. Internet was slow and spotty. Often defaulted to one device, plugged in, as a hot spot for everyone. Especially if working. Overall, excellent property and location.
Stayed 5 nights in Apr 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Easy Breezy

Island life in lush gardens. Great property.
Stayed 5 nights in Mar 2022