In the heart of Old Town Key West, The Cigar House offers a secluded retreat with rustic charm. This 100+ year old cottage features a vaulted ceiling, Dade County Pine floors, and turn-of-the-century trim. With a private pool deck and heated Jacuzzi, enjoy outdoor living in this Caribbean-inspired setting.
Reviews
1010 out of 10
Exceptional
Entire home
2 bedrooms2 bathroomsSleeps 41000 sq ft
Popular amenities
Kitchen
Washing machine
Dryer
Free Wi-Fi
Add dates for prices
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 washer 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 first 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 countertops, 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, garbage 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 washer 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 center 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 roosters, 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 roosters. You will definitely see and hear chickens and roosters 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.
Property amenities
Beach
Beach towels
Pool/Spa
Communal pool
Heated pool
Hot tub
Outdoor pool
Internet
Available in the house: Free WiFi
Parking and transport
Electric car charging station on site
Car not required
Parking on site
Kitchen
Blender
Coffee/tea maker
Cookware, dishware, and utensils
Electric kettle
Hob
Microwave
Oven
Paper towels
Refrigerator
Toaster
Bedrooms
2 bedrooms
Bedsheets provided
Sofa bed
Bathroom
1.5 bathrooms
Bathtub
Bidet
Hair dryer
Shampoo
Shower
Shower/bathtub combination
Soap
Toilet paper
Towels provided
Living spaces
Living room
Entertainment
Books
DVD player
Smart TV with cable/satellite channels
Outdoor areas
Barbecue grill
Garden
Outdoor furniture
Patio
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Heating
Pets
No pets allowed
Suitability/Accessibility
If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
Hardwood flooring in public areas
No lift (single-level property)
Visual alarms in hallways
Well-lit path to entrance
Smoke-free property
Services and conveniences
Change of towels on request
Housekeeping on request
Iron/ironing board
Location highlights
In a village
Near a health/beauty spa
Near a hospital
Near the marina
Near the sea
Things to do
Bicycle parking
Bicycles
Heated pool
Basketball nearby
Birdwatching nearby
Cycling nearby
Ecotours nearby
Fishing nearby
Golfing nearby
Hiking/biking trails nearby
Jet skiing nearby
Kayaking nearby
Motor boating nearby
Parasailing nearby
Sailing nearby
Scuba diving nearby
Snorkelling nearby
Swimming nearby
Water skiing nearby
Wildlife walks nearby
Windsurfing nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
The house arrival and departure information, house and property rules, and guest registration will be emailed to the guest prior to arrival.
Pets
Pets not allowed
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
We should mention
A car is not required for transport to and from this property
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 ecotours and hiking/biking trails nearby. Visit our Key West travel guide
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 Fort Zachary Taylor Historic State Park are also within 15 minutes.
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Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4 Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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.
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.
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!!!
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:)
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.
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.
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.
Was down for July 4th week this year (2019) and loved this spot. Two blocks off Duval and centrally located North to South so everything we wanted to do was within walking distance. Nice, clean, great A/C (it was really hot this week) and some very attentive assistance from Abbey. Great little compound with pool. Would definitely stay here again.
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!
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.
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.
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.
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.
Jason R.
Stayed 4 nights in Dec 2021
Verified
6/10 Okay
Rindy A.
12 Jun 2025
Liked: Check-in, communication, location
The property is not maintained. Every plate and cup had a chip in it - you can find much better cups at flea market…When we came, the property had a dingy or moldy smell. No matches or firewood to lit up fireplace. The toilet clogged twice for us during 2 nights stay. Bathtub didn't drain. Its not a 5 star place for sure. But the location is nice and owner was very responsive
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.
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.