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Monthly historic old town rental Key West quaint 1 block to Duval

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Beach
TV, DVD player
Outdoor dining
Exterior detail
Interior

Reviews

8.0 out of 10
Very good

Entire apartment

2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪2 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪2 min walk‬
  • Place, Southernmost Point
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪14 min drive‬

Room options

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About the neighborhood

Key West

Located in Old Town Key West, this apartment is next to popular attractions like Duval Street and Ernest Hemingway Home and Museum. The apartment includes a kitchen, a balcony, and a refrigerator.
View more Apartments in Key WestOpens in a new window

What's nearby

  • Duval Street - 2 min walk - 0.1 miles
  • Ernest Hemingway Home and Museum - 2 min walk - 0.1 miles
  • Key West Lighthouse and Keeper's Quarters Museum - 2 min walk - 0.1 miles
  • South Beach - 6 min walk - 0.4 miles
  • Southernmost Point - 8 min walk - 0.4 miles

Getting around

  • Key West Intl. Airport (EYW) - 10 min drive

Restaurants

  • ‪Circle K - ‬3 min walk
  • ‪Blue Heaven - ‬5 min walk
  • ‪Cuban Coffee Queen (Duval) - ‬4 min walk
  • ‪Moondog Cafe & Bakery - ‬2 min walk
  • ‪801 Bourbon Bar - ‬5 min walk

About this property

Monthly historic old town rental Key West quaint 1 block to Duval

Historic 2-Bedroom Cigar Maker’s Cottage – A Key West Gem!

Step back in time and experience Old Key West charm in this delightful 2-bedroom Cigar Maker's Cottage, built in the 1880s. Nestled at 1008 Whitehead Street, the cottage sits just across from where a bustling cigar factory once stood on Truman Avenue. The home's rich history includes ownership by David Kaufelt, a beloved Key West author and literary figure.

From the front porch, enjoy views of the iconic Key West Lighthouse, a perfect spot for relaxing and people-watching. Just a half block from the Hemingway House and one block from vibrant Duval Street, the location offers both tranquility and easy access to the heart of Key West’s culture and nightlife.

Inside, the home offers:

2 cozy bedrooms: one with a full-size bed and the second with two twins (which can be converted into a king upon request)

A bright, art-filled living room featuring works by local Key West artists and equipped with a TV and DVD player

A fully equipped kitchen with French doors that open to a lush tropical deck—ideal for indoor-outdoor living

Step outside to your private deck oasis—perfect for grilling on the large gas BBQ, dining al fresco, or unwinding with a cold drink under swaying palms.

Whether you’re looking to write the next great novel, reconnect with island life, or simply relax in comfort and history, this lovingly maintained cottage is your perfect piece of paradise.

Good to Know
Minimum stay: 28 nights
Ideal for month-long getaways, writers’ retreats, or snowbird escapes
Pet-friendly on approval (inquire first)

Prime Location
1/2 block to Hemingway House
1 block to Duval Street
Short walk to beaches, galleries, bars, and restaurants
Located on Whitehead Street, full of local history and charm

Outdoor Living
Enjoy lush tropical landscaping and Key West breezes
Sip coffee on the front porch with views of the Key West Lighthouse

Amenities
Fully equipped kitchen with French doors opening to the deck
Smart TV & DVD player
High-speed WiFi
Air conditioning & ceiling fans
Private tropical deck with:
Dining area
Lounge seating
Large gas BBQ grill

The Space
2 Bedrooms, 1 Bath
Bedroom 1: Full-size bed
Bedroom 2: Two twin beds (can be converted to a king upon request)
Sleeps up to 4 guests
Tastefully decorated with original Key West artwork
Historic touches meet modern comfort
The apartment is air-conditioned and features a kitchen and a balcony, and there's space to spread out with 2 bedrooms. Guests can expect to find free WiFi and a TV with a DVD player. Other standard amenities include a washing machine, a coffee maker, and an ironing board.

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  • Dryer
  • Free WiFi
  • Air conditioning
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Property amenities

Internet

  • Available in the apartment: Free WiFi

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Ice maker
  • Microwave
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • DVD player
  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near a hospital
  • Near the marina
  • Near the sea

Things to do

  • Bicycles
  • Boat
  • Golf
  • Kayak
  • Tennis
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Snorkeling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water skiing nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Bicycles

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available

Check-out

Check-out before 10:00 AM

Special check-in instructions

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

Pets

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.

Property is also known as

1680-71533

Frequently asked questions

What is there to do close to this apartment?

This apartment is situated in Old Town Key West, just steps from Duval Street and Ernest Hemingway Home and Museum, and within a short walk of Florida Keys Beaches. You'll also find Southernmost Point and South Beach less than a mile away.

Is parking available on site at Monthly historic old town rental Key West quaint 1 block to Duval?

No, this apartment doesn't offer parking.

Is this apartment next to a casino?

No, this apartment is not connected to a casino.

Is there an indoor pool at this apartment?

No, there is no indoor pool at this apartment.

What amenities will couples enjoy at Monthly historic old town rental Key West quaint 1 block to Duval?

Couples staying at this apartment will value amenities like a kitchen, a kitchen in some apartments, as well as tennis.

Does Monthly historic old town rental Key West quaint 1 block to Duval have a hot tub?

No, there isn't a spa tub at this apartment.

Does this apartment offer breakfast?

No, this apartment doesn't offer breakfast.

Does this apartment allow pets to stay for free?

No, pets aren't allowed at this apartment.

Does Monthly historic old town rental Key West quaint 1 block to Duval have connecting rooms available?

No, this apartment doesn't feature connecting guestrooms.

How close is the airport from this apartment?

The closest major airport to this apartment is Key West Intl. Airport (EYW), which is 3.7 mi away (10 minutes by car).

Are there rooms with balconies that I can book at Monthly historic old town rental Key West quaint 1 block to Duval?

Yes, every apartment at Monthly historic old town rental Key West quaint 1 block to Duval comes with a balcony.

Monthly historic old town rental Key West quaint 1 block to Duval Reviews

Reviews

8.0

Very Good

Rating 10 - Excellent. 3 out of 6 reviews
Rating 8 - Good. 1 out of 6 reviews
Rating 6 - Okay. 1 out of 6 reviews
Rating 4 - Poor. 1 out of 6 reviews
Rating 2 - Terrible. 0 out of 6 reviews

Reviews

From a partner site

10/10 Excellent

A guest from Pennsboro, WV

Busy Heart of Key West

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We greatly enjoyed our stay. The apartment is located steps away from the lighthouse, Hemingway House, Buoy, and Duval. We look forward to next winter at 1008 Whitehead.
From a partner site

10/10 Excellent

Scott J.

Great Stay

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was more than happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We loved the location, the cute little two bedroom. the house was well equipped with kitchen utensils. we really enjoyed being in the quieter section of town at night but during the day sitting on the porch and all the people watching was just great. Love the property and we will be back for sure in a year.
From a partner site

8/10 Good

A month of fun in Key West

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We enjoyed staying at the Cigar Makers Apartment. Interesting how it is A part of history. We were there a month visiting friends and attending 3 big week long events. Bicycling and the Duval loop bus stop being close by made for easy transportation to everywhere we wanted to go. We had friends visit us during the month. Everyone was pleased.
Archival

6/10 Okay

robin L.

Good basic housing

Rating Details: The property manager was very helpful. The vacation rental was clean. I was more than happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Nothing special but the price was right. We gave up our usually required pool to save $50 a day. Cottage is tiny and kitchen has no range, just a small convection oven and 2 burner top. Old and quaint it does have a slight mildew problem. Location, near southernmost point, good for beach access, but quite a walk from Mallory Sq. and all the action.
Stayed 30 nights in Nov 2017
Archival

4/10 Poor

Tony A.

Cigar Makers Cottage 1008 Whitehead St. KW

Rating Details: The property manager was more than helpful. The vacation rental was very dirty. I was very happy with the location. I was very dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: The cottage is old and has character. There are several areas of the building that needs to be repaired and or replaced. We only stayed in the first floor 2 bedroom section which was large enough for 2 couples. The second bedroom with twin beds did not have good A/C since it is located in the living room and the windows cannot be opened. Several bugs were able to get into the room due to the window not being sealed properly and it has mold around the edges. The WiFi was great and so was the kitchen. The TV only had 14 workable channels and looks like an oversized monitor. The bathroom shower works good, but there are several tiles that have mold and the caulking is cracked or broken off. The bathroom does not have a fan so you have to use the window to vent the room and it has a missing piece of glass. We liked sitting on the back deck, but we had to sweep the deck at least twice a day from all of the trees dropping leaves and sticks. The outside steeps leading to the second floor deck are not safe to use since it is to small to walk up and it is wrapped around a tree that you have to lean under to use the steps. The stairs need to be fixed for safety reasons. There is no on or off street automobile parking within 50 feet of the cottage. The management and maintenance staff are very nice and respond to requests. The location of the cottage is great, but there is a lot of street noise that start at 7am with trucks and street sweepers. If you are looking for a quite location this is not where you want, but it is a good location to DuVall and KW historical places.
Archival

10/10 Excellent

Stan E.

Cigar Makers cottage Oct-Nov 2014

Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Very pleasant stay--ideal for 2 people--great location very near Hemingway House--interior as pictured--very cozy--tree-shaded deck great for outdoor living--parking was not a problem even though you have to park on street--only drawback was no closet in cottage and might be a little tight for 2 couples to stay--good value for the price compared to other small houses in KWest.

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