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

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

Exterior
Living area
Miscellaneous
Living area
Outdoor dining

Reviews

8.0 out of 10
Very good
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Kitchen
  • Washing machine
  • Air-conditioning
  • Outdoor barbecue
  • Balcony
  • Free Wi-Fi

Explore the area

View 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.)
    ‪13 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

1 bathroom

Bathroom 1

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Balcony

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

Add dates for prices

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House Rules

Check in after 4:00 PM
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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
On-site 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

About the area

Key West

Located by the sea, this apartment is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. MLK Community Pool & Community Center and Key West Butterfly and Nature Conservatory are also worth visiting. Discover the area's water adventures with jet skiing and snorkelling nearby, or enjoy the great outdoors with cycling and ecotours.
View more Apartments in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Duval Street - 2 min walk - 0.2 km
  • Ernest Hemingway Home and Museum - 2 min walk - 0.2 km
  • Key West Lighthouse and Keeper's Quarters Museum - 2 min walk - 0.2 km
  • South Beach - 6 min walk - 0.5 km
  • Southernmost Point - 8 min walk - 0.7 km

Getting around

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

Restaurants

  • ‪801 Bourbon Bar - ‬5 min walk
  • ‪Circle K - ‬3 min walk
  • ‪Old Town Tavern - ‬3 min walk
  • ‪Rams Head Southernmost - ‬4 min walk
  • ‪Moondog Cafe & Bakery - ‬2 min walk

Frequently asked questions

Is Monthly historic old town rental Key West quaint 1 block to Duval pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Monthly historic old town rental Key West quaint 1 block to Duval?

As of 16 Apr 2026, prices found for a 1-night stay for 2 adults at Monthly historic old town rental Key West quaint 1 block to Duval on 23 Mar 2026 start from AU$250, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

What time is check-in at Monthly historic old town rental Key West quaint 1 block to Duval?

Check-in begins at 4:00 PM.

What time is check-out at Monthly historic old town rental Key West quaint 1 block to Duval?

Checkout is at 10:00 AM.

Where is Monthly historic old town rental Key West quaint 1 block to Duval located?

Located in Old Town Key West, this apartment building is steps away from Key West Lighthouse and Keeper's Quarters Museum, Duval Street and Ernest Hemingway Home and Museum. Florida Keys Beaches and Southernmost Point are also within 10 minutes.

Reviews

8.0

Very good

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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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.
Response from VrboOwner on 20 Sept 2023
Look forward to your return
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.
Response from VrboOwner on 20 Sept 2023
Thank you Jeffrey, Great to hear. We hope we will see you guys again.
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
Response from VrboOwner on 20 Sept 2023
Thanks for your review. Yes it is affordable for Old Town.
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.
Response from VrboOwner on 20 Sept 2023
Thank you for your review. We will certainly let the Owner know of your comments. The Property is a historic home in the Old Town Area and is not advertised as anything else. It is also excellent value for the high demand period that you stayed.
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.
Response from VrboOwner on 20 Sept 2023
Thanks for staying with us Stan, it was good to meet you. I will be in contact in regards to the other properties for next year.

About the host

Hosted by All Florida Keys Property Management

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