Apartment

Monthly historic old town rental Key West

Overview
Amenities
Policies
Location
Host

Very good

2 bedrooms1 bathroomSleeps 4

Popular amenities

Dryer
Washer
Kitchen
Barbecue grill
Air conditioning
Outdoor space

Explore the area

Key West, Florida

Duval Street
‪2 min walk‬
Ernest Hemingway Home and Museum
‪2 min walk‬
Southernmost Point
‪8 min walk‬
Key West, FL (EYW-Key West Intl.)
‪9 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

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

Property manager

All Florida Keys Property Management

Premier Host

Languages

English, Spanish

Add dates for prices

Amenities

Kitchen

Washer

Dryer

Free WiFi

Air conditioning

Outdoor space

Have a question?

Beta

Get instant answers with AI powered search of property information and reviews.

Ask a question

Similar properties

Kitchen
Washer
Dryer
Free WiFi

House Rules

Check in after 4:00 PM

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets 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

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 Fort Zachary Taylor Historic State Park and Florida Keys Beaches. 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 ecotours and cycling.

Key West, Florida

What's nearby

Duval Street - 2 min walk - 0.2 km
Ernest Hemingway Home and Museum - 2 min walk - 0.2 km
South Beach - 6 min walk - 0.5 km
Southernmost Point - 8 min walk - 0.7 km
Mallory Square - 18 min walk - 1.6 km

Getting around

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

Restaurants

‪Blue Heaven - ‬5 min walk
‪Bourbon Street Pub - ‬5 min walk
‪801 Bourbon Bar - ‬5 min walk
‪Moondog Cafe & Bakery - ‬2 min walk
‪Old Town Tavern Key West - ‬3 min walk

Frequently asked questions

Is Monthly historic old town rental Key West pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Monthly historic old town rental Key West?

Check-in begins at 4:00 PM.

What time is check-out at Monthly historic old town rental Key West?

Checkout is at 10:00 AM.

Where is Monthly historic old town rental Key West 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.

8.0

Very good

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

A guest from Pennsboro, WV

3 Apr, 2024

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.

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Scott J.

15 Dec, 2019

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.

This review comes from a trusted partner site and has not been verified.

8/10 Good

18 Oct, 2019

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.

This review was submitted before 2018 and has not been verified.

6/10 Okay

robin L.

3 Dec, 2017

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

This review was submitted before 2018 and has not been verified.

4/10 Poor

Tony A.

1 Oct, 2016

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.

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Stan E.

21 Oct, 2014

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.