Apartment in Key West, FL
4 guests · 2 bedrooms · 1 bath
Reasons to book
Well priced for this locationPriced under area average
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Includes essentials and more
About this apartment rental
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
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
Amenities at Monthly historic old town rental Key West quaint 1 block to Duval
Non-smoking
No pets allowed
Family friendly
Map of Key West, FL
Ratings and reviews
Summary of reviewsGuests praised the helpful property manager, cleanliness, great location, and overall satisfaction with vacation rentals.
10 / 10Outstanding·Apr 2024
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.
10 / 10Outstanding·Jan 2020
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.
8 / 10Excellent·Dec 2019
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.
6 / 10Average·Dec 2017
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.
$$$$
Top rated by guests
8Excellent
(6 Ratings)
Guests praised the helpful property manager, cleanliness, great location, and overall satisfaction with vacation rentals.
From real guest reviews summarized by AIDon't miss out! Price and availability may change
