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
2 Bedroom one bath, hard wood floors, back deck, BBQ, internet and
Minimum number of persons: 1
Maximum number of persons: 4
House is well suited to go sailing
Snorkeling
Bathtub
Laundromat
Marina
Crèche/day care
Located Downtown
Water-skiing
Staff follow all safety protocols as directed by local authorities
Terrace
ATM on site
House is well suited to go fishing
Available for letting for a longer period
Business center
Canoeing
Stereo
No-pets version possible
Fan
Evening Entertainment
Golf
Bath
Cooking basics (pots and pans)
Shared tennis court
House is well suited to go surfing
Disinfectant is used when cleaning the property
Bicycle routes
Contactless check-in and checkout
Number of toilets: 1
Walking routes
Boat (for rent) (S)
Beach
Grocery shopping service
Windsurfing
Shower
Garden
Located Near the Ocean
Restaurant (M)
No Booking or Service Fees
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Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
---|---|---|---|---|---|
Jul 18 - Oct 19 2025 | $309 | 3 nights | |||
Oct 29 - Dec 23 2025 | $309 | 3 nights | |||
Mar 01 2026 - May 31 2028 | $309 | 3 nights |
Fees:
Notes:
County tax: 5%
Reservation fee: 3%
State tax: 7.5%
Last updated on July 08, 2025