Apartment in Key West, FL
4 guests · 2 bedrooms · 1 bath
Reasons to book
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
Includes essentialsFamily friendly 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
Family friendly
Map of Key West, FL
Things to know
Additional fees to expect
Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Vrbo properties are professionally cleaned after each stay.
Booking feeNo booking fees, easy credit card payments.
Service feeThis helps Vrbo provide a safer and more secure booking experience.
TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.
Customer support
Customer support is handled by our partner Vrbo
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Top rated by guests
8.0Excellent
(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
