Cigar Makers Apartment KW Monthly
Address: 1008 Whitehead Street #1
Location: Key West, Florida
Type: Apartment
Property ID: 24605
About This Home
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
Neighborhood
Bedroom Configuration
bedroom
1
Queen
bedroom
2
Twin
Things To Know
- Cancellation Policy: Full refund 30 days prior to arrival and no refunds after that.
- Check-in Time: 4:00 PM
- Check-out Time: 10:00 AM
- Parking Available: yes
- Parking Price Type: charges may apply
- Pets Allowed: no
- Smoking Allowed: No
House Rules
- Quick Snap Shot: Historic 2BR Cigar Maker’s Cottage | Lighthouse View | Walk to Duval & Hemingway House Stay in the heart of Old Town Key West in this beautifully preserved 1880s Cigar Maker’s Cottage—just steps from all the action, yet tucked away for total relaxation
- Please do not park in spots marked RP- these are for Monroe County residents only. They will ticket you. There is a side street ½ block away on Julia which can be easier to find a space. Please be courteous to your neighbors in regards to noise levels. The AC should be turned to 78 when you are out and upon departure. Trash & re-cycling can be placed in the green trash and recycling bin on the righthand side of the property. There is one pick up a week on a Tuesday morning. Keys should be dropped at the rental office prior to departure. If you are leaving outside of business hours please call to make arrangements. The maximum occupancy in this apartment is 4 Do not move around furniture, any damage done is the responsibility of the guest.
Amenities
Activities
- Tennis court
- Golf
- Water skiing
- Jet-ski
Bathroom
- Bathroom amenities
- Bathtub
- Bathtub or Shower
- Hairdryer
- Private bathroom
Food and Drink
- BBQ/Picnic area
- Coffee/Tea maker
Media and technology
- Cable television
- TV
Miscellaneous
- Free Parking
Outdoor and view
- Library
- City View
Policy
- Off-Site parking
- Wireless Internet Connection
- No Pets Allowed
Pool and Spa
- Fitness center
Room amenities
- Washer/dryer
- Ceiling fan
- Air Conditioning
- Luxury linen type
- Dining room seats
- Iron
- Ironing board
- Kitchen supplies
- Washer
- Living room
- Outdoor furniture
- Kitchenette
- High-Speed Wifi
- Microwave
- Balcony/Lanai/Terrace
- Barbecue grills
- Refrigerator
- Refrigerator with ice maker
- Silverware/utensils
Shops
- Grocery shopping service available
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