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2 Br Apartment Vacation Rental In Key West, Florida

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Monthly historic old town rental Key West quaint 1 block to Duval

Type Apartment
Bedrooms 2
Bathrooms 1
House Rules
  • No pets allowed
  • Children allowed: ages 0-17
  • Smoking is not permitted
  • No events allowed
Max Occupancy 4
Host Language English Spanish
Property Id 3627965
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
Located by the sea, this apartment is in Old Town Key West, a neighborhood in Key West. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Discover the area's water adventures with jet skiing and snorkeling nearby, or enjoy the great outdoors with cycling and ecotours.
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    Policy

    Pet policy

    • Pets not allowed

    Check out time

    • 10:00 AM

    Check in policy

    • Check-in time starts at 4:00 pm
    • Contactless check-in available

    Payment policy

    • Localcurrency: USD

    Check out policy

    • Check-out before 10:00 am

    Check in start time

    • 4:00 PM

    Check in instructions

    • Information provided by the property may be translated using automated translation tools
    • You will receive an email from the host with check-in and check-out instructions

    Special instructions

    • 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
    • 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
    • Onsite parties or group events are strictly prohibited
    • Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
    • This property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

    Children and extra bed policy

      • Children are welcome.
    Amenities

    Popular amenities

    • Ac
    • Balcony
    • Barbecue
    • Dryer
    • Internet
    • Kitchen
    • Laundry
    • Living area
    • Microwave
    • No smoking
    • Patio
    • Tennis court
    • Tv
    • Washer

    Property amenities

    • Pets:
      • No pets allowed
    • Dining:
      • Dining table
    • Safety:
      • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
      • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)
    • Bedroom:
      • 2 bedrooms
      • Bed sheets provided
    • Kitchen:
      • Coffee/tea maker
      • Cookware/dishes/utensils
      • Ice maker
      • Microwave
      • Refrigerator
      • Stovetop
      • Toaster
    • Laundry:
      • Laundry facilities
      • Near laundromat
      • Washing machine and dryer
    • Internet:
      • Free WiFi, with speed of 250+ Mbps (good for 3–5 people or up to 10 devices)
    • Outdoors:
      • Balcony
      • Barbecue grill
    • Bathrooms:
      • 1 bathroom
      • Bathtub or shower
      • Hair dryer
      • Towels provided
    • Langs Spoken:
      • English
      • Spanish
    • Things To Do:
      • Bicycle on site
      • Boat on site
      • Ecotours nearby
      • Fitness facilities nearby
      • Golf nearby
      • Golfing on site
      • Jet skiing nearby
      • Kayak on site
      • Marina nearby
      • Sailing nearby
      • Snorkeling nearby
      • Swimming nearby
      • Tennis on site
      • Water skiing nearby
      • Windsurfing nearby
    • Entertainment:
      • DVD player
      • TV with cable/satellite service
    • Living Spaces:
      • Living room
    • Climate Control:
      • Air conditioning
    • Location Highlights:
      • In the city center
      • Near a hospital
      • Near the sea
    • Services And Conveniences:
      • Iron/ironing board
    • Suitability/accessibility:
      • Smoke-free property
 

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