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Monthly historic old town rental Key West

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Fridge, microwave, stovetop, coffee/tea maker
TV, DVD player
Interior
Outdoor dining
Exterior

Reviews

8.0 out of 10
Very good

Entire apartment

2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Dryer
  • Washer
  • Kitchen
  • Barbecue grill
  • Air conditioning
  • Outdoor space

Explore the area

View map
Key West, FL
  • Duval Street
    ‪2 min walk‬
  • Ernest Hemingway Home and Museum
    ‪2 min walk‬
  • Southernmost Point
    ‪8 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪9 min drive‬

Room options

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Fridge, microwave, oven, stovetop

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About the area

Key West

A stay at this apartment places you in the heart of Key West, steps from Duval Street and Ernest Hemingway Home and Museum. .This apartment is 0.2 mi (0.4 km) from Florida Keys Beaches and 0.3 mi (0.5 km) from Southernmost Point.
View more Apartments in Key WestOpens in a new window

What's nearby

  • Duval Street - 2 min walk - 0.2 km
  • Ernest Hemingway Home and Museum - 2 min walk - 0.2 km
  • South Beach - 6 min walk - 0.5 km
  • Southernmost Point - 8 min walk - 0.7 km
  • Mallory Square - 18 min walk - 1.6 km

Getting around

  • Key West Intl. Airport (EYW) - 10 min drive

Restaurants

  • ‪Old Town Tavern - ‬3 min walk
  • ‪Banana Cafe - ‬5 min walk
  • ‪La Grignote - ‬5 min walk
  • ‪Better Than Sex - ‬4 min walk
  • ‪By George Bar At La-Te-Da - ‬4 min walk

About this property

Entire place

You'll have the entire apartment to yourself and will only share it with other guests in your party.

Monthly historic old town rental Key West

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
Make yourself comfortable in this air-conditioned apartment, featuring a kitchen with a refrigerator and a stovetop. There's a private balcony. Complimentary wireless internet access keeps you connected, and a DVD player is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.
This smoke-free apartment features a tennis court on site, ecotours nearby, and snorkeling nearby. Recreational activities include surfing/body boarding nearby, sailing nearby, and water skiing nearby.
Guests will find features like internet access.

Property amenities

Internet

  • Available in the apartment: Free WiFi

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Hob
  • Ice maker
  • Microwave
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • DVD player
  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre
  • Near a hospital
  • Near the marina
  • Near the sea

Things to do

  • Bicycles
  • Boat
  • Golf
  • Kayak
  • Tennis
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Snorkelling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water skiing nearby
  • Windsurfing nearby

Safety features

  • 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)

General

  • Bicycles

Policies

Check-in

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

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets not allowed

Children and extra beds

Children are welcome

Important information

You need to know

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
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
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
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

Property is also known as

1680-71533

Monthly historic old town rental Key West Reviews

Reviews

8.0

Very good

Rating 10 - Excellent. 3 out of 6 reviews
Rating 8 - Good. 1 out of 6 reviews
Rating 6 - Okay. 1 out of 6 reviews
Rating 4 - Poor. 1 out of 6 reviews
Rating 2 - Terrible. 0 out of 6 reviews

Reviews

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