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

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Beach
Outdoor dining
Interior
TV, DVD player
Exterior detail

Reviews

8.0 out of 10
Very good

Entire apartment

2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Explore the area

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

Room options

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About the neighborhood

Key West

Located in Old Town Key West, this apartment is next to popular attractions like Duval Street and Ernest Hemingway Home and Museum. The apartment includes a kitchen, a balcony, and a refrigerator.
View more Apartments in Key WestOpens in a new window

What's nearby

  • Duval Street - 2 min walk - 0.1 miles
  • Ernest Hemingway Home and Museum - 2 min walk - 0.1 miles
  • Key West Lighthouse and Keeper's Quarters Museum - 2 min walk - 0.1 miles
  • South Beach - 6 min walk - 0.4 miles
  • Southernmost Point - 8 min walk - 0.4 miles

Getting around

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

Restaurants

  • ‪801 Bourbon Bar - ‬5 min walk
  • ‪Circle K - ‬3 min walk
  • ‪Old Town Tavern - ‬3 min walk
  • ‪Rams Head Southernmost - ‬4 min walk
  • ‪Moondog Cafe & Bakery - ‬2 min walk

About this property

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

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
The apartment is air-conditioned and features a kitchen and a balcony, and there's space to spread out with 2 bedrooms. Guests can expect to find free WiFi and a TV with a DVD player. Other standard amenities include a washing machine, a coffee maker, and an ironing board.

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Property amenities

Internet

  • Available in the apartment: Free WiFi

Kitchen

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

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the marina

Things to do

  • Bicycles
  • Boat
  • Golf
  • Kayak
  • Tennis

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
Information provided by the property may be translated using automated translation tools

Pets

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

Smoking

Smoking is not permitted

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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.

Property is also known as

1680-71533

Frequently asked questions

What is there to do close to this apartment?

This apartment is situated in Old Town Key West, just steps from Duval Street and Ernest Hemingway Home and Museum, and within a short walk of Florida Keys Beaches. You'll also find Southernmost Point and South Beach less than a mile away.

Is there parking available at Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024?

No, there isn't parking available at the apartment.

Is this apartment next to a casino?

No, this apartment is not connected to a casino.

Is there an indoor pool at this apartment?

No, there is no indoor pool at this apartment.

Is Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024 good for couples?

Couples staying at this apartment will value amenities like a kitchen, a kitchen in some apartments, as well as tennis.

Does Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024 have a hot tub?

No, there isn't a spa tub at this apartment.

Does this apartment offer breakfast?

No, this apartment doesn't offer breakfast.

Does this apartment allow pets to stay for free?

No, pets aren't allowed at this apartment.

Does Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024 have connecting rooms available?

No, this apartment doesn't feature connecting guestrooms.

How close is the airport from this apartment?

The closest major airport to this apartment is Key West Intl. Airport (EYW), which is 3.7 mi away (10 minutes by car).

Are there rooms with balconies at Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024?

Yes, every apartment at Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024 comes with a balcony.

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