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Monthly historic old town rental Key West

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Exterior
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Combined shower/tub, hair dryer, towels
Exterior
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

Map
Key West, Florida
  • 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

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About the neighborhood

Key West

Seaside stay .A stay at this Old Town Key West apartment places you steps from Ernest Hemingway Home and Museum and a 5-minute walk from Duval Street. Key West Lighthouse and Keeper's Quarters Museum and Tennessee Williams Key West Exhibit are also within half a mile (1 km).
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
  • South Beach - 6 min walk - 0.4 miles
  • Southernmost Point - 8 min walk - 0.4 miles
  • Mallory Square - 18 min walk - 1.0 mile

Getting around

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

Restaurants

  • ‪Blue Heaven - ‬5 min walk
  • ‪Bourbon Street Pub - ‬5 min walk
  • ‪801 Bourbon Bar - ‬5 min walk
  • ‪Moondog Cafe & Bakery - ‬2 min walk
  • ‪Old Town Tavern Key West - ‬3 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

Property manager

All Florida Keys Property Management

Languages

English, Spanish

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  • Washer
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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

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • 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
  • Snorkeling 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

  • No pets 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited.

Property is also known as

1680-71533

Frequently asked questions

How close is Best Downtown Location Monthly Rental open March 7th 2025 Great deal to the airport?

This apartment is 3.7 mi (10-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Best Downtown Location Monthly Rental open March 7th 2025 Great deal have an airport shuttle?

Airport shuttle services are not available at this apartment.

How close is Best Downtown Location Monthly Rental open March 7th 2025 Great deal to the beach?

This apartment is a short 4-minute walk from Florida Keys Beaches and 8-minute walk from South Beach. Don't forget your sunscreen!

Does Best Downtown Location Monthly Rental open March 7th 2025 Great deal offer free breakfast?

This apartment does not offer free breakfast.

Is there a casino at Best Downtown Location Monthly Rental open March 7th 2025 Great deal?

No, there is no casino at this apartment.

What time is check-in at Best Downtown Location Monthly Rental open March 7th 2025 Great deal?

Check-in begins at 4:00 PM.

Is there free parking at Best Downtown Location Monthly Rental open March 7th 2025 Great deal?

Free parking is not available at this apartment.

Does Best Downtown Location Monthly Rental open March 7th 2025 Great deal have a pool?

This apartment does not have a pool.

Does Best Downtown Location Monthly Rental open March 7th 2025 Great deal have a spa?

There are no spa services available at this apartment.

How close is Best Downtown Location Monthly Rental open March 7th 2025 Great deal to downtown Key West?

This apartment is 0.3 mi away from Key West.

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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