Entire apartment

Monthly historic old town rental Key West

Choose dates to view prices

Where to?

Dates

July 2025

22

August 2025

Fridge, microwave, stovetop, coffee/tea maker

Overview
Amenities
Policies
Location
Host

Entire apartment

2 bedrooms1 bathroomSleeps 4

Popular amenities

Dryer
Washer
Kitchen
Barbecue grill
Air conditioning
Outdoor Space

Explore the area

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

Room options

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 West

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

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.

Property manager

All Florida Keys Property Management

Languages

English, Spanish

Similar properties

Kitchen
Washer
Dryer
Free WiFi

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

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

This property doesn't allow pets

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 this apartment?

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.

What amenities will couples enjoy at Monthly historic old town rental Key West?

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

Are there hot tubs at Monthly historic old town rental Key West?

No, this apartment doesn't have a spa tub.

Does this apartment offer breakfast?

No, this apartment doesn't offer breakfast.