Apartment

The Maloney - Luxury Modern Downtown Penthouse

Photo gallery for The Maloney - Luxury Modern Downtown Penthouse

The Maloney - Exterior
Kitchen Overview
Living Room
Living Room Alt. View
Entertainment Space

Reviews

10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 6188.1 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪3 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪9 min walk‬
  • Place, Mallory Square
    ‪10 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪14 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Living Room 1

2 Double Beds

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Spaces

Deck or patio
Kitchen
Office
Balcony
Dining area

About this property

The Maloney - Luxury Modern Downtown Penthouse

Summary:

Woven throughout this 2,000+ square foot luxury penthouse is a story that can only be revealed by experience.



The Maloney encompasses the entire second story of the historic red brick building on the corner of Fleming and Simonton. Originally built in 1908 as the first pharmacy in Key West, the building now houses two penthouse units and a first-floor clothing and arts boutique.



**The Maloney is only available as a monthly rental at this time. All bookings require a 30-day minimum stay.**



The Space:

Idyllic Key West mornings are sure to take place at the Maloney, where the soft light of sunrise meanders through the 19th century brick framed windows, offering the perfect pairing for a velvety cup of cafe con leche and a slow drip of energy to start your day. Enjoy vibrant Key West evenings where the curated collection of local paintings and carvings compete with the glow of the 100 year-old Dade county pine floors make the perfect setting to host a quiet dinner or serve cocktails to friends.



The Neighborhood:

Located on one of the best corners in Key West, the Maloney places our guests within one block of award-winning restaurants, coffee and sandwich shops, wine bars, craft cocktail bars, a local grocery store and world-famous Duval Street.



Getting Around:

One of the best parts of staying in Key West is how close in proximity you are to everything. Don’t feel like walking? Peddle your way to breakfast, or take a bike ride along the water at sunset. Rent your bikes from Fury or Island Bicycles who offer both pick up & drop off services to your home! Feel like you’re on island time when you rent from Minty’s where you can enjoy exploring Key West on a scooter or golf cart. In addition to these non-traditional modes of transportation, you can also Uber, Lyft or Taxi to your next destination. Pink Taxi is an easy, reliable and affordable way for getting to your rental from the airport.



Other Things to Note:

There is no parking included with your stay.

Mid-stay cleans are available upon request.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
• Damages to the property or additional cleaning due to excessive mess are subject to charges.

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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

Frequently asked questions

Is The Maloney - Luxury Modern Downtown Penthouse pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at The Maloney - Luxury Modern Downtown Penthouse?

As of 5 April 2026, prices found for a 1-night stay for 2 adults at The Maloney - Luxury Modern Downtown Penthouse on 8 April 2026 start from NZ$1,054, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

What time is check-in at The Maloney - Luxury Modern Downtown Penthouse?

Check-in begins at 4:00 PM.

What time is check-out at The Maloney - Luxury Modern Downtown Penthouse?

Checkout is at 11:00 AM.

Where is The Maloney - Luxury Modern Downtown Penthouse located?

Located in Old Town Key West, this apartment building is steps away from San Carlos Institute - Casa Cuba and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 15 minutes.

About the host

Hosted by Brightwild

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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