536 Fleming St, Key West, FL 33040

The advertised rate of $18,964/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 6, 2026.

Rates vary depending on... the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be higher if billed in multiple payments.
Experience the allure of this luxurious 2,000+ square foot penthouse, The Maloney, which occupies the entire second story of a historic red brick building at the corner of Fleming and Simonton. Originally constructed in 1908 as Key West's first pharmacy, this building now features two penthouse units and a first-floor boutique. The Maloney is available exclusively for monthly rentals, requiring a 30-day minimum stay.
Start your day with idyllic Key West mornings at The Maloney, where the soft light of sunrise filters through 19th-century brick-framed windows, perfectly complementing a velvety cup of cafe con leche. The vibrant evenings offer a curated collection of local paintings and carvings, set against the glow of 100-year-old Dade County pine floors, creating an ideal ambiance for hosting a quiet dinner or serving cocktails to friends.
Mid-stay cleans are available upon request.
Situated on one of Key West's prime corners, The Maloney places you within a block of award-winning restaurants, coffee and sandwich shops, wine bars, craft cocktail bars, a local grocery store, and the world-famous Duval Street. The neighborhood's walkability is complemented by options to rent bikes from Fury or Island Bicycles, which offer pick-up and drop-off services. For a unique island experience, rent a scooter or golf cart from Minty’s. Traditional transportation options like Uber, Lyft, and taxis, including the reliable Pink Taxi, are also available for convenient travel.
There is no parking included with your stay. Damages to the property or additional cleaning due to excessive mess are subject to charges. [SI] Read More