Old Town Homes for Rent

This 2/1 Old Town apartment is in good condition with a new shower and combination window and ductless a/c units. Stack laundry in the unit and 1 off street parking spot included. Available August 1st. F/L/S to move in. Please contact David Austin, Anchor Line Realty, Licensed Real Estate Broker for showings.

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

Beautiful 3-bedroom, 2-bath monthly rental located on Key West's famous Duval Street. Guests enjoy easy access to shopping, dining, and entertainment options. The Green Pineapple offers charming architecture and an authentic taste of Key West’s unique culture and lifestyle. Visit The Green Pineapple storefront for a refreshing wellness journey. Discover a curated selection of nourishing foods,

Casa Azul is a luxurious modern cottage featuring an open-concept living area that is bathed in natural sunlight. Enjoy a dip in the heated saltwater plunge pool with a waterfall feature and night lighting. Located in Old Town Key West, just two blocks from Duval Street, this pet-friendly home offers private parking and is perfect for your next extended stay.Casa Azul perfectly blends comfort

"Lil Bit" is a rare find in the historic Bahama Village neighborhood. This classic "conch" home is modern and renovated to have an elevated feel but retains the charm and character of old Key West. Perfect for a couple or visitors looking for a monthly stay, this home is equipped with everything you need. While it is a "Lil Bit," the space feels large, open, and fresh, and is a short walk to Fort

Southernmost View is a modern and luxurious waterfront home located in a private seven-home gated community, just steps from the beach and the Southernmost Point of the continental USA. Enjoy turquoise blue waters from the rooftop sundeck, perfect for tanning, reading, and sipping your morning coffee. Relax under the southernmost stars or watch the sunset over the horizon.This upscale beach

Very cute little garden studio available Early August. Small but in the very HEART of it all! Walk to everything Old Town has to offer! Tenant pays electric and cable/internet. F/S/S. Sorry No Pets!

Clean furnished downstairs apt near Bayview Park in Key West. One BR is furnished, 2nd room can be used as an office or as 2nd BR. Additional outdoor shower, fenced, landscaped, and very private. Rent includes All utilities! NO Pets or animals and NO Smoking! Private laundry and off street parking! Perfect for single professional or Military.6 mo lease plus. Call Mark for more details

Lovely upstairs loft style apartment available Nov.1st, 2025 Located in upper old town Key West, near Bayview Park. Apartment is completely furnished, private w/d, gas range, large tiled shower, and covered deck for outside living! All utilities are included! First and last mo rent required to move in. Property is very well maintained, and suitable for a clean and quiet single professional. NO

922A EATON STREET, KW1/1 AVAILABLE NOVEMBER 1.90 cu. ft. of private lockable storage.Second floor, PRIVATE entrance, near Old Town Bakery. Nice rooms and storage. Ample room for scooters and bikes. W/D coin-operated 1 block away. Refrigerator, microwave, oven and stove. 2 A/C unitsLooking for long term steady tenant. Pets OK with pet deposit.