Allotjaments vora Ernest Hemingway Home & Museum

Duval Vibes • Pool • 10 Guests

Located only 30 seconds from Duval Street, this house will be your Key West headquarters for bachelor parties, family reunions, or any celebration that bring you to town. This 3 bedroom/ 2.5 bathroom home has a full kitchen, spacious outdoor living space, outdoor shower, private second story sundeck, and a pool. Your group of up to 10 will love being steps away from all KW has to offer- be Hemingway's neighbor! Add this listing to your wishlist by clicking the ♥ in the upper right hand corner.

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

Stay on Roxie - free transport & snacks, BYOB.

Read our reviews and relax with last minute weather cancellation! 🌞 Shower, toilet and power to recharge phones, full cellular. Enjoy a peaceful night or two on the water! Free parking and one free round trip transport to/from Roxie per night stay! Roxie is anchored in ~3ft lagoon. We live on a boat a half-mile away if you need anything at all! Roxie has a Keurig, coffee pods, bread, peanut butter-jelly, and bottled waters. No cooking but you may bring to-go food, beer/booze/wine. 🛥️🌴🎣

Key West Outpost: eco-vacation

The Outpost is a unique experience. This is a place where you can be completely off the grid, but still have all of the amenities. Private conch cottage on the backcountry waters surrounding Key West. Enjoy watching the amazing wildlife from your private deck. You can paddle board, kayak or do some light tackle fishing right off the boat. You can even add eco-tours to enhance the adventure. We will take you out for arrival and bring you back on your departure day, via one of our other boats.

NEW! - The Jolly Rooster Cottage - Walk to Duval

We’re thrilled to welcome you to our newly renovated, standalone cottage. Nestled just one block from vibrant Duval Street, you’ll be steps from Key West’s best dining, shopping, and nightlife Thoughtfully designed for relaxation and comfort, the Jolly Rooster comfortably hosts up to six guests and blends island charm with modern convenience. Our cottage comes fully equipped for a memorable stay. Come unwind, explore, and experience the best of island living at the Jolly Rooster!

Bright Condo in Paradise

The ideal location of this super-comfortable, 2nd floor, corner property makes it the perfect blend of convenience, tranquility, and tropical Key West scenery. Sit back and relax as you sip cocktails on the balcony and unwind in front of the living room smart TV after a day at Fort Zachary Beach. Or head down to the community's newly renovated, heated swimming pool. The Shipyard Condo is just a short walk from Duval Street's renowned shops, restaurants, and nightlife.

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs & DVD players.

Tropical Heron Hideaway w/ Hot Tub + Pool

Welcome to our charming 1932 Key West retreat in the peaceful Meadows neighborhood. This unique getaway features a private porch, a private hot tub, access to a shared pool and BBQ grill, and all the comforts of home. Blending historic island charm with modern amenities, it’s just minutes from Duval Street, the Historic Seaport, beaches, restaurants, and local attractions—the perfect place to relax and experience authentic Key West.

Sky Suite with Balcony Overlooking Duval Street

Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. The front house of Sky Suite is a rare find on the 700 block of Duval Street. History meets luxury here in this 1935 home that has been updated with modern designs and finishes. The location provides a great home base for all of your activities on the island and a place to kick off your night on the town.

Tiki Suites ~ Original Tiki ~ Floating Bungalows

Stay on the water in this one-of-a-kind Tiki Suite in Key West. This private floating bungalow blends boat life with comfort, featuring a custom bed, panoramic views, and direct access to the ocean. Swim, paddle, or relax in a hammock surrounded by nature. A peaceful, off-grid glamping experience you won’t find anywhere else. Accessible by boat only.

Duval Street Suites full kitchen and heated pool

The Little Palm Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlooking the pool in historic Old Town, Key West. Located in the middle of everything yet quiet and away from it all. This space is truly unique and sure to please all ages.

Duval Balcony Spanky's Retreat

Located in the heart of Duval Street, this one bedroom, one bathroom apartment with kitchen, and living area puts you right in the middle of all the action on Duval Street. Restaurants, bars, shops and attractions are just minutes away!