Holiday rentals in Wisteria Island

Casa Rosa: 4BR/4BA house, pool, near Duval

Casa Rosa, a historic eyebrow home in Key West, offers 4 bedrooms, 4 bathrooms, a private pool, hot tub, and prime location just a block from Duval Street. Enjoy charming décor, a fully equipped kitchen, and outdoor dining surrounded by tropical foliage. Relax in the serene backyard oasis or explore nearby attractions like the Hemingway Home, Mallory Square, and Southernmost Point. Pool heat available for $250+ tax per week. Book now for an unforgettable stay! Saturday-to-Saturday Rentals Only.

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. 🛥️🌴🎣

Waterfront Condo Dock Pool Downtown Near Duval

Time to relax and vacation in this spacious 1,350 sq ft waterfront corner condo in downtown Key West. Bring your family and friends and enjoy a private balcony with marina views, full kitchen, and open living space. Dockage available with a fish cleaning station and commercial ice maker, perfect for boating and fishing. Amenities include a heated pool, tiki area, BBQ grills, free parking, elevator access, and secure entry. Located about 1 mile from Duval Street and 10 minutes from EYW airport.

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.

Gorgeous Ocean View in Paradise, Close to Key West

This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

#201 Key West Suites

Welcome to your charming, private studio apartment located right on Duval Street! Originally built in 1919, this historic building was once known as the Central Hotel, reflecting its prime location at the heart of Duval Street at Southard. While this is a vacation rental rather than a traditional hotel (there is no lobby or on-site services), we’ve preserved the nostalgic character by naming it “Key West Suites Hotel” in honor of its rich history.

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.

Duval Corner - Pet friendly with Balcony

Welcome to Duval Corner! A beautifully updated one-bedroom condo in the heart of Downtown Key West. This second-floor retreat is perfect for travelers wanting to be steps from it all. Within walking distance to iconic attractions like the Southernmost Point, The Ernest Hemingway Home, and Mallory Square, plus dining hotspots such as Blue Heaven, 7 Fish, and Louie's Backyard; Duval Corner is the ideal base for your Key West adventure.

Parking & Shared Pool - Casa Key West

- Located on the south end of Duval Street steps from the Southernmost Point! - Large open-concept condo with private balconies overlooking Duval Square restaurants & shops. - On the intersection of Truman Avenue and Duval Street, just a 10 minute walk to downtown bars, restaurants and Key West's famous attractions. - Private off-street parking included with your stay along with access to the rooftop pool overlooking Duval Street.

Pilar House

Charming 3BR/2BA townhouse in the heart of Old Town Key West. Just steps from restaurants, bars, shops, and attractions, yet on a quieter street for a relaxing stay. Two queen bedrooms downstairs, a king master with a balcony upstairs, plus a queen sofa bed to sleep 8. Enjoy a large private deck perfect for morning coffee, lounging, or BBQs. The ideal mix of comfort, space, and unbeatable walkability.

Island Color Suite

Stay in the heart of Key West! This modern, spacious 2-story apartment is located directly on famous Duval Street, steps from dining, shopping and entertainment. Enjoy 2 bedrooms, 1.5 baths, a fully equipped chef’s kitchen, comfortable living area, Smart TVs, high-speed Wi-Fi and quality linens. Sip a tropical cocktail from your private balcony while people-watching below. Free parking included! 🌴

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.