Vacation rentals in Sunset Key
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Top-rated vacation rentals in Sunset Key
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Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.
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 & BlueTooth stereo system with CD player & radio.
Ocean front 1BR/1BA Suite w/ kitchen & living rm
1BR 1BA ocean front suite with a living room, kitchen and one bedroom. Doors that open to a balcony overlooking the Atlantic Ocean. Heated pool, hot tub, sun deck and a private sandy beach on the Atlantic ocean. 5 minutes walk to Duval street and the most Southern Point. Located between the prestigious Casa Marina and the top restaurant on the island Louise Back Yard. Free garage parking. Washer, dryers and ice maker are available for guests. Powerful, but sometimes noisy central a/c.
Tropical Old Town Bungalow
Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.
Amazing houseboat with 2nd floor observation deck
Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Soencers boat yard Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.
Studio Blu -Hip Studio/Old Town
*Recent Update (2025): We’ve made a wonderful upgrade to the studio bathroom — it’s now fully enclosed with walls extending to the ceiling and a new exhaust fan for ventilation. Situated in the heart of the Cuban district, just steps from arguably the best café con leche in Key West, this bright and breezy studio apartment is minutes from everything on the island. No car needed — bikes and beach chairs are provided free of charge so you can explore at your own pace.
Condo de Paradise/Salt Water Pool/Boat Dock
This is one of the best kept secret locations. Can be a very romantic escape. This is a good place for honeymooners, guys or gals getaway, fishermen/fisherwomen weekend get away or family time. A private unit in paradise in a gated community. Only 10 miles to Duval Street and all that Key West has to offer. There is a dock that can be used to dock up to a 26 foot boat that can be launched at Geiger Key, a mile down the road and they will store your trailer.
The Bartlum - Steps to Duval Street
Welcome to the Bartlum, a historic and luxurious studio apartment just steps to Duval Street. This studio, located on Caroline St, has been designed with comfort in mind, offering large windows for natural sunlight and plenty of space to spread out. Enjoy an updated kitchen, spacious bathroom, open concept layout, and all the hot spots of Key west within walking distance!
Key West • 2 Cabin • Yacht by Luxury Sea Charters
Skip the hotel room—own the horizon. Step aboard FREE TIME, your 50-foot floating suite in Key West. Two ensuite staterooms, a sun-soaked salon, and a private deck made for sunrise coffee or champagne sunsets. Docked in a premier marina with resort-style perks, this yacht redefines luxury travel—it’s not a stay, it’s a story you’ll tell for years.
Prime Downtown Key West Spot - Walk Everywhere!
Welcome to The Cozy Little Cottage! A REAL ISLAND GETAWAY IN KEY WEST!!! Nestled in the heart of Key West, The Cozy Little Cottage, welcomes you to a sanctuary of comfort and convenience. As your host, we're delighted to extend our warmest greetings and ensure your stay is nothing short of exceptional.
Beach Club Ocean Front 2BR Condo
Come fall in love with Key West in our luxurious ocean front condo. The Key West Beach Club is located directly on the Atlantic in a quiet residential secured building. It is a 2BR, 2 1/2 Bath located in Mid-Town.
Namaste: A blissful one bedroom cottage
Secluded in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing cottage. One bedroom, two bathrooms and a private courtyard create a restful vacation experience.
Popular amenities for Sunset Key vacation rentals
Other great vacation rentals in Sunset Key
Luxurious Stay | Snorkeling. Outdoor Pool
Nuns Room, A single travelers delight!
King Room (Limited Pet Friendly Rooms)
Poinciana Patio @ Tropical Inn
Mallory House Room #1
Marrero's Guest Mansion Adult Only (21+) Room 6
The Galleon, Key West
Duval St Apartment w/ Balcony w/parking Adult Only
All about Sunset Key
Sunset Key’s origins are inglorious: the United States Navy built it as a fuel tank depot during the Cold War. Today it's a very different place. This privately owned island community of multimillion-dollar homes is ringed by waving palm trees, white sand, and bright blue waters accessible only via ferry. Those lucky enough to stay in one of the house rentals here can avail themselves of a swimming pool, tennis courts, spa treatments, and yoga on the beach. It would be easy to play luxury island castaway for your entire vacation, but Sunset Key is located just off the coast of the island of Key West, whose serene beaches and bustling saloons have tempted artists and writers to its shores for decades. Go island hopping to get the best of both worlds.
What are the top things to do in Sunset Key?
Key West Museum of Art & History at the Custom House
Housed in a grand circa-1891 four-story brick building, this museum chronicles the last two centuries of art and history in Key West through two floors of exhibits. The collection includes displays devoted to notable locals and the sinking of the battleship USS Maine in Cuba’s Havana Harbor in 1898.
Key West Cemetery
The residents of Key West have as relaxed an attitude about memorials as they do about life. Dotted among the grand monuments and crypts of Key West Cemetery are cheeky tombstone messages such as “I told you I was sick” and “I’m just resting my eyes.” Established in 1847, this is an active cemetery with an estimated 100,000 people buried within. Self-guided tour maps are available at the cemetery entrance.
Fort Zachary Taylor State Park
It took 21 years to build the circa-1866 fort that lends this park its name. Used by the Union during the Civil War, and later in the Spanish-American War, the fort included then-state-of-the-art features such as a desalination plant and toilets flushed by the tide. After you’ve had your fill of history, head to the park’s gorgeous beach, where tropical fish put on a show for snorkelers. Head underwater and you may catch a glimpse of parrotfish, yellowtail snapper, lobster, and brilliant coral. Speaking of coral, there’s a lot of it at this beach, so wear water shoes (sold in the gift shop if you didn’t pack your own).
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