Vacation rentals in Sunset Key
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Top-rated vacation rentals in Sunset Key
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ATLANTIS...Ocean Front Cottage Retreat!
ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!
KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK
Your own private Key West hideaway awaits. Surrounded by lush tropical landscaping, this peaceful home offers a large pool, outdoor shower, grill, and fire pit — perfect for relaxing days and starlit evenings. Enjoy complete privacy indoors and out, with three comfortable bedrooms, a fully equipped kitchen, washer/dryer, and 66' of canal frontage- bring your own boat or ask one of our favorite captains to pick you up! Whether out on the town or relaxing in your own home, you will love it here!
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.
Cozy Tiny Houseboat: Find Your Peace and Balance
Welcome aboard your cozy houseboat, Balance Key! Perfect for couples, friends, or solo travelers seeking a unique and creative experience that transcends conventional travel. Disconnect from the everyday hustle and bustle and enjoy a refreshing ocean getaway or embark on adventures exploring vibrant marine life, all while taking in 360-degree views through our glass doors whether you’re indoors or outdoors. Two free Kayaks and a dinghy (only for experienced users, $50 one time fee)
Waterfront Cozy Cottage with Boat Ramp & Dock!
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!
Starlight Serenity - Hideaway with Stunning Views
Escape to paradise at this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key sleeping up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance. Whether you're relaxing indoors or savoring the outdoors, this home offers the perfect blend of comfort and tranquility. Book your next getaway for 3 nights or more!
Waterfront Dock Pool Condo Near Duval St Pet OK
Bring friends and family to this spacious 1,350 sq ft waterfront corner condo in historic downtown Key West. Enjoy a full kitchen, open living space, and a private balcony with marina and pool views. Dockage available with a fish cleaning station and commercial ice maker, perfect for boating and fishing. Located about 1 mile from Duval Street, the Historic Seaport, and Hemingway House. Amenities include a heated pool, tiki area, BBQ grills, parking, elevator, and secure entry.
Cudjoe Key Home with a View
We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.
Palm Breezes! Room for Everyone on the Ocean.
This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.
*Emerald Seas*-Florida Keys Ocean Front Paradise!
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.
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.
Popular amenities for Sunset Key vacation rentals
Other great vacation rentals in Sunset Key
Condo de Paradise/Salt Water Pool/Boat Dock
White House - Receive $400 towards a Boat Rental!
3BR In Resort Village, Pools, Free Kayak & Shuttle
Bright Condo in Paradise
Casa Rosa: 4BR/4BA house, pool, near Duval
Waterfront Boat Stay + Resort Amenities
NEW! - The Jolly Rooster Cottage - Walk to Duval
September special 119/nt-walk to Duval, Mallory
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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