
Alquileres para vacaciones en Upper Sugarloaf Key
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Los alojamientos para vacaciones mejor valorados en Upper Sugarloaf Key
Los viajeros coinciden: estos alojamientos tienen valoraciones excelentes por su ubicación, su limpieza y mucho más.

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!
Valoración media de 4,89 sobre 5, 177 evaluaciones
Oceanfront Cottage with Open Water Views
Oceanview Serenity provides stunning open water views, and a 60 foot seawall for your boat. Comes with paddle board, kayaks, and more. Newly renovated 2BR cottage sleeps MAXIMUM OF FOUR (4) GUESTS, with a King in the Master BR and one Queen size bed Guest BR (both with new JW Marriott mattresses for comfort). All new appliances! Enjoy resort amenities like a pool, hot tub, tennis, and marina store. Just 30 minutes from Key West. One-time $125 RESORT FEE DUE AT CHECK-IN (PER STAY, NOT PER PERSON
Valoración media de 5,0 sobre 5, 47 evaluaciones
Oceanside home 109, dock,kayaks,bikes,pool,fishing
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #109 and I also rent adjacent homes 111 and 107 in case you need more than one. We are 80 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.
Valoración media de 4,94 sobre 5, 33 evaluaciones
Tropical Paradise
Oceanfront home with private pool, boat dock, kayaks, and private beach Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24' boat allowed) screened in porch for dining There are 2 king bedrooms, 3rd bedroom has a queen with trundle 2 1/2 bath. This home has an open floor plan and recently remodeled kitchen.
Valoración media de 4,67 sobre 5, 9 evaluaciones
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!
Valoración media de 4,97 sobre 5, 36 evaluaciones
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!
Valoración media de 4,89 sobre 5, 184 evaluaciones
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!
Valoración media de 4,95 sobre 5, 38 evaluaciones
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.
Valoración media de 4,96 sobre 5, 209 evaluaciones
Yellow Home - Receive $400 towards a Boat Rental!
Receive a $400 gift certificate towards a boat rental. When you reserve a week for any of the dates and house below. When you book a full week at one of our homes staying between the dates of Sept 1, 2026 through Dec 19, 2026 Except for Nov 21-28, 2026 Please reach out before booking for boat availability. Beautiful 3 bedroom 2 bath home. Kayaks included. Private heated pool and deck with a view of the Atlantic Ocean. Boat dockage available with parking.
Valoración media de 4,88 sobre 5, 42 evaluaciones
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.
Valoración media de 4,83 sobre 5, 111 evaluaciones
Ocean front classic keys cottage
This classic keys cottage is tucked among the palm trees on the open water of Niles Channel. Enjoy the breathtaking sunrises and romantic moonrises, seabirds,dolphins, and a nearly south-easterly breeze. This lovely hideaway is next to last home on dead end street, this 3 BRs, 2 baths ground level home has a large kitchen and Master suite. this location is only 30 minutes from the historic key west, close to restaurants and a nearby marina.
Valoración media de 4,95 sobre 5, 20 evaluaciones
*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.
Valoración media de 4,87 sobre 5, 135 evaluacionesComodidades populares en casas para vacaciones en Upper Sugarloaf Key
Otros alojamientos para vacaciones perfectos en Upper Sugarloaf Key

2Bd/1Ba Waterfront Retreat w/35’ Dock
Valoración media de 4,83 sobre 5, 35 evaluaciones
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
Valoración media de 5,0 sobre 5, 4 evaluaciones
Tiki Time in Cudjoe Key 136
Valoración media de 4,97 sobre 5, 58 evaluaciones
Relaxing and Inviting home with 35' Private Dock
Valoración media de 4,85 sobre 5, 60 evaluaciones
101- Oceanside House with Pool
Valoración media de 4,89 sobre 5, 258 evaluaciones
The Tarpon Retreat
Valoración media de 5,0 sobre 5, 19 evaluaciones
FL Keys Retreat - Community pool and hot tub
Valoración media de 5,0 sobre 5, 8 evaluaciones
Kelly’s Kabin - Private FL Keys Cottage
Valoración media de 4,77 sobre 5, 92 evaluacionesDestinos por descubrir
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- Parque Estatal Bahía Honda
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- Parque Histórico Estatal Fort Zachary Taylor
- Cayo Hueso
- Acuarios de Encuentros de los Cayos de Florida
- Dolphin Research Center
- Conservatorio de Mariposas y Naturaleza de Key West
- Cayo Hueso Faro Museo
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- Curry Hammock State Park
- Acuario de Key West





