Holiday rentals in West Summerland Key

Cottage 30 min from Key West, free parking, pool

Escape the everyday and unwind under the stars in this charming, nature-surrounded getaway where deer are frequent visitors. This cozy tiny house of offers 1 bedroom, 1 bathroom, and 3 beds, comfortably sleeping up to 4 guests. Enjoy peaceful surroundings, fresh air, and convenient double parking with space for a truck and boat trailer—perfect for outdoor adventures and total relaxation. Ideal for couples, families, or friends seeking quiet nights, wildlife views, and a simple, memorable stay!

Castillo Del Mar- Ocean access from your backyard

Welcome to PARADISE! — perfect for salty families, fishing lovers and beach goers • Prime Location – In Key Colony Beach with access to Cabana Club pool & private beach • Walk to Dining – Steps from Sparky’s Landing & Island Company • Boater’s Paradise – Backyard dockage for boats up to 30 ft • Spacious Kitchen – Family-style layout with 4-person bar top • Boho Dining Room – Perfect for cozy dinners and entertaining • Amenities include washer + dryer, fully stocked kitchen, Cozy Tv Room

Lagoona-Matata

A truly magical place "Lagoona-Matata" sits on the edge of Vaca Cut showcasing fabulous views of the Gulf. The outdoor area flows from the patio to the pool deck, private sandy beach, tidal pool and then to the pier dock. "Vaca Cut" is a fast-moving body of water from incoming to outgoing tides with fish of every kind moving through that makes fishing from the dock great entertainment. The continuous plethora of sea life in the lagoon makes this property an experience unlike any other.

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Welcome to Paradise Palms: ⭑ 1750 sqft liveable space on 10,500 sqft estate ⭑ Private home, deck, patio & backyard, overlooking a beautiful scenic landscape ⭑ Crystal pool, hot tub, movie theater, remote workspace, game room with arcade & more ⭑ Secure parking for up to six vehicles, boat trailer parking, RV and EV charging ⭑ 10 min to sombrero beach & just minutes to all island attractions ⭑ Fully stocked kitchen ⭑ Extremely safe neighborhood License #VACA-24-20 License #VACA-24-32

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!

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!

b watervibe

Disfruta de los sonidos de la naturaleza cuando te quedes en este lugar único. Es algo diferente para disfrutar con tu pareja de un momento romántico y divertido y así relajarse y olvidarse de la vida cotidiana. Puedes disfrutar de la pesca ,de paseos en kayak ,vivir una aventura y disfrutar de otras actividades locales. Toda una experiencia de camping para los huéspedes que les gusta lo divertido y diferente. Prueben y ustedes dirán. Ofrece un espacio para 2 personas

Gorgeous Ocean View Home!

Beautiful family friendly ocean view home centrally located in the heart of Marathon (only 10min from Sombrero Beach) were you’ll be able to do many things like snorkeling, fishing, boating, Scuba, museums, visit the aquarium, and/or the dolphin research center, and even dine on the water with many restaurants selections near by. This property does NOT have dock space for a boat or trailer parking. Licensed and inspected by the city of Marathon Lic.# VACA-23-144

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)

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.

Angler’s Terrace Conde Nast Traveler’s Best Airbnb

As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

Slack Tide Cove Welcome to Slack Tide Cove, a stunning 3-bedroom, 2-bathroom waterfront retreat in the heart of Marathon, FL. This brand-new construction is chicly decorated with a coastal theme, offering the perfect blend of luxury and relaxation. Take in breathtaking views of Boot Key Harbor from the pool or balcony, and enjoy 50 feet of deep-water dockage with a fish cleaning station for your day’s catch.