Holiday rentals in Boot Key Harbor

Sombrero Beach Tropical Paradise Hotel

Spacious 1 Bedroom Condo at Skip Jacks Resort in the heart of Marathon, located at Mile Marker 50 Positions you in the perfect spot to explore all that the Florida Keys has to offer, Just 1 hour to Key West or Key Largo Spend your day,Boating,Snorkeling, Fishing, Lounging by the Pool or spend the Day at Sombrero Beach. The Condo has TV's with Wifi and a Fully Stocked Kitchen if you just want to Stay in sit on the Balcony and Enjoy the Music coming from the Live band at the Tiki bar VACA-24-205

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

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.Prueba de la expericiensa y ya ustedes diran.Esta casa flotante ofrece un espacio para 2 adultos. Está Esta es una experiencia de Acampada

Tiny Home Aqua Lodges 2/1

This memorable place is anything but ordinary. Experience the Keys like a local. Stay in our fully equipped aqua lodge with private surroundings. This lodge has 1 queen bed, 1 full bed, a sofa sleeper full size on the main floor, and 1 twin in the loft. It has a full kitchen, mini split ac, and full bathroom with hot water. This location has great sunset views and private BBQ waterfront area. All lodges have all bedding and dishes and cooking utensils.

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

Exquisite Oceanfront Paradise - Key Colony Beach

Experience a wonderful ocean view from our beachfront condo in Key Colony Beach. Newly renovated ground floor with a stunning, clean white interior and just a few steps from our private beach and heated pool. Continental Inn Unit #10 offers one King size bed that sleeps two people. A fully equipped kitchen with essentials (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Reliable WiFi and Smart TV.

Waterfront Cozy Modern Retreat w/Deep Canal

Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.

Canal View Condo w/ Pool, Balcony & Bar

Celebrate the season in paradise at THE DAPPER DOLPHIN, an updated coastal-themed 1-bedroom, 1-bathroom condo, accommodating up to 4 guests. Featuring a complete kitchen, balcony, and access to resort amenities including a pool, Tiki Bar, restaurant, Marina, and more! Situated in the heart of Marathon, it offers proximity to the beach, restaurants, activities, and all the essentials for an unforgettable vacation experience right on-site!

Couples Getaway, Suites-Marlin Bay Resort & Marina

Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort featuring 13 luxury vacation homes, 74 private marina slips and a centrally located pool deck and clubhouse. We provide unparalleled service in an intimate setting allowing you to relax and unwind. We are located in Marathon in The Middle Keys, so you can easily explore all that The Keys have to offer.

Spacious! 70ft Dock, Near Beach VACA23-16

Enjoy the boutique decor of our large, spacious home. Our place is a short distance from Sombrero Beach, with bicycles available to ride there. Our property is on a wide and deep canal, with both ocean and gulf access. Our dock is 70 ft, so ideal place for large boats, or you can even bring 2 boats. Free parking, with space to park boat trailer. We include free passes to the Sea Turtle Hospital to guests.

Private Pool, Kayaks, Deep Water Dock, Near Golf

Welcome to the Salt Cottage Sombrero Tucked away in Marathon’s exclusive Flamingo Island neighborhood, this stunning 3-bedroom, 2-bath waterfront retreat offers the perfect blend of island charm, coastal luxury, and outdoor adventure — complete with a 30’ dock (Boat lift is not for Guest use), private pool, and thoughtful amenities.

Waterfront 2-bedroom Home w/Pool and Spa

Enjoy the Florida Keys living at its finest. This home features a private pool and spa, tropical landscaping, and a large backyard with lounge chairs, a BBQ, and an outdoor dining table. It is perfect for boaters and water lovers, with easy access to the ocean and the Gulf for some of the best fishing in The Florida Keys!