Vacation rentals in Boot Key

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Top-rated vacation rentals in Boot Key

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
Home in Marathon
4.92 out of 5 average rating, 72 reviews

Beach House, Private Pool, Dock, Gulf View Sunsets

You don’t come to the islands to stay in a town—you come to slow down. Welcome to our tropical keys beach home, tucked away from the traffic and noise of US Hwy #1. Sway with the palms on the wraparound deck, soak in wide-open panoramic bay views, and catch fiery sunsets right off your dock. Fire up the BBQ, brew a Keurig, float in the private pool, or cast a line from the 300’ private pier/dock. Easy going island living with ocean / gulf breezes, comfy beds, quality linens, Wi-Fi, and cable TV.

Top guest favorite
A boat is docked beside a light blue cottage, featuring large windows that reflect on the water's surface. Lush palm trees surround the property, enhancing the tropical atmosphere and offering a serene view of the canal.
Home in Marathon
4.98 out of 5 average rating, 57 reviews

Flamingo Palms-April availability

Flamingo Palms Cottage located on a deep-water canal with dockage and easy access to world-class fishing in the Atlantic and the Gulf. Nestled in a tropical setting amongst the native palms, Royal Poinciana and tropical landscape. Enjoy all the amenities needed for a perfect island vacation: airy open living areas, cozy screened porch, office nook off the kitchen, updated bedrooms and bathrooms, SUPs, beautiful yard, gas grill, parking for 2 cars/boat trailer. Marathon License #VACA-22-164

Top guest favorite
A private deck overlooks lush greenery leading to the ocean. A circular table with six chairs sits under a large umbrella, providing a shaded spot. The scene features bright blue skies and a calm sea, creating a serene atmosphere.
Home in Marathon
4.99 out of 5 average rating, 67 reviews

Oceanview Escape

Enjoy the stunning ocean views, sunshine, and warm breeze while you relax on your private deck. Centrally located to beaches and world class fishing and diving, this recently renovated home sits on the Atlantic and is situated within walking distance to shops and restaurants. Enjoy the spectacular sunrises and sweeping views from the open concept living/kitchen area. The vaulted ceilings and huge kitchen island make for the ideal gathering space, perfect for your Florida Key's tropical getaway.

Top guest favorite
A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.
Home in Key Colony Beach
4.93 out of 5 average rating, 134 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Top guest favorite
A serene outdoor space features two wooden lounge chairs positioned on a grassy area beside calm waters. A small table is placed nearby, and a private dock extends towards the water, flanked by lush greenery in the background under a bright blue sky.
Townhouse in Key Colony Beach
5 out of 5 average rating, 11 reviews

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

Top guest favorite
A wooden dock extends over calm waters, flanked by posts leading to a serene view of the sky at sunset. Lush palm trees are visible in the background, enhancing the tranquil atmosphere of the canal.
Guest suite in Key Colony Beach
4.99 out of 5 average rating, 133 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

Superhost
Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.
Villa in Marathon
4.89 out of 5 average rating, 538 reviews

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!

Top guest favorite
A cozy sleeping area featuring a quilted bedspread in various patterns. A kitchenette with modern appliances is visible, complemented by cabinetry. Two refrigerators are nestled in the corner, and a large mirror reflects the space. Ambient lighting and decorative touches add character.
Houseboat in Marathon
4.95 out of 5 average rating, 63 reviews

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 .

Top guest favorite
A modern two-story home with a spacious outdoor area featuring a private pool. Comfortable lounge chairs surround the pool, and a staircase leads to the upper level. The structure is complemented by a rooftop terrace with a sail shade, enhancing the coastal atmosphere.
Home in Marathon
4.97 out of 5 average rating, 137 reviews

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

Top guest favorite
A modern interior showcases a spacious living area with a sectional sofa adorned with decorative cushions. Adjacent, a bright kitchen is visible, alongside a dining table. A cozy bedroom features a bed with plush linens. Outdoor seating is arranged on a covered patio, surrounded by greenery.
Home in Marathon
4.9 out of 5 average rating, 183 reviews

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.

Superhost
Home in Marathon
5 out of 5 average rating, 4 reviews

A Paradise Point by Sombrero Beach

Modern Tropical Paradise | Marathon, FL Stylish home in exclusive Flamingo Isle, minutes from Sombrero Beach, marinas, fishing piers, indoor surf-style shop, and the Florida Keys Country Club. 3 bed | 2 bath + den Downstairs full bath with handicap-accessible walk-in shower Living room + playroom (pool table, games) Outdoor: Heated pool , Jacuzzi, BBQ, tiki hut Corner lot with parking for boat trailer & RV (full hook-ups)

Top guest favorite
Home in Marathon
4.94 out of 5 average rating, 199 reviews

Spacious 3Br/3Ba, 70ft Dock, March avail 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.

Popular amenities for Boot Key vacation rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Marathon
  6. Boot Key