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Holiday houses in Boot Key Harbor

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Top-rated holiday rentals in Boot Key Harbor

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Top Guest favourite
A spacious sleeping area includes a king-sized bed with crisp white bedding and decorative pillows. Metal fish sculptures adorn the wall, complemented by two bedside lamps. A dark sectional sofa is positioned nearby, creating a comfortable seating area for relaxation.
Condo in Key Colony Beach
4.92 out of 5 average rating, 311 reviews

Key Colony Beach Luxury Condo, New Modern Interior

Private studio condo at Key Colony Beach with a private balcony, heated pool and sandy beach. Unit #15 was recently renovated and offers one comfy King size bed and a fully equipped kitchen with essentials (stove, oven, toaster, microwave, blender, fridge, cooking utensils). Wifi, Amazon Echo and a TV. Enjoy a short walk to Sunset Park next door to experience a stunning Florida Keys sunset. Guests also have access to a private beach with lounge chairs, patio tabales, tiki huts, and BBQ grills.

Superhost
A welcoming sign for Skipjack Resort and Marina is prominently displayed, surrounded by lush palm trees and manicured greenery. The blue sky adds a bright backdrop, enhancing the inviting atmosphere of the resort.
Apartment in Marathon
4.84 out of 5 average rating, 49 reviews

Sombrero Beach Tropical Paradise

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

Guest favourite
A welcoming living area features a dark gray sofa and armchair, complemented by patterned cushions. A light wooden coffee table sits atop beige tile flooring. A large flat-screen TV is mounted on the wall, and natural light filters through window coverings, creating a bright atmosphere.
Apartment in Marathon
4.94 out of 5 average rating, 70 reviews

Dock POOL Kayaks Bikes Beach2mi WalkToStores

Come enjoy tranquil Atlantic breezes at our DUPLEX. Enjoy all the keys islands & adventure in three (3) bedrooms & two (2) bathrooms with full tubs. Enjoy cooking & baking for family & friends On-site gated parking and dock space for ocean toys/ boat (35 ft max) on the 75 ft waterfront concrete seawall & wood dock complete with fish cleaning station and outdoor kitchen & grill to prepare your daily catches. Enjoy the multiple spacious outdoor spaces (shared) for playing, relaxing & dining.

Top Guest favourite
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, 122 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
Home in Marathon
4.73 out of 5 average rating, 49 reviews

Fisherman's Catch- 3BR Home with 60' Dock & Pool

License # VACA-23-219 - Discover paradise at this Flamingo Island retreat in Marathon boasting everything you'll need for the ideal Florida Keys getaway including a 20' Private, Heated Pool, Jacuzzi Spa Tub (not Hot Tub...this is the same temp as the Pool) and 60' Slip Space poised for easy access to the waters of the Atlantic. Don't spend your leisure crammed into the average 325 sq. ft. hotel room; this Canal Front Vacation Home features 1,658 sq. ft. of generous space to move about.

Top Guest favourite
A spacious outdoor area is surrounded by tropical landscaping, featuring a BBQ grill and a hot tub. Comfortable lounge chairs are available under umbrellas, with a gravel walkway leading to various seating arrangements. Sunlight filters through the palm fronds, creating a relaxing atmosphere.
Home in Marathon
4.95 out of 5 average rating, 42 reviews

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

License#VACA-23-370. Hot Tub, BBQ. Bring Your Boat, RV Parking. Conch Home located in the Heart of Marathon. Home sits on 8,000+sf lot w/2 bed (king in main BD & 2 twins in 2nd BD) 1 bath home w/ fully equipped kitchen & full bath w/shower & tub + lots of natural light & garden view all around. W/D, new mini split ACs in living room, & both bedrooms, back deck has a BBQ, Hot Tub & huge yard w/plenty of parking for a boat and trailer. YOUTUBE VIDEO TOUR: SEARCH sandys conch cottage

Top Guest favourite
An open living space is featured, highlighted by a round dining table surrounded by comfortable seating. A large television is mounted on the wall, while light-colored walls enhance the bright atmosphere. A serene coastal artwork depicting a pier adds a calming touch to the decor.
Home in Key Colony Beach
5 out of 5 average rating, 32 reviews

Bohemian Beach Bungalow

Cabana Club Access Included! Escape to our newly built 2-bd, 2-bath duplex in KCB, where relaxation meets luxury. Located on the golf course, this stylish home boasts professional decor with modern amenities. While not directly waterfront, ample parking for your boat/trailer. Fully equipped kitchen meets all your culinary needs. Savor effortless access to Havana Jacks, Cabana Club, and Sunset Park, all within walking/biking distance, making this the ultimate Florida Keys retreat

Guest favourite
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
4.9 out of 5 average rating, 472 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 favourite
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
4.91 out of 5 average rating, 35 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

Guest favourite
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
4.89 out of 5 average rating, 174 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.

Guest favourite
Condo in Marathon
5 out of 5 average rating, 9 reviews

*New* Turtles Pace-Private Beach

Discover the perfect getaway in this beachfront condo in Key Colony Beach, FL. With direct access to a private beach, you’ll enjoy breathtaking ocean views and endless relaxation. This condo features modern amenities, a fully equipped kitchen, and comfortable living spaces. Whether you’re soaking up the sun on the beach or exploring local attractions, this is the ultimate coastal escape. Don't miss the chance to experience paradise!

Top Guest favourite
Home in Marathon
4.94 out of 5 average rating, 197 reviews

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.

Popular amenities for Boot Key Harbor holiday rentals

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