Marathon vacation rentals

An outdoor space features a sparkling in-ground pool surrounded by a sun deck with several lounge chairs. A shaded screened-in porch is visible in the background, along with a gas grill and a cornhole game set nearby. Lush palm trees provide a tropical atmosphere.

4.99 out of 5 average rating, 138 reviews

Cancellation Deal: 08/02 thru 08/09

2025 - New concrete dock, fenders & fish filet table. This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

4.97 out of 5 average rating, 176 reviews

A spacious outdoor patio is visible, featuring a wooden dining table and chairs. Beyond the patio, a serene waterway is showcased, lined with lush greenery and palm trees. A sailboat can be seen moored nearby, with a blue sky and fluffy clouds overhead.

Townhouse in Marathon

Marathon Keys Coral Lagoon Unit 2 Waterfront Villa

*Currently the seawall repair is not affecting our side of the property, our view is unobstructed and not affected. Also, our marina is 100% open and operational should you need to rent a slip during your stay Welcome to paradise! We are proud to offer you one of the nicest waterfront units in Coral Lagoon! Please Note: For your safety, the entire house is sanitized prior to your arrival. Along with our standard cleaning practices we have a local company that comes in and fogs the entire house

A large outdoor swimming pool is surrounded by palm trees, offering a serene atmosphere. Lounge chairs line the poolside, and several umbrellas provide shade. A hot tub is positioned in the foreground, with clear, inviting water reflecting the sky.

4.98 out of 5 average rating, 107 reviews

Waterfront House with 37 ft Dock & Cabana Club

Right in the middle of the action between Miami and Key West. This 2/2 house has been nicely renovated and furnished with new stainless kitchen appliances and a gorgeous granite countertop. Comfortable outside/inside living space perfect for a getaway in paradise. Walk out to the porch and backyard, and you will be engulfed by the beauty of the sunset views while lying on the cozy hammock. It features lots of outdoor entertaining: fishing, paddling, BBQ or just plain hanging out in the shade.

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.

4.96 out of 5 average rating, 107 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.

Guest suite in Key Colony Beach

A wooden dock extends over calm waters, flanked by white pilings and gently swaying palm trees. The warm hues of twilight fill the sky, reflecting softly on the water's surface, creating a serene atmosphere perfect for evening relaxation.

4.99 out of 5 average rating, 110 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!

The kitchen area features a modern sink with a view of the water through large sliding glass doors. A casual seating area with blue sofas and bright chairs can be seen, alongside a mounted TV. The waterfront setting is visible through the windows.

4.94 out of 5 average rating, 35 reviews

Florida Keys Oceanside Utopia

Create amazing memories at this beautiful oceanside home in Marathon, FL. Relax in the backyard or outdoor bar, watching boats cruise by on the aqua waters of Vaca Cut. Enjoy a fully equipped, newly remodeled and furnished duplex, beautifully decorated and ready to be your home away from home. Our waterfront location can’t be beat. Marathon has everything you need for a vacation to do it all on one Key. We can’t wait for you to experience our vacation home. Must be 25+ years old to book.

4.8 out of 5 average rating, 274 reviews

A modern houseboat is anchored on calm waters during sunset. The structure features large windows and a spacious front deck with a grill station. The warm glow of the setting sun illuminates the exterior, reflecting off the water, creating a serene atmosphere.

Boat in Marathon

Paradise awaits on this cozy houseboat!

Our vision is for you to kick back, relax, and find your home away from home! Wether you want to celebrate with your loved one or retreat by yourself this floating home offers comfortable space for 2 adults. Located near the 7 mile bridge in Marathon Florida on the Atlantic Ocean nestled in a quiet, reserved mangrove area. This spot is fantastic because you have unparalleled access to out of this world sunset/sunrise views. Kayak through the mangrove and explore the surrounding areas.

4.95 out of 5 average rating, 118 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

A serene waterfront scene showcases calm blue waters meeting a rocky shoreline. Palm trees provide gentle shade alongside a wooden dock extending into the sea. The clear sky and distant boats enhance the inviting coastal atmosphere, ideal for relaxation and outdoor activities.

4.91 out of 5 average rating, 11 reviews

Endless Summer

Welcome to Marathon the heart of the Florida Keys! Here in Marathon we have several restaurants and Sombrero beach minutes away. The home is located in Grassy Key (Marathon) it features its own private pool and spa, instant gulf access with plenty of parking for trucks and trailers. Each Bedroom has its own private bathroom. Pool heat is an additional charge. Chartered fishing trips, snorkeling trips, kayak, boat and Golf Cart available for rent upon request. VACA-23-60

4.9 out of 5 average rating, 332 reviews

Three colorful Adirondack chairs, yellow, turquoise, and green, are positioned on a sandy beach facing a calm blue ocean. A rocky shore and sparse greenery surround the seating area, while fluffy white clouds drift in a bright sky, enhancing the serene water view.

Villa in Marathon

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!

A black and white Jeep is parked in the gravel driveway of a charming yellow house. The house features large windows and is surrounded by palm trees, under a partly cloudy blue sky. A blue recycling bin is visible in the foreground.

4.9 out of 5 average rating, 162 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.

An airy kitchen space is highlighted by modern pendant lighting with woven shades. A wooden dining table takes center stage, complemented by open shelving showcasing decorative dishes. Large glass doors invite natural light while providing views of the surrounding greenery.

4.92 out of 5 average rating, 12 reviews

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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Marathon vacation rentals

Marathon beach vacation rentals

4.67 out of 5 average rating, 285 reviews

Two striped swings are suspended from a thatched roof, overlooking tranquil waters. The serene reflection of nearby palm trees and docks can be seen in the water, while soft lights hang overhead, enhancing the cozy ambiance of the outdoor space.

Tiny home in Key Largo

Waterfront Pool, Beach, Dock, Kayaks, Paddleboards

4.55 out of 5 average rating, 269 reviews

The exterior of a sleek travel trailer is showcased under soft patio lights, offering a welcoming glow. A thatched tiki hut is nearby, accompanied by lounge chairs and a small dining area, creating a relaxed outdoor atmosphere for gatherings.

Camper/RV in Key Largo

2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental

A serene outdoor space features a clear swimming pool surrounded by palm trees. A covered lounge area provides shade, while lounge chairs offer spots for relaxation. The tranquil waters are visible in the background, enhancing the overall atmosphere of the private retreat.

5 out of 5 average rating, 12 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

4.78 out of 5 average rating, 208 reviews

A wooden dock extends over tranquil waters, featuring two colorful lounge chairs facing the serene landscape. A boat is moored nearby, and the scene is surrounded by lush palm trees and thatched-roof structures in the background.

Tiny home in Key Largo

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

A private pool and spa are framed by tropical palm trees, with a serene canal visible beyond. The scene captures bright blue skies and lush greenery, emphasizing the outdoor oasis. Lounge chairs are positioned nearby for relaxation.

5 out of 5 average rating, 16 reviews

Waterfront 2-bedroom Home w/Pool and Spa

A private pool is surrounded by a paved patio, featuring lounge chairs and a small table. Lush tropical plants provide a natural backdrop. In the distance, a boat dock is visible along with outdoor dining furniture and an umbrella. Soft lighting enhances the inviting outdoor space.

5 out of 5 average rating, 16 reviews

Waterfront home w/pool, dock & close to beach

The private saltwater pool is framed by tropical plants and bright blue sky. Lounge chairs are positioned nearby, alongside decorative elements and pots. The serene atmosphere offers a refreshing retreat, inviting relaxation and enjoyment in the beautiful surroundings.

Cottage in Key Colony Beach

5 out of 5 average rating, 11 reviews

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach

A stilted beach house stands beside a serene canal, with lush green foliage lining the wooden dock. A kayak rests on the dock, while palm trees sway gently in the background, all under a bright blue sky.

4.91 out of 5 average rating, 23 reviews

Walk to Sombrero Beach, 50’Dock, SPA, Kayaks,Bikes

Show all

Vacation rentals with pools in Marathon

A modern two-story home features a clean white exterior with navy blue accents. A set of black stairs leads to a covered balcony adorned with potted plants. Large windows allow natural light to enter, while a gravel driveway provides ample space in front.

5 out of 5 average rating, 38 reviews

Waterfront Escape -VACA-23-408

A serene view is presented from the pool area, featuring gentle waves lapping at the shore and numerous sailboats anchored in the harbor. Two palm trees provide shade, and a well-maintained lawn borders the pool, enhancing the coastal ambiance.

5 out of 5 average rating, 9 reviews

Sandbox

Condo in Key Colony Beach

An aerial view captures the oceanfront property showcasing lush greenery and inviting private beach access. Bright blue rooftops of the buildings contrast with the turquoise waters. Lounge areas with tiki huts and a heated pool are visible near the shore, promoting a relaxed outdoor atmosphere.

4.92 out of 5 average rating, 239 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

4.95 out of 5 average rating, 140 reviews

A private heated pool is surrounded by a spacious patio with laid brick flooring. Palm trees frame the scene, while a vibrant sunset casts warm colors across the sky. Lounge chairs are positioned by the pool, inviting relaxation by the serene water view.

Villa in Marathon

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

A spacious beachfront home is depicted, featuring a large outdoor area with neatly arranged tropical plants. A well-maintained pool is visible in the backyard, alongside a staircase leading to wraparound balconies that provide ample views of the surroundings.

4.89 out of 5 average rating, 66 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

The spacious canal-front home is showcased from an aerial view, highlighting its private pool and lush palm trees. A dock with boat access extends into the water, while comfortable outdoor seating is positioned nearby, creating a relaxed atmosphere for guests.

5 out of 5 average rating, 24 reviews

Spacious lux home, private pool/spa, 80' dock

A spacious pool area is framed by cool Turkish marble pavers and lush greenery. The large heated pool reflects the clear blue sky. Underneath the elevated structure, shaded seating areas provide inviting spots for relaxation. The overall atmosphere emphasizes outdoor living and waterfront enjoyment.

5 out of 5 average rating, 37 reviews

Amazing Bayfront New House with Dock and Pool!

An inviting swimming pool is illuminated with soft blue light, creating a serene ambiance at night. The nearby outdoor dining area features a covered patio with seating for ten, enhancing the space for gatherings. The house provides a cozy backdrop, with warm lights glowing from the windows.

4.98 out of 5 average rating, 56 reviews

Waterfront Heated Pool 120 ft Boat Dock

Show all

Pet-friendly vacation rentals in Marathon

The exterior of a charming waterfront home is depicted, showcasing a canal with clear turquoise water. Lush palm trees frame the property, and well-maintained landscaping adds to the serene environment. The two-story building features a spacious porch and multiple balconies, enhancing outdoor living.

4.95 out of 5 average rating, 66 reviews

Coral Lagoon #23- Private Villa Home

The image captures a sparkling private pool overlooking the water, with a sandy beach and a wooden dock in the distance. A yellow kayak is positioned nearby, and several lounge chairs are arranged by the pool, inviting relaxation under the tropical sky.

4.89 out of 5 average rating, 37 reviews

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

Cottage in Little Torch Key

A waterfront property is surrounded by lush palm trees, with a gravel area leading to a private dock. The home is painted in soft blue tones, reflecting a comfortable coastal vibe. The expansive water views offer shimmering reflections under the clear sky.

4.9 out of 5 average rating, 167 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

4.97 out of 5 average rating, 193 reviews

The living area features a comfortable light blue sofa and a glass-top coffee table, complemented by tropical-themed decor. A ceiling fan circulates air above, while a kitchen bar with high chairs is visible in the background. Natural light enters through multiple windows, enhancing the welcoming atmosphere.

Home in Islamorada

Flakey's

4.89 out of 5 average rating, 121 reviews

A cozy living space features a navy blue sofa adorned with nautical-themed throw pillows. A dining area with a glass table and chairs is visible in the background, alongside a decorative display of framed art and a potted plant. Natural light filters through the windows.

Houseboat in Marathon

Houseboat Getaway In Marathon

Aerial view of the property along a wide canal, showcasing lush landscaping and a private Tiki Hut. The pristine water reflects a clear blue sky, bordered by palm trees and neighboring homes. Dock space is visible, indicating direct water access.

4.91 out of 5 average rating, 56 reviews

*Newly Renovated Single Family Home w/Private Pool

4.96 out of 5 average rating, 144 reviews

A shaded outdoor dining area features a wooden table surrounded by chairs, with a view of the private canal lined with palm trees. Nearby boats are docked along the lush green banks, creating a serene waterfront setting.

Townhouse in Marathon

Boater’s Paradise 3br/2.5ba at Coral Lagoon

An oceanfront pool area is featured with a clear blue water surface and several lounge chairs arranged around the deck. A striped umbrella is positioned over a decorative table, offering shade. Palms frame the view, enhancing the relaxed atmosphere.