Family-friendly holiday rentals in Marathon

4.73 out of 5 average rating, 26 reviews

Sunset Key Escape/Pool, Dock, Kayaks & Gulf Access

Welcome to Sunset Key Escape Your Private Waterfront Retreat in Marathon Bask in the beauty of the Florida Keys at Sunset Key Escape, a stylish and serene 3 bedrooms, 3 bathroom waterfront getaway designed for comfort, adventure, and unforgettable views. Whether you are unwinding poolside, launching a kayak at sunrise, enjoying dinner by the water under the stars, or challenging friends and family to a ping pong match, this home offers a true Keys escape surrounded by nature and coastal charm.

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.

4.93 out of 5 average rating, 154 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.

4.77 out of 5 average rating, 161 reviews

Houseboat in Marathon

Tiny Home Aqua Lodges 2/1

This memorable place is anything but ordinary. 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. You will also have access to the Cabana Club located in Key Colony Beach.

4.92 out of 5 average rating, 120 reviews

The image showcases a vibrant living space within the Dapper Dolphin condo, featuring a stylish kitchen with granite countertops, a cozy dining area, and a comfortable bedroom with a king-sized bed. The outdoor area displays a large pool surrounded by lounge chairs, highlighting the resort's inviting atmosphere.

Apartment in Marathon

Dapper Dolphin | Canal View + Breakfast + Pool

Escape to The Dapper Dolphin, a beautifully updated coastal 1-bedroom, 1-bath condo located at Skipjack Resort & Marina in the heart of Marathon. Sleeping up to 4 guests, this stylish retreat features a full kitchen, private balcony, and 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!

5.0 out of 5 average rating, 6 reviews

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace

The outdoor area features a sandy patio surrounded by palm trees, with several blue Adirondack chairs facing a shaded seating area under a white gazebo. The spacious home stands in the background, showcasing multiple balconies and a light-colored exterior.

4.84 out of 5 average rating, 100 reviews

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

The two-story home is complemented by lush palm trees and surrounded by water, reflecting the vibrant colors of the sunset. Lounge chairs are positioned on the patio, and lights from the home illuminate the water, creating a serene atmosphere.

4.96 out of 5 average rating, 56 reviews

🏝Beautiful🏖 Water🏊‍♀️ View🌅 Pool Gym🏋️ Room, Private⛵️ Dock⚓️

Over 100ft of water frontage, with expansive bay view of all the beautiful wildlife that Marathon has to offer! Pets are always welcome but you MUST‼️indicate how many guest and pets when you make the booking. If cleaning crew discover sign of pets, guest will be charge $350/entire stay due to the extra cleaning work from the cleaning crew. With an outdoor heated pool, paddle boards, and kayaks, you and your family will never need to leave the home for activities!

An inviting outdoor area features a clear swimming pool surrounded by a paved patio. The two-story structure above includes spacious balconies with multiple seating options. Sunlight brightens the scene, and lush greenery is visible in the background, enhancing the tranquil environment.

4.97 out of 5 average rating, 114 reviews

Angler's Eden

Amazing get-away in the beautiful Florida Keys! This property (constructed in 2018) is a haven for families seeking to escape to paradise year-round. Situated on a deep water canal with ocean access and enough dock space to park your boat for the week. A floating dock is also provided with kayaks. Enjoy the large pool or ping pong table, or lounging in the sun! Beautiful Sombrero Beach is within walking distance (approx 1.5 miles) via a paved bike path.

5.0 out of 5 average rating, 5 reviews

Waterfront Pool Home w/ Private Dock, Tiki Hut & B

Captain’s Hideout, your 4BR waterfront escape in Marathon’s Little Venice, built for boaters, families, anglers, and easy Keys living with quick access near Vaca Cut to the Gulf. 🏊‍♂️ Private backyard pool ⛵ 28’ dock with fish cleaning table 🌴 Huge tiki hut hangout area 🍳 Outdoor kitchen + dining space 🧊 Commercial ice machine + bait freezer 🛏️ Ground-level comfort for 10 🐾 Pet & kid friendly with pack ’n play + highchair

4.95 out of 5 average rating, 152 reviews

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

Perfect for families, couples, groups, or solo travelers, this spacious home offers 5 bedrooms, 3 bathrooms, an open living room, and a fully stocked kitchen. Easy to reach and simple to access, it’s set in a peaceful neighborhood close to island fun and water adventures. Just a short walk to Sweet Savannah’s Ice Cream & Sweets Parlor, this retreat is ideal for relaxing or exploring. We look forward to hosting you!

4.94 out of 5 average rating, 206 reviews

70ft Dock, Bikes, Beach, Spacious, 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.

The backyard features a pool surrounded by a marble deck, with lounge chairs and an umbrella for shade. A tiki hut with seating stands nearby, complemented by landscaped greenery and palm trees. The multi-level home is illuminated softly against the evening sky.

5.0 out of 5 average rating, 18 reviews

Luxury Oasis, Pool, Kayaks, Dock, Near Beach

Welcome to Casa De Cayo 🏆 Featured in Rolling Stone as one of the best Airbnbs for large groups Exactly what you want from the Florida Keys—just 1 mile from Sombrero Beach. This modern 3BR retreat shines outdoors with a pool, tiki hut kitchen, hammock, and 40’ deep-water dock (no lift use), plus kayaks & paddleboard for the perfect island stay.

Popular amenities for Marathon family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Upper Sugarloaf Key

The bungalow stands illuminated against a night sky, surrounded by swaying palm trees. Soft reflections shimmer on the water's surface, while the sandy beach extends along the shoreline. The structure features large windows, showcasing a welcoming interior visible from outdoors.

The Lighthouse - Beach Houses Key West

4.93 out of 5 average rating, 134 reviews

4.95 out of 5 average rating, 108 reviews

4BR 3B, Heated Pool & Spa, 60' Dock

The image captures a private dock setup with several tall pilings along the water's edge. Two adirondack chairs are placed on a grassy area, and a palm tree provides partial shade. The serene bay views and clear blue sky enhance the tranquil atmosphere of the outdoor space.

4.85 out of 5 average rating, 189 reviews

Waterview from three sides, Cabana Club, 30' Docks

4.96 out of 5 average rating, 213 reviews

An aerial view showcases a coastal community with a spacious beach area, palm trees, and turquoise waters. The two-story unit features a large balcony above the entrance, with the surrounding buildings and lagoon clearly visible, highlighting the vibrant landscape of the area.

Home in Cudjoe Key

Cudjoe Key Home with a View

4.88 out of 5 average rating, 102 reviews

A bright living area features a comfortable gray sofa, decorative chairs, and a coffee table on a patterned rug. Natural light floods the space through large windows, creating a relaxed atmosphere. A wall-mounted TV and a small desk can also be seen, along with coastal decor.

Flat in Tavernier

When Paradise is Key: Tropical Oceanfront Condo

4.83 out of 5 average rating, 112 reviews

A heated pool is surrounded by a spacious deck, featuring lounge chairs and a dining table with blue chairs. Beyond the pool, a pathway leads to lush greenery and the ocean view under a partly cloudy sky.

Home in Cudjoe Key

Palm Breezes! Room for Everyone on the Ocean.

A renovated house is set on a corner lot, surrounded by palm trees and coral stone landscaping. The exterior features light yellow walls and white accents. A gravel driveway offers ample parking space, complementing the tranquil tropical environment.

4.93 out of 5 average rating, 164 reviews

Marathon Star - home with hot tub

The living area features contemporary furnishings and large windows, allowing for bright natural light and views of the waterways. A dining table is positioned beside the seating area. The spacious lanai showcases an outdoor dining setup with a view of the dock and water.

4.95 out of 5 average rating, 148 reviews

Paradise in Key Colony Beach + Cabana Club

Family- and pet-friendly home rentals

4.86 out of 5 average rating, 619 reviews

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

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

4.95 out of 5 average rating, 173 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 Villa with Slip!

A private wooden dock extends over calm waters, featuring a boat with a blue canopy and a small table with colorful umbrellas nearby. Palm trees line the waterfront, and a series of pastel-colored homes are visible across the canal, creating a serene setting.

5.0 out of 5 average rating, 126 reviews

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

A serene view of a canal populated by several pelicans floating on the water's surface. Palm trees line the shore, and colorful houses are visible in the background. A boat is docked nearby, enhancing the peaceful coastal scene.

4.98 out of 5 average rating, 129 reviews

Waterfront House with 37 ft Dock & Cabana Club

4.91 out of 5 average rating, 160 reviews

An aerial view showcases the resort's layout, featuring a sparkling pool surrounded by palm trees and lounge chairs. A canal runs parallel to the property, with well-maintained pathways visible alongside the greenery and buildings.

Townhouse in Marathon

*Sept $pecial pricing* CLBoathouse/Marathon FL

5.0 out of 5 average rating, 10 reviews

A Paradise Point by Sombrero Beach

5.0 out of 5 average rating, 6 reviews

Entire private two family water front home.

5.0 out of 5 average rating, 5 reviews

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

Family-friendly home rentals with a pool

A two-story house is surrounded by lush greenery and palm trees. A spacious backyard features a heated pool and a wooden dock. Loungers are arranged near the pool, providing a relaxing outdoor space. The exterior showcases large windows and a balcony with seating.

4.98 out of 5 average rating, 88 reviews

Sombrero beach vacation paradise, great location

4.93 out of 5 average rating, 82 reviews

Beach House, Private Pool, Dock, Gulf View Sunsets

Aerial view of a two-story yellow home is shown, surrounded by a fenced yard with a spacious pool and patio area. Several sun loungers are positioned near the pool. Nearby, a boat dock and a grassy area can be seen, alongside other similar homes.

4.89 out of 5 average rating, 98 reviews

Summer Sale~New 4/3/pool/40f dock

A spacious pool area is framed by tropical landscaping, showcasing a large, clear swimming pool. Sun loungers are arranged around the pool, providing places to relax. A tiki hut offers shaded seating options, enhancing the outdoor living experience with serene water views.

4.84 out of 5 average rating, 50 reviews

Waterfront Keys Home | Pool, Hot Tub & 35’ Dock

5.0 out of 5 average rating, 5 reviews

*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!

A welcoming living area is highlighted by large windows that let in natural light. Two armchairs and a small table are positioned in front of a light-colored sofa. An elegant green console table is placed along one wall, enhancing the space's charm.

5.0 out of 5 average rating, 15 reviews

Kingsail Resort Home

A private pool with crystal-clear water reflects sunlight, featuring a large inflatable flamingo floating serenely. The surrounding area is bright and spacious, with a view of a light-colored house and tropical greenery in the background.

4.99 out of 5 average rating, 81 reviews

Casa Blue Flamingo