Family-friendly vacation rentals in Marathon

5.0 out of 5 average rating, 4 reviews

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

Wake up to endless open-water views at your private Marathon oceanfront retreat. Designed for families, boaters and groups, this 4-bedroom Florida Keys home combines a private pool, spectacular sunset views and a 60 foot private dock with direct access to the water. Bring your boat, fish from the dock, cool off in the pool, or settle in with a drink. The dock includes water for rinsing boat and flushing engines, while the spacious two story layout gives everyone room to gather and room to relax.

4.95 out of 5 average rating, 161 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

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

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, 150 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.

5.0 out of 5 average rating, 5 reviews

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

Searenity is a newly updated ground level vacation rental! A direct shot to the Gulf in about two minutes and nestled in a nice quiet neighborhood on Dolphin Drive in Marathon, this home is in a great central location! There is plenty of dockage for your boat and a gorgeous tropical back yard with everything you need for the perfect Keys vacation - pool with jets, tiki hut, grill, outdoor refrigerator, fish cleaning station, two kayaks, two bikes, back porch, and plenty of outdoor furniture!

5.0 out of 5 average rating, 5 reviews

Lagoona-Matata

A truly magical place "Lagoona-Matata" sits on the edge of Vaca Cut showcasing fabulous views of the Gulf. The outdoor area flows from the patio to the pool deck, private sandy beach, tidal pool and then to the pier dock. "Vaca Cut" is a fast-moving body of water from incoming to outgoing tides with fish of every kind moving through that makes fishing from the dock great entertainment. The continuous plethora of sea life in the lagoon makes this property an experience unlike any other.

4.97 out of 5 average rating, 219 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

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

A tropical backyard features a private saltwater pool surrounded by seating areas. A thatched-roof Tiki Hut is adorned with string lights. A gas fire pit sits centrally, while walls are embellished with colorful fish murals. Lush greenery completes this inviting outdoor space.

4.91 out of 5 average rating, 116 reviews

Tiki Time! Private Pool~Tiki Hut~Kayak~Grill!

Tiki Time ~ your private paradise in beautiful Marathon, heart of the Florida Keys! This is the perfect place for a family vacation or relaxing getaway. Gorgeous 3BR home with your own private salt water pool, Tiki Hut, space to park a 30' boat/trailer, and ocean views from the balcony~Kayak, grill, beach toys await you for your beautiful day in the Florida Keys! Less than 5 min to Sombrero Beach, Dining & Local Bars! Experience the Florida Keys like a local and book Tiki Time today!

4.93 out of 5 average rating, 391 reviews

A solar and wind powered houseboat is moored on calm waters, featuring bright yellow shutters and a roof deck. Wind turbines and an American flag adorn the top, contrasting with the soothing blue sky and fluffy clouds in the background.

Boat in Islamorada

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

A private backyard features a swimming pool bordered by lounge chairs in a cool turquoise hue. Nearby, a shaded seating area with a round structure is visible. Lush greenery surrounds the space, enhancing the tropical ambiance.

4.93 out of 5 average rating, 100 reviews

Valhalla Beach House

Discover Valhalla (paradise) with everything you'll need for the perfect Florida Keys private getaway of a lifetime! Relax with the whole family at this peaceful tropical resort style backyard. Spend your day lounging by the private pool while enjoying your favorite drink, while the rest of the family can enjoy the pool table, ping-pong table, Dominoes and much more! This centrally located, fully equipped home is ready for your ultimate family vacation getaway!

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.

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.

4.97 out of 5 average rating, 147 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

4.95 out of 5 average rating, 108 reviews

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

Enjoy breathtaking views of the Gulf and Ocean from the screened in patio of this beautiful 4 BEDROOM/3 BATH canal front home. Bring your boat to the 60' dock on a 200' wide canal just 10' away from the Ocean. Relax by the pool/spa area after a day of fishing. A pool heater is offered as an option for your convenience. Please inquire about water heater fee and operating instructions before booking. (VR Lic # PLR2020-00104)

Popular amenities for Marathon family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a pool

A sparkling in-ground pool is visible in the foreground, surrounded by a spacious patio. Lounge chairs are positioned along the deck, offering views of the lagoon. Lush palm trees provide shade, while a clear sky enhances the tranquil atmosphere of the waterfront setting.

4.99 out of 5 average rating, 176 reviews

Oct. Cancellation Deals: 10/17 thru 10/31

5.0 out of 5 average rating, 116 reviews

A private backyard features a heated pool surrounded by tropical landscaping. Lounge chairs are positioned on the wooden deck beside the pool. The two-story home includes large glass doors that open onto the deck, providing easy access to outdoor spaces.

Home in Duck Key

Private Pool Tropical Oasis - Centrally Located

A wooden dock extends over calm water leading to a circular stone embankment. Lush greenery and palm trees surround the scene, alongside a distant white building with green roofing. The clear blue sky and gentle water highlight the serene waterfront setting.

4.92 out of 5 average rating, 12 reviews

3/2 Home w Dock, lagoon, kayaks!

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.

4.91 out of 5 average rating, 86 reviews

Beautiful Beachfront Home w/ Pool/Tiki/Dock

5.0 out of 5 average rating, 5 reviews

Entire private two family water front home.

5.0 out of 5 average rating, 4 reviews

Coastal Keys Escape - New Pool, Dock & Quick Ocean

The exterior features a two-story turquoise house with large windows. A private saltwater pool is surrounded by lounge chairs, offering a relaxing space. Kayaks are visible in the background, with palm trees framing the scene under a colorful sky.

4.98 out of 5 average rating, 40 reviews

Ocean's Edge Retreat

A heated pool is situated in the backyard, surrounded by lounge chairs. Lush palm trees and a view of the waterfront create a serene outdoor space, with gentle clouds drifting across a bright blue sky.

4.93 out of 5 average rating, 46 reviews

Coco Plum Paradise - Marathon 5 BR 4 BA Waterfront

Family-friendly home rentals with air conditioning

4.77 out of 5 average rating, 146 reviews

Houseboat in Marathon

Tiny Home Aqua Lodges 2/1

A waterfront property is depicted, featuring a contemporary two-story design with light blue and yellow exterior accents. A private dock is visible alongside the house, and a clear sky reflects over the calm water, enhancing the serene coastal environment.

5.0 out of 5 average rating, 21 reviews

Boating Paradise Villa rental Lic# VACA-25-124

An inviting outdoor space features comfortable seating and a hot tub, surrounded by lush greenery. A large screen is set up for movie nights, and ambient lighting enhances the evening atmosphere as the sun sets.

5.0 out of 5 average rating, 80 reviews

Tropical Keys Retreat | Pool | Hot Tub | Cinema

5.0 out of 5 average rating, 24 reviews

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

4.93 out of 5 average rating, 94 reviews

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

b watervibe

This aerial view captures a canal front home, showcasing two private pools on the lawn and a dock for boat access. The surrounding greenery complements the spacious outdoor areas, while the coastal setting is highlighted by the water's edge.

4.97 out of 5 average rating, 32 reviews

Get Hooked private pool & dock

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.

4.92 out of 5 average rating, 48 reviews

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

5.0 out of 5 average rating, 14 reviews

Waterfront Pool Home w/ 30’ Dock, Kayaks & Outdoor

Family-friendly home rentals with a kitchen

A resort-style pool is surrounded by lounge chairs, set on a brick patio with a view of palm trees and the ocean. The scene is bright and open, showing a clear sky with scattered clouds, enhancing the outdoor leisure space.

4.8 out of 5 average rating, 15 reviews

Oceanview Rooftop Retreat 3BR 3BA in Marathon FL

A clear view of a swimming pool framed by lush greenery and manicured grass, extending toward the Atlantic Ocean. The tranquil water reflects the blue sky above, enhancing the serene setting.

4.89 out of 5 average rating, 19 reviews

SAY'S BY THE SEA

Vacation home in Marathon

A spacious living area features a gray sectional sofa adorned with blue accent pillows. Light wood tables complement the hardwood floor. A large painting of a coastal scene is displayed on the wall, and natural light filters in through shuttered windows.

4.93 out of 5 average rating, 55 reviews

Cabana Club Condo: Key Colony Beach, FL

5.0 out of 5 average rating, 17 reviews

A two-story house is set against a clear blue sky, featuring balconies and a light blue exterior. A wooden dock extends into tranquil water, with paddleboards and kayaks visible. A heated pool is surrounded by palms, offering a relaxing outdoor space.

Villa in Marathon

Marathon Villa w/ Priv Pool/Dock Sombrero Beach

A shaded outdoor area features a small private pool surrounded by lounge chairs. A white table sits nearby, offering a space for refreshments. A view of the boat dock and palm trees creates a relaxing atmosphere perfect for enjoying sunny days.

4.96 out of 5 average rating, 46 reviews

Villa Bella 3/3 with Private Pool & NEW Dock!

An aerial view captures a waterfront property featuring multiple pools surrounded by lush greenery. The colorful houses are highlighted against the clear blue water, with the distant horizon blending into the sky. Nearby homes and a small marina are visible, adding to the serene setting.

4.98 out of 5 average rating, 48 reviews

Waterfront Home| Heated Pool + Dock+Kayaks

A spacious hot tub is positioned beside a large saltwater pool, overlooking the Atlantic Ocean. Two lounge chairs face the water, creating a serene spot for relaxation. Lush greenery and a rocky shoreline enhance the coastal ambiance.

5.0 out of 5 average rating, 33 reviews

Direct Oceanfront Private Paradise - Pool/Spa/Dock

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.