Family-friendly holiday rentals in Marathon

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, 172 reviews

Sea Ray Cove w/ 80' Dock, Pool, Beach & Tiki Hut

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.

A stunning view of 'The Islander' Villa overlooks open water, showcasing a spacious heated pool with surrounding patio areas. Lush palms sway in the breeze, and the two-story home features large balconies designed for enjoying the scenic surroundings.

5 out of 5 average rating, 27 reviews

World-Class Oceanfront Pool/Hottub Sunset Escape

Escape to Oceans Cay Villas—luxury oceanfront in the Florida Keys. Why you’ll love the Islander: ✨ Heated swimming pool + Relaxing HOT TUB! ✨ Fire pit with perfect sunset views ✨ Fishing, snorkeling, and swimming in your backyard ✨ Free kayaks, paddle boards, and bicycles ✨ Walk or ride to Seven Mile Bridge ✨ Walking distance to restaurants and attractions ✨NO SEAGRASS SMELLS! ✨ Ping pong table ✨ Private dock for your boat ✨ Stylish, modern villa design ✨ Breathtaking SUNRISE and SUNSET views

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, 141 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 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.

4.99 out of 5 average rating, 137 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!

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 out of 5 average rating, 76 reviews

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Welcome to Paradise Palms: ⭑ 1750 sqft liveable space on 10,500 sqft estate ⭑ Private home, deck, patio & backyard, overlooking a beautiful scenic landscape ⭑ Crystal pool, hot tub, movie theater, remote workspace, game room with arcade & more ⭑ Secure parking for up to six vehicles, boat trailer parking, RV and EV charging ⭑ 10 min to sombrero beach & just minutes to all island attractions ⭑ Fully stocked kitchen ⭑ Extremely safe neighborhood License #VACA-24-20 License #VACA-24-32

A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.

4.94 out of 5 average rating, 140 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.

4.93 out of 5 average rating, 117 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.

Condo in Marathon

Waterfront Condo, daily housekeeping & breakfast!

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!

4.93 out of 5 average rating, 384 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.

An aerial view of the waterfront area shows vibrant turquoise waters and lush greenery. The scene includes several residential buildings along the coastline and a nearby marina, with boats visible on the water and the horizon illustrating a scenic expanse.

4.93 out of 5 average rating, 242 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in the beautiful Florida Keys! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

4.87 out of 5 average rating, 582 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

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!

5 out of 5 average rating, 110 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

Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.

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, 144 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

Popular amenities for Marathon family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 150 reviews

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

4.95 out of 5 average rating, 106 reviews

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

4.92 out of 5 average rating, 323 reviews

Home in Key West

Family House, 2 K BR's, Private Spa/Deck, 2 pools.

Townhouse in Key Colony Beach

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.

5 out of 5 average rating, 12 reviews

Castillo Del Mar- Ocean access from your backyard

5 out of 5 average rating, 84 reviews

Luxury Boating Paradise+Pool+Sailing Kayaks

5 out of 5 average rating, 17 reviews

P87 - Modern 4 bedroom, 4 bath home on open water

4.83 out of 5 average rating, 110 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.

The waterfront patio features a wooden dock leading into the calm water, surrounded by neatly arranged lounge chairs and palm trees. The single-story home is seen in the background with large glass doors and windows, allowing for ample natural light.

5 out of 5 average rating, 41 reviews

Boat Dock+King Bed & Cabana Club

Family- and pet-friendly home rentals

A bright living area is showcased with a sectional sofa and a round coffee table. Natural light fills the space, highlighted by decorative lamps and greenery visible through the windows. A woven rug adds texture to the wooden floor, contributing to a relaxed atmosphere.

4.96 out of 5 average rating, 55 reviews

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

An outdoor area features a fenced pool surrounded by colorful chairs. Palm trees provide shade, and the spacious deck above is visible. The setting reflects a relaxed atmosphere with nearby greenery enhancing the tranquil environment.

4.87 out of 5 average rating, 30 reviews

Soothing Nest

4.75 out of 5 average rating, 130 reviews

Houseboat in Marathon

Tiny Home Aqua Lodges 2/1

4.91 out of 5 average rating, 44 reviews

Dog-Friendly • Pool & Boat Dock • Sombrero Beach

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.

4.89 out of 5 average rating, 92 reviews

Gorgeous Ocean View Home!

4.9 out of 5 average rating, 41 reviews

Golf Coast Oasis near Sombrero Beach

An outdoor theater area is outlined by a modular seating arrangement with blue cushions and dark wicker. A large projection screen is mounted on a wooden wall, creating an inviting space for movie nights. Soft lighting from overhead strands completes the ambiance.

4.93 out of 5 average rating, 45 reviews

Oceanview Marathon - Screened Porch, Theater & Bar

The living area features a comfortable sofa arranged around a coffee table, with large windows offering views of the balcony. A modern kitchen with granite countertops and stainless steel appliances is visible, providing ample space for meal preparation.

4.86 out of 5 average rating, 14 reviews

Sombrero Getaway Poolside Retreat with Canal Views

Family-friendly home rentals with a pool

A modern three-story home is depicted, showcasing a charming facade with a balcony above two sets of large windows. Lush greenery surrounds the entrance, while a pathway of pavers leads to the front door. The architecture reflects a contemporary style with natural elements.

5 out of 5 average rating, 6 reviews

Home Away from Home Pet Friendly - Marlin Bay

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, 83 reviews

Sombrero beach vacation paradise, great location

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.

5 out of 5 average rating, 7 reviews

3/2 Home w Dock, lagoon, kayaks!

5 out of 5 average rating, 54 reviews

Heated&Cooled PrivatePool/CabanaClub/Bikes/PaddleB

A serene pool area is framed by palm trees and lush greenery, offering views of the ocean. Comfortable lounge chairs are positioned around the pool, which features a spa. The scene includes bright umbrellas, enhancing a relaxing outdoor space under a clear blue sky.

4.98 out of 5 average rating, 62 reviews

Oceanfront with Pool near Sombrero Beach

An aerial view captures the property's prime location along the waterfront, highlighting proximity to Sombrero Beach and the 7 Mile Bridge. The tranquil waters and nearby coastal homes enhance the inviting atmosphere of this tropical getaway.

5 out of 5 average rating, 6 reviews

Waterfront Oasis3/2 Direct Ocean

4.92 out of 5 average rating, 76 reviews

Beach House, Private Pool, Dock, Gulf View Sunsets

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.