Family-friendly vacation rentals in Fire Island

A vibrant blue exterior of the cottage is complemented by wooden decking, leading to an inviting entry. A couple of white chairs provide a space to relax, while colorful buoys hang decoratively. Glass bottles scatter along the ground, adding character to the outdoor area.

4.94 out of 5 average rating, 192 reviews

Fire Island Pines Mid-Century Beach Cottage

This Fire Island Pines house is an Early-Pines artist's paradise. Our house was once written up in House & Garden (photo spread at house), and provides an authentic bohemian Pines lifestyle: Layered decks descend the hill for sun and shade with main decks surrounding, plus a roof-top deck for 4, all make for a party-friendly space; secluded on two old-growth lots for plenty of get-away privacy. Beautiful white-sand beach only 150 steps away. You'll fall in love with this unique Pines experience.

Guest suite in Fire Island

The cabin's entrance is framed by lush greenery and flowering plants. A wooden walkway leads to the door, and a small set of steps offers access. The rustic exterior features dark wood siding and a window for natural light.

4.96 out of 5 average rating, 105 reviews

Fire Island Pines: Studio Cabin

Studio cabin (approx. 13.5 x 15 ft.) Functional, basic, rustic, atmospheric—It's just a little cabin in the woods. The shack can accommodate only 2 people max. Queen bed (sheets, blankets) Bathroom (shower/towels) Kitchenette (fridge, microwave, sink, dishwasher, dishes, cutlery, glasses) A/C (window unit) Fan Basic tv Internet Beach chairs/umbrellas, Outside shower The Pines is primarily a gay community, but welcoming to all. We love our wild deer and squirrels but no pets in the cabin

An outdoor deck space is surrounded by lush bamboo. Several wooden chairs and a picnic table are arranged for seating, offering a serene environment for relaxation. The area is shaded by leafy trees, contributing to a calm atmosphere.

4.84 out of 5 average rating, 123 reviews

Fire Island Getaway! Weeks/Weekends/Midweeks!

VILLA ÉTOILE: 100 Yards/meters from Fire Island's best beach in a quieter, family area. Our simple 3-bedroom classic bungalow sleeps up to 6. Two bathrooms (1 w/shower). Whole-house A/C in summer! Screened windows & fans; front & back decks + balcony. Huge outdoor shower, BBQ, bikes, wagon, port-a-crib, games, 2 TVs, Netflix, beach chairs/umbrellas/toys, full cooking gear, condiments, etc. We rent to families & QUIET groups who agree to STRICT noise rules. Parties NOT allowed! Minimum age 25.

4.96 out of 5 average rating, 139 reviews

A charming red barn-style house is framed by a vibrant field of wildflowers. Various hues of blue, red, and white blossoms create a colorful foreground, while lush greenery surrounds the property, contributing to a serene natural setting.

Barn in Katonah

Magic Red Barn with Heated Salt Pool (opened now)

Escape to magic, just one hour from NYC. No car really necessary. Immerse yourself in nature’s wonderland: wildflowers blooming in June, scenic trails, and vibrant local farmers’ markets. Unwind in a heated saltwater pool and cedar soaking tub. Sleep in a stunning renovated loft — 1,000 sq ft of luxury in a private barn. Ideal for family or friends: 1 king, 2 queens, and a toddler bed. Full kitchen with oven, microwave, and half fridge. Fiber optic Wi-Fi. Privacy guaranteed: no other guests.

Superhost

A spacious living area features large glass windows that frame a stunning sunset over the water. The open design enhances natural light, illuminating the room's elegant furnishings and wooden accents. A dining table is positioned near the windows, inviting relaxed meals with a view.

Cabin in Shirley

4.83 out of 5 average rating, 206 reviews

A-Frame cabin with private beach & epic sunsets

Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

4.98 out of 5 average rating, 175 reviews

A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.

Cottage in Riverhead

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

4.89 out of 5 average rating, 169 reviews

An outdoor deck is seen featuring a spacious octagonal hot tub. It overlooks a calm canal bordered by green grass and trees. Nearby boats are docked, and the tranquil water reflects the clear sky, creating a peaceful atmosphere.

Home in Oakdale

Waterfront Round House View

A unique little beach house on the south shore of long island with the most beautiful view. The house is located on a canal. Dock is available! **We have Paddle Boards, Surf Boards and 3- 2 person Kayaks onsite for you to use during your stay. You can get to the Great South Bay by paddling to the mouth of the canal. And you can get to Fire Island by hiring a Water Taxi to pick you up! The octagon house was built in the 1970s. It's recently been refreshed with all new beds & linens.

4.97 out of 5 average rating, 221 reviews

A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

4.94 out of 5 average rating, 401 reviews

A welcoming living area features a comfortable couch and a textured ottoman, complemented by natural wood accents on the ceiling. Light fills the space from multiple windows, highlighting the hardwood floors and decorative stone wall that adds character to the room.

Cottage in Milford

Summer Sale! CozyCottage/Pet-friendly/ WalktoBeach

Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

4.95 out of 5 average rating, 172 reviews

Home in Centerport

The Harbor House: Beachfront Home 1 hour from NYC

FEATURED #1 on Refinery29's "11 Best Beach Houses Near NYC" Welcome to Long Island’s iconic Gold Coast! Wake up to sweeping waterfront views and, if you’re lucky, catch a glimpse of our local bald eagle family soaring overhead! Explore nearby gems like the Vanderbilt Mansion & Planetarium, Caumsett State Historic Park Preserve, Del Vino Vineyards, and the lively Paramount Theatre. Stroll through Downtown Huntington or Northport Village for boutique shopping, great restaurants.

4.99 out of 5 average rating, 106 reviews

The exterior of a charming cottage displays a white facade with dark blue trim and a welcoming front door. A well-manicured lawn featuring stepping stones leads up to the porch, surrounded by colorful flower beds and greenery.

Home in Patchogue

Hamptons Style Cottage close to everything!

Hamptons style cottage home is family friendly with a wonderful, fully equipped, kitchen to cook-in and spa inspired marble bathroom with huge shower and soaking tub to relax in. Rear patio with nicely landscaped yard shaded or unshaded by a large retractable awing. Located in Patchogue on a quiet block just a short walk to the fire island ocean ferries, restaurants, town's bustling main street, local bay beaches, and parks. Perfect for a weekend getaway or an extended stay!

4.99 out of 5 average rating, 121 reviews

The living area features two rattan chairs facing a coffee table, surrounded by vibrant wall art. A cozy sofa and plants add life to the space. Natural light streams through large windows, creating a bright and inviting atmosphere.

Home in Montauk

3 BR/Pool. Walk to Beach & Town!

Welcome to Good Tauk – a cheerful, retro-inspired 3BR, 2BA cottage tucked in the heart of Montauk and walkable to town and the beach. Thoughtfully renovated and full of personality, it’s perfect for families or longer stays. The vibe is fun, relaxed, and unmistakably Montauk. Outside, unwind in your private backyard with a pool, grill, and dining patio—ideal for lazy afternoons and sunset dinners. Just minutes from the beach, town, and everything that makes Montauk magical.

Popular amenities for Fire Island family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a pool

Superhost

The home theater features a large screen and 15 electric recliner seats arranged in a semi-circle. Dark blue walls and patterned carpeting create a cozy movie-watching environment. Subtle lighting enhances the overall ambiance without overwhelming brightness.

Guest suite in Northport

4.91 out of 5 average rating, 143 reviews

Coastal Villa Suite pool•sauna•gym•theater•beach

4.93 out of 5 average rating, 151 reviews

A patio is shown with a wooden table and a dark wicker chair overlooking a scenic view. A clear sky with scattered clouds is visible in the background, along with open fields and distant structures. Utility poles line the road, adding context to the setting.

Home in Patchogue

Joyful Beach House, viewing The Great South Bay

4.96 out of 5 average rating, 203 reviews

A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.

Cottage in Guilford

Luxury cottage by the sea with hot tub and pool

4.95 out of 5 average rating, 124 reviews

An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.

Cottage in Putnam Valley

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

4.92 out of 5 average rating, 132 reviews

Home in Springs

Chic, 1 block to waterfront dining,8 mins Main St

Home in Westhampton Beach

A spacious saltwater pool is surrounded by a well-manicured yard, featuring lounge chairs and large umbrellas. Water features create gentle splashes, enhancing the serene environment. The area is framed by trees, providing a natural backdrop for relaxation.

4.97 out of 5 average rating, 108 reviews

Brand new house with an all year round hot tub.

4.96 out of 5 average rating, 112 reviews

Home in North Fork

Stunning Farmhouse in NoFo I Heated Pool, Wineries

4.9 out of 5 average rating, 154 reviews

Two blue Adirondack chairs are positioned on a manicured lawn, facing a vibrant sunset over the ocean. The sky displays pink and orange hues as the sun sets on the horizon, creating a serene outdoor setting.

Condo in Greenport

Beachside Waterview 2Br Condo w/ Pool in Greenport

Family-friendly home rentals with air conditioning

4.86 out of 5 average rating, 70 reviews

A two-story house is set among tall grasses, showcasing light grey siding with teal accents. Large windows dominate the upper level, allowing natural light to fill the interior. A spacious deck is visible, providing outdoor space for relaxation.

Home in Ocean Beach

Fire Island 4BR; Bay Views; Big Deck (no cars!)

A bright living space features two comfortable chairs with patterned cushions facing a marble coffee table. A television is mounted on the wall, and large glass doors lead to an outdoor area, allowing natural light to fill the room.

5 out of 5 average rating, 6 reviews

2BR Bungalow: Fire Island Pines

Guesthouse in Fire Island

An outdoor deck area features a gas grill, a small round table with two blue chairs, and a wooden privacy screen. Surrounding greenery offers a natural backdrop, and the sunlight enhances the inviting space for relaxation or outdoor dining.

4.92 out of 5 average rating, 92 reviews

One Bedroom Cottage in Cherry Grove

4.97 out of 5 average rating, 74 reviews

A well-maintained outdoor area features two blue lounge chairs facing a sandy beach. Pathways of stepping stones lead towards the water, framed by green grass and beach access. A gazebo is positioned nearby, complementing the serene coastal view.

Cottage in Patchogue

Toes in the Sand Beach Cottage

Guesthouse in Fire Island

A group of eight individuals stands in front of a brightly lit sign displaying the word 'PINES' in multicolored letters. The wooden deck is visible beneath them, with a vibrant atmosphere created by colorful lighting in the background.

5 out of 5 average rating, 32 reviews

2 BR Private Suite w/Private Living Room & Kitchen

4.95 out of 5 average rating, 74 reviews

An open living area features a comfortable dark sofa adorned with decorative pillows. Behind it, high stools are situated at a breakfast bar connected to the kitchen. Natural light enters through window treatments, while wooden beams create a warm ambience overhead.

Cottage in Fire Island

Charming Beach Cottage in OCEAN BAY PARK

A wooden deck extends toward a multi-level home set amidst lush greenery. Stairs lead to the entrance, which features railings and a large window, surrounded by trees and grass, contributing to a natural setting.

5 out of 5 average rating, 49 reviews

Fair Harbor, Fire Island sunny 3 bedroom

A serene heated pool is framed by lush greenery and flowering plants. The pool's clear water reflects the sky, while wooden decking provides a natural finish. Brightly colored pots add vibrancy to the surrounding landscape.

5 out of 5 average rating, 7 reviews

Charming Quintessential Beach House

Family-friendly home rentals with a kitchen

4.97 out of 5 average rating, 75 reviews

A spacious private deck is furnished with various seating options, including lounge chairs and a dining table. An umbrella provides shade over the seating area, while a gas grill is positioned nearby. Lush greenery surrounds the deck, creating a serene outdoor environment.

Home in Ocean Beach

4BR Spacious Beach House in Ocean Beach

5 out of 5 average rating, 52 reviews

A serene night scene showcases a heated salt water pool, illuminated in calming blue hues. Several lounge chairs are positioned around the pool area on a paver patio, surrounded by a white privacy fence that enhances the tranquil ambiance.

Home in East Quogue

Hamptons Getaway/ Backyard OASIS/EV charger

4.98 out of 5 average rating, 44 reviews

An expansive view shows a huge heated saltwater pool surrounded by a lawn. Lounge chairs are positioned poolside, and an umbrella offers shade. The home is seen in the background, featuring a spacious deck and access stairs. Lush greenery lines the property, contributing to a tranquil atmosphere.

Home in Center Moriches

40x20 Heated Salt Pool · Sun Deck · Sleeps 6

The image captures a sandy beach area bordered by lush grass, leading to two nearby wooden houses. A sunset sky illuminates the scene with soft hues, while the water gently reflects the changing colors. Relaxation and coastal charm are evident in this serene setting.

4.85 out of 5 average rating, 53 reviews

Bay Front Upper Level Cottage 47E

A spacious living area features a large blue sectional sofa adorned with tropical throw pillows. A white coffee table sits in front, complemented by a small side table. Natural light fills the space through multiple windows, and a striped rug adds texture to the wooden floor.

4.95 out of 5 average rating, 44 reviews

Spacious "Playhouse" - Ocean Bay Park

5 out of 5 average rating, 36 reviews

An outdoor deck features a large dining table surrounded by multiple chairs, shaded by a sun umbrella. In the background, beach chairs and an umbrella are set on the sand, with calm waters extending toward the horizon.

Home in North Fork

Hang by the (Chel)SEA

Superhost

The exterior of a green cottage features a white picket fence and neatly trimmed hedges. An American flag is displayed from the porch, where a door with a decorative window adds character. Large windows allow natural light to brighten the space.

Home in Ocean Beach

4.88 out of 5 average rating, 17 reviews

Beach and Town House Steps to ALL!

An open-roofed porch features a large table surrounded by six chairs, with a sun umbrella providing shade. An outdoor BBQ unit and a cozy seating area create an inviting space for gatherings, all complemented by bright natural light and wooden elements.