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Family-friendly holiday rentals in Flanders

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Flanders

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.
Home in Hampton Bays

Stylish + Modern Cozy Cape - 5 min to beach

Stylish+Modern Cape Beach House nestled in Hampton Bays South of the highway, 5 min drive to beaches. Heated Saltwater Pool. 4 Bedrooms+Crib room & Office. 2 Bathrooms. Outdoor deck w/family dining+BBQ. Fully-fenced, tree-lined back yard w/ beautiful sunsets. Upstairs King bedroom w/ensuite bthrm + Twin bedroom directly off master. Main floor has another King bedroom+Twin bedroom, master bath, lounge+kitchen w/huge sit-around island. TV Den. Central AC. 15 min walk/ 2 min drive to shops+train.

FamilyKitchenCleanliness

4.98 out of 5 average rating, 160 reviews
Guest favourite
A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.
Home in Mattituck

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Indoor spacesFamilyQuiet

4.94 out of 5 average rating, 139 reviews
Top guest favourite
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.

Indoor spacesFamilyCleanliness

4.98 out of 5 average rating, 184 reviews
Guest favourite
A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.
Home in Hampton Bays

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views and sunset from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Our pool will close on September 15th, 2026 and will reopen May 29, 2027.

Indoor spacesFamilyHeating

4.87 out of 5 average rating, 144 reviews
Guest favourite
A charming beach cottage is set against a clear blue sky, featuring a welcoming enclosed front porch. Surrounding gardens are filled with vibrant pink and purple flowers, framing the path leading to the front door and adding to the property’s tranquil ambiance.
Cottage in North Fork

Charming Beach Cottage, Vineyards & Sunset Views

Take it easy at this unique and tranquil beach getaway. Steps to white sandy beach and walk to nearby steak & seafood restaurant as well as our local Post Office & Book Depisitory . Enjoy harvest season festivities, all in the heart of Long Island wine country! Exclusive & Historic South Jamesport is conveniently located on the Peconic Bay and scenic North Fork of Long Island. Explore vineyards, breweries, farm stands, restaurants combined with beautiful beaches.

Indoor spacesKitchenBeach

4.88 out of 5 average rating, 33 reviews
Guest favourite
A spacious backyard is showcased with a large saltwater pool, featuring a floating inflatable and sun loungers arranged along the edge. The house stands in the background, framed by trees and an inviting grassy area, enclosed by a black fence.
Home in Hampton Bays

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

Unwind in Hamptons Bliss! A coastal oasis awaits at this exquisite vacation house. Immerse yourself in luxury, from the elegant interiors to the serene outdoor retreat including a massive fenced-in salt water heated pool (Memorial Day to Labor Day) that will leave you in awe. Indulge in beachside bliss, upscale shopping, and culinary delights. Create memories that will linger long after the sun sets over the horizon. Your dream Hamptons getaway starts here!

FamilyIndoor spacesCheckout

4.94 out of 5 average rating, 119 reviews
Top guest favourite
A modern living area is highlighted by a gray sofa centered on a low coffee table. Two armchairs are placed to one side, while a textured area rug complements the space. Wall art hangs above the sofa, and natural light enters through large windows.
Home in North Fork

Walk to Beautiful Beach in Heart of Wine Country

Enjoy bright, comfortable and modern home in the heart of North Fork wine and farm country located just a quick walk from a gorgeous Peconic Bay beach with tennis/pickleball courts, volleyball and playground right on the beach. You'll have easy and quick access to the best of the east end: beautiful beaches, boating, fishing, fine and casual dining, vineyards, wineries, breweries, farms and farm stands offering fresh local produce, antique and local shops.

KitchenFamilyAccuracy

4.96 out of 5 average rating, 167 reviews
Guest favourite
Flat in Flanders

Stylish & Modern Touches Move-In-Ready

Musu&Oscar Residential is a home away from home, located in a cool and serene environment on the East End of Long Island, Flanders, New York. It is a stand-alone, self-contained 2-Bedroom apartment that stands out in the attractive town of Southampton for travellers and visitors looking to have quality time away with friends, loved ones, family or just for that "me time" that you have always wanted all by yourself in a relaxed and hospitable atmosphere.

KitchenIndoor spacesAmenities

4.79 out of 5 average rating, 48 reviews
Top guest favourite
A charming cottage exterior features wood shingles and white trim. An American flag hangs proudly from the front, while window boxes with greenery add a touch of color. The light blue front door complements the natural elements, inviting guests inside.
Home in Westhampton Beach

Luxury Hamptons Home with Heated Saltwater Pool

Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.

KitchenFamilyComfort

4.98 out of 5 average rating, 179 reviews
Top guest favourite
Home in Hampton Bays

Luxury Hamptons Getaway w/ Private pool- sleeps 14

Escape to this private Hamptons retreat in the exclusive Bay-Woods enclave of Hampton Bays. Set on a beautifully landscaped acre, the home is just 10 minutes to ocean beaches, 5 minutes to the bay, and 10–15 minutes to Southampton Village for dining, shopping, nightlife, and Cooper’s Beach. Enjoy peaceful luxury, outdoor living, and the perfect location for a relaxing Hamptons getaway. Shinnecock Hills Golf Club is also just minutes away.

FamilyKitchenLocation

4.84 out of 5 average rating, 131 reviews
Top guest favourite
An outdoor deck features a dining table surrounded by six chairs, positioned over the water. The scene includes a marina with boats and lush greenery. A tranquil sunset casts soft hues across the landscape, enhancing the serene environment.
Cottage in Flanders

Bayside bliss - Charming 2bdrm on the water w dock

Lovely 2 bedroom cottage located on the water with your own private dock. 2 queen beds, 1 bathroom, and full kitchen. Enjoy a blissful kayak along the shores of the Peconic Bay. Easy access to the North and South Forks of Long Island, famous wine trails, Ocean Beaches, and amazing farms. 2 kayaks included in the rental. Experience the food, drink, and beautiful scenery with a short drive to all of the Hamptons and the North Fork.

FamilyKitchenCleanliness

4.95 out of 5 average rating, 75 reviews
Guest favourite
Flat in Hampton Bays

Charming Apt in the Heart of the Hamptons

Welcoming studio apartment with queen bed, living room and spacious full bathroom. Kitchenette complete with laundry. Small deck with delightful creek-side views. And this unit includes cable TV and Wi-Fi. Please note that there is an extra fee of $75. per stay for each pet, There is a queen sofa bed in living area for quests at $75 additional fee. This unit is attached to the main house.

Indoor spacesKitchenTV

4.96 out of 5 average rating, 107 reviews

Popular amenities for Flanders family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favourite
A contemporary ranch-style home is surrounded by lush greenery. The custom-shaped heated pool features a waterfall and is bordered by a stone patio with lounge chairs and umbrellas. A state-of-the-art hot tub is positioned nearby, enhancing the outdoor relaxation space.
Home in Westhampton Beach

Hampton's Haven

FamilyKitchenCheck-in

4.93 out of 5 average rating, 167 reviews
Guest favourite
The exterior of a modern two-story home features a sleek white facade with large windows allowing for ample natural light. A covered porch provides a welcoming entrance, alongside neatly arranged greenery and stone pathway leading to the front door.
Home in Southampton

Southampton Village Newly Built Gem

KitchenIndoor spacesNearby

4.97 out of 5 average rating, 103 reviews
Guest favourite
A modern farmhouse is set on a spacious lot. The architecture features a blend of dark and light siding with a white chimney. A well-maintained path leads to a front porch, surrounded by landscaped greenery, enhancing the inviting curb appeal.
Home in Sound Beach

Luxury modern farmhouse with heated pool & hot tub

KitchenFamilyTV

4.93 out of 5 average rating, 148 reviews
Guest favourite
A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.
Home in North Fork

Private Oasis W/Stunning Vinyard and Pool Views

FamilyIndoor spacesAir conditioning

4.97 out of 5 average rating, 218 reviews
Guest favourite
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

FamilyKitchenAccess

4.95 out of 5 average rating, 212 reviews
Top guest favourite
Home in Commack

GOOD VIBEZ HOUSE! Mini Golf+Pool+Hot Tub+Game Room

FamilyKitchenHot tub

4.99 out of 5 average rating, 188 reviews
Top guest favourite
Home in Branford

Steps to Beach • Hot Tub • Game Room • Water Views

Indoor spacesFamilyAmenities

4.99 out of 5 average rating, 113 reviews
Guest favourite
Flat in Flanders

Hamptons Waterfront Suite | Private Hot Tub

Indoor spacesFamilyHospitality

4.94 out of 5 average rating, 106 reviews

Family- and pet-friendly home rentals

Guest favourite
A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.
Home in Shinnecock Hills

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong

KitchenFamilyComfort

4.95 out of 5 average rating, 206 reviews
Top guest favourite
The exterior of a historic Tudor home is shown, featuring a blend of brick and wood accents. A winding driveway leads to the entrance, surrounded by lush greenery and a decorative black fence. Trees provide shade, enhancing the serene outdoor setting.
Guest suite in North Fork

Walk to Vineyards, Beaches, Farms & Town

FamilyIndoor spacesHospitality

4.88 out of 5 average rating, 755 reviews
Guest favourite
Home in East Quogue

Est.1840 Farmhouse | Heated Pool & by Bay

KitchenFamilyNearby

4.94 out of 5 average rating, 102 reviews
Top guest favourite
A calm waterfront scene shows a serene body of water reflecting the sky. A sandy beach is visible, framed by natural vegetation, with a wooden barrier along the shoreline. The peaceful setting invites relaxation and enjoyment of the outdoors.
Flat in Hampton Bays

Private & Cozy Cottage with short walk to beach!

KitchenFamilyWalkability

4.97 out of 5 average rating, 449 reviews
Guest favourite
A spacious backyard is framed by mature trees, featuring a fire pit surrounded by white Adirondack chairs. A children’s playground with swing set is visible nearby, while the home, illuminated by warm lights, stands invitingly in the background.
Villa in Southampton

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

FamilyKitchenValue

5.0 out of 5 average rating, 118 reviews
Guest favourite
A modern cottage is set amidst lush greenery, featuring a spacious rear deck and a lower patio area with two lounge chairs. The second story includes a covered deck with an awning, while large windows invite natural light into the interior.
Home in Mattituck

Walk to Breakwater Beach in Heart of Wine Country

FamilyIndoor spacesAir conditioning

4.93 out of 5 average rating, 120 reviews
Guest favourite
Home in Flanders

East End Escape

Indoor spacesKitchenCheckout

4.86 out of 5 average rating, 35 reviews
Top guest favourite
Home in East Quogue

Cozy Home with Pool - Near Beach and Restaurants

FamilyKitchenCheck-in

4.97 out of 5 average rating, 58 reviews

Family-friendly home rentals with a pool

Guest favourite
An expansive ocean view is showcased from the studio, featuring calm waters that reflect the sunlight. Soft waves gently lap at the sandy shore, while lush greenery lines the foreground, contrasting with the clear blue sky above.
Flat in Montauk

Ocean View Studio with King Bed

FamilyIndoor spacesComfort

4.89 out of 5 average rating, 142 reviews
Guest favourite
The living area features high ceilings and large windows that fill the space with natural light. A neutral-colored sofa and loveseat provide comfortable seating, complemented by a simple coffee table. A ceiling fan enhances air circulation, while a welcoming rug adds warmth to the wooden floor.
Home in Hampton Bays

*Hamptons Oasis* 4BR Cool Getaway

FamilyIndoor spacesValue

4.89 out of 5 average rating, 115 reviews
Top guest favourite
A landscaped outdoor area features a stone fire pit surrounded by bright blue chairs on a gravel surface. Lush greenery and tall trees provide privacy, while a spacious pool bordered by lounge chairs is situated in the background.
Home in East Quogue

Beach House Feel - Newly renovated Backyard Oasis

Indoor spacesKitchenBack garden

4.99 out of 5 average rating, 153 reviews
Top guest favourite
Home in Hampton Bays

Hampton Bays 6 bed/5 bath large secluded property

Indoor spacesFamilyDecor

4.97 out of 5 average rating, 73 reviews
Guest favourite
A large outdoor pool is surrounded by lounge chairs and umbrellas, inviting relaxation. Well-maintained gardens and trees frame the area, with a spacious deck along one side. The bright blue sky enhances the tranquil atmosphere of this inviting outdoor retreat.
Home in Shinnecock Hills

Spectacular Southampton Retreat!

FamilyIndoor spacesOutdoor spaces

4.95 out of 5 average rating, 62 reviews
Guest favourite
Home in Westhampton

Chic Hamptons Gateway | Pool, Hot Tub, Beach

Indoor spacesKitchenAmenities

5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Westhampton

NEW DECK! Private, Heated Pool, Home Office & Gym

KitchenIndoor spacesGrill

4.98 out of 5 average rating, 65 reviews
Guest favourite
A grassy backyard area features a circular arrangement of four wooden Adirondack chairs surrounding a fire pit. In the background, a saltwater heated pool is visible, framed by lush trees and shrubs, creating a serene outdoor space.
Home in Hampton Bays

Designer Home w/ Heated, Salt-Water Pool

FamilyKitchenSleep quality

4.94 out of 5 average rating, 63 reviews

Destinations to explore