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Family-friendly holiday rentals in Flanders

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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.

4.98 out of 5 average rating, 160 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.

4.98 out of 5 average rating, 184 reviews
Top guest favourite
A contemporary home with large windows overlooks a serene pool area. Lush greenery surrounds the property, providing a natural backdrop. Sun loungers are positioned beside the pool on spacious stone decking, inviting relaxation and outdoor enjoyment.
Home in Westhampton Beach

Hamptons Oasis: pool, grill, lush landscape

Kick back and relax in this calm, stylish, contemporary masterpiece. 4 beds, 3 baths, eco pool, and expansive outdoor living space. Architecturally impressive structure surrounded by lush landscape and tastefully decorated. The outdoor space includes a pool, a new outdoor grill, a fire pit, pool lounge chairs, a dining table under a wisteria pergola and an outdoor sofa area big enough to fit your entire party. Fully equipped kitchen. Short drive to the beach and to downtown Westhampton.

4.95 out of 5 average rating, 146 reviews
Guest favourite
Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

4.96 out of 5 average rating, 189 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.

4.87 out of 5 average rating, 144 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!

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.

4.96 out of 5 average rating, 168 reviews
Guest favourite
A bright living area features light-colored walls and wooden flooring. A comfortable sofa and a plush chair are arranged around a rustic coffee table. A ceiling fan hangs above, while a kitchen with a blue island is visible in the background, enhancing the space's openness.
Home in Mattituck

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

4.92 out of 5 average rating, 180 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.

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.

4.84 out of 5 average rating, 131 reviews
Top 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

Can't beat autumn in the Hamptonsl. The beaches, sun, shopping, restaurants & nightlife. Or just stay at the house. It has everything you might need for a family vacation. With a spacious deck and firepit, the backyard might be all you need. And it's walking distance from town (groceries, coffee, train station & more). The neighborhood is super quiet. 55in LG TV, WiFi, X-Box, board games. Pool closes in September. Families only please.

4.89 out of 5 average rating, 115 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.

4.95 out of 5 average rating, 75 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

4.93 out of 5 average rating, 167 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

4.97 out of 5 average rating, 218 reviews
Guest favourite
Flat in Flanders

Hamptons Waterfront Suite | Private Hot Tub

4.94 out of 5 average rating, 106 reviews
Top guest favourite
Home in Branford

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

4.99 out of 5 average rating, 113 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

4.95 out of 5 average rating, 212 reviews
Guest favourite
The image captures a spacious outdoor area featuring a large heated pool with a fountain and surrounding stone patio. Nearby, lounge chairs are arranged for relaxation, while a generous lawn stretches in the background, accompanied by a well-designed home nestled among trees.
Home in East Hampton

Sprawling Hamptons Estate with Hot Tub & Amenities

4.78 out of 5 average rating, 146 reviews
Superhost
The open living area features a custom slate pool table with a vibrant arrangement of billiard balls. A modern kitchen is visible in the background, including sleek cabinetry and a refrigerator. A tasteful seating area includes a fireplace and a large wall-mounted television.
Home in Shirley

By NYC & Hamptons - Hot Tub, Pool Table, Speakeasy

4.93 out of 5 average rating, 272 reviews
Top guest favourite
The farmhouse, constructed in 1856, is showcased with its classic white exterior and black accents. Large windows allow natural light to fill the space, while lush greenery surrounds the property. A pebble pathway leads to the entrance, enhancing the inviting atmosphere.
Home in Old Lyme

Modern Farmhouse with Hot Tub in Old Lyme, CT

4.97 out of 5 average rating, 231 reviews

Family- and pet-friendly home rentals

Guest favourite
Home in East Quogue

Est.1840 Farmhouse | Heated Pool & by Bay

4.94 out of 5 average rating, 102 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

4.88 out of 5 average rating, 755 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!

4.97 out of 5 average rating, 449 reviews
Top guest favourite
A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.
Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

4.96 out of 5 average rating, 222 reviews
Guest favourite
The living room features a bright and airy arrangement with a large white sectional sofa and a coffee table at the center. Natural light streams through the wide windows, creating a welcoming environment. A front door and a lamp add to the cozy feel of the space.
Cottage in Hampton Bays

Hamptons Cottage 3-minute walk to breezy bay beach

4.92 out of 5 average rating, 151 reviews
Guest favourite
Home in Flanders

East End Escape

4.86 out of 5 average rating, 35 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

4.88 out of 5 average rating, 33 reviews
Guest favourite
A calm beach scene is depicted at sunset, with vibrant colors reflecting off the water's surface. The sandy shore stretches into the distance, bordered by gently lapping waves. Soft clouds create a gradient of hues in the evening sky, enhancing the tranquil atmosphere.
Home in Riverhead

The Perfect Bay House Escape

4.91 out of 5 average rating, 57 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

4.89 out of 5 average rating, 142 reviews
Guest favourite
A serene pool area is surrounded by lush greenery and colorful hydrangea flowers. Lounge chairs offer relaxation under large umbrellas, while the inviting pool reflects the clear blue sky. A charming home stands in the background, adding to the peaceful setting.
Home in Southampton

Southampton Charmer, 5 bedrooms w pool - Location

4.93 out of 5 average rating, 139 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

4.99 out of 5 average rating, 153 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!

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

Chic Hamptons Gateway | Pool, Hot Tub, Beach

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

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

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

4.94 out of 5 average rating, 63 reviews
Guest favourite
A spacious salt-water pool is framed by a paved patio and secured by a black fence. White lounge chairs are positioned nearby, with two adirondack chairs visible under trees in the background. String lights are hung along the patio area, enhancing the outdoor setting.
Home in East Quogue

After Beach Family Retreat

4.95 out of 5 average rating, 65 reviews

Destinations to explore