Family-friendly holiday rentals in Southampton

4.91 out of 5 average rating, 141 reviews

Home in Springs

Serene + private ~ 1 block to waterfront dining

Enjoy zen living at this serene, chic, Hamptons oasis! Ideally located 1 block to waterfront dining, 8 minutes to beaches + 9 minutes to Main St! Relax poolside w/ tons of greenery + nature views. Spark up the BBQ + firepit under the starry sky. Listen to the crickets + spot a deer on the property. Curl up to the wood burning fireplace, cook in your Chef's kitchen + stream on your 80' TV Enjoy coffee on the sea + dinner w the best sunsets just 1 block away. A perfect escape + place to unwind!

4.94 out of 5 average rating, 334 reviews

An enclosed outdoor living space features a wooden deck overlooking a heated pool. Furnished with a large round table and comfortable seating, natural light floods through the screens, creating an airy atmosphere. Elegant trees and lounge chairs visible outside enhance the serene environment.

Home in Bridgehampton

Amazing Home close to Everything -

Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grounds are smoke-free.

4.96 out of 5 average rating, 109 reviews

A vibrant pool scene is captured, featuring a colorful unicorn float positioned on the water. Lush hydrangea blooms frame the area in shades of pink, complementing the surrounding greenery and the wooden fence that provides privacy.

Apartment in Southampton

Swimming pool w/Hot tub Fire Pit Coffee Bar

Relax in this cozy loft filled with amenities that will create lasting memories. Recently renovated so fresh and clean. Located on a wooded lot. Large fenced in landscaped yard with hammocks and firepit. Heated pool seasonal. We are just minutes from the beach. Spend time in our 6 person jacuzzi. 10 min to Southampton village. 15 min to Sag Harbor. Centrally located. Fresh farm (home of Tate’s Cookies) around the corner with fresh meats and produce. A tasty restaurant near by and a deli too.

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.

4.97 out of 5 average rating, 154 reviews

Stylish+Modern Cape w/Saltwater Pool-5min 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.

4.91 out of 5 average rating, 202 reviews

Home in Sag Harbor

Barefoot Bliss | Quiet Family Retreat Heated Pool

Welcome to your Hamptons retreat. This bright single-level home sits in a quiet neighborhood just minutes from Main Street and the ocean. The private fenced yard overlooks a peaceful nature preserve and features a heated pool (June–Sept, heating available for a fee), hot tub, outdoor fireplace, and outdoor shower—perfect after a beach day. Family-friendly amenities include a sandbox, toys, crib, and highchair, with a separate safety fence surrounding the pool for added peace of mind.

5.0 out of 5 average rating, 113 reviews

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

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

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.

4.87 out of 5 average rating, 138 reviews

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.

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.

4.94 out of 5 average rating, 116 reviews

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!

Home in Westhampton Beach

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.

4.98 out of 5 average rating, 173 reviews

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.

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.

4.95 out of 5 average rating, 204 reviews

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong

Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

4.94 out of 5 average rating, 166 reviews

A well-maintained outdoor pool area is surrounded by a wooden deck and lush greenery. Lounge chairs are positioned along the pool, with a shaded area provided by a large tree. The clear blue water of the pool reflects the sunlight, inviting relaxation.

Home in Water Mill

Astounding Watermill 5 Bedroom home with Pool

Situated off of a quiet lane on a half-acre of land, updated, modern residence offers a peaceful and quiet Hamptons getaway. 5 bedrooms / 3 modern bathrooms offers a relaxing escape. Large open kitchen leads out to the back garden, pool and indoor-outdoor eating areas. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

Apartment in Shinnecock Hills

A wide sandy beach stretches towards the horizon, where soft waves gently lap at the shore. Tall lifeguard stands are positioned along the beach, with a few distant figures walking. The sky features a gradient of muted colors as the sun sets, creating a serene atmosphere.

4.95 out of 5 average rating, 244 reviews

Sunny Southampton Studio

Newly renovated sun drenched, spacious studio in Southampton. Five minute drive to Main Street, while still in close proximity to some of the most beautiful beaches. Queen size bed and queen size pull out couch. Full kitchen with new appliances and full bathroom. BEACH PASS for Coopers beach is available upon advanced request—please let me know the day before you arrive

Popular amenities for Southampton family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Superhost

The living area is characterized by high vaulted ceilings and large windows allowing natural light. A sofa with light cushions is centered around a wooden coffee table on a neutral rug. A decorative fireplace is framed with a modern mantle, adding warmth to the space.

Home in Southampton

4.83 out of 5 average rating, 220 reviews

Stylish & Chic w hot tub/ Near Beaches & Village

4.96 out of 5 average rating, 184 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

4.98 out of 5 average rating, 145 reviews

A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.

Home in East Hampton

Explore the Water & Woods at a Relaxing Retreat

4.78 out of 5 average rating, 145 reviews

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

4.97 out of 5 average rating, 218 reviews

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, 163 reviews

A contemporary house exterior features a combination of wood and metal finishes, set against a backdrop of lush greenery. Large glass windows provide ample natural light, and a pathway of stepping stones leads through a manicured lawn, enhancing the inviting atmosphere.

Home in East Hampton

East Hampton (walking distance to village)

Home in Westhampton Beach

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.

4.93 out of 5 average rating, 165 reviews

Hampton's Haven

Superhost

A cozy bedroom features a queen bed with a light blue quilt and a green loveseat nearby. Natural light enters through sliding glass doors, revealing a serene outdoor space. A decorative plant and framed artwork add a touch of interest to the room.

Guesthouse in East Hampton

4.82 out of 5 average rating, 349 reviews

Detached bungalow w/ private bath

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 123 reviews

Cottage in Hampton Bays

Hamptons Cottage.

Apartment in Hampton Bays

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.

4.97 out of 5 average rating, 443 reviews

Private & Cozy Cottage with short walk to beach!

4.93 out of 5 average rating, 134 reviews

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

4.92 out of 5 average rating, 130 reviews

The exterior of a two-story home is visible, featuring large glass windows that promote natural light. A spacious wooden deck hosts a dining area with a white umbrella. Lush green grass and trees surround the area, creating a serene outdoor setting.

Home in Water Mill

Elegant Modern Artist's Residence

Campervan/RV in Southampton

A travel trailer is nestled among tall trees, surrounded by a gravel area. Outdoor seating, including metal chairs and a table, is arranged nearby. The trailer features large windows and an awning that provides shade, creating a serene outdoor space for relaxation.

4.83 out of 5 average rating, 191 reviews

Large Camper, Weekend Getaway from it all

Superhost

The airy living space features white shiplap walls and a high ceiling, accented by natural light from multiple windows. A gray sofa is paired with a glass coffee table, while a decorative fireplace adds charm. A ceiling fan provides airflow, enhancing the inviting atmosphere.

Home in Southampton

4.89 out of 5 average rating, 309 reviews

PICTURE PERFECT SOUTHAMPTON HOME-

4.93 out of 5 average rating, 108 reviews

A bright living area is furnished with a leather sofa and a dark coffee table, positioned on a textured rug. Natural light filters through large windows, illuminating the space. A staircase leads to an upper level, with wooden accents enhancing the modern design.

Home in Bridgehampton

Pool Central Private Bridgehampton Home

4.95 out of 5 average rating, 523 reviews

A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.

Home in Springs

Silver House: 3BR Home with Private Beach Access

Family-friendly home rentals with a pool

4.9 out of 5 average rating, 136 reviews

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.

Apartment in Montauk

Ocean View Studio with King Bed

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.

4.89 out of 5 average rating, 114 reviews

*Hamptons Oasis* 4BR Cool Getaway

4.99 out of 5 average rating, 151 reviews

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

4.93 out of 5 average rating, 140 reviews

A spacious backyard is highlighted by a blue in-ground pool surrounded by lounge chairs. Red umbrellas provide shade, while a tall wooden fence adds privacy. Lush green grass complements the natural setting, and a rustic home is visible in the background among the trees.

Home in Springs

Private & Pristine with Pool and Kid’s Playard

4.91 out of 5 average rating, 11 reviews

Home in Southampton

Southampton Village Escape

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.

4.95 out of 5 average rating, 59 reviews

Spectacular Southampton Retreat!

A bright and airy outdoor space features a long pool bordered by lounge chairs and greenery. The white house stands in the background, with large windows reflecting the blue sky. An umbrella provides shade beside the pool, promoting relaxation.

4.98 out of 5 average rating, 61 reviews

Luxe Southampton Home w/Pool 5 Min To Town & Beach

A sparkling pool reflects the clear blue sky, surrounded by a sleek stone patio. Lounge chairs are positioned nearby, inviting relaxation. Lush greenery and vibrant gardens frame the space, enhancing the private outdoor setting.