Family-friendly vacation rentals in Water Mill

A modern, sleek structure is surrounded by lush greenery, featuring a private pool and spacious patio area. Chaise lounges are positioned beside the clear water, while large glass doors provide a view of the interior, inviting natural light into the space.

4.89 out of 5 average rating, 156 reviews

Modern House close to the beach

This modern home has all the amenities and comfort you would expect. You are 5 minutes from Southampton Village, 5 minutes from Flying Point Beach by car. Spacious back yard with beautiful patio furniture which gives onto beautiful pond. Fully equipped kitchen with Wolf stove. Lots of sun on this property. Quiet back patio area with barbecue and patio furniture. Fireplace available in the winter months. We use cotton linen and towels. Pool open in May. Pool heating is an additional cost.

KitchenFamilyCheckout

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.

Indoor spacesKitchenNearby

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.

FamilyIndoor spacesTV

4.91 out of 5 average rating, 202 reviews

Home in Sag Harbor

Offseason Monthly, Utilities Included

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.

Indoor spacesFamilyDecor

4.96 out of 5 average rating, 175 reviews

Family Friendly House in Southampton Village

Cozy, spacious Southampton Village house in family neighborhood. Great for families & large groups or mid-week meetings for your business team. Fully equipped kitchen for cooking & serving family meals for up to 20 people. Also, great space for business meetings to meet in person during these times where everyone is working remotely. Secluded yet walkable to Village, train & Jitney. Beach minutes away. Ping pong, Movie/TV room, Fuss Ball table, bicycles & many spaces for quiet thought.

Indoor spacesFamilyCheck-in

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.

Indoor spacesKitchenDecor

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.

4.89 out of 5 average rating, 310 reviews

PICTURE PERFECT SOUTHAMPTON HOME-

Picture Perfect 3 bedroom 1.5 Bath Cottage located in the heart of Southampton. The home is conveniently located close to Southampton, Bridgehampton and Sag Harbor towns. Additionally, there is close access to both Bay and Ocean Beaches. The Newly renovated home gives you a peaceful and serene feeling everyday. Dogs are accepted on a case by case basis. Cats are not permitted. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

Indoor spacesKitchenSleep quality

4.94 out of 5 average rating, 116 reviews

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!

FamilyKitchenDecor

4.95 out of 5 average rating, 204 reviews

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

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.

FamilyKitchenAccess

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

Longer stay and reduced rate please email 169bridgehamptoncottage@gmail.com. NOTE* Rest assured, as always, even more so now, our housekeeper is aware to put in the extra tedious clean needed for a happy healthy stay! 7 minute drive to Hampton classic or less 20 min bike ride. Restaurants, studio 89 gym, on same rd. Ocean+bay 5-10 min drive. Bike to 1 ocean Yoga/winery. Halfway to Sag Harbor+Bridgehampton. There is pet fee.

KitchenIndoor spacesSleep quality

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.

4.92 out of 5 average rating, 130 reviews

Elegant Modern Artist's Residence

This simple and serene home is set against a farm preserve, exposed to beautiful light and views and biking distance to the beach. Very relaxing - a terrific, creative space for a couple or small group. We are a pet friendly home so if allergic please be aware. A large vegetable garden is maintained on the property and is available for guests to harvest as they like. Fresh salad greens, herbs, vegetables for you to enjoy!

KitchenIndoor spacesWalkability

A bright living area features a white sofa adorned with patterned blue pillows, positioned beside a rustic wooden coffee table. Large glass doors open to reveal a glimmering pool and lush outdoor landscaping, enhanced by vibrant potted plants and a shaded seating area.

4.89 out of 5 average rating, 149 reviews

Serene 3 Bed 2.5 Bath House w/Heated Pool

Situated off a quiet lane on a half-acre, this designer, updated, modern residence offers a peaceful and quiet Hamptons getaway. 3 wonderful bedrooms 2 modern bathroom and a heated saltwater pool ( See Pool heat and Pool Closure Details ) with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

KitchenFamilyBackyard

Popular amenities for Water Mill family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.83 out of 5 average rating, 220 reviews

Stylish & Chic w hot tub/ Near Beaches & Village

Indoor spacesFamilySleep quality

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.

4.98 out of 5 average rating, 145 reviews

Explore the Water & Woods at a Relaxing Retreat

FamilyKitchenLong stay

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.

4.78 out of 5 average rating, 145 reviews

Sprawling Hamptons Estate with Hot Tub & Amenities

KitchenIndoor spacesValue

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

FamilyKitchenHospitality

4.96 out of 5 average rating, 184 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

FamilyIndoor spacesOutdoor spaces

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.

4.97 out of 5 average rating, 163 reviews

East Hampton (walking distance to village)

KitchenFamilyWifi

4.92 out of 5 average rating, 145 reviews

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

Indoor spacesFamilyLocation

Guesthouse in East Hampton

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.

4.82 out of 5 average rating, 350 reviews

Detached bungalow w/ private bath

FamilyIndoor spacesSolo travel

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 164 reviews

A private entrance features a white door set against a backdrop of textured wooden siding. Colorful purple irises bloom along the stone pathway, complemented by lush greenery, contributing to the inviting exterior of the studio apartment.

Apartment in Southampton

Southampton Village Studio

Indoor spacesKitchenHospitality

4.87 out of 5 average rating, 138 reviews

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

KitchenIndoor spacesTV

4.93 out of 5 average rating, 135 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

KitchenFamilyCleanliness

4.96 out of 5 average rating, 199 reviews

A spacious living area features high ceilings and natural light streaming through large windows. A white sofa is paired with wooden chairs, while a glass coffee table sits on a woven rug. An elegant dining area is visible in the background with a large table.

Cottage in Southampton

Charming Southampton Light filled Cottage

FamilyKitchenHeating

4.95 out of 5 average rating, 266 reviews

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

Home in Springs

Private beach, fully updated house, on 2 acres.

FamilyIndoor spacesCondition

4.97 out of 5 average rating, 155 reviews

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 Cape w/Saltwater Pool-5min to Beach

Indoor spacesFamilyAmenities

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

Indoor spacesKitchenGrill

4.83 out of 5 average rating, 191 reviews

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.

Camper/RV in Southampton

Large Camper, Weekend Getaway from it all

FamilyIndoor spacesAccuracy

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 11 reviews

Southampton Village Escape

KitchenFamilyWalkability

The outdoor area features a large, heated saltwater pool surrounded by lounge chairs. Lush hydrangeas bloom nearby, adding color to the landscape. A two-story home stands in the background, accented by patio umbrellas and trees, contributing to a relaxed garden atmosphere.

4.93 out of 5 average rating, 59 reviews

Awesome Watermill 5 Bedroom with a heated pool

Indoor spacesKitchenHospitality

An aerial view showcases a modern house surrounded by greenery, featuring large glass windows and multiple outdoor decks. A heated pool is nestled below, flanked by lounge chairs and umbrellas, creating an inviting space for relaxation and enjoyment.

5.0 out of 5 average rating, 18 reviews

Modern Oasis in Southampton

KitchenFamilyAmenities

4.91 out of 5 average rating, 74 reviews

Southampton Labor Day Private House Pool

FamilyKitchenOutdoor spaces

4.87 out of 5 average rating, 76 reviews

Home in Shinnecock Hills

Chic Southampton Home. Mins to Village and Beach!

FamilyKitchenGrill

An inviting outdoor seating area features multiple lounge chairs and a central table surrounded by manicured grass. A heated inground pool is visible in the background, framed by lush greenery and a blue sky. Colorful cushions add a touch of comfort to the space.

5.0 out of 5 average rating, 11 reviews

Perfect SouthHampton getaway

FamilyCheck-inBackyard

4.95 out of 5 average rating, 42 reviews

A spacious living room is featured, characterized by whitewashed beams and large windows allowing natural light. A soft, neutral sofa is positioned in front of a gold-accented coffee table. Decorative plants and a subtle area rug add warmth to the space, enhancing the inviting atmosphere.

Cottage in Bridgehampton

Hamptons Designer Cottage w Pool by Wölffer Estate

KitchenFamilyWalkability

A private swimming pool reflects clear blue skies, surrounded by lounge chairs and umbrellas. Lush greenery frames the scene, while a wooden deck leads to the main house, which features a modern architectural design. A swing set adds an element of leisure to the serene outdoor space.