Family-friendly vacation rentals in Southampton

4.87 out of 5 average rating, 102 reviews

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

5 out of 5 average rating, 104 reviews

A lush backyard features a children's playset alongside a hammock. Adirondack chairs are arranged around a fire-pit, framed by trees and greenery. A serene waterfront view is visible, with a dock extending into the calm waters, enhancing the natural landscape.

Villa in The Hamptons

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.

4.96 out of 5 average rating, 163 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 The Hamptons

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

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, 284 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 –

4.83 out of 5 average rating, 195 reviews

The studio features a queen-sized bed adorned with a floral-patterned blanket. A comfortable sofa and armchair are positioned nearby, along with a small table. Natural light filters through a nearby door, illuminating the warm wood flooring.

Condo in The Hamptons

Coastline View Studio

This sun drenched studio apartment is perfect for families, couples or friends looking to get away and discover Montauk! Located in Montauk's harbor district. This unit is perfectly located to experience all that Montauk has to offer... Sit back on the balcony and enjoy a glass of wine as the sun sets perfectly over Culloden Point. A short walk to the Harbor, the Dock, Gosmans, TTs, Salivars, Sunday Funday, La Fin, Viking Fleet (fishing, Whale watching & Ferry).

A modern kitchen space features a granite countertop with high-backed bar stools positioned for dining. Glass-front cabinets display dishware, and a sliding door opens to a sunny outdoor area with a pool and patio seating.

4.97 out of 5 average rating, 263 reviews

Stunning 3 bed 2 bath home W Pool

Nestled on a serene an acre off a tranquil lane, this contemporary, designer-updated residence provides an idyllic Hamptons retreat. With 3 delightful bedrooms, 2 sleek bathrooms, and a seasonal heated pool amidst mature landscaping, you're promised a calming respite. We kindly ask that you familiarize yourself with the detailed disclosures, & guidelines. We maintain a strict policy against events, parties, and smoking. our home and property grouds are smoke-free.

Guesthouse in The Hamptons

A cozy living space features a brown leather sofa and a white coffee table on a geometric patterned rug. A large window allows natural light to fill the room, showcasing a wall-mounted fish decor and colorful accents. A decorative plant sits on the table.

4.96 out of 5 average rating, 452 reviews

Tiny Home in Prime Spot in Southampton Village

Price drop! Located in the heart of Southampton Village, this intimate cottage is the perfect getaway! Nestled in an accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station or to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet.

4.94 out of 5 average rating, 129 reviews

A spacious room features a queen-size bed adorned with a light gray quilt. Bedside tables with lamps flank either side, and a decorative bench sits at the foot of the bed. Natural light filters through the sheer curtains, enhancing the calming color palette.

Apartment in North Fork

J&J's BnB Lovely, BR/Bath w/ Private Entrance!

Welcome to Jeanette and Jims Airbnb! We are avid travelers and look forward to hosting you on your trip to beautiful Long Island! Lovely, clean updated private room with private separate entrance and bathroom. Great location on a quiet wooded acre. 2 miles from Splish Splash. 3.6 miles from the Long Island Aquarium. 8.7 miles from Cupsogue Beach. 4.8 miles from Baiting Hollow Farm Vineyard. So much to do near by. Head easily to the north or south fork!

4.93 out of 5 average rating, 148 reviews

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 North Fork

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.

A bright and airy living space features large windows allowing natural light to fill the room. Wooden dining chairs surround a rectangular table, while comfortable seating is arranged in a cozy arrangement. Indoor plants add a touch of greenery, enhancing the inviting atmosphere.

4.93 out of 5 average rating, 123 reviews

Classic Southampton Village Home w/ Pool

Newly renovated Southampton village home with great light, offering the best of indoor-outdoor living. A beautiful backyard with a pool surrounded by lush privet hedges for privacy. Perfectly situated in the heart of the village, one block from restaurants, shopping, and one mile from the ocean beaches. Perfect with space to spread out, play or work remotely! Ask about special rates for long-term summer rental!

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.

4.94 out of 5 average rating, 144 reviews

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 – no exceptions!

Apartment in The Hamptons

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, 221 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

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 210 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

4.96 out of 5 average rating, 117 reviews

A two-story oceanfront home features a light gray exterior with large windows and a turquoise front door. A spacious ground level is accessible via white railings, leading to an outdoor sitting area. The serene beach and water views are visible in the background.

Home in Milford

Oceanfront Retreat with Hot Tub

4.93 out of 5 average rating, 170 reviews

1800 Historical EH Home, 1 Mile to Town!

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, 147 reviews

East Hampton (walking distance to village)

4.98 out of 5 average rating, 132 reviews

A vibrant sunset fills the sky with hues of pink, orange, and purple, reflecting on the tranquil water. Silhouettes of two birdhouses are visible on posts in the foreground, framed by lush vegetation along the shore.

Home in Milford

3 Bedroom Beach House with Hot Tub!

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, 136 reviews

Explore the Water & Woods at a Relaxing Retreat

4.83 out of 5 average rating, 170 reviews

A serene pond is complemented by a charming wooden bridge leading to a small island bordered by smooth stone landscaping. The lush greenery surrounds the tranquil water, with trees providing dappled sunlight, enhancing the peaceful ambiance of the outdoor space.

Home in Bayport

Luxury Waterfront Oasis • Modern Retreat for 8

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, 217 reviews

Stylish & Chic w hot tub/ Near Beaches & Village

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 136 reviews

A cozy living space features exposed wooden beams and natural light streaming through the windows. A small kitchenette with modern appliances is visible, alongside a comfortable sofa and a rustic wooden coffee table. Decorative shelves and a unique tree branch accent add character to the room.

Tiny home in Mastic

Cozy craftsman style home close to beaches

A cozy living area features a light-colored sofa adorned with blue and white throw pillows. Woven armchairs flank a wooden coffee table, while a stone fireplace adds warmth. Two large windows allow natural light to fill the space, complemented by greenery and decorative accents.

4.98 out of 5 average rating, 102 reviews

Sea Roost

Guesthouse in The Hamptons

A serene view of a spacious barn with a deck illuminated by the golden light of sunset. Surrounded by lush foliage, the barn features large windows and a welcoming porch, providing a glimpse of modern yet comfortable architecture.

4.9 out of 5 average rating, 214 reviews

Beautiful Airy Barn in Springs

5 out of 5 average rating, 120 reviews

An aerial view captures the beachside neighborhood with the glimmering water in the background. The Tyde wedding venue is marked, along with the listing's address. Lush greenery and residential homes are visible, showcasing the proximity to the shore and nearby amenities.

Home in Milford

HGTV reno! Fall Foliage, near New Haven, Firepit!

A dining set featuring a large wooden table with eight matching chairs is positioned under a spacious umbrella, offering shade. Lush greenery and a serene waterfront view are visible nearby, providing a peaceful outdoor setting.

4.98 out of 5 average rating, 104 reviews

Breezy Waterfront Home With private Dock

Apartment in The Hamptons

A compact entryway features a mirrored console table with lighting, enhancing the sense of space. A small dining area with two stools is positioned beside a refrigerator. A plant sits on the table, adding a touch of greenery. Soft seating and a rug complete the inviting atmosphere.

4.93 out of 5 average rating, 215 reviews

Private paradise 3 min from town ice skating pond!

4.91 out of 5 average rating, 632 reviews

A bright studio cottage features a spacious bed with light linens and a working fireplace. A round table with two white chairs sits on a soft area rug, while a blue accent chair is positioned in the corner. Soft light enters through large windows.

Bungalow in The Hamptons

Montauk Oceanview with Fireplace (2)

4.95 out of 5 average rating, 350 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

Fall Sale! CozyCottage/Pet-friendly/Walk to Beach

Family-friendly home rentals with a pool

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.

4.94 out of 5 average rating, 32 reviews

Designer Home w/ Heated, Salt-Water Pool

A contemporary home is depicted with a clear blue pool in the foreground, surrounded by a spacious wooden deck. Lush greenery and autumn foliage frame the property, while sliding glass doors provide views of the interior.

4.93 out of 5 average rating, 145 reviews

Peaceful Retreat in Immaculate Architect’s House

Superhost

A light-filled living area features a cozy neutral sofa, accompanied by a matching armchair. A decorative coffee table sits in the center, and a Smart TV is mounted on the wall. Sliders lead to a private waterfront deck with seating, enhancing the space's openness.

Condo in North Fork

4.85 out of 5 average rating, 155 reviews

2 BR Waterfront Autumn Escape in Wine Country

The exterior of the home features a modern facade with natural wood siding and a green lawn surrounding a heated pool. Two umbrellas provide shade for patio seating, while large windows allow for ample natural light. Trees frame the backdrop for a serene atmosphere.

4.97 out of 5 average rating, 36 reviews

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

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.

4.96 out of 5 average rating, 83 reviews

Southampton Village Newly Built Gem

A modern studio room features a spacious bed beside a seating area with a comfortable sofa and a small coffee table. Large windows with slatted shades allow natural light in, while a round mirror enhances the decor. Soft green and brown tones are present in the furnishings.

5 out of 5 average rating, 38 reviews

A Fall/Winter Escape from the City

4.96 out of 5 average rating, 99 reviews

The image showcases a spacious outdoor area featuring a heated gunite pool surrounded by manicured grass. Four loungers with umbrellas are positioned near the pool, while a cozy seating arrangement is visible on the patio. A charming cottage is seen in the background.

Cottage in The Hamptons

Modern Southampton Cottage | Heated Pool & Peloton