Family-friendly holiday rentals in East Hampton North

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

Spacious & private Hamptons Oasis. High speed WiFi. Family friendly. Massive home on 1.4 acres hosts 15 guests across 6 bedrooms, 8 beds, 4 full baths plus crib & pack 'n play. Gorgeously decorated by Judy Posey Large heated gunite pool (42 x 20 feet) hot tub and sundeck. Fireplace, over-sized kitchen w/ 3 fridges, electric wood-fired grill, huge yard, firepit, bar/lounge, Golden Tee arcade™, bikes & kayaks. Just 2 miles from towns of East Hampton and Amagansett and several white sand beaches

Indoor spacesKitchenValue

4.91 out of 5 average rating, 141 reviews

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!

FamilyIndoor spacesCheckout

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.

4.95 out of 5 average rating, 266 reviews

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

FamilyKitchenAmenities

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.

4.95 out of 5 average rating, 523 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

Indoor spacesFamilyOutdoor spaces

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.

FamilyKitchenSleep quality

4.99 out of 5 average rating, 125 reviews

A spacious backyard is highlighted, featuring a well-maintained lawn and a refreshing pool. Black wooden chairs surround a fire pit in the foreground, while a small shed and lush greenery can be seen creating a serene atmosphere for relaxation.

Villa in East Hampton

East Hampton Escape | Heated Pool + Outdoor Living

Escape to a 5* rated Hamptons retreat designed for effortless summer living. Set on a quiet property surrounded by mature landscapes, this light-filled designer home offers the perfect balance of privacy, comfort, and indoor-outdoor flow. The open concept layout is filled with natural light, feat a modern kitchen, multiple living areas, and thoughtfully designed bedrooms for a relaxed, and comfortable stay. Ideal for small groups looking for elevated escape minutes from beaches and town.

KitchenIndoor spacesLocation

Guest suite in East Hampton

A rustic wooden fence displays a sign reading 'BEACHGLASS BARN' in light blue paint. Colorful flowers peek through the fence, adding a touch of nature to the setting. The surrounding greenery enhances the inviting atmosphere of the property.

Bchglass Barn Gated prop King suite 2bths Central

Clean beautiful bright King suite Cozy Fireplace 2 ensuite Bths & prvt separate Poolside Entrance. Pool is all yours (Closes9/15) Adults only Solo travelers welcome We r just mins to Beaches, shopping, golf, hiking, biking, yoga, eateries and wineries. Play games, grill or cozy up fireside w a good book or movie. The space is creatively designed with a nod to natural elements and Luxe comfort. Sleep your very best on our Deluxe King Bed w/your choice of pillows. Coffee/tea/treats provided!

FamilyKitchenWalkability

4.97 out of 5 average rating, 184 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.

4.98 out of 5 average rating, 145 reviews

Explore the Water & Woods at a Relaxing Retreat

Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway. (No AI used in these photos!)

KitchenFamilyLaundry

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.

KitchenFamilySleep quality

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)

Relax by the hot tub and fire pit with local wines or walk to the village for shopping and dining. House is just a few blocks from Serafina and the famous Nick and Toni’s. Complimentary cruiser bikes included to get around town. IGA supermarket is around the corner and gas grill is on site and ready to use. The house is also walking distance to the train station if your coming from Manhattan. The second bedroom features a Murphy Bed that folds out of the wall and over the couch pictured.

FamilyIndoor spacesLayout

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.

4.93 out of 5 average rating, 140 reviews

Private & Pristine with Pool and Kid’s Playard

INSTANT BOOK/ dates are current. Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Heated Pool open: Memorial Day - Sept 30.

KitchenFamilyAccuracy

A modern kitchen is featured, equipped with sleek stainless steel appliances and an island with seating for four. Pendant lights hang above the counter, illuminating the space, while the white cabinetry provides a clean look. Large windows allow natural light to fill the room.

4.88 out of 5 average rating, 103 reviews

Contemporary East Hampton 4 Bedroom, Pool

Newly Built East Hampton home, a 5-minute drive from the ocean beaches and the Village center. The contemporary interior boasts 4 bedrooms equipped with 5 beds, all thoughtfully furnished, complemented by 2.5 well-designed bathrooms. Prepared to perfection for guests, the home offers a chef's kitchen, matching linens, both interior and beach towels, among other amenities. The outside space is highlighted by meticulous landscaping, a spacious yard, a patio with a a Non heated pool.

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Popular amenities for East Hampton North family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

Detached bungalow w/ private bath

FamilyKitchenCheckout

4.82 out of 5 average rating, 349 reviews

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

FamilyIndoor spacesAmenities

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

FamilyIndoor spacesLong stay

4.92 out of 5 average rating, 514 reviews

A spacious living area features a dark leather sofa adorned with colorful throw pillows, complimented by a patterned area rug. A ceiling fan is positioned above, and natural light streams through multiple windows. An adjoining dining area with a black table and chairs is visible.

Home in Greenport

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

KitchenFamilyWi-Fi

5.0 out of 5 average rating, 260 reviews

Two wooden Adirondack chairs are positioned on a spacious sun deck, overlooking expansive views of lush greenery and the waterfront. The bright blue sky complements the serene atmosphere, creating an inviting space for relaxation and enjoyment of the natural surroundings.

Condo in Montauk

Montauk Waterfront Condo w/ Sunset Views

KitchenIndoor spacesCleanliness

4.87 out of 5 average rating, 124 reviews

A spacious living area features exposed wooden beams and a cozy brick fireplace. Comfortable seating includes a brown sofa and recliner, with decorative pillows adding warmth. A glass coffee table stands on a colorful area rug, while large windows overlook the greenery outside.

Cabin in North Fork

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

KitchenIndoor spacesSleep quality

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.

Hampton's Haven

Indoor spacesFamilyBarbecue

4.93 out of 5 average rating, 165 reviews

4.99 out of 5 average rating, 211 reviews

A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.

Home in Greenport

Greenport Village walking distance to all

FamilyIndoor spacesOutdoor spaces

Family- and pet-friendly home rentals

A modern home is set on a spacious green lawn, featuring a combination of wood and metal siding. Large windows allow natural light to fill the interior. A stone pathway leads to the entrance, framed by lush landscaping and trees, enhancing the outdoor tranquility.

4.89 out of 5 average rating, 117 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

FamilyIndoor spacesLong stay

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

FamilyKitchenAccuracy

A tranquil saltwater pool area is surrounded by lush greenery, featuring four sun loungers with colorful cushions. A large blue umbrella provides shade on the paved deck, enhancing the outdoor relaxation space.

4.88 out of 5 average rating, 236 reviews

HeatedPool, Walk2Beach, Yard4Pup, Spotless, GasBBQ

FamilyIndoor spacesAir conditioning

4.98 out of 5 average rating, 132 reviews

The living area features two rattan chairs facing a coffee table, surrounded by vibrant wall art. A cozy sofa and plants add life to the space. Natural light streams through large windows, creating a bright and inviting atmosphere.

Home in Montauk

3 BR/Pool. Walk to Beach & Town!

Indoor spacesKitchenParking

4.94 out of 5 average rating, 111 reviews

A portable cabana is placed on a sandy beach with a view of the ocean. Two blue beach chairs are positioned underneath the cabana, providing shade. The shoreline and gentle waves are visible in the background, framed by a clear blue sky.

Cottage in Amagansett

Amagansett Dunes Gem

KitchenIndoor spacesHiking

Guesthouse in East Hampton

The exterior of the cottage is surrounded by lush, vibrant greenery, with climbing plants and flowering shrubbery. Natural light illuminates the soft colors of the cottage, which features multiple windows and a door framed by greenery, presenting an inviting and tranquil setting.

Enchanting studio cottage, walk everywhere

Indoor spacesKitchenAir conditioning

4.95 out of 5 average rating, 19 reviews

4.89 out of 5 average rating, 18 reviews

A heated pool is surrounded by a spacious wooden deck, providing ample room for relaxation. Sun loungers are positioned neatly nearby, offering comfortable seating options. A colorful inflatable float is visible on the water's surface, with lush greenery framing the tranquil setting.

Cabin in East Hampton

Close to all! Peaceful Heated Pool! *Month

FamilyIndoor spacesPool

4.77 out of 5 average rating, 13 reviews

A charming exterior view of a home is featured, surrounded by lush greenery and colorful landscaping. A tranquil swimming pool is positioned in the foreground, with a well-maintained lawn leading up to the house, which includes multiple large windows and a spacious patio area.

Home in Amagansett

Beautiful Cozy Home in East Hampton

Indoor spacesFamilyAccuracy

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

Indoor spacesFamilyView

4.99 out of 5 average rating, 126 reviews

A well-maintained outdoor space features a large swimming pool surrounded by a wooden deck. Lounge chairs are placed around the pool, with red umbrellas providing shade. Adjacently, a patio area includes a dining table. Lush greenery frames the area, contributing to a serene ambiance.

Guesthouse in Springs

The Quail’s Nest

FamilyIndoor spacesDecor

4.91 out of 5 average rating, 265 reviews

An inviting in-ground pool is surrounded by lush greenery and vibrant trees. Sunlight reflects off the clear blue water, enhancing the serene atmosphere. Outdoor seating can be seen nearby, providing a tranquil spot to relax amidst the natural setting.

Guest suite in Springs

Private Cozy Cottage with Pool / Private Beach

FamilyIndoor spacesSleep quality

4.86 out of 5 average rating, 138 reviews

A bright living area features large windows that offer views of the nearby pond. Comfortable seating includes a white sofa, patterned chairs, and a coffee table, all arranged on a natural fiber rug. Light from the windows enhances the serene atmosphere.

Home in Sag Harbor

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

KitchenIndoor spacesPool

A spacious living area features large windows dressed with natural shades, allowing ample light to filter in. Comfortable seating includes a plush sofa with blue accents, woven chairs, and a wooden coffee table. A modern kitchen area with a wine fridge is visible in the background.

5.0 out of 5 average rating, 46 reviews

Stunning Central E. Hampton Home w/ gunite pool.

FamilyIndoor spacesOutdoor spaces

The charming exterior of a cedar shingle house is framed by lush greenery. A welcoming entryway features a blue front door, complemented by symmetrical windows on either side. The landscaped front yard includes low shrubs and a gravel pathway leading to the entrance.

4.79 out of 5 average rating, 72 reviews

Beautiful E. Hampton Home w/ Brand New heated pool

KitchenIndoor spacesTV

A spacious backyard features a large pool surrounded by a wooden deck. Two lounge chairs are positioned beside the pool, and an umbrella provides shade nearby. Lush greenery lines the property, creating a serene and private environment for relaxation and recreation.

4.94 out of 5 average rating, 53 reviews

Sunny, walk to beach, large pool

KitchenIndoor spacesHeating

A two-story home features a welcoming front porch with steps leading up to it. A gravel driveway is visible, bordered by lush greenery and flowering bushes. Bicycles can be seen propped against the house, surrounded by a peaceful, natural setting.