Family-friendly holiday rentals in Springs

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, 251 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.

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, 484 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

Guest house in The Hamptons

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, 339 reviews

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house w/ use of amenities (shared with our family of 4) including sauna & hot tub. The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 2 guests. 2 Adult guests ONLY, no children due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets

4.9 out of 5 average rating, 112 reviews

Serene + private, 1 block to waterfront dining

Come enjoy this chic, serene private home; located just 1 block to waterfront dining and minutes to Main St.! Bask in your Hamptons oasis at this half-acre property. Enjoy outdoor/indoor living, hang on the porch during Summer, swim in your pool all day + night, spark up the BBQ + firepit under the starry sky! Stroll 1 block to waterfront dining + cafe to enjoy the most magnificent sunsets in the area, You'll be 5 minutes to Main St. of East Hampton + Amagansett, restaurants, beaches + more!

Guest suite in The Hamptons

A cozy sleeping area is highlighted by a spacious bed with light blue bedding, positioned near a working fireplace. A television is placed on a wooden stand across from the bed. Soft lighting from bedside lamps creates a warm ambiance, complemented by a decorative artwork on the wall.

4.9 out of 5 average rating, 386 reviews

Artists Sag Harbor Village Retreat

This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat with it’s own thermostat controls & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.

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.

4.92 out of 5 average rating, 127 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.

An outdoor area features a rectangular pool surrounded by a wooden deck. Lounge chairs are positioned along the pool's edge, and a shaded seating area is located nearby under an umbrella. Lush trees provide privacy and a natural backdrop.

4.83 out of 5 average rating, 126 reviews

East Hampton Oasis - Pool and Hot Tub

Nestled at the end of a private road in the Springs section of East Hampton, this classic Hamptons home will keep you and your friends/family entertained. Living room with sonos sound system, kitchen, 3 bedrooms, 2 bathrooms, outdoor living area with lounge chairs, a bbq, bar, pool and hot tub. All 3 bedrooms have AC. Towels and linens provided. Washer/dryer available. CLOSE TO BEACH AND EH VILLAGE. The pool is open May 5 through October 5. The hot tub remains open year round.

A spacious and heated swimming pool is surrounded by a brick patio and lush green landscaping. Two lounge chairs are positioned nearby, offering a tranquil spot to relax. The serene setting is enhanced by mature trees bordering the pool area.

4.87 out of 5 average rating, 117 reviews

Cheerful East Hampton home with Pool

Situated off of a quiet lane on one and a half-acres of land, this amazing residence offers a peaceful and quiet Hamptons getaway. The home consists of 4 wonderful bedrooms, 3.5 modern bathrooms, a heated pool & mature landscaping. Additionally, please read my disclosures and "rules". Not a party house. No Events, parties & No smoking will be permitted. The house is beautiful, tranquil and very comfortable. THANK YOU!

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, 148 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!

4.97 out of 5 average rating, 358 reviews

The living area features two comfortable sofas, a wooden coffee table, and a dining table set for four. A window allows natural light to fill the space, while decor accents create a relaxed environment. Air conditioning unit is visible on the wall.

Cottage in The Hamptons

Carriage House - Cottage in East Hampton Village

Darling cottage in East Hampton Village. Situated in a historic picturesque tree-canopied neighborhood. Easy stroll to Newtown Lane and Main Street shops. (1/2 mile). Classic atmosphere. Very comfortable, bright, and clean. A perfect place from which to enjoy East Hampton and the surrounding area. Fully renovated (2019).

The exterior of the house is depicted, showcasing a light-colored siding with brick accents. The entrance features a covered porch supported by white columns. Two windows are visible on the front, framed with white shutters, and a well-maintained yard adds to the setting.

4.92 out of 5 average rating, 180 reviews

Charming Quiet Cottage

Escape to a quiet area of East Hampton. Access to a private Bay beach, nearby Farmer's market and art galleries. Only 5 miles from unique shops, movie theater, trendy restaurants and performance center Guild Hall. House is equipped with Smart TV and wi-fi. *Minimum Stay in July and August is (5) Five Nights

A spacious backyard features a heated swimming pool surrounded by a sun deck, adorned with loungers. Lush greenery and trees provide a natural backdrop to the inviting setting, while a charming house is visible in the distance.

4.88 out of 5 average rating, 130 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

Rent a beautiful and spacious 4 bedroom/3 bathroom property in East Hampton with a heated swimming pool in the backyard. This three level house with large kitchen, central A/C, BBQ in the backyard, and a garage is the perfect place to entertain guests or to relax and escape in East Hampton.

Popular amenities for Springs family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.97 out of 5 average rating, 212 reviews

Private Oasis W/Stunning Vinyard and Pool Views

4.97 out of 5 average rating, 31 reviews

A spacious backyard is bordered by lush greenery and has a view of the tranquil water. Two surfboards are propped against the house, and a set of bright pink chairs surrounds a dining table. Pathways made of stones lead to the water's edge.

Home in Shelter Island

Waterfront shelter island gem

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.

4.98 out of 5 average rating, 199 reviews

Greenport Village walking distance to all

4.92 out of 5 average rating, 13 reviews

A spacious living area displays a large sectional couch adorned with assorted cushions. A wooden dining table is surrounded by black chairs. Natural light filters through multiple windows, highlighting the cozy atmosphere, while decorative baskets add an organic touch.

Bungalow in The Hamptons

Stylish East Hampton Surf Cabin: Hot Tub & Office

4.98 out of 5 average rating, 100 reviews

Brand new house with an all year round hot tub.

4.87 out of 5 average rating, 113 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

4.95 out of 5 average rating, 101 reviews

An open-concept living space features a modern dining area with a wooden table set for six, complemented by sleek metallic chairs. A comfortable sectional sofa is positioned across from a wall-mounted television, with a fireplace and green outdoor views visible through large windows.

Cottage in The Hamptons

Calf Creek Cottage (Water Mill/Bridgehampton)

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, 153 reviews

East Hampton (walking distance to village)

Family- and pet-friendly home rentals

The exterior of a modern cottage is presented with a black wood facade and multiple windows. A front porch is seen, partially enclosed with slatted wood. Lush green grass and shrubbery frame the entrance, creating a welcoming approach to the home.

4.9 out of 5 average rating, 39 reviews

Waterfront NoFo Cottage w/ public beach access

The exterior of the cottage is framed by lush greenery and a gravel driveway that leads to a welcoming entrance. A garage is visible on the left, and a wooden fence outlines the property, providing a sense of privacy. Natural light filters through the windows.

4.82 out of 5 average rating, 11 reviews

Cozy Springs Getaway

A cozy living area is highlighted by a chandelier, providing soft illumination. Two stylish chairs flank a round table, while a decorative sculpture and a vintage fireplace enhance the space. Large windows allow natural light to fill the room, offering views of the surrounding greenery.

4.89 out of 5 average rating, 108 reviews

The Cooper-Burke House

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, 104 reviews

Sea Roost

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.

4.92 out of 5 average rating, 156 reviews

Modern Farmhouse Steps to Beach & Love Lane

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.

4.87 out of 5 average rating, 117 reviews

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

An aerial view captures the layout of the property, showcasing a well-maintained lawn surrounded by lush greenery. A swimming pool is visible adjacent to a wooden deck with lounge chairs, while an outdoor space is equipped with umbrellas for shade.

5 out of 5 average rating, 8 reviews

Chic, Modern, & a Walk to Beach!

4.93 out of 5 average rating, 105 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 The Hamptons

Amagansett Dunes Gem

Family-friendly home rentals with a pool

A spacious backyard is showcased, featuring a large saltwater pool surrounded by six lounge chairs. Lush green grass is complemented by a flowerbed, while tall trees provide shade. The house, with a wooden deck, is visible in the background.

4.92 out of 5 average rating, 12 reviews

Hamptons Home w/ Salt Water Pool

A tranquil outdoor space features a sparkling pool surrounded by greenery. A light-colored bench with patterned cushions is positioned beside the water, offering a comfortable spot to relax. Bright flowers add a splash of color to the scene, enhancing the inviting atmosphere.

4.79 out of 5 average rating, 38 reviews

The Hummingbird House: E Hampton Beach House

A charming house is presented, featuring a blend of shingled and brick exterior. The porch is outlined by neatly trimmed hedges, and a gravel pathway leads to the entrance. Lush greenery surrounds the home, accentuating its inviting curb appeal.

4.94 out of 5 average rating, 34 reviews

East hampton 3 bedroom home w/ pool great location

Guest house in The Hamptons

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.

5 out of 5 average rating, 109 reviews

The Quail’s Nest

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 out of 5 average rating, 43 reviews

Stunning Central E. Hampton Home w/ gunite pool.

An in-ground salt-water pool is surrounded by natural stone, set amidst lush greenery. Sun loungers are positioned alongside the pool, and a shaded seating area is visible to the right. A wooden structure stands in the background, blending with the tranquil landscape.

4.87 out of 5 average rating, 46 reviews

East Hampton Secluded Escape with Gunite Pool

Guest suite in The Hamptons

4.97 out of 5 average rating, 173 reviews

Private central cozy king suite 2 baths fireplace

A spacious dining area is highlighted by a long wooden table surrounded by white upholstered chairs. Large windows allow natural light to fill the room, enhancing the bright, minimalist design. Contemporary light fixtures complement the clean lines and neutral color palette.