Family-friendly vacation rentals in Springs

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, 522 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

KitchenIndoor spacesOutdoor spaces

4.91 out of 5 average rating, 141 reviews

Serene + private ~ 1 block to waterfront dining

Serene, chic, Hamptons oasis! During summer enjoy waterfront dining just 1 block from the house + your large pool Settle into your private home in East Hampton near all of the best attractions. Relax poolside, spark up the BBQ + firepit and enjoy the nature all throughout the property. Stream on your 80' TV + curl up to the wood burning fireplace. The home is perched back on a private piece of property! You'll be 8 mins. to Main St + 8 mins. to beaches. A truly perfect escape any time of year!

FamilyKitchenCleanliness

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.

KitchenFamilyTV

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

FamilyKitchenCheck-in

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

Peace and serenity in East Hampton and minutes from the Village. This exquisite modern home features high-end finishes such as Sub-Zero and Wolf appliances, quartzite waterfall kitchen island and counters, marble tiled bathrooms, designer mid-century decor and separately zoned air conditioning. The heated saltwater pool is surrounded by a bluestone patio, Ipe lighted deck and huge yard. The house features two wood-burning fireplaces in the living room and den and an outdoor fire-pit. RR# 26-891

Indoor spacesKitchenGrill

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

Meticulous easy home.Tranquil family neighborhood in historic artist's beach community.Lush private yard! Heated saltwater pool.Wood burning fireplace.Private fenced-in backyard.Half mile to private bay beach. Bike great trails & savor delicious meals prepared in fully equipped kitchen.Enjoy Clearwater Beach's renowned sunset.We welcome all respectful guests.East Hampton's best restaurants are nearby.Smoke free.Small dogs permitted.Cell reception booster! Ask about EVcharger.RentalR-25-705

Indoor spacesKitchenBathroom

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

A beautifully landscaped tranquil oasis. Newly constructed private two bedroom, one bathroom guest extension to owner occupied house. Guests share large yard and pool with owner, and have private deck and seating area. Private entry and parking. Guest's may enjoy outdoor shower and BBQ. Please note there is no kitchen, however a small fridge, Keurig coffeemaker and microwave, plates/utensils are provided. Conveniently located to beaches, shopping and local restaurants in East Hampton.

KitchenFamilyBathroom

4.91 out of 5 average rating, 201 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.

FamilyIndoor spacesAmenities

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.

FamilyKitchenCondition

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.

KitchenFamilyBathroom

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

**POOL CLOSES SEPTEMBER 30TH** **POOL opens last week of May** This is a guest house for 1 or 2 adults. Its separate from the main house. Kids are allowed but must bring own sleeping arrangements. You do NOT have to do any chores before checking out. **PETS NOT ALLOWED** I hate to do this but someone ruined it for everyone. Max Occupancy: 4 Guests can only bring 1 vehicle since there is not enough room in the driveway

Indoor spacesKitchenOutdoor spaces

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.

4.93 out of 5 average rating, 193 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

KitchenIndoor spacesBeach

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 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, 144 reviews

Explore the Water & Woods at a Relaxing Retreat

FamilyKitchenAmenities

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, 349 reviews

Detached bungalow w/ private bath

Indoor spacesKitchenOutdoor 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)

Indoor spacesFamilyWalkability

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

FamilyKitchenSleep quality

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)

KitchenIndoor spacesOutdoor spaces

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

FamilyKitchenBathroom

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

KitchenFamilyDecor

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 spacesComfort

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 115 reviews

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.

Home in Montauk

Sea Roost

KitchenFamilyBiking

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

KitchenFamilyCleanliness

4.94 out of 5 average rating, 185 reviews

1800 Historical EH Home, 1 Mile to Town!

FamilyKitchenParking

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 -

Indoor spacesKitchenAccuracy

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

FamilyKitchenCheckout

A serene river scene is captured under a partly cloudy sky. Tall grasses line the water's edge, while trees provide shade along the bank. The calm water reflects the surrounding landscape, creating a peaceful atmosphere.

4.86 out of 5 average rating, 22 reviews

Private Beach Community with exceptional light

Indoor spacesKitchenAmenities

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.

4.76 out of 5 average rating, 108 reviews

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend

Indoor spacesFamilyQuiet

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.

4.91 out of 5 average rating, 65 reviews

East Hampton Secluded Escape with Gunite Pool

Indoor spacesFamilyParking

Family-friendly home rentals with a pool

A spacious deck surrounds a heated pool, featuring a light blue surface reflective of the sky. Four sun lounge chairs are positioned for relaxation, and an outdoor dining area with a retractable awning is available. Lush trees provide a natural backdrop to the serene setting.

5.0 out of 5 average rating, 93 reviews

East Hampton Rental w/ Pool, Moments to Amenities

FamilyIndoor spacesSleep quality

4.67 out of 5 average rating, 3 reviews

East Hampton Retreat w/ Heated Pool

KitchenFamilyAccuracy

4.87 out of 5 average rating, 70 reviews

Spacious East Hampton house with heated pool + WFH

FamilyKitchenOutdoor spaces

A charming vacation home is set against a backdrop of lush greenery, featuring a heated saltwater pool surrounded by a spacious patio. The backyard includes contemporary lounge furniture, umbrellas for shade, and a stylish cabana, offering an inviting space for outdoor relaxation and entertainment.

4.9 out of 5 average rating, 86 reviews

East Hampton Family Vacation Home

KitchenFamilySleep quality

The kitchen and dining area feature modern cabinetry in muted tones against light wood flooring. A vintage-inspired Smeg fridge stands opposite a sleek kitchen layout with a black stove. Eye-catching circular wall art accents the space, complemented by a wooden dining table surrounded by six chairs.

4.97 out of 5 average rating, 31 reviews

Secluded Oasis salt water pool near beach

Indoor spacesFamilyBeach

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

FamilyIndoor spacesOutdoor spaces

The charming exterior of a two-story home is framed by lush greenery and a manicured lawn. A vintage blue vehicle is parked on a gravel driveway, leading up to the inviting front porch with white railings and a welcoming entryway.

4.93 out of 5 average rating, 45 reviews

Luxury 4-bedroom in East Hampton [w/private beach]

Indoor spacesKitchenHeating

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.