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, 253 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.

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, 340 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

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, 116 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 deck and huge yard. The house also features two wood-burning fireplaces in the living room and den and an outdoor fire-pit. RR# 24-656

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, 137 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!)

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.

4.99 out of 5 average rating, 110 reviews

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.

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, 128 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, 129 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.

Guest suite in The Hamptons

4.97 out of 5 average rating, 174 reviews

Super sweet king en-suite prvt access pool central

Beautiful, bright, spacious King suite w fireplace, two en-suite bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga 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 super deluxe king sized bed w/your choice of pillows. Complimentary coffee/tea/treats

Guest suite in The Hamptons

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.

4.9 out of 5 average rating, 252 reviews

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

4.98 out of 5 average rating, 370 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).

4.97 out of 5 average rating, 130 reviews

A bright living area is depicted, featuring a sleek sofa, a wooden coffee table, and a round dining table surrounded by red chairs. The space incorporates a large potted plant, and light streams through a nearby window, illuminating the whitewashed wood floors.

Flat in The Hamptons

Renovated Guest Cottage close to E.Hampton Village

This modern beach guesthouse has white washed wood floors, all new stainless steel appliances , central air, and very conveniently located . We are a short walk to East Hampton Village and 1.9 miles to the nearest beach.There is a private back patio with a cedar outdoor shower and sitting area in a serene setting .

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, 182 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

Popular amenities for Springs 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, 214 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

4.99 out of 5 average rating, 205 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 North Fork

Greenport Village walking distance to all

4.93 out of 5 average rating, 15 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

5 out of 5 average rating, 10 reviews

Offseason Hamptons Escape!

Apartment in The Hamptons

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.

5 out of 5 average rating, 254 reviews

Montauk Waterfront Condo w/ Sunset Views

A spacious saltwater pool is surrounded by a well-manicured yard, featuring lounge chairs and large umbrellas. Water features create gentle splashes, enhancing the serene environment. The area is framed by trees, providing a natural backdrop for relaxation.

4.97 out of 5 average rating, 103 reviews

Brand new house with an all year round hot tub.

4.86 out of 5 average rating, 116 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

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

4.99 out of 5 average rating, 121 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 The Hamptons

East Hampton Escape | Heated Pool + Outdoor Living

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.

4.99 out of 5 average rating, 116 reviews

3 BR/Pool. Walk to Beach & Town!

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.

4.75 out of 5 average rating, 102 reviews

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend

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.

4.89 out of 5 average rating, 55 reviews

East Hampton Secluded Escape with Gunite Pool

A well-maintained outdoor pool area features a crystal-clear heated saltwater pool surrounded by smooth stone decking. Comfortable lounge chairs and a sectional sofa with colorful cushions provide ample seating, while umbrellas offer shade. Lush greenery and flowering plants create a serene and inviting environment.

4.97 out of 5 average rating, 69 reviews

Stylish Oasis, Gorgeous Pool, Private Beach Access

4.87 out of 5 average rating, 45 reviews

Family Fun Close to Montauk

4.97 out of 5 average rating, 191 reviews

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

4.85 out of 5 average rating, 144 reviews

Hamptons Oceanfront Oasis

Family-friendly home rentals with a pool

4.8 out of 5 average rating, 40 reviews

East Hampton Sunny Heated Swimming Pool. Sunroom.

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 home with a shingle exterior sits amidst a well-kept lawn. Green grass stretches across the yard, with a defined path leading to the entrance. Bushes and trees provide natural landscaping, enhancing the inviting appearance of the property.

4.98 out of 5 average rating, 57 reviews

Exhale...and relax in East Hampton!

4.9 out of 5 average rating, 112 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.

Flat in The Hamptons

Ocean View Studio with King Bed

4.92 out of 5 average rating, 12 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 The Hamptons

Close to all! Peaceful Heated Pool! *Month

Guest suite in The Hamptons

A spacious living area is presented with a cozy blue sofa and an accent chair, complemented by a decorative rug. A dining table for four is positioned nearby, and a large TV center is visible. The room is well-lit with natural light streaming through skylights.

4.98 out of 5 average rating, 146 reviews

Hamptons Dream Suite

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.

4.8 out of 5 average rating, 10 reviews

Beautiful Cozy Home in East Hampton

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.