Family-friendly vacation rentals in Wainscott

4.91 out of 5 average rating, 142 reviews

Serene + private ~ 8 mins to Main Street + beaches

The perfect Hamptons getaway! Near all of the best attractions. Enjoy this chic, serene home surrounded by the beauty of Hamptons nature + birds' chirping, deer sauntering. Cozy up to the wood burning fireplace, 80' TV + Chef's kitchen. Spark up the BBQ + firepit under the starry sky! Enjoy the bucolic views from every room. Here, you will be 8 minutes to Main St of East Hampton + Amagansett for endless dining + shopping options! Also 5-10 minutes to gorgeous beaches (great any time of year!).

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

A modern exterior of a two-story home is showcased, with large glass windows reflecting the surrounding greenery. Loungers and umbrellas are positioned near the clear blue pool, which invites relaxation. A grill is visible on the deck, providing options for outdoor dining.

4.89 out of 5 average rating, 104 reviews

Stylish Artist's Home in EH 4B, Pool, Paradise

Enjoy time in a stylish and comfortable artist's home in East Hampton. Quick access to beaches and activities in East Hampton, Sag Harbor, Bridgehampton and Wainscott. Also enjoy trendy dining in East Hampton/Sag Harbor. Outdoor fun can be had at the pool, around the fire pit and with the grill. This house can sleep up to 8 people and brings stylish comfort to your Hamptons experience. The home has all amenities. Open to longer rentals - discounts are available for weekly and monthly rentals.

4.93 out of 5 average rating, 136 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

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Guest suite in East Hampton

4.97 out of 5 average rating, 185 reviews

Beachglassbarn cozy suite retreat Be our guest!

Clean serene spacious King Suite fireplace 2 en-suite baths private poolside entry. Pool is 4 u only (Closes9/15) Play games grill or cozy up fireside w/a good book or movie. We r just mins to beaches, shopping, golf, hiking, biking, yoga, eateries and wineries. ~Adults only ~Solo travelers are welcome and safe here. The space is creatively designed with a nod to natural elements and Luxe comfort. Sleep your best on our Deluxe King Bed with choice of pillows. Coffee/tea/treats provided!

4.98 out of 5 average rating, 242 reviews

A cozy living area is shown with two comfortable sofas and a coffee table. Natural light enters through two windows adorned with bamboo shades. A flat-screen television is mounted on the wall, and a decorative rug adds warmth to the wooden flooring.

Apartment in Sag Harbor

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

The backyard showcases a serene oasis with a sparkling pool surrounded by lush greenery. A sunroom is visible, providing a view of the inviting outdoor space. The setting offers a sense of privacy, enhanced by the natural landscape.

4.94 out of 5 average rating, 106 reviews

Oasis backyard, Pool, Gym, and Sunroom!

Oasis pool and landscaping makes it feel like your on a private island. Sunroom with smart TV over looking oasis back yard. Decks in the back yard with lounge chairs and 2 patio dining tables. Front deck with lounge chairs. Outdoor gym located in the corner of the yard. Paddle boards, boogie boards, beach chairs, and beach towels provided. Walk to EHP Resort (SiSi Restaurant), and Harbor Bistro featured on Delicious Destinations. Paddle Diva paddle board/kayak rentals also nearby.

4.94 out of 5 average rating, 155 reviews

A comfortable living room area is presented, featuring a light-colored sectional sofa arranged around a wooden coffee table. Natural light enters through a large window, illuminating a piece of artwork on the wall and adding a cozy touch to the space.

Apartment in Sag Harbor

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

4.9 out of 5 average rating, 117 reviews

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.

Home in Sag Harbor

The Cooper-Burke House

Many Main Street restaurants such as the American Hotel, Lulu's, Page 63, Wolffer Kitchen, Sen, Sag Pizza and Goldberg's, etc are a few minutes away. On Main Street one finds the Sag Harbor Cinema, The Bay Street Theater, Schiavoni's Market and Yoga Shanti. The house is a 12-minute walk to Haven's Beach. 1-minute around the corner from the house is Cavaniola's Wine, Cheese and Kitchen shops as well as the Sag Harbor Beverage store.

4.93 out of 5 average rating, 109 reviews

A bright living area is furnished with a leather sofa and a dark coffee table, positioned on a textured rug. Natural light filters through large windows, illuminating the space. A staircase leads to an upper level, with wooden accents enhancing the modern design.

Home in Bridgehampton

Pool Central Private Bridgehampton Home

Longer stay and reduced rate please email 169bridgehamptoncottage@gmail.com. NOTE* Rest assured, as always, even more so now, our housekeeper is aware to put in the extra tedious clean needed for a happy healthy stay! 7 minute drive to Hampton classic or less 20 min bike ride. Restaurants, studio 89 gym, on same rd. Ocean+bay 5-10 min drive. Bike to 1 ocean Yoga/winery. Halfway to Sag Harbor+Bridgehampton. There is pet fee.

5.0 out of 5 average rating, 102 reviews

A two-story house features a light blue exterior beneath a gray shingled roof. Large windows allow natural light into the enclosed porch area, which is accentuated by landscaped flower beds with pink flowers and well-maintained green grass in the front yard.

Home in Sag Harbor

Sag Harbor Village Gem

Sag Harbor Village Gem. 3 br, 2.5 ba., Enclosed Porch, Great Room with Fireplace, Charming Patio and Yard, Grill, Garage. Nicely landscaped property. House is immaculate. Spacious Master Bedroom with high ceiling. All bedrooms have beautiful dressers and TVs. Washer / Dryer. 10 minute drive to Ocean Beaches and 1 to 2 minute drive to Harbor Beach. 8 to 10 minute stroll to heart of Sag Harbor Village Main St.

4.95 out of 5 average rating, 324 reviews

A welcoming living area is illuminated by natural light from large windows. A comfortable gray sofa is complemented by light-colored armchairs and a coffee table adorned with books and decorative items. The neutral color palette is accentuated by indoor plants and a textured rug.

Home in Sag Harbor

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

Popular amenities for Wainscott 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, 147 reviews

Explore the Water & Woods at a Relaxing Retreat

4.96 out of 5 average rating, 186 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

Superhost

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, 143 reviews

East Hampton Oasis - Pool and Hot Tub

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 wIth Fire Pit /Coffee Bar

4.95 out of 5 average rating, 110 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 Bridgehampton

Calf Creek Cottage (Water Mill/Bridgehampton)

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, 352 reviews

Detached bungalow w/ private bath

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

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)

Family- and pet-friendly home rentals

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, 267 reviews

Private beach, fully updated house, on 2 acres.

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.

4.87 out of 5 average rating, 237 reviews

Fall-Getaway, WoodFireplace, Walk2Beach, Spotless

4.94 out of 5 average rating, 166 reviews

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.

Home in Water Mill

Astounding Watermill 5 Bedroom home with Pool

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, 141 reviews

5 min to EH town w/pool, playground, self check-in

4.87 out of 5 average rating, 139 reviews

A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.

Home in Hampton Bays

Stunning Hamptons Waterfront Escape w/ Sunset View

4.98 out of 5 average rating, 183 reviews

A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.

Cottage in Riverhead

Savor Ocean Sunsets at a Soothing Beachfront Haven

Superhost

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.

4.86 out of 5 average rating, 108 reviews

Contemporary East Hampton 4 Bedroom, Pool

A private swimming pool reflects clear blue skies, surrounded by lounge chairs and umbrellas. Lush greenery frames the scene, while a wooden deck leads to the main house, which features a modern architectural design. A swing set adds an element of leisure to the serene outdoor space.

4.94 out of 5 average rating, 51 reviews

¤¤¤ Wonderful retreat on 4 acres with pool ¤¤¤

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 138 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

Home in Westhampton Beach

A charming cottage exterior features wood shingles and white trim. An American flag hangs proudly from the front, while window boxes with greenery add a touch of color. The light blue front door complements the natural elements, inviting guests inside.

4.98 out of 5 average rating, 175 reviews

Luxury Hamptons Home with Heated Saltwater Pool

Superhost

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, 118 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

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.

4.9 out of 5 average rating, 40 reviews

East hampton 3 bedroom home w/ pool great location

4.95 out of 5 average rating, 42 reviews

A spacious living room is featured, characterized by whitewashed beams and large windows allowing natural light. A soft, neutral sofa is positioned in front of a gold-accented coffee table. Decorative plants and a subtle area rug add warmth to the space, enhancing the inviting atmosphere.

Cottage in Bridgehampton

Hamptons Designer Cottage w Pool by Wölffer Estate

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.

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

The exterior of a spacious home is illuminated by soft twilight, showcasing a private pool with a smooth, blue surface. A shaded dining area beneath a pergola sits next to the inviting outdoor seating area, featuring a fire table. The wooden deck surrounds the house.