Family-friendly vacation rentals in Sag Harbor

4.91 out of 5 average rating, 141 reviews

Serene w/ large pool ~1 block to waterfront dining

Serene, chic Hamptons oasis! Located 1 block to waterfront dining + 8 mins to Main St. A perfect escape for any time of year! During summer, swim all day + walk 1 block to waterfront dining for dinner, drinks, coffee on the sea! During fall/winter, enjoy the firepit, indoor wood burning fireplace, 80' streaming TV + large fully stocked Chef's kitchen! The home is nestled in nature and serenity, perched back on a large piece of private property. Perfect for a serene escape to relax and unwind!

KitchenFamilyBathroom

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, 521 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

FamilyKitchenCondition

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.

Indoor spacesFamilyCheck-in

4.91 out of 5 average rating, 201 reviews

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.

FamilyKitchenAccuracy

4.98 out of 5 average rating, 240 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!

FamilyKitchenBathroom

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.

4.86 out of 5 average rating, 137 reviews

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

Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds, 2.5 baths - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond -Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action. NOTE: Due to water leakage issues, the bath in pool house is not available

Indoor spacesKitchenWifi

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 .

KitchenFamilyWalkability

Guest suite in Sag Harbor

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.

4.91 out of 5 average rating, 410 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. Fully self contained and private. 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 in driveway close to entrance. Not suitable for infants or children.

Indoor spacesKitchenHot tub

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.

4.9 out of 5 average rating, 117 reviews

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.

FamilyKitchenCondition

4.93 out of 5 average rating, 107 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.

KitchenIndoor spacesSleep quality

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.

5.0 out of 5 average rating, 101 reviews

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.

KitchenIndoor spacesComfort

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.

4.95 out of 5 average rating, 323 reviews

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.

KitchenFamilySleep quality

Popular amenities for Sag Harbor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a 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 w/Hot tub Fire Pit Coffee Bar

Indoor spacesFamilyAccess

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

KitchenFamilyHospitality

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 spacesKitchenWifi

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.

4.84 out of 5 average rating, 142 reviews

East Hampton Oasis - Pool and Hot Tub

FamilyIndoor spacesAir conditioning

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

KitchenFamilyLayout

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, 348 reviews

Detached bungalow w/ private bath

KitchenIndoor spacesPool

4.83 out of 5 average rating, 220 reviews

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.

Home in Southampton

Stylish & Chic w hot tub/ Near Beaches & Village

FamilyIndoor spacesComfort

Guesthouse in Southampton

A charming outdoor area features a black cottage in the background, with large glass doors reflecting the surroundings. The deck is adorned with potted red geraniums and wooden seating. A hot tub is positioned adjacent to the cottage, emphasizing a tranquil retreat atmosphere.

4.98 out of 5 average rating, 120 reviews

5 Star Rated Private Cottage Southampton/Sag Hrbr

FamilyKitchenShared spaces

Family- and pet-friendly home rentals

A flower-filled back deck is highlighted by comfortable seating arrangements and a small dining table. Potted flowers in vibrant colors complement the wooden decking, while a table reflects the surrounding greenery. Various lounge chairs invite relaxation in this serene outdoor space.

4.91 out of 5 average rating, 117 reviews

Walk to Village Sag Harbor Victorian

Indoor spacesFamilyCheck-in

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.

Indoor spacesFamilyHospitality

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

FamilyKitchenCleanliness

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

Indoor spacesKitchenBeach

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, 138 reviews

Private & Pristine with Pool and Kid’s Playard

FamilyKitchenAmenities

5.0 out of 5 average rating, 113 reviews

A spacious backyard is framed by mature trees, featuring a fire pit surrounded by white Adirondack chairs. A children’s playground with swing set is visible nearby, while the home, illuminated by warm lights, stands invitingly in the background.

Villa in Southampton

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

FamilyKitchenLocation

4.94 out of 5 average rating, 184 reviews

1800 Historical EH Home, 1 Mile to Town!

Indoor spacesKitchenNearby

4.85 out of 5 average rating, 172 reviews

Sag Harbor House for rent.

Indoor spacesFamilyAccess

Family-friendly home rentals with a pool

4.9 out of 5 average rating, 134 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

FamilyIndoor spacesSleep quality

A spacious living room is featured, showcasing a light-colored sectional sofa adorned with decorative pillows. A wooden coffee table sits centrally on a textured area rug. Built-in shelves hold various items, and large windows allow natural light to illuminate the room.

5.0 out of 5 average rating, 21 reviews

Sag Harbor Charming Forest Home

Indoor spacesFamilyPool

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

FamilyIndoor spacesOutdoor spaces

A single-story house features a combination of light-colored siding and a welcoming front porch. Lush green grass surrounds the home, with neatly trimmed bushes adding to the curb appeal. Tall trees provide a natural backdrop, and the American flag hangs from the porch.

5.0 out of 5 average rating, 24 reviews

Perfect Beach Home in Sag Harbor

FamilyKitchenSleep quality

A spacious dining area features a large wooden table surrounded by white chairs. Natural light streams through multiple windows, highlighting the warm tones of the decor. Stylish woven pendant lights hang from the ceiling, creating an inviting atmosphere for gatherings.

4.96 out of 5 average rating, 24 reviews

Tasteful Hampton 4 Bedroom w Heated Pool EH / Sag

KitchenFamilyAmenities

A spacious outdoor area features a large swimming pool surrounded by lush green grass. Four lounge chairs are positioned nearby, alongside a parasol offering shade. A quaint shed with red accents is visible in the background, complemented by seating areas. Tall trees provide a natural backdrop.

5.0 out of 5 average rating, 17 reviews

Sag Harbor Dream Home: Heated Pool

FamilyKitchenCheck-in

The image captures a spacious backyard featuring a heated swimming pool with a gentle waterfall. Surrounding the pool, lounge chairs are neatly arranged. A charming house with multiple windows and outdoor seating is visible in the background, complemented by mature trees and colorful flower beds.

5.0 out of 5 average rating, 18 reviews

Sag Harbor Hamptons hideaway

Indoor spacesFamilyOutdoor spaces

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.