Family-friendly vacation rentals in Shirley

A spacious deck is furnished with a wooden table surrounded by six white chairs, offering ample space for relaxation. Two large umbrellas provide shade, while a view of the calm water and distant horizon can be seen in the background.

4.97 out of 5 average rating, 100 reviews

Stunning sunset charming waterfront home 4 seasons

Want to relax and enjoy the water and sunsets? This home has a very relaxed vibe, whether you are grilling outside, kayaking, going to the beach, reading a book as the sound of the waves gently wash up on shore or even enjoying a glass of your preferred beverage on the deck as you gaze into the horizon, there is a sense of comfort and tranquility. Very nice open kitchen looking out into the bay. It really is a nice getaway and an environment to take a break and recharge the senses. Enjoy!

KitchenFamilyGrill

An expansive deck offers a view of the Great South Bay, with a mix of comfortable seating options, including lounge chairs and a sectional sofa. The area is complemented by manicured green grass and a wooden railing, providing a serene backdrop for outdoor relaxation.

4.98 out of 5 average rating, 243 reviews

Luxurious Waterfront Beach House On The Bay

Relax and enjoy your time at this beautiful east end waterfront getaway. This house is located right on the relaxing and exclusive Great South Bay with private beach... The experience will bring you the feel of tranquility everyone desires with vacationing out east. While offering all the enjoyments the island has at your fingertips. Centrally located to all island destinations. 90 minutes from Manhattan - 15 minutes to West Hampton - 15 minutes to Fire Island Ferrys. Visit top winery’s WiFi

Indoor spacesFamilyGrill

Superhost

Apartment in Ridge

4.76 out of 5 average rating, 196 reviews

Spacious 1Bedroom Apartment By Wineries & Beaches

Relax and unwind in this private, spacious 1-bedroom apartment designed for comfort, convenience, and a peaceful stay. Whether you’re here for a weekend getaway, visiting the North Fork wineries, or need a quiet place to work remotely, this space has everything you need. Enjoy fully private apartment with its own entrance and yard - giving you uninterrupted freedom. Comfortable bedroom, cozy living area & full kitchen Relax in or after a day exploring nearby beaches, wineries, and attractions.

Indoor spacesFamilyQuiet

Superhost

A living area features a gray futon adorned with decorative pillows, complemented by a small coffee table. A red accent chair provides additional seating. Soft lighting from the ceiling enhances the space, while wall art depicts blooming flowers, contributing to a welcoming atmosphere.

Apartment in East Patchogue

4.85 out of 5 average rating, 277 reviews

Private 1br Apartment on Long Island

Bright & clean 1br apartment with private entrance on a quiet street. Refrigerator, microwave, keurig incl 2 miles to downtown restaurants, bars, breweries, shopping 10 miles to winery & vineyards 3 miles to beaches 3 miles to Fire Island Ferry 30miles to NYC 3 miles to Baseball Heaven 10 miles to Stonybrook University & hospital 1 mile to public horse farm & stable 3 miles to St Joseph's College .5 mile to Long Island Community Hospital 1 mile to hiking 45min to JFK 10min to McArthur airport

FamilyKitchenBathroom

4.97 out of 5 average rating, 220 reviews

A modern living area features a dark sectional sofa accented by cushions and a stylish area rug. In the background, a dining space with four chairs and a kitchen area is visible. Natural light enters through multiple windows, creating a bright, inviting environment.

Apartment in Medford

Charming 2 Bedroom apartment

Enjoy our charming 2 Bedroom apartment that is in a quiet and friendly neighborhood in a cul-de-sac. Private entrance on first floor of our house with 2 Bedrooms, 1 Bathroom, Living room, Dining area, and a Kitchen. Close to: Main highways (Sunrise HWY/Long Island Expressway), Grocery stores, Winery & Vineyards, Davis park ferry, Downtown Patchogue village (Restaurants, bars, breweries, shopping), Beaches, Top Golf, MacArthur airport, Long Island Community Hospital, St Joseph’s College.

KitchenIndoor spacesWifi

4.88 out of 5 average rating, 153 reviews

Home in Bellport

The Stella ~ A 1920s Beach Bungalow

Welcome to The Stella, a thoughtful 1920's home set in the heart of Bellport Village. This is the place for a summer romance, a family gathering, or a creative re-centering. Inspired by the subtle palette and refined geometry of the American artist Frank Stella—who often spent time on Long Island—The Stella enjoys close proximity to many beaches and wetlands. Our original 1920's Cape Cod style home is full of old and new finds that appeal to curious journeyers and creative weekenders.

Indoor spacesKitchenAir conditioning

4.92 out of 5 average rating, 142 reviews

A calm waterfront scene features a vibrant sailboat gliding across the bay, surrounded by green marshland. A wooden dock leads into the water, with several colorful chairs positioned for relaxation. Soft hills and houses line the distant shore under a gentle mist.

Home in Mastic Beach

Gorgeous Waterfront and Indoor Pool Family Oasis!

Breathtaking Waterfront home with 37 foot heated indoor pool. 3 Bedrooms plus a 800 Sq/Ft master bedroom with wood burning fireplace. WiFi, 3rd floor entertainment room with 120 inch screen movie projector, karaoke, fooseball, pool table. Wraparound terrace, sunroom, 45ft dock with launching ramp, putting green, sand trap, outdoor kitchen, bar & stone patio with tables & BBQ grills & fire pit. Ability to catch abundant fish & blue crabs right from the dock. Picture tells a thousand words.

KitchenIndoor spacesNearby

4.93 out of 5 average rating, 158 reviews

A patio is shown with a wooden table and a dark wicker chair overlooking a scenic view. A clear sky with scattered clouds is visible in the background, along with open fields and distant structures. Utility poles line the road, adding context to the setting.

Home in Patchogue

Joyful Beach House, viewing The Great South Bay

Amazing Great South Bay view with access to Shorefront and Rider Parks. This Ranch has an unobstructed view of the Shorefront Band Shell. Watch concerts and sunsets from the comfort of your patio. Walk down to the Patchogue Beach Club and enjoy the pool and beach. This open-concept home has 2 bedrooms, one bath, a remodeled bathroom, and a kitchen. The kitchen has stainless steel appliances, a farm sink, and a butcher block countertop with natural lighting that will brighten the home.

FamilyIndoor spacesHospitality

Superhost

The open living area features a custom slate pool table with a vibrant arrangement of billiard balls. A modern kitchen is visible in the background, including sleek cabinetry and a refrigerator. A tasteful seating area includes a fireplace and a large wall-mounted television.

4.93 out of 5 average rating, 271 reviews

By NYC & Hamptons - Hot Tub, Pool Table, Speakeasy

Welcome to Coast to Coast - the perfect getaway from NYC! You may have heard about our new little secret - but you’ll have to come see it for yourself to believe it! Step back into prohibition era Long Island in our hidden speakeasy! Right by Smith Point Beach, we provide accommodations that go above and beyond- this is not your average AirBnB! Soak up the sun at one of LI's top beaches, then enjoy complimentary Netflix, Hulu, cable and more while you shoot pool or play games.

Indoor spacesKitchenQuiet

A charming entrance features a white gate framed by decorative stonework. American flags adorn the front of the house, which is surrounded by lush greenery. The pathway is lined with manicured grass, creating a welcoming approach to the front door.

4.87 out of 5 average rating, 109 reviews

House of peace.

Welcome to my families heart. This house may be old but it is filled with so much love its truly the heart of our family. For many generations we have gathered here. Lovely 3 bedroom house with large property on quiet road. Dining room, kitchen, living room, laundry room. Small sitting room off the master bedroom . There are puzzles and some games for children. Please feel free to use what you want. Close to shopping, beach, casino, ferry, LIRR, LIE, sunrise and The Hamptons.

KitchenIndoor spacesValue

4.94 out of 5 average rating, 161 reviews

A cozy living space features exposed wooden beams and natural light streaming through the windows. A small kitchenette with modern appliances is visible, alongside a comfortable sofa and a rustic wooden coffee table. Decorative shelves and a unique tree branch accent add character to the room.

Tiny home in Mastic

Cozy craftsman style home close to beaches

Feel refreshed when you stay in this rustic gem. 10 minutes from the fire island beaches this newly renovated home will take your breath away. 20 minutes from local wineries theres no shortage of things to do. This is a single dwelling home. There is a basement apartment with a separate entrance. The tenant does not have access to the house. Everything pictured is yours to use! Kick your feet up and enjoy the details of this handcrafted home. Tree house inside and out!

KitchenFamilyDecor

4.99 out of 5 average rating, 107 reviews

A cozy living area is presented, featuring a full-size couch and love seat in soft brown fabric. A round black coffee table sits at the center, complemented by a patterned area rug. Natural light enters through a skylight and glass doors, creating a warm ambiance.

Apartment in Shirley

Welcome to Bill & Debbies AirBnb

Welcome to our AirBNB. We hope you will enjoy your stay in your private apartment. You will appreciate the off street parking & private entrance. We are only a short drive away from Long Island’s North Fork Vineyards, Skydiving, Smith Point County Beach, Fire Island and much, much more. We are also only 2.5 miles from Brookhaven National Laboratory. Only a short drive from a huge selection of stores & restaurants. We are in easy walking distance to a deli and 7/11.

KitchenIndoor spacesHeating

Popular amenities for Shirley family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.92 out of 5 average rating, 145 reviews

A modern farmhouse is set on a spacious lot. The architecture features a blend of dark and light siding with a white chimney. A well-maintained path leads to a front porch, surrounded by landscaped greenery, enhancing the inviting curb appeal.

Home in Sound Beach

Luxury modern farmhouse with heated pool & hot tub

Indoor spacesFamilyGetting around

4.9 out of 5 average rating, 177 reviews

An outdoor deck is seen featuring a spacious octagonal hot tub. It overlooks a calm canal bordered by green grass and trees. Nearby boats are docked, and the tranquil water reflects the clear sky, creating a peaceful atmosphere.

Home in Oakdale

Waterfront Round House View

KitchenIndoor spacesAccess

4.99 out of 5 average rating, 187 reviews

Home in Commack

GOOD VIBEZ HOUSE! Mini Golf+Pool+Hot Tub+Game Room

FamilyKitchenOutdoor spaces

4.91 out of 5 average rating, 202 reviews

Home in Sag Harbor

Offseason Monthly, Utilities Included

KitchenIndoor spacesWalkability

Home in Westhampton Beach

A contemporary ranch-style home is surrounded by lush greenery. The custom-shaped heated pool features a waterfall and is bordered by a stone patio with lounge chairs and umbrellas. A state-of-the-art hot tub is positioned nearby, enhancing the outdoor relaxation space.

4.93 out of 5 average rating, 165 reviews

Hampton's Haven

Indoor spacesKitchenCheckout

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

KitchenFamilyBiking

4.87 out of 5 average rating, 124 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

KitchenIndoor spacesCleanliness

4.91 out of 5 average rating, 156 reviews

The home theater features a large screen and 15 electric recliner seats arranged in a semi-circle. Dark blue walls and patterned carpeting create a cozy movie-watching environment. Subtle lighting enhances the overall ambiance without overwhelming brightness.

Guest suite in Northport

Coastal Villa Suite pool•sauna•gym•theater•beach

KitchenIndoor spacesLaundry

Family- and pet-friendly home rentals

4.82 out of 5 average rating, 126 reviews

A cozy bedroom features a spacious bed layered with soft bedding and decorative pillows. Pendant lights hang on either side, illuminating the room. Simple wall art and round mirrors add visual interest to the neutral walls, while natural light filters through a sheer curtain.

Apartment in Medford

Blue apartment in Long Island, Ny

Indoor spacesKitchenCheck-in

4.93 out of 5 average rating, 135 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

Indoor spacesFamilyQuiet

4.87 out of 5 average rating, 138 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

KitchenIndoor spacesTV

4.98 out of 5 average rating, 182 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

FamilyIndoor spacesAccess

4.93 out of 5 average rating, 150 reviews

A spacious living area features a red sofa and a cozy armchair, situated around a wooden coffee table. Natural light floods the room, highlighting a framed painting above the sofa. The open kitchen is visible in the background, equipped with dark cabinetry and modern appliances.

Guest suite in Patchogue

Charming Garden Hideaway near downtown Patchogue

Indoor spacesKitchenBiking

4.95 out of 5 average rating, 204 reviews

A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.

Home in Shinnecock Hills

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong

KitchenIndoor spacesAccess

4.88 out of 5 average rating, 592 reviews

A serene beach scene illustrates a vast stretch of shoreline, with gentle waves lapping at the sand. The water is a mix of blue and green hues under a clear sky, providing a calming seaside atmosphere.

Cabin in Rocky Point

Little, cozy place near beach for a couple.

Indoor spacesKitchenCondition

4.99 out of 5 average rating, 67 reviews

Home in Mastic

Modern Hamptons Home

Indoor spacesFamilyCheck-in

Family-friendly home rentals with a pool

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, 174 reviews

Luxury Hamptons Home with Heated Saltwater Pool

KitchenIndoor spacesPool

Home in Westhampton Beach

A contemporary home with large windows overlooks a serene pool area. Lush greenery surrounds the property, providing a natural backdrop. Sun loungers are positioned beside the pool on spacious stone decking, inviting relaxation and outdoor enjoyment.

4.94 out of 5 average rating, 144 reviews

Hamptons Oasis: pool, grill, lush landscape

Indoor spacesFamilyValue

4.97 out of 5 average rating, 156 reviews

A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.

Home in Hampton Bays

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

KitchenIndoor spacesValue

4.88 out of 5 average rating, 24 reviews

A cozy living room features two comfortable sofas, one in light fabric and the other in gray. A unique wooden coffee table holds a vibrant flower arrangement at its center. A stone fireplace is accented by a mirror above, and a bookshelf is adjacent.

Home in Bellport

*NEW* Reno Bellport Village Home + Saltwater Pool

Indoor spacesKitchenPets

5.0 out of 5 average rating, 6 reviews

Home in East Moriches

Cedargate The East End’s 1830’s Seaside Farmhouse

KitchenFamilyBackyard

4.93 out of 5 average rating, 15 reviews

A private pool area features a rectangular blue pool with colorful floats, surrounded by a stone patio. Sun loungers are arranged on one side, while a shaded gazebo stands with outdoor bar seating nearby. Lush greenery and flowering shrubs provide a natural backdrop.

Home in Center Moriches

Bayside paradise w/ huge yard

FamilyIndoor spacesQuiet

4.91 out of 5 average rating, 32 reviews

An outdoor patio area features a rectangular dining table surrounded by several woven chairs. A private pool sparkles in the background, framed by lush greenery. Shaded areas created by large umbrellas provide comfort for outdoor gatherings.

Villa in Centereach

Summer Retreat: Heated Pool, Game Room, Playground

KitchenFamilyWalkability