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Family-friendly vacation rentals in Shirley

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Shirley

  • Total vacation rentals

    Explore 40 vacation rentals in Shirley

  • Nightly prices starting at

    Shirley vacation rentals start at ﺩ.ﺇ 551 per night before taxes and fees

  • Verified guest reviews

    Over 3,460 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Shirley vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Shirley rentals

  • 4.9 Average rating

    Shirley stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Shirley

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
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.
Home in Shirley

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

FamilyKitchenWifi

4.98 out of 5 average rating, 243 reviews
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

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

FamilyKitchenCondition

4.85 out of 5 average rating, 276 reviews
Superhost
A spacious living area features large glass windows that frame a stunning sunset over the water. The open design enhances natural light, illuminating the room's elegant furnishings and wooden accents. A dining table is positioned near the windows, inviting relaxed meals with a view.
Cabin in Shirley

A-Frame cabin with private beach & epic sunsets

Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

KitchenIndoor spacesBeach

4.82 out of 5 average rating, 216 reviews
Top guest favorite
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.

FamilyIndoor spacesDecor

4.97 out of 5 average rating, 219 reviews
Guest favorite
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.

Indoor spacesKitchenLayout

4.92 out of 5 average rating, 142 reviews
Guest favorite
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.

FamilyKitchenAir conditioning

4.88 out of 5 average rating, 152 reviews
Guest favorite
Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

Indoor spacesKitchenBathroom

4.96 out of 5 average rating, 184 reviews
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.
Home in Shirley

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.

FamilyKitchenCheck-in

4.93 out of 5 average rating, 271 reviews
Guest favorite
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.
Home in Shirley

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 spacesGrill

4.87 out of 5 average rating, 108 reviews
Guest favorite
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!

Indoor spacesFamilyNearby

4.94 out of 5 average rating, 161 reviews
Top guest favorite
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 spacesParking

4.99 out of 5 average rating, 107 reviews
Guest favorite
A spacious living room features a large sectional sofa adorned with colorful cushions, offering comfort and relaxation. A sleek television is mounted on the wall, while natural light streams through wide windows, illuminating a wooden coffee table and a decorative fireplace in the corner.
Home in Mastic

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Indoor spacesFamilySleep quality

4.87 out of 5 average rating, 150 reviews

Popular amenities for Shirley family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
Home in Commack

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

FamilyIndoor spacesPets

4.99 out of 5 average rating, 186 reviews
Top guest favorite
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 spacesOutdoor spaces

4.9 out of 5 average rating, 177 reviews
Guest favorite
Home in Sag Harbor

Barefoot Bliss | Quiet Family Retreat Heated Pool

FamilyKitchenPool

4.91 out of 5 average rating, 202 reviews
Superhost
A charming red cottage is set among lush greenery, showcasing a manicured lawn leading to the porch. The house features a rustic stone chimney and a welcoming front porch adorned with white railings. Nearby, a small structure complements the main home with a rounded window.
Home in Port Jefferson

The Hilltop Harborview

KitchenFamilyHospitality

4.81 out of 5 average rating, 421 reviews
Guest favorite
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 spacesKitchenBackyard

4.96 out of 5 average rating, 109 reviews
Guest favorite
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

KitchenFamilyAir conditioning

4.91 out of 5 average rating, 156 reviews
Top guest favorite
An outdoor deck is viewed, featuring a swimming pool surrounded by lounge chairs and shaded by red umbrellas. A dining table with ample seating is situated on one side, enhancing the open-air space with lush greenery in the background.
Apartment in Fire Island

"SOUTH APT." Renovated 1 Br Apt. In Great Location

FamilyIndoor spacesQuiet

4.98 out of 5 average rating, 131 reviews
Top guest favorite
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.
Home in Westhampton Beach

Hampton's Haven

Indoor spacesKitchenWifi

4.93 out of 5 average rating, 165 reviews

Family- and pet-friendly home rentals

Guest favorite
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

FamilyIndoor spacesGetting around

4.93 out of 5 average rating, 158 reviews
Superhost
Apartment in Ridge

Spacious 1Bedroom Apartment By Wineries & Beaches

Indoor spacesKitchenSleep quality

4.76 out of 5 average rating, 196 reviews
Guest favorite
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 spacesFamilyCheck-in

4.82 out of 5 average rating, 126 reviews
Top guest favorite
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 spacesKitchenBackyard

4.93 out of 5 average rating, 134 reviews
Top guest favorite
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

KitchenFamilyLong stay

4.93 out of 5 average rating, 150 reviews
Guest favorite
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

Indoor spacesFamilyAccess

4.87 out of 5 average rating, 137 reviews
Top guest favorite
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

KitchenFamilyCheckout

4.98 out of 5 average rating, 182 reviews
Guest favorite
A spacious backyard is showcased with a large saltwater pool, featuring a floating inflatable and sun loungers arranged along the edge. The house stands in the background, framed by trees and an inviting grassy area, enclosed by a black fence.
Home in Hampton Bays

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

FamilyIndoor spacesLayout

4.94 out of 5 average rating, 116 reviews

Family-friendly home rentals with a pool

Guest favorite
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.
Home in Westhampton Beach

Luxury Hamptons Home with Heated Saltwater Pool

KitchenIndoor spacesCheckout

4.98 out of 5 average rating, 173 reviews
Top guest favorite
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.
Home in Westhampton Beach

Hamptons Oasis: pool, grill, lush landscape

Indoor spacesKitchenParking

4.94 out of 5 average rating, 143 reviews
Guest favorite
A cozy corner of the apartment is showcased, featuring a round mirror above a narrow table with two stools. A comfortable armchair with a plush cushion is positioned nearby. Natural light enters through a window adorned with sheer green curtains, enhancing the inviting space.
Apartment in Farmingville

LOVELY STUDIO APT W/ PRIVATE ENTRANCE & PATIO

KitchenIndoor spacesWalkability

4.82 out of 5 average rating, 158 reviews
Guest favorite
A dining area is presented featuring a dark wooden table surrounded by four white chairs. A decorative potted plant is centered on the table, complementing the modern decor. A doorway leads to a softly lit bedroom in the background.
Home in Port Jefferson

Port Jefferson Convenient, Cozy and Chic!

KitchenFamilyAir conditioning

4.93 out of 5 average rating, 157 reviews
Guest favorite
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

KitchenFamilyCheckout

4.95 out of 5 average rating, 204 reviews
Top guest favorite
A spacious backyard features a large heated pool, surrounded by multiple lounge chairs. A gazebo provides shaded seating, and a wooden deck extends towards the house, which is complemented by lush greenery and trees in the background under a clear blue sky.
Home in Shirley

Beach Retreat - Heated Pool, Game Room & Bar

KitchenIndoor spacesBackyard

4.99 out of 5 average rating, 88 reviews
Guest favorite
Home in East Moriches

Cedargate The East End’s 1830’s Seaside Farmhouse

FamilyKitchenGrill

5.0 out of 5 average rating, 6 reviews
Top guest favorite
An aerial view captures the heated saltwater pool surrounded by a spacious patio. Lounge chairs and shaded seating areas are arranged near the pool, with outdoor furniture positioned for relaxation. Lush greenery and a landscaped garden frame the space, providing a serene environment.
Home in Yaphank

Long Island Getaway w/ Heated Pool & Lake

KitchenFamilyCheckout

5.0 out of 5 average rating, 51 reviews

When is the best time to visit Shirley?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 992ﺩ.ﺇ 1,087ﺩ.ﺇ 1,098ﺩ.ﺇ 1,010ﺩ.ﺇ 1,197ﺩ.ﺇ 1,340ﺩ.ﺇ 1,407ﺩ.ﺇ 1,469ﺩ.ﺇ 1,234ﺩ.ﺇ 1,127ﺩ.ﺇ 1,124ﺩ.ﺇ 1,021
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