
Family-friendly holiday rentals in Shirley
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Shirley
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Cozy Apartment with King Bed - Separate Entrance
Enjoy your stay in this private, clean and comfy environment. Space offers a bedroom with a king size bed and a desk for at-home work. Living room includes a smart TV and a sectional. Unleash your inner chef! Access to kitchen utensils, dinnerware, and pots/pans. Free parking on premises. Convenient location with many necessities nearby (mall/gas station/restaurants). We are located 2 mins from I-495 and 15 mins from Macarthur airport. Great for visiting family in Port Jefferson, Patchogue, etc!

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

Beautiful & Independent Guest House near the water
Welcome to our beautiful yet very private guest house in Brookhaven. You are walking distance from the Deer Run Farm (fresh eggs every morning), Post-Morrow Nature Trails and a short drive to Bellport Village Historic District. We are also very close to Wine Country, The Hamptons & Fire Island. We offer all the accommodations you might need for longer stays Washer & Dryer; Dishwasher; High Speed internet and TVs with all the premium channels. EV Charger available (Tesla - Fees applies).

Cozy studio
We are 10 minutes away to MacArthur Airport in Islip, 5 minutes to shopping center where you can find supermarkets, restaurants, and stores. We are 10 minutes away from LIRR train station where you can get a ride to Manhattan. Although the studio is centrally located a car or Uber is recommended,. You'll have your own bathroom, kitchen with microwave, coffee maker, toaster, fridge, air conditioner, tv with cable and internet. Our study is a FREE SMOKING PLACE! Not smoking or vaping!

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!

Boho Beach Vibez Retreat! Private entrance
"Experience a different kind of stay with our unique Airbnb, the 'Boho Beach Vibez” This cozy 1-bedroom apartment , that’s approximately 500sqft is situated on the first level of our home with a separate entrance . Located in a prime area of our town, you'll find yourself just minutes away from all the stores, restaurants, highways, and within walking distance of hiking trails, the Carman’s river, and 5 miles from Smith Point beach. NOTE : hosts live on top level .

Blue apartment in Long Island, Ny
Welcome to our blue apartment a Peaceful, comfy one bedroom apartment suitable for 4 people. Private bedroom has a Queen size bed with comfy mattress and two small closets to keep your belongs. Living room has two twin comfy beds, tv and desk. Kitchenette is equipped with necessities for a quick meal and coffee maker. You can also enjoy the shared backyard with the fire pit. Keep in mind if you stay past our check out time you will be charge an extra night.

Studio in Stony Brook
We have contactless check-in procedure & fully private entrance. Please contact with any questions! Large clean studio space that is totally private from the main residence. Private bathroom with toiletries included. Close to beaches, shopping, and SUNY hospital and campus by car or bus. Pull-out loveseat with twin size mattress available for an extra charge. (Book for “3 Guests” for this regardless of occupancy so we know to prepare the bed.)

Quaint Cottage on Long Island's South Shore.
The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

Modern style Spacious Getaway
This apartment offers a living room, dining area, bathroom, and a bedroom. The apartment is very spacious so you will never feel cramped and is stylish giving it a unique, creative vibe. The apartment is attached to the side of a house with the owners living on one side. The apartment is partitioned from the main house making it private. There is potential for noise sometimes. There are no hidden fees.

Charming “hotel inspired” Retreat
Relax and recharge at this peaceful, centrally located retreat. Your private room features a cozy full-size bed, desk and chair for work or study, TV for entertainment, and a coffee station with microwave and mini fridge for quick bites. Enjoy the privacy of your own bathroom and entrance, with easy on-street parking right in front of the house.

In-Law apt a block away from Patchogue Bay
Entire In-Law apartment in Patchogue NY! Ideal location: 10min walk to Davis Park ferry, 2min walk to the bay and Great South Bay Festival, 15min walk to the town, 10min walk to the train station! 1 bedroom, 2 beds (1 queen, 1 futon: full size). Private entrance, on the second floor of our house. Bikes available on request to cruise around.
Popular amenities for Shirley family-friendly rentals
Family-friendly home rentals with a hot tub

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

Luxury cottage by the sea with hot tub and pool

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

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

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!

Beach Haven - waterfront, near Yale, sunsets

Hampton's Haven

Paradise Citadel hottub, Htd pool, sauna, golf.
Family- and pet-friendly home rentals

Romantic, Cozy and Private, 1 Block from Beach

Small Studio. Private Entrance and bathroom

Charming Garden Hideaway near downtown Patchogue

Fall Sale! Cozy Bungalow/Walk2Beach/Pet-friendly

Great little place just for a couple

Port Jefferson Convenient, Cozy and Chic!

Eco-friendly studio with Private entrance

Walk to Vineyards, Beaches, Farms & Town
Family-friendly home rentals with a pool

Joyful Beach House, viewing The Great South Bay

Beautiful Airy Barn in Springs

Amazing Home close to Everything -

Southampton Charmer, 5 bedrooms w pool - Location

Spacious East Hampton Getaway with Pool

Modern farmhouse w/ pool, beach, horses and winery

A Lovely Cottage in the Woods

The Pond Mill Retreat w/ 2 Bdrms & Pool
Quick stats about holiday rentals that are family-friendly in Shirley
Total holiday rentals
Explore 40 holiday rentals in Shirley
Nightly prices starting at
Shirley holiday rentals start at £90 per night before taxes and fees
Verified guest reviews
Over 3,600 verified reviews to help you choose
Pet-friendly holiday rentals
Find 10 rentals that welcome pets
Holiday rentals with a pool
10 properties feature pools
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
40 of Shirley holiday rentals include wifi 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!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Rentals with a washing machine and dryer Shirley
- Rentals with a patio Shirley
- Rentals with pools Shirley
- Rentals with a fireplace Shirley
- Rentals with a firepit Shirley
- Flat rentals Shirley
- Pet-friendly rentals Shirley
- Rentals with outdoor seating Shirley
- House rentals Shirley
- Rentals with beach access Shirley
- Waterfront rentals Shirley
- Family-friendly rentals Suffolk County
- Family-friendly rentals New York
- Family-friendly rentals United States
- Yale University
- Jones Beach
- Fairfield Beach
- Southampton Beach
- Rye Beach
- Cooper's Beach, Southampton
- Gilgo Beach
- Robert Moses State Park
- Walnut Public Beach
- Rowayton Community Beach
- Shinnecock Hills Golf Club
- Bethpage State Park
- Rye Playland Beach
- Napeague Beach
- Cedar Beach
- Jones Beach State Park
- Silver Sands Beach
- Woodmont Beach
- Sunken Meadow State Park
- Jennings Beach
- Sandy Beach
- Wildemere Beach
- Seaside Beach
- Outer Beach at Smith Point County Park