Family-friendly vacation rentals in Shirley

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Top-rated family-friendly rentals in Shirley

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Guest favorite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

Nov 4 – 11

ﺩ.ﺇ2,735 per night

Guest favorite

Guest suite in Fairfield

4.92 out of 5 average rating, 112 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; for stays of 1 week or less: exclusive use of main kitchen; private entrance to space. Includes continental breakfast, 2 large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

Jan 16 – 23

ﺩ.ﺇ432 per night

Guest favorite

Home in Shirley

4.98 out of 5 average rating, 179 reviews

Luxurious Waterfront Beachouse 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

Mar 13 – 20

ﺩ.ﺇ1,908 per night

Guest favorite

Home in Center Moriches

4.98 out of 5 average rating, 188 reviews

Walk to beach and playground. Outdoor hot tub.

My goal is for all guests to relax & enjoy my quaint home. Have a Keurig coffee on the covered front porch, kick back on the second floor & rooftop outdoor decks. Bay beach and playground are a 3 min. walk from the house. Sunsets are beautiful. Ocean beaches are a 15 min. drive to the west (Smith Point) and to the east (Westhampton). The street borders a 263 acre park with trails. There is an outdoor shower (April thru Oct), hot tub, gas BBQ, fire pit, wifi & AC. 20 min. to wineries.

Dec 20 – 27

ﺩ.ﺇ1,502 per night

Guest favorite

Apartment in Smithtown

4.98 out of 5 average rating, 184 reviews

Mimi's Retreat -Private street level basement apt.

Walk-in street level one bedroom basement apartment with keypad entry in a quiet, safe neighborhood. Fully equipped kitchen includes cooking essentials, microwave, air fryer, electric tea kettle, Keurig coffee machine and toaster. Premium cable TV, excellent 5G Wi-Fi and Smart TV. Free parking on premise. Outside Security Camera's. Within walking distance to LIRR, restaurants and shopping. Centrally located between NYC, LI beaches & North Fork wine country. *NO PETS and NO SMOKING +

Dec 30 – Jan 6

ﺩ.ﺇ632 per night

Guest favorite

Guest suite in Bay Shore

4.95 out of 5 average rating, 240 reviews

Bay Shore's Private Guest Suite

Welcome to our cozy guest suite nestled within walking distance of the Fire Island ferries and conveniently close to local amenities! This private unit, attached to the main part of our home, offers a comfortable retreat for your stay. Step through your own private entrance into a welcoming living room, where you can unwind after a day of exploration. The bedroom features a queen-sized bed, providing a restful night's sleep, and an adjoining bathroom offers convenience and privacy.

Oct 17 – 24

ﺩ.ﺇ491 per night

Guest favorite

Apartment in Stony Brook

4.78 out of 5 average rating, 544 reviews

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.)

Sep 18 – 25

ﺩ.ﺇ403 per night

Guest favorite

Apartment in Islip Terrace

4.87 out of 5 average rating, 175 reviews

PHILS COZY Private studio(new kitchen/fresh paint)

My place is close to restaurants and dining, the beach, and family-friendly activities. You’ll love my place because of light, comfy bed, the kitchen, the coziness, and the high ceilings and privacy. Good for couples, solo, business travelers, and furry friends (pets). Located near the airport and train station. I ESPECIALLY PREFER MONTHLY OR SEASONAL LENGTHY VISITORS.

Nov 1 – 8

ﺩ.ﺇ429 per night

Guest favorite

Guest suite in New Haven

4.99 out of 5 average rating, 157 reviews

Cozy cottage in historic neighborhood

Housed in a 100-year-old building nestled between the Victorian houses in New Haven's historic City Point neighborhood, once the center of New England's oyster trade, our cottage is a two-block walk from the marina (and its award-winning restaurant), a 10 minute-drive from the West Haven beaches and a few minutes' drive to Yale.

Jun 24 – Jul 1

ﺩ.ﺇ550 per night

Guest favorite

Home in Ronkonkoma

4.86 out of 5 average rating, 147 reviews

Convenient home in Ronkonkoma

Charming cape that is completely private. This is not an apartment within a house. The entire home and yard are yours to enjoy with complete privacy. Conveniently located 6 blocks from LIRR Ronkonkoma Station, 2 miles from Islip MacArthur Airport, and 1 mile from Long Island Expressway. 5.5% Occupancy Tax included.

Jun 7 – 14

ﺩ.ﺇ424 per night

Guest favorite

Guest suite in Lake Ronkonkoma

4.99 out of 5 average rating, 235 reviews

Private New Apartment

Open concept living. Cathedral ceilings. 1 Bedroom, Full Bath. Private parking. Patio. 5 minutes from train, 15 minutes to MacArthur Airport. Close to Stony Brook, South shore ocean beaches, and the north shore of Long Island. Perfect if you are planning on heading out east to the wineries!

Sep 27 – Oct 4

ﺩ.ﺇ735 per night

Superhost

Home in East Patchogue

4.79 out of 5 average rating, 140 reviews

Bay's Edge Vacation Get a Way

Newly renovated home with views of the Great South Bay. Formal dining room, living room and spacious family room which opens up to a outdoor patio. The perfect spot for a quiet beach vacation. There are 3 bedrooms, two of which have full size beds, the third bedroom has a set of twin beds.

Apr 16 – 23

ﺩ.ﺇ1,156 per night