Vacation rentals in Shirley

4.87 out of 5 average rating, 150 reviews

A bright living room area features a sectional sofa and a coffee table set on light carpet. A smart TV is positioned on a low stand, and natural light enters through a skylight. Decorative curtains frame the window, adding a touch of style.

Apartment in Medford

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!

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, 219 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

4.87 out of 5 average rating, 229 reviews

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 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

4.97 out of 5 average rating, 158 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 Patchogue

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.

4.74 out of 5 average rating, 171 reviews

A cozy living area features a sectional sofa with decorative pillows and a glass side table. A dynamic area rug adds warmth, while wall art and a mirror enhance the space. Natural light is provided by a lamp and nearby windows, creating a welcoming environment.

Apartment in Ridge

The Silver Pine Cone

Welcome to the hamlet of Ridge. The gateway to Long Islands many treasures. Whether you are venturing out to the North Fork wineries or a scenic drive on the south shore beaches on your way to the Hamptons. A beautiful cozy private (not a shared space) full one bedroom downstairs lower level apartment, living room w/full size sofa sleeper, kitchen/dining room, full bathroom and a completely separate yard with patio furniture exclusively for your use. Everything you need to enjoy your stay.

4.96 out of 5 average rating, 195 reviews

An aerial view captures a private guest house surrounded by lush green landscaping. Outdoor furniture is arranged around a small table, complemented by two sun beds. A barbeque grill is visible near the house, with vibrant flowers accentuating the backyard space.

Home in Brookhaven

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).

A modern kitchen features a central wooden island with a light wood countertop. White cabinets line the walls, complemented by sleek stainless-steel appliances. A farmhouse sink is located beneath a double window, and a decorative sign reading 'eat' is mounted on the wall.

4.76 out of 5 average rating, 331 reviews

Beautiful home with Game Room

Beautiful home with modern farmhouse decor located near the beach, the vineyards and the Hamptons! We have board games, a ping pong table, a poker table and a tv with Hulu! Hangout by the firepit on chilly nights or stay in the Central A/C on those hot days. Play outside with the kids or watch them play from the hammock. Grill some burgers and hang on the back patio. Everything you need for a fantastic stay. Come check it out! We promise you won’t be disappointed :) *No Parties*

4.99 out of 5 average rating, 114 reviews

A well-appointed sleeping area features a queen bed with crisp white linens, flanked by two illuminated nightstands. Above the bed, an abstract art piece adds a pop of color to the neutral walls. A small plant is positioned near the bed, enhancing the calming atmosphere.

Place to stay in Coram

T&T Unique Space

NEW ! Private renovated studio attached to a single family home. Private entrance queen bed w/full bathroom, sofa, 55”smartTV, kitchenette(no stove)free street parking in front of house.This is a drug free, non-smoking, no pets and no party unit. Minutes from Port Jefferson pier, LIRR, Connecticut Ferry, 15 min. to Mac Arthur airport. Shopping in Riverhead at Tanger Outlets a few exits from the LIE. 10min. to John T Mather Hospital & St Charles Hosp. Near Jakes 58 Casino and Top Golf.

4.95 out of 5 average rating, 123 reviews

A cozy living area features a plush gray couch adorned with decorative pillows. Vibrant blue walls complement the stylish kitchen cabinetry in the background. A large flat-screen television displays a scenic beach image, while a sleek desk sits nearby. Soft lighting adds to the inviting ambiance.

Apartment in Shirley

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 .

Guest suite in Stony Brook

A spacious studio features a queen-sized bed with patterned bedding, flanked by bedside lamps. A small dining table with two chairs is positioned near a window, allowing for natural light. A wooden bench is placed at the foot of the bed, enhancing the room's functionality.

4.8 out of 5 average rating, 659 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.)

A well-maintained putting green is positioned in the front yard, surrounded by soft turf and bordered by gravel. Small flags are placed on the green, with nearby shrubs and trees adding to the outdoor landscape. The house is visible in the background.

4.96 out of 5 average rating, 150 reviews

Beach Waterview, 3 KING Beds, Golf Putting Green

Take it easy at this 3 story waterview beach home with a putting green and fire pit. The Bellport Bay is across the street. Shirley Beach: 0.4 mile walk Smith Point Beach: 1.8 miles Featuring: 3 luxurious KING beds 👑 (and 2 fulls) Watch Netflix, Disney+ on the 70" living room TV and 3 50" bedroom TVs Fully equiped kitchen/dining room Enjoy BBQ Grill, fire pit on premium soft turf Highspeed mesh WiFi, keyless entry.

4.94 out of 5 average rating, 248 reviews

A spacious living area displays rustic log walls and a mix of wooden and upholstered furniture. A comfortable leather sofa is positioned near a stone wood stove, while a colorful armchair adds charm. Natural light fills the room through windows adorned with patterned curtains.

Cottage in Patchogue

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.

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Popular amenities for Shirley vacation rentals

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Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Shirley

An open-concept living area is showcased with a light gray sofa adorned with patterned pillows. A plush area rug lies beneath it, while wooden cabinets and essential appliances are visible in the kitchenette area, complemented by a patterned floor mat.

4.86 out of 5 average rating, 51 reviews

Home Sweet Home by the Beach

4.53 out of 5 average rating, 165 reviews

A quaint cottage exterior is framed by lush greenery, including ornamental grasses and shrubs. A wooden path leads to the entry, highlighting a welcoming entrance set under a tree. The soft colors of the cottage blend harmoniously with the natural surroundings.

Home in Mastic Beach

Cottage with Seashells

4.87 out of 5 average rating, 92 reviews

A cozy sleeping area is presented with a plush, upholstered bed featuring a tall, tufted headboard. Soft, light-colored bedding complements decorative pillows. A stylish nightstand with a lamp adds functional decor beside the bed, while natural light illuminates the space.

Guest suite in Shirley

A&D Airbnb.

5 out of 5 average rating, 34 reviews

A living room area features a cozy gray sofa adorned with dark cushions, facing a simple white coffee table. A round mirror reflects the warm lighting from a modern floor lamp. Natural light enters through a nearby window, highlighting the smooth wooden flooring.

Apartment in Shirley

1 BR Zen Den Apt in Safe & Beautiful Neighborhood

Apartment in Center Moriches

An open studio space features a spacious bed with a light duvet and decorative pillows. A leather couch complements the area, while large windows provide natural light, framed by white blinds. A bedside table and warm lighting create a cozy ambiance.

4.86 out of 5 average rating, 94 reviews

Quiet and comfy studio near the Hamptons

4.96 out of 5 average rating, 101 reviews

A comfortable sleeping area features a spacious bed with a blue quilt and decorative pillows. Two side tables with lamps are placed beside the bed. A small arrangement of flowers adds a touch of color. Blinds cover the window, allowing for adjustable natural light.

Guesthouse in Shirley

La casita J place

4.98 out of 5 average rating, 65 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

A cozy living room features a light beige sectional sofa adorned with decorative pillows. A wooden coffee table rests on a patterned area rug. Natural light enters through large windows, complemented by bamboo shades, creating a bright and inviting space.