Holiday rentals with outdoor seating in Shirley

4.93 out of 5 average rating, 227 reviews

A light-filled bedroom features a spacious bed with striped linens, situated next to a cozy sofa. A flat-screen TV is mounted on the wall opposite the bed. A large window allows natural light, with sheer curtains enhancing the bright ambiance.

Apartment in Coram

Private Apartment- close to shops, Pt. Jeff., SBU

Separate apartment with private keyless entrance. Cozy one bedroom king suite and sofa with full pull out bed. Full kitchen and dining area. Bathroom with standing shower. Free parking on premise for up to 2 cars. Quiet, family friendly neighborhood. Located in the heart of Long Island. Close to everything! Wineries, Farms, breweries, golf, shopping, great dining. NYC is a only a train ride away! Conveniently located within a mile of groceries and laundromat. High speed WiFi, 55in smart tv

4.98 out of 5 average rating, 226 reviews

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

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.

4.84 out of 5 average rating, 105 reviews

Quiet and comfy studio near the Hamptons

*If you have good prior reviews book our place and receive an offer within 24hrs! A well equipped cozy studio only 20 minutes from the Hamptons and 10 minutes away from LIRR train station to go into NYC (free parking at the train station!) This studio has a small kitchenette to warm up meals, a full size fridge, we include some snacks for those late night cravings. A queen size bed, a separate desk and chair to study or work, a couch, smart TV, and a peaceful environment to relax and unwind.

4.85 out of 5 average rating, 188 reviews

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.

Guest suite in North Fork

A bright yellow door with a window covered by blinds is framed by gray shingles. Two exterior lamps are mounted on either side, and a small porch area features a decorative mat in front of the door.

4.91 out of 5 average rating, 288 reviews

Beachy En Suite /Gateway to The North Fork

Adorable,quiet,clean, w private entrance, private bedroom and bathroom,breakfast nook and patio.We are located in a beach front town dubbed“Gateway to the North Fork”.Walking/driving directions to local beaches,15minute walk to our community beach,Wildwood StPk(.6mi away).Niks deli nearby.Minutes by car to wineries,breweries,farm stands,EastWind,TangerOutlets15min away,35min to Hamptons,Greenport!Hosts live in adjoining house.NoTV but Wifi is good so bring your device for entertainment.

4.88 out of 5 average rating, 102 reviews

Apartment in Ridge

The Golden Acorn

Welcome to the hamlet of Ridge. The gateway to Long Islands many treasures. Whether you are adventuring out to the North Fork wineries or a scenic drive on the south shore on your way to the Hamptons. A peaceful cozy private (not shared space) full studio apartment on the main level portion of house. Full size bed, with additional small futon couch in sitting area, kitchenette with dining area, full bathroom and private yard with outdoor seating. Everything you need to enjoy your stay.

4.94 out of 5 average rating, 257 reviews

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.

4.9 out of 5 average rating, 114 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

Welcome to our cozy private guest suite, nestled in a tranquil neighborhood walking distance to Main Street. This space has a comfortably-sized bedroom and living room with a well-equipped kitchen and bathroom. Relax in the living area after a day of exploring nearby attractions or unwind in the garden where your pets can run and play in the fenced yard. With easy access to local dining and shopping, this space offers the ideal blend of comfort and convenience for your stay.

4.95 out of 5 average rating, 138 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, 692 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.)

4.88 out of 5 average rating, 120 reviews

A living room is highlighted by a cozy sofa draped with a light throw. A glass coffee table sits atop a soft rug. A fireplace is set within a white mantel, complemented by plants and framed art that add a touch of character.

Home in Bellport

The Stella ~ Bellport Beach ~ Monthly Winter Rates

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. ~ ask about our monthly winter rates for 2025-2026 ~

4.95 out of 5 average rating, 258 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.

Popular amenities for Shirley outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

5 out of 5 average rating, 129 reviews

Home in Milford

Feb/Mar longer stays avail! Inquire! New Firepit!

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, 125 reviews

Hamptons Oasis: pool, grill, lush landscape

A spacious and heated swimming pool is surrounded by a brick patio and lush green landscaping. Two lounge chairs are positioned nearby, offering a tranquil spot to relax. The serene setting is enhanced by mature trees bordering the pool area.

4.87 out of 5 average rating, 115 reviews

Cheerful East Hampton home with Pool

4.91 out of 5 average rating, 175 reviews

The kitchen is designed with white cabinetry and stainless-steel appliances, including a refrigerator and gas stove. A large island with seating is positioned across from the sink, illuminated by natural light from nearby windows. Hardwood flooring adds warmth to the space.

Home in Bay Shore

The Harbor House

A bright living area features large windows that offer views of the nearby pond. Comfortable seating includes a white sofa, patterned chairs, and a coffee table, all arranged on a natural fiber rug. Light from the windows enhances the serene atmosphere.

4.87 out of 5 average rating, 117 reviews

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

4.94 out of 5 average rating, 380 reviews

A bright living room features a comfortable gray sofa against a neutral wall, complemented by a light-colored rug with geometric patterns. A wooden coffee table sits in front, with a lounge chair nearby. Natural light enters through multiple windows, creating a spacious feel.

Home in North Fork

The Sandpiper

A welcoming living area is illuminated by natural light from large windows. A comfortable gray sofa is complemented by light-colored armchairs and a coffee table adorned with books and decorative items. The neutral color palette is accentuated by indoor plants and a textured rug.

4.95 out of 5 average rating, 308 reviews

Sag Harbor Cottage, Walk to the Beach!

A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.

4.95 out of 5 average rating, 483 reviews

Silver House: 3BR Home with Private Beach Access

Apartment rentals with outdoor seating

4.89 out of 5 average rating, 254 reviews

The property features a white two-story house with a covered front porch and lush green landscaping. A red barn stands nearby, contrasting against the blue sky, while a paved driveway leads up to the residence, offering ample space for off-street parking.

Apartment in Milford

Renovated Apartment in a Historic Farmhouse Estate

4.89 out of 5 average rating, 132 reviews

The balcony features a charming outdoor dining set with a table and two folding chairs. A spread of sliced bread, apples, and glasses of sparkling drink is arranged, overlooking a view of downtown Stamford, with a mix of buildings and greenery visible in the distance.

Apartment in Stamford

Honey Spot Studio | Downtown City Views

Apartment in Islip Terrace

An outdoor seating area is set up with wicker chairs surrounding a gas fire pit, glowing warmly in the evening light. A well-maintained green lawn and white privacy fence create a serene backdrop, with soft string lights enhancing the inviting atmosphere.

4.96 out of 5 average rating, 196 reviews

Near all 1 BR - Full Kitchen, Backyard & Fire Pit!

4.94 out of 5 average rating, 303 reviews

The entrance features a welcoming porch adorned with decorative railings and a prominent front door. Potted plants and blooming flowers line the pathway, leading to a well-maintained yard with lush green grass and neatly trimmed shrubs on either side.

Apartment in Northport

NORTHPORT APARTMENT: Private, Clean, Cozy

4.95 out of 5 average rating, 333 reviews

A spacious bedroom features a large bed with crisp white linens, surrounded by vibrant artwork and colorful cabinetry. Warm wood paneling lines the ceiling, and two bedside lamps provide soft illumination, contributing to a bright and inviting environment.

Apartment in Southport

2BR Flat above Historic Cider Mill

4.94 out of 5 average rating, 101 reviews

A modern living area is presented, featuring a comfortable gray sofa adorned with soft pillows. A round coffee table sits on a black and white patterned rug, complemented by a small plant. A television is positioned in front, with natural light filtering through a window.

Apartment in Lindenhurst

2BR Gem/Private Driveway Entry

4.98 out of 5 average rating, 126 reviews

A modern kitchen features white cabinetry and sleek stainless steel appliances. The spacious layout includes a large refrigerator, a built-in oven, and a dishwasher. Natural light enters through nearby windows, illuminating the stylish countertops and a decorative rug that adds warmth to the space.

Apartment in Stamford

Luxurious 1BR Downtown Stamford

Apartment in Farmingville

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.

4.81 out of 5 average rating, 143 reviews

LOVELY STUDIO APT W/ PRIVATE ENTRANCE & PATIO

Condo rentals with outdoor seating

A living area features shiplap walls and ample natural light from large windows. A dark sectional sofa is positioned next to a glass coffee table with a small plant. An open kitchen area is visible, along with access to a screened porch through sliding doors.

4.86 out of 5 average rating, 129 reviews

Beautiful condo on Long Islands Northfork

A light-filled living area features a cozy neutral sofa, accompanied by a matching armchair. A decorative coffee table sits in the center, and a Smart TV is mounted on the wall. Sliders lead to a private waterfront deck with seating, enhancing the space's openness.

4.84 out of 5 average rating, 160 reviews

2 BR Waterfront Autumn Escape in Wine Country

4.84 out of 5 average rating, 146 reviews

A well-appointed bedroom features a spacious bed with decorative pillows, complemented by a cozy armchair with a vibrant red cushion. Natural light fills the room through large windows adorned with blinds, while an elegant painting adorns the wall above the bed.

Condo in Fairfield

Cozy 3-Bed 2-Bath Condo | Parking and Laundry!

A tranquil waterfront scene is captured at sunset, with the sky painted in shades of pink and purple. The calm water reflects the vibrant colors, creating a mirrored effect. A dock can be seen in the foreground, adding to the serene atmosphere of the setting.

Condo in Freeport

4.51 out of 5 average rating, 78 reviews

Waterfront Zen - Private 2 Bedroom

The living area features a spacious dark gray couch, a light wooden coffee table, and a white dining table with woven chairs. Natural light filters through the window with plantation shutters, while decorative elements like a round mirror and wall art create a welcoming ambiance.

4.9 out of 5 average rating, 175 reviews

Beautiful Waterview Condo on the North Fork of LI

4.95 out of 5 average rating, 41 reviews

Two people are seen swimming in a calm body of water, surrounded by gentle ripples reflecting sunlight. Lush greenery lines the distant shoreline, creating a serene backdrop against the shimmering surface.

Condo in Mount Sinai

1856 Trading House close to water

A sandy landscape is visible, with gentle dunes leading towards the calm ocean. Fencing made of wooden slats runs parallel to the beach, guiding towards the waterfront. Coastal grasses and sparse vegetation are present, complemented by a clear blue sky.

Condo in Long Beach

5 out of 5 average rating, 3 reviews

January dates- west end oceanfront condo

The living area showcases a comfortable sofa adorned with decorative cushions, complemented by a coffee table. A kitchen area with modern appliances is visible, alongside a dining cart. Art pieces frame the walls, and natural light enters through sliding glass doors.