Holiday rentals with outdoor seating in Shirley

4.92 out of 5 average rating, 217 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.

Flat 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

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, 225 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, 108 reviews

Home in The Hamptons

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

4.85 out of 5 average rating, 184 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, 286 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.

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.

4.94 out of 5 average rating, 254 reviews

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.

4.94 out of 5 average rating, 137 reviews

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!

4.98 out of 5 average rating, 191 reviews

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.

Flat in Islip Terrace

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

Come stay at this beautifully renovated 1 bedroom apartment! Well-appointed for long-term stays or quick trips. ~ Propane Fire Pit ~ Private Sun-soaked backyard. ~ Full kitchen ~ Living room with sofa/futon for a 3rd guest ~ Queen bed ~ Full bathroom ~ Off-street parking for 1 car. This is a first-floor, ground-level apartment that gets lots of natural light. It is not a basement! :) Located in a quiet neighborhood and near all major highways. SmartTV. No cable TV. 21+

4.95 out of 5 average rating, 135 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.

Flat 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, 678 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.)

Guest suite in Rocky Point

A serene beach scene illustrates a vast stretch of shoreline, with gentle waves lapping at the sand. The water is a mix of blue and green hues under a clear sky, providing a calming seaside atmosphere.

4.89 out of 5 average rating, 539 reviews

Great little place just for a couple

It's quiet and cozy here. The yard is completely fenced with tall, green, living shrubs. There's no high stone or wooden fence. The garden is full of flowers, shrubs, and trees. There's a gas grill, a fire pit, and a place to eat under an umbrella. Parking is free. I rent out half the house and the sitting area to guests. You won't be disturbed. The other half is empty; I only go there occasionally. I don't charge extra for pets.

4.89 out of 5 average rating, 112 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 ~

Popular amenities for outdoor seating rentals in Shirley

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.93 out of 5 average rating, 136 reviews

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

4.96 out of 5 average rating, 247 reviews

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

Designer Beach Retreat on Exclusive Cedar Beach

5 out of 5 average rating, 123 reviews

Home in Milford

HGTV reno! Fall Foliage, near New Haven, Firepit!

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.

4.84 out of 5 average rating, 58 reviews

Home Sweet Home by the Beach

4.94 out of 5 average rating, 144 reviews

A modern kitchen is showcased, featuring a large center island with four wooden bar stools. Stainless steel appliances and white cabinetry are complemented by granite countertops. Natural light filters in through a window above the sink, illuminating the inviting space.

Home in North Fork

Modern Farmhouse Retreat North Fork Wine Country

An aerial view showcases a spacious outdoor area featuring a heated pool, hot tub, and multiple seating arrangements. A patio dining table accommodates ten, while lounge chairs surround a fire pit. String lights illuminate the space, enhancing the inviting atmosphere for relaxation and entertainment.

4.94 out of 5 average rating, 70 reviews

Beach Getaway w/ Heated Pool & Hot tub

4.99 out of 5 average rating, 158 reviews

Home in Commack

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

4.92 out of 5 average rating, 118 reviews

A serene pool area is surrounded by lush greenery and colorful hydrangea flowers. Lounge chairs offer relaxation under large umbrellas, while the inviting pool reflects the clear blue sky. A charming home stands in the background, adding to the peaceful setting.

Home in The Hamptons

Southampton Charmer, 5 bedrooms w pool - Location

Apartment rentals with outdoor seating

4.92 out of 5 average rating, 112 reviews

A comfortable seating area features a dark gray sofa adorned with decorative pillows, positioned beside a lamp and a small side table. Natural light filters through sheer curtains, illuminating the space. A rug with intricate patterns adds warmth, while a display cabinet holds personal items.

Flat in Oceanside

Beautiful apartment available

4.94 out of 5 average rating, 293 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.

Flat in Northport

NORTHPORT APARTMENT: Private, Clean, Cozy

4.98 out of 5 average rating, 120 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.

Flat in Stamford

Luxurious 1BR Downtown Stamford

4.81 out of 5 average rating, 142 reviews

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.

Flat in Farmingville

LOVELY STUDIO APT W/ PRIVATE ENTRANCE & PATIO

4.95 out of 5 average rating, 333 reviews

A well-appointed sleeping area is furnished with a cozy queen-size bed dressed in light bedding. Two bedside lamps provide soft lighting, while a decorative wall poster adds character. Window treatments consist of striped curtains, framing the natural light that filters through.

Flat in West Babylon

The Cozy Apartment

4.98 out of 5 average rating, 130 reviews

A sandy path leads through beach grass, flanked by wooden fencing, toward a tranquil ocean beyond. Clear blue skies complement the scene, where gentle waves are visible on the horizon.

Flat in The Hamptons

Walk to Bay and Ocean-Newly Renovated

4.94 out of 5 average rating, 235 reviews

A balcony is equipped with outdoor furniture, including two chairs and a small table. The scene is enhanced by a view of the city skyline during sunset, with soft, warm lighting reflecting off the buildings. Glasses are placed on the table.

Flat in Stamford

Sugar Shack Studio | Downtown Skyline Views

4.97 out of 5 average rating, 130 reviews

A modern living room is highlighted by a set of white sofas with tufted detailing, accented by blue cushions. A light fixture with a circular design illuminates the space, while sheer curtains frame the windows. A coffee table and two armchairs complement the room’s layout.

Flat in Freeport

Quiet Waterfront Entire Apartment

Apartment rentals with outdoor seating

4.81 out of 5 average rating, 79 reviews

Two individuals are seen enjoying a swim in a calm body of water, with sunlight reflecting off the surface. Lush greenery is visible in the background, creating a serene natural setting.

Apartment in Mount Sinai

1856 Trading House w/ walk to water

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.

4.87 out of 5 average rating, 126 reviews

Beautiful condo on Long Islands Northfork

An inviting living space features a light-colored wooden floor and white paneled walls. A cozy couch and soft ottoman complement a TV mounted on the wall. A dining table with chairs is positioned next to a window, allowing natural light to brighten the room.

Apartment in Ocean Bay Park

4.43 out of 5 average rating, 51 reviews

1BR Apt. in Ocean Bay Park with rooftop deck

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.

4.85 out of 5 average rating, 156 reviews

2 BR Waterfront Autumn Escape in Wine Country

4.84 out of 5 average rating, 143 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.

Apartment in Fairfield

Cozy Condo by Fairfield U/SHU | Patio | Wshr/Dryr

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.

Apartment in Freeport

4.55 out of 5 average rating, 77 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, 172 reviews

Beautiful Waterview Condo on the North Fork of LI

Two blue Adirondack chairs are positioned on a manicured lawn, facing a vibrant sunset over the ocean. The sky displays pink and orange hues as the sun sets on the horizon, creating a serene outdoor setting.