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Places to stay in Shirley

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Top-rated places to stay in Shirley

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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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

4.88 out of 5 average rating, 138 reviews

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!

A dining table set on the deck displays plates of oysters garnished with lemon slices, accompanied by glasses of white wine. A bottle of wine stands nearby, with the Great South Bay and a sunset in the background, creating a serene outdoor dining atmosphere.

Home in Shirley

4.98 out of 5 average rating, 201 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

A modern living area is showcased with a gray futon adorned with decorative pillows. A white coffee table sits on a soft area rug, while a microwave and refrigerator are positioned against the wall. Soft lighting enhances the clean tile flooring.

Apartment in Patchogue

4.88 out of 5 average rating, 217 reviews

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

Large windows allow natural light to fill the open living space, showcasing the stunning view of the Great South Bay. A comfortable sofa with decorative pillows faces the water, complemented by a dining area nearby. Warm wood tones enhance the cozy atmosphere of the room.

Cabin in Shirley

4.87 out of 5 average rating, 161 reviews

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.

Top guest favorite

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

4.96 out of 5 average rating, 141 reviews

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.

A calm beach scene at dusk is presented with soft hues of pink and blue in the sky. The sandy shore is visible, with a large rock positioned near the water's edge. Two signs marked 'PRIVATE BEACH' stand upright in the foreground.

Guest suite in North Fork

4.9 out of 5 average rating, 271 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.

A hot tub is surrounded by a wood pergola adorned with string lights, creating a warm ambiance in the evening. A spacious backyard features various seating areas, including a hammock and decorative elements, while soft lighting enhances the relaxing atmosphere.

4.95 out of 5 average rating, 146 reviews

Paradise Citadel hottub, Htd pool golf basketball

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 🚗 Free Parking 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

A Stiga ping pong table is displayed in a well-lit game room, featuring a sleek black surface with red accents. Nearby, a foosball table and framed sports memorabilia can be seen, creating an inviting space for fun and entertainment.

Home in Shirley

4.94 out of 5 average rating, 235 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.

A set of stone stairs is illuminated by soft pathway lights, leading to the entrance of the home. The surrounding area features low greenery, creating a serene atmosphere during nighttime.

Apartment in Farmingville

4.88 out of 5 average rating, 105 reviews

Studio Apt W/Private Entrance & Patio

Enjoy your stay in this private space offers a bedroom with a Queen size bed . Living room includes a smart TV 43" with twin sofa bed and desk for at-home work, kitchen where to find enough crockery for four people, microwave, refrigerator,coffee maker, Free parking on premises. Convenient location with many necessities nearby (gas station/restaurants). We are located 2 mins from I-495 and 14 mins from Macarthur airport. Keep it simple at this peaceful and centrally-located place.

The interior features a bright, open space with wooden beams and rustic decor. A comfortable couch with a plaid throw faces a wall-mounted TV. A staircase with unique railings leads to the upper level, while a dining area is visible to the side.

Tiny home in Mastic

4.93 out of 5 average rating, 121 reviews

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!

A cozy bedroom features a spacious bed with layered bedding, complemented by decorative pillows. Artwork depicting a beach scene adorns the walls. A TV is mounted for entertainment. Natural light filters in through large windows, enhancing the inviting atmosphere.

Apartment in Shirley

4.94 out of 5 average rating, 107 reviews

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 .

The rear view of the three-story beach home is shown, highlighting a spacious backyard. A fire pit is centered on the soft turf, surrounded by a stone border. Outdoor seating is positioned on the upper deck, with steps leading from the deck to the yard.

Home in Shirley

4.96 out of 5 average rating, 126 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.

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Popular amenities for Shirley places to stay

Laptop-friendly workspace

Other great vacation rentals in Shirley

A spacious garden is framed by tall, leafy trees, featuring a circular seating arrangement with several Adirondack chairs surrounding a fire pit. Soft hues of pink and purple fill the sky at dusk, while pathways lead deeper into the verdant landscape filled with blooming plants.

Home in Brookhaven

4.97 out of 5 average rating, 92 reviews

Nature Lovers Paradise at Zephaniah Conklin Farm

YaldaRating, 5 stars9 months ago

Had a wonderful stay at Paul's. He was incredibly responsive and lovely to interact with. The house is tastefully designed - it's such a pretty cottage, lovely touches throughout and his design sensibility shines through. The backyard was really the highlight for us. The landscaping is stunning (imagine a backyard full of hydrangeas) and you could spend all of your time out there - between the pool, the firepit, the lighting, outdoor shower and patio, we found ourselves not wanting to leave. There is even a beautifully restored and, I imagine historical, restored family cemetery at the back of the property. We enjoyed the short trips over to Smith Point and Fire Island, and wandering Bellport and Brookhaven, where there are many beautiful homes and terrific local farms. Definitely recommend!

A living area features a sleek black leather couch facing a modern electronic fireplace. A flat-screen TV is mounted on a decorative brick wall. A light-colored armchair complements the space, alongside a low coffee table and a textured area rug, creating an inviting atmosphere.

Apartment in Mastic

5 out of 5 average rating, 5 reviews

1 Bed room Apartment in Manorville.

AyajRating, 5 stars4 days ago

We absolutely loved our stay at C & S – it truly felt like a home away from home. The hosts were incredibly friendly and responsive, going above and beyond to make us feel welcome. We were especially touched by the thoughtful toy corner they set up for our 2-year-old daughter—she walked in and exclaimed, “Wow, this is so amazing!” It was a wonderful experience from start to finish. Thank you so much for hosting us—we’d love to return if we’re ever in the area again!

Guesthouse in Middle Island

5 out of 5 average rating, 10 reviews

Private newly renovated apt

WesleyRating, 5 stars2 weeks ago

Clean place everything was just like the images posted ,Arielle went above and beyond on communication made check in seamless and provided everything I needed for a comfortable stay.

A modern bathroom features a glass-enclosed shower with a rainfall showerhead. The toilet is positioned beside a white sink, and a towel rack holds neatly stacked towels. Natural light enters through a window, complemented by patterned curtains. Neutral tiles create a calming ambiance.

Home in Shirley

4.87 out of 5 average rating, 139 reviews

Cope near the beach

LatashaRating, 5 stars1 month ago

I really enjoyed my stay I was very comfortable and the host was extremely nice I would definitely stay again

A bright bathroom features dual sinks with vintage-style faucets, paired with a spacious, antique claw-foot bathtub. Natural light filters through a window, casting a soft glow on the room's clean, neutral walls. Towels are neatly arranged on a towel rack, adding to the room's functional elegance.

Cottage in Yaphank

4.86 out of 5 average rating, 64 reviews

Beautiful Waterfront Cottage

GlennRating, 5 stars1 week ago

A beautiful house that felt very spacious for its size. It was very stylish and super comfortable. The backyard was huge with a little bridge that went over the pond, and had daily visits from a rabbit, groundhog and turtle. This house is a great choice if you are visiting the area, with the Expressway a minute away, a Walmart at the next exit going east, and a deli, pizza place and gas station at the corners of your street. Looking forward to staying again

A well-lit bathroom features light blue patterned wallpaper, a sleek white door, and a vintage-style sink. A mirror with a decorative frame is mounted above the sink, while a towel holder and a cushioned bench add functional elements to the space.

Home in Bellport

5 out of 5 average rating, 4 reviews

Bellport Village Retreat

Dean And AnneRating, 5 stars1 month ago

Karen’s home was so beautiful, well decorated and comfortable. The home was very well equipped with everything we needed including high end amenities all throughout the home and a chefs kitchens dream. We have stayed in Airbnb’s in many parts of the country and the home far exceeded our expectations. On top of that Karen was a kind and responsive host. We really would give this host and home 10 stars if that was possible. Highly recommend that you book the home of you have the opportunity.

A white shelving unit features neatly arranged, packaged slippers. Two gray slippers with a soft fabric surface are placed side by side, while a single black slipper with a patterned bottom is positioned on the left.

4.88 out of 5 average rating, 8 reviews

Luxe Home Escape

CrystalRating, 5 stars1 week ago

Nerlly's space was exactly how she described it. Plenty of space for my family and I of 3. We had everything we needed for our stay and more. The basement unit was very clean upon arrival and Nerlly allowed us to check in early. It was very comfortable and peaceful. Her and her husband are so sweet and very attentive hosts! Our stay couldn't have been any better. Thank you so much for being awesome hosts! We would definitely recommend them and their home to anyone looking for a comfortable, clean and friendly stay.

Home in Mastic Beach

5 out of 5 average rating, 8 reviews

Newly Renovated Home in Mastic Beach!

JoshRating, 5 stars6 days ago

Great host. The place was nice and as described. Julianne responded quickly when messaged. Overall fantastic host.

Quick stats about vacation rentals in Shirley

Total rentals
90 properties
Total number of reviews
5K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Shirley?
Yes! Work meets play with ease at over 50 vacation rentals in Shirley featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Shirley?
Enhance your stay in our House Rentals with the most popular amenities: over 70 homes with wifi, over 10 homes with self check-in, over 30 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Shirley?
Four-legged friends are welcome in Shirley. Choose from more than 20 vacation rentals for guests traveling with pets.
Do house rentals in Shirley have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in Shirley. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Shirley have wifi?
Absolutely! We offer over 70 house rentals with wifi in Shirley. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Shirley have a bbq area?
Absolutely! We offer over 30 house rentals with a bbq area in Shirley. Enjoy a tailored experience with all the comforts you desire.
Are there Shirley house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Shirley, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly house rentals in Shirley?
Shirley has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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