
Holiday rentals in Shirley
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Shirley
Guests agree: these stays are highly rated for location, cleanliness and more.

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!

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

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

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.

Cozy studio
We are 10 minutes away to MacArthur Airport in Islip, 5 minutes to shopping center where you can find supermarkets, restaurants, and stores. We are 10 minutes away from LIRR train station where you can get a ride to Manhattan. Although the studio is centrally located a car or Uber is recommended,. You'll have your own bathroom, kitchen with microwave, coffee maker, toaster, fridge, air conditioner, tv with cable and internet. Our study is a FREE SMOKING PLACE! Not smoking or vaping!

Fall Sale! CozyCottage/Pet-friendly/Walk to Beach
Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

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 .

Blue apartment in Long Island, Ny
Welcome to our blue apartment a Peaceful, comfy one bedroom apartment suitable for 4 people. Private bedroom has a Queen size bed with comfy mattress and two small closets to keep your belongs. Living room has two twin comfy beds, tv and desk. Kitchenette is equipped with necessities for a quick meal and coffee maker. You can also enjoy the shared backyard with the fire pit. Keep in mind if you stay past our check out time you will be charge an extra night.

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.)

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.

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.

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 holiday rentals
Other great holiday rentals in Shirley

J&J's BnB Lovely, BR/Bath w/ Private Entrance!

Home Sweet Home by the Beach

Cozy studio w/ private entrance

Modern Farmhouse Decor With Washer/Dryer

Cottage with Seashells

Beach Getaway w/ Heated Pool & Hot tub

Welcome to Bill & Debbies AirBnb

Cozy Guest Suite 10 min to Ocean
When is the best time to visit Shirley?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $247 SGD | $221 SGD | $227 SGD | $236 SGD | $249 SGD | $267 SGD | $288 SGD | $323 SGD | $236 SGD | $253 SGD | $227 SGD | $247 SGD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 15°C | 21°C | 24°C | 23°C | 19°C | 13°C | 8°C | 3°C |
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.
Do house rentals in Shirley have air conditioning?
Absolutely! We offer over 60 house rentals with air conditioning in Shirley. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Shirley have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Shirley. Enjoy a tailored experience with all the comforts you desire.
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.
Are there family-friendly vacation rentals in Shirley?
Shirley has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Shirley have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Shirley. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Shirley?
Experience the best of Shirley with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Shirley vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Shirley, available on Airbnb. Make a splash and soak up the sun in style!
What are the most popular amenities for Apartment Rentals in Shirley?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Shirley have free parking?
Absolutely! We offer over 60 house rentals with free parking in Shirley. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Shirley

Total holiday rentals
Explore 90 holiday rentals in Shirley

Nightly prices starting at
Shirley holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 5,600 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
90 of Shirley holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Shirley rentals

4.9 Average rating
Shirley stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with pools Shirley
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- Rentals with a firepit Shirley
- Family-friendly rentals Shirley
- Rentals with a patio Shirley
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- House rentals Shirley
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