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Shirley Holiday Rentals

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Holiday Rentals in Shirley

Modern Vacation home. Close to The Hamptons

10.0 out of 10, Exceptional, (3)
"good time"
The price is NZ$1,096
includes taxes & fees
6 Oct - 7 Oct
Modern Vacation home. Close to The Hamptons

Relaxing Smith Point Beach House on private canal

9.6 out of 10, Exceptional, (59)
"The property is clean and it great working order with everything you need for your stay. Aceess to Smith Point Beach is easy we fished and had time in the sun while visiting with family and friends. The owners are kind, accommodating and easy to communicate with. "
Relaxing Smith Point Beach House on private canal

3 Story Beach Waterview, 3 KING bed, golf putting green!

10.0 out of 10, Exceptional, (21)
"Great costal location on Long Island. Eddie is a rockstar and took great care of us. Very unique architecture with lots of cool angles. Awesome family gettaway...!"
The price is NZ$1,072
includes taxes & fees
8 Oct - 9 Oct
3 Story Beach Waterview, 3 KING bed, golf putting green!

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

9.4 out of 10, Exceptional, (29)
"its small but very nice for a short stay would recommend."
The price is NZ$283
includes taxes & fees
9 Oct - 10 Oct
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Spacious Home Located Close to Stony Brook!

7.0 out of 10, Good, (20)
"Great stay great people great costumer care definitely reccomend"
The price is NZ$1,210
includes taxes & fees
10 Oct - 11 Oct
Spacious Home Located Close to Stony Brook!

Newly Renovated Luxury Beach House Ocean Bay Park

10.0 out of 10, Exceptional, (71)
"Very nice place for a family to stay"
The price is NZ$2,028
includes taxes & fees
8 Oct - 9 Oct
Newly Renovated Luxury Beach House Ocean Bay Park

East End Cottage Retreat - Dock, Fireplace, Beaches, Wineries & More!

10.0 out of 10, Exceptional, (99)
"Great indoor and outdoor spaces to hang out. Took SUP on the water - so nice and calm. "
The price is NZ$870
includes taxes & fees
2 Nov - 3 Nov
East End Cottage Retreat - Dock, Fireplace, Beaches, Wineries & More!

10 Bedroom Hampton House with a regulation size Pickleball court

10.0 out of 10, Exceptional, (32)
"Cannot say enough good things. Unique, sprawling, beautiful property with more than enough room for a large group. Endless entertainment, great pool, walking distance from a few bars and restaurants. Great communication and accommodation from our host. Would recommend and rent again."
10 Bedroom Hampton House with a regulation size Pickleball court

Walk to Beach 2BR Near Dining & Shopping

6.6 out of 10, (20)
"The beach is private and you need to be a Brookhaven resident to be admitted. This is not specified anywhere on the listing. Communication about this with the owner via app was rather poor. "
The price is NZ$474
includes taxes & fees
8 Oct - 9 Oct
Walk to Beach 2BR Near Dining & Shopping

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (33)
"We had a amazing stay and plan to come back next July again"
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

10.0 out of 10, Exceptional, (190)
"Had a lovely relaxing time with family and friends. Very convenient and great size."
The price is NZ$2,218
includes taxes & fees
17 Oct - 18 Oct
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (137)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Beautiful historic home in Stony Brook!

2.0 star property
8.4 out of 10, Very good, (15)
"Was a great place is a small town. Everything was clean and nice just wish there was a small sheer curtain in the bathroom where you shower. "
Beautiful historic home in Stony Brook!

OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!

9.0 out of 10, Wonderful, (53)
"Has a very nice stay."
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
8.4 out of 10, Very good, (7)
"prefect experience! The house is clean and well decorated with a large organized yard. Many parking spaces. "
The price is NZ$1,569
includes taxes & fees
3 Oct - 4 Oct
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

9.0 out of 10, Wonderful, (32)
"This is a charming little guest house that allows dogs and is steps away from the beach. What more can I say…"
One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

2.0 star property
10.0 out of 10, Exceptional, (7)
"What a nice place to stay! Key code entry, clean, quiet, comfortable and spacious. This basement apartment exceeded expectations and met all our needs. We would definitely rent this space again."
The price is NZ$307
includes taxes & fees
9 Oct - 10 Oct
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

9.4 out of 10, Exceptional, (73)
"Enjoyed our time. Thank you "
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Private beach on a fenced in property sunset views

10.0 out of 10, Exceptional, (12)
"We liked our stay there. Clean house, beautiful sunset as described. Close to the beach. Very nice stay."
The price is NZ$2,070
includes taxes & fees
5 Oct - 6 Oct
Private beach on a fenced in property sunset views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Shirley Hotel Reviews

Find out more about Shirley

Find out more about Shirley

Everything you need to know about Shirley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shirley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shirley holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Shirley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shirley. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shirley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shirley holiday rentals we have selected for you start as low as NZ$283 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shirley rentals

At Expedia, we put the best Shirley holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Shirley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shirley holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shirley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Shirley?

Yes, there are holiday rentals close to the most popular sights in Shirley, or you can select a more secluded option if you're looking for a relaxing stay. Shirley is known for its parks.

What are some of the best holiday rentals that Shirley has to offer?

Modern Vacation home. Close to The Hamptons: This highly rated holiday home rental in Shirley is located on the waterfront, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Shirley?

With 19 Expedia holiday rentals, you're guaranteed to find just the right place for your Shirley stay.

What can I see and do in Shirley?

Great South Bay and Carmans River are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Lasorda Legacy Park and TWA Flight 800 International Memorial.

What are holiday rentals like in Shirley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shirley. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.