Photo by AnnMarie Guli Photography

Shirley Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Shirley

Modern Vacation home. Close to The Hamptons

Shirley
10.0 out of 10, Exceptional, (3)
"good time"
United States
Roy T.
The price is NZ$1,066
includes taxes & fees
30 Nov - 1 Dec
Modern Vacation home. Close to The Hamptons

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

Shirley
10.0 out of 10, Exceptional, (21)
"Eddie was a great host, we loved the area and will definitely keep him in mind when we plan on returning."
United States
Faraz S.
The price is NZ$1,094
includes taxes & fees
18 Nov - 19 Nov
3 Story Beach Waterview, 3 KING bed, golf putting green!

Tranquil Stay

Shirley
8.4 out of 10, Very good, (9)
"We were pleased with our stay! The living room was spacious for family interaction, the kitchen was well appointed. My kids loved getting a visit from the neighboring chickens each morning! We enjoyed a day at nearby Smith Point beach as well."
United States
Jules D.
Tranquil Stay

LUXURY BAY SHORE HOME

2.0 star property
Bay Shore
2.0 out of 10, (1)
The price is NZ$1,834
includes taxes & fees
18 Nov - 19 Nov
LUXURY BAY SHORE HOME

Cozy 2 bedroom retreat in long island

2.0 star property
Central Islip
8.0 out of 10, Very good, (1)
"Some noise at night. Great shower and great water pressure but shower head suction cup does not stay on wall."
United States
Suzanne S.
The price is NZ$446
includes taxes & fees
18 Nov - 19 Nov
Cozy 2 bedroom retreat in long island

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

2.0 star property
Kings Park
10.0 out of 10, Exceptional, (12)
"IF I COULD COULD 10 STARS I WOULD, APARTMENT WAS CLEAN , EVERYTHING WORKED PROPERLY, WAS A PLEASURE"
United States
Thomas
The price is NZ$315
includes taxes & fees
18 Nov - 19 Nov
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

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

Brentwood
9.6 out of 10, Exceptional, (34)
"Jennifer was a nice host, very communicative. We felt very at home and safe. There was no noise and it was peaceful, I would definitely book here again, thanks Jeniffier!!!"
United States
Cindy E.
The price is NZ$290
includes taxes & fees
18 Nov - 19 Nov
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Cozy Country Cottage #3

Miller Place
10.0 out of 10, Exceptional, (29)
"Place was very clean and quaint, exactly what we were looking for for the week. Owner was responsive prior to arriving but didn’t need anything during our stay. "
United States
Grace D.
The price is NZ$575
includes taxes & fees
29 Nov - 30 Nov
Cozy Country Cottage #3

Walk to Beach 2BR Near Dining & Shopping

Rocky Point
6.6 out of 10, (25)
"The home is cute and cozy--located close enough to attractions and restaurants but off the beaten path."
United States
Lori M.
The price is NZ$404
includes taxes & fees
18 Nov - 19 Nov
Walk to Beach 2BR Near Dining & Shopping

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Centereach
10.0 out of 10, Exceptional, (44)
"Great experience and stay!"
United States
Annie P.
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Serenity Haven: Cozy 2-Bedroom Home with Spacious Living & Big Backyard

Coram
9.4 out of 10, Exceptional, (6)
"Great first time doing Vrbo great experience would do again "
United States
Rodrigo M.
Serenity Haven: Cozy 2-Bedroom Home with Spacious Living & Big Backyard

Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

Jamesport
10.0 out of 10, Exceptional, (8)
"Found this location and seemed too good to be true when we had an unplanned trip that we were able to take. House was great and location really worked for our needs. Food and winery recommendations were spot on and getting around was easy. Thanks for helping us make some great memories in NY!"
United States
Brent M.
Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

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

Hampton Bays
9.6 out of 10, Exceptional, (143)
"Had a lovely time at our stay! Only regret was that we couldn’t stay longer, there were so many amenities we couldn’t take full advantage of. Such a beautiful property!"
United States
Gina K.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

Ocean Bay Park
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…"
United States
Lois G.
One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc

Islip
9.8 out of 10, Exceptional, (21)
"Worked well for our visit."
United States
Mark G.
fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc

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

Westhampton Beach
10.0 out of 10, Exceptional, (194)
"House was more then I can imagine , host was great , house literally have anything you forgot at home . "
United States
Isiah L.
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

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

Hampton Bays
9.4 out of 10, Exceptional, (75)
"We loved our stay. The house was roomy and very comfortable for our family of 15. The very private yard, which includes a pool, hot tub, fire pit and tennis/basketball court were a hit with everyone and helped make this family vacation very memorable!"
United States
Linda C.
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs

Sound Beach
9.6 out of 10, Exceptional, (105)
"Great location! Beautiful view with sunrise and sunsets. Easy beach access! House was clean and pictures are accurate."
United States
Debbie B.
Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs

1856 Trading House w/ walk to water

Mt Sinai
9.6 out of 10, Exceptional, (52)
"The place was lovely and well appointed.. Beds were comfy. The spiral staircase was a bit tight to maneuver but location was perfect. It was a great spot for us, close to family in Sound Beach and Miller Place."
United States
Sally D.
1856 Trading House w/ walk to water

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

Ocean Beach
9.0 out of 10, Wonderful, (53)
"What a great place! Second time staying here and it was as awesome as last year! The location is perfect! Peter is the most excellent host! Can’t wait to come back!"
United States
Jill K.
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Shirley Hotel Reviews

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$290 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 18 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.