Photo by AnnMarie Guli Photography

Shirley Vacation 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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Shirley

Fridge, microwave, oven, stovetop
Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons

Shirley
10.0 out of 10, Exceptional, (3)
"good time"
United States
Roy T.
The price is ￥55,030
￥102,123 total
includes taxes & fees
Nov 17 - Nov 18
Modern Vacation home. Close to The Hamptons
Property grounds
3 Story Beach Waterview, 3 KING bed, golf putting green!

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 ￥27,577
￥94,519 total
includes taxes & fees
Nov 16 - Nov 17
3 Story Beach Waterview, 3 KING bed, golf putting green!
2 bedrooms, WiFi, bed sheets
Cozy 2 bedroom retreat in long island

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 ￥14,790
￥39,078 total
includes taxes & fees
Nov 14 - Nov 15
Cozy 2 bedroom retreat in long island
Outdoor dining
Newly Renovated Luxury Beach House Ocean Bay Park

Newly Renovated Luxury Beach House Ocean Bay Park

Ocean Beach
10.0 out of 10, Exceptional, (71)
"We had a fantastic experience. Beautiful home, excellent communication with the owner. Highly recommended."
United States
Laura S.
Newly Renovated Luxury Beach House Ocean Bay Park
Outdoor pool, a heated pool
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

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

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!
1 bedroom, iron/ironing board, free WiFi, bed sheets
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

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

Brentwood
9.6 out of 10, Exceptional, (33)
"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 ￥15,252
￥25,349 total
includes taxes & fees
Nov 18 - Nov 19
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Property grounds
Walk to Beach 2BR Near Dining & Shopping

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 ￥12,479
￥36,260 total
includes taxes & fees
Nov 14 - Nov 15
Walk to Beach 2BR Near Dining & Shopping
Full-size fridge, cookware/dishes/utensils
LUXURY BAY SHORE HOME

LUXURY BAY SHORE HOME

2.0 star property
Bay Shore
2.0 out of 10, (1)
The price is ￥59,626
￥160,558 total
includes taxes & fees
Nov 14 - Nov 15
LUXURY BAY SHORE HOME
Exterior
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

Bayport
10.0 out of 10, Exceptional, (88)
"Great location. Very peaceful. Great house"
United States
Richard D.
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville
Terrace/patio
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

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

Hampton Bays
9.6 out of 10, Exceptional, (142)
"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!
2 bedrooms, iron/ironing board, WiFi, bed sheets
Stylish 2BR House Near Stony Brook University and shopping, fully renovated

Stylish 2BR House Near Stony Brook University and shopping, fully renovated

2.0 star property
Stony Brook
The price is ￥35,357
￥81,056 total
includes taxes & fees
Nov 14 - Nov 15
Stylish 2BR House Near Stony Brook University and shopping, fully renovated
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

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

2.0 star property
Kings Park
10.0 out of 10, Exceptional, (11)
"IF I COULD COULD 10 STARS I WOULD, APARTMENT WAS CLEAN , EVERYTHING WORKED PROPERLY, WAS A PLEASURE"
United States
Thomas
The price is ￥18,718
￥27,547 total
includes taxes & fees
Nov 15 - Nov 16
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Fridge, microwave, oven, stovetop
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!

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!
Dining
One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

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
Fridge, microwave, oven, stovetop
Home Away from Home – 3BR Retreat with Amenities

Home Away from Home – 3BR Retreat with Amenities

Hauppauge
10.0 out of 10, Exceptional, (7)
Home Away from Home – 3BR Retreat with Amenities
Microwave, oven, stovetop, dishwasher
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

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.
Fridge, microwave, oven, stovetop
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Eastport
9.6 out of 10, Exceptional, (34)
"We had a lot of fun and created some nice memories"
United States
Scott T.
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
Outdoor pool, a heated pool
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

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

Hampton Bays
9.4 out of 10, Exceptional, (75)
"As always everything was excellent, This is our third stay at this property and we are booked for 2026"
United States
Michael R.
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Interior
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches

3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches

Stony Brook
6.0 out of 10, (2)
"Very comfortable and welcoming Only problem was only one bathroom door closed the other one appeared to be in disrepair Other then that all was well"
United States
Kathleen
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shirley Hotel Reviews

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

10/10 Excellent
"There was a Hole in the rug other than that fine "
Yasmine 1-night trip
Posted 23 hours ago
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

Find out more about Shirley

Search for holiday rentals in Shirley on Expedia! You can easily find your home rentals, villas, holiday apartments in Shirley using one of the methods below:

  • View our selection of featured holiday rentals in Shirley
  • Use the map to find apartments and other holiday homes in the Shirley neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Shirley while they last

Look no further and take a look at our great range of rental properties in Shirley!

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Shirley?

Yes, you can find vacation rentals near the most popular sights in Shirley, or you can choose a more remote option if you're looking for a relaxing stay. Shirley is known for its parks.

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

Modern Vacation home. Close to The Hamptons: This highly rated vacation 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 you can cook with friends or family.

How many vacation rentals are there in Shirley?

With 18 Expedia vacation rentals, you're sure 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 larger area, you’ll find Lasorda Legacy Park and TWA Flight 800 International Memorial.

What are vacation rentals like in Shirley?

Vacation rentals are private properties you can reserve for several days or more in Shirley. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family gatherings.