Shirley Holiday Rentals

  • 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
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for Shirley holiday rentals

Interior

Holiday Home in Shirley

Waterfront Designer Retreat | Stunning Sunsets! 5 minutes to the beach!
The price is HK$2,161
HK$4,159 total
includes taxes & fees
17 Mar - 18 Mar
Waterfront Designer Retreat | Stunning Sunsets! 5 minutes to the beach!
Fridge, microwave, oven, stovetop

Holiday Home in Shirley

Modern Vacation home. Close to The Hamptons
10.0 out of 10, Exceptional, (4 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is HK$1,954
HK$3,986 total
includes taxes & fees
17 Mar - 18 Mar
Modern Vacation home. Close to The Hamptons
Dining

Holiday Home in Shirley

3 Story Beach Waterview, 3 KING bed, golf putting green!
10.0 out of 10, Exceptional, (22 reviews)
"The house was beautiful and the owner was incredibly easy to work with! Will be trying to stay here every year! "
United States
Red F.
The price is HK$2,482
HK$6,297 total
includes taxes & fees
14 Apr - 15 Apr
3 Story Beach Waterview, 3 KING bed, golf putting green!
1 bedroom, iron/ironing board, free WiFi, bed sheets

Holiday Home in Brentwood

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
9.4 out of 10, Exceptional, (39 reviews)
"We had a good experience and we brought our little pup and she was welcome there. Clean and quiet stay "
United States
janice s.
The price is HK$810
HK$1,328 total
includes taxes & fees
17 Mar - 18 Mar
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Exterior

Apartment in Kings Park

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
10.0 out of 10, Exceptional, (18 reviews)
"Perfect spot for a quick trip"
United States
James P.
The price is HK$969
HK$1,420 total
includes taxes & fees
17 Mar - 18 Mar
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
1 bedroom, free WiFi, bed sheets

Apartment in Mastic

South Shore Studio in Mastic
10.0 out of 10, Exceptional, (3 reviews)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is HK$1,057
HK$1,744 total
includes taxes & fees
17 Mar - 18 Mar
South Shore Studio in Mastic
Smart TV

Holiday Home in Lake Grove

Spacious Home Located Close to Stony Brook!
7.6 out of 10, Good, (26 reviews)
"Amazing host and amazing house. Thank you!!"
United States
AJ L.
Spacious Home Located Close to Stony Brook!
Smart TV, books

Holiday Home in Rocky Point

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
10.0 out of 10, Exceptional, (25 reviews)
"It was perfect for what we needed and the hostess made it very simple and easy to check in and check out and answer any questions thank you"
United States
ken g.
The price is HK$2,098
HK$4,186 total
includes taxes & fees
17 Mar - 18 Mar
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
TV

Apartment in Centereach

Spacious one Bedroom Apt with private entrance
7.8 out of 10, Good, (10 reviews)
"The host was extremely attentive to any questions or needs. Excellent and immediate communication. Good, quiet location between Islip airport and Port Jefferson. The size of the unit was very adequate for two people. Bathroom was clean and adequately stocked with towels and wash cloths.The reason for 2 stars is we thought the apartment was not very clean from floor to ceiling. This apartment has huge potential to be very cute. In my option, it needs an entire over haul."
United States
Russell R.
The price is HK$881
HK$2,652 total
includes taxes & fees
23 Mar - 24 Mar
Spacious one Bedroom Apt with private entrance
Smart TV

Apartment in Coram

JC Entire Apartment remodeled, close to Airport and Ferry
10.0 out of 10, Exceptional, (3 reviews)
"Would definitely stay again "
United States
Katherine R.
The price is HK$665
HK$1,574 total
includes taxes & fees
31 Mar - 1 Apr
JC Entire Apartment remodeled, close to Airport and Ferry
Terrace/patio

Holiday Home in Ronkonkoma

The Royal Suite - Ronkonkoma
10.0 out of 10, Exceptional, (4 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is HK$1,233
HK$3,144 total
includes taxes & fees
24 Mar - 25 Mar
The Royal Suite - Ronkonkoma
1 bedroom, free WiFi, bed sheets

Apartment in East Quogue

Hamptons apartment getaway
6.0 out of 10, (3 reviews)
"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "
United States
Hilary K.
The price is HK$1,174
HK$2,236 total
includes taxes & fees
17 Mar - 18 Mar
Hamptons apartment getaway
Exterior detail

Holiday Home in Calverton

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
8.6 out of 10, Excellent, (8 reviews)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
The price is HK$3,516
HK$6,557 total
includes taxes & fees
17 Mar - 18 Mar
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
2 bedrooms, WiFi, bed sheets

Apartment in Smithtown

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
6.8 out of 10, (3 reviews)
"We enjoyed our stay. The apartment was simple, clean, and comfortable. The neighborhood felt safe, and it was easy to call Uber for rides. LIRR access was also convenient, which made traveling to New York City and Stony Brook very manageable. The highlight was the beautiful backyard, which made the place feel relaxing."
United States
Jing L.
The price is HK$1,221
HK$1,753 total
includes taxes & fees
17 Mar - 18 Mar
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
Interior

Apartment in Centereach

Private 1 bedroom apt in a quiet neighborhood, close to all!
9.6 out of 10, Exceptional, (26 reviews)
"It was the perfect landing pad for a family reunion. We hope to stay there again next year."
United States
Amanda
The price is HK$1,353
HK$2,234 total
includes taxes & fees
22 Mar - 23 Mar
Private 1 bedroom apt in a quiet neighborhood, close to all!
Interior

Apartment in Coram

Cozy king suite with kitchen and dining area.
9.6 out of 10, Exceptional, (7 reviews)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is HK$1,370
HK$2,039 total
includes taxes & fees
19 Mar - 20 Mar
Cozy king suite with kitchen and dining area.
Terrace/patio

Holiday Home in Mastic

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
10.0 out of 10, Exceptional, (28 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is HK$3,930
HK$9,221 total
includes taxes & fees
23 Mar - 24 Mar
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Terrace/patio

Holiday Home in Hampton Bays

Black Swan Beachfront Home with Jacuzzi year round
9.6 out of 10, Exceptional, (15 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is HK$2,458
HK$8,840 total
includes taxes & fees
23 Mar - 24 Mar
Black Swan Beachfront Home with Jacuzzi year round
Dining

Holiday Home in Stony Brook

3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches
6.0 out of 10, (2 reviews)
"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
The price is HK$2,957
HK$5,436 total
includes taxes & fees
18 Mar - 19 Mar
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

Holiday Inn Long Island-Islip Arpt East by IHG

Holiday Inn Long Island-Islip Arpt East by IHG

8/10 Good
"Clean room, helpful Staff, Very Comfortable Pillows & Mattresses. Could use better quality Refrigerator, & a room safe is needed."
Gregory 4-night trip
Posted 2 hours ago
Holiday Inn Long Island-Islip Arpt East by IHG

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 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?

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!: This holiday home rental outside of Shirley is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Shirley?

With 14 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 Wertheim National Wildlife Refuge and Lasorda Legacy Park.

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.