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Shirley Holiday Rentals

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan

Holiday Rentals in Shirley

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

Modern Vacation home. Close to The Hamptons

10.0 out of 10, Exceptional, (3)
"good time"
The price is HK$2,661
HK$4,997 total
includes taxes & fees
12 Oct - 13 Oct
Modern Vacation home. Close to The Hamptons
Relaxing Smith Point Beach House on private canal
Outdoor dining

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!
Property grounds

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 HK$1,393
HK$4,854 total
includes taxes & fees
15 Oct - 16 Oct
3 Story Beach Waterview, 3 KING bed, golf putting green!
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
1 bedroom, iron/ironing board, free WiFi, bed sheets

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 HK$770
HK$1,280 total
includes taxes & fees
12 Oct - 13 Oct
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Spacious Home Located Close to Stony Brook!
Property grounds

Spacious Home Located Close to Stony Brook!

7.0 out of 10, Good, (20)
"Great stay great people great costumer care definitely reccomend"
Spacious Home Located Close to Stony Brook!
Newly Renovated Luxury Beach House Ocean Bay Park
Outdoor dining

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 HK$4,896
HK$9,185 total
includes taxes & fees
10 Oct - 11 Oct
Newly Renovated Luxury Beach House Ocean Bay Park
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
Smart TV, fireplace, video games, stereo

East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

10.0 out of 10, Exceptional, (102)
"Great indoor and outdoor spaces to hang out. Took SUP on the water - so nice and calm. "
The price is HK$3,074
HK$5,744 total
includes taxes & fees
2 Nov - 3 Nov
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
Walk to Beach 2BR Near Dining & Shopping
Property grounds

Walk to Beach 2BR Near Dining & Shopping

6.6 out of 10, (20)
"Stay away"
The price is HK$875
HK$2,156 total
includes taxes & fees
14 Oct - 15 Oct
Walk to Beach 2BR Near Dining & Shopping
10 Bedroom Hampton House with a regulation size Pickleball court
Pool

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

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (34)
"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
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (191)
"Had a lovely relaxing time with family and friends. Very convenient and great size."
The price is HK$6,187
HK$9,931 total
includes taxes & fees
17 Oct - 18 Oct
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Terrace/patio

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

9.6 out of 10, Exceptional, (140)
"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!
Interior

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!
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Oven, stovetop, dishwasher

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 HK$3,883
HK$7,104 total
includes taxes & fees
10 Oct - 11 Oct
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!
Fridge, microwave, oven, stovetop

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

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
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

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 HK$945
HK$1,391 total
includes taxes & fees
22 Oct - 23 Oct
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Outdoor pool, a heated pool

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
Terrace/patio

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 HK$2,763
HK$11,985 total
includes taxes & fees
23 Oct - 24 Oct
Private beach on a fenced in property sunset views
Summer getaway
Outdoor dining

Summer getaway

9.0 out of 10, Wonderful, (14)
"Perfect location for a family holiday "
Summer getaway
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

Hampton Inn Long Island/Islandia

Hampton Inn Long Island/Islandia

10/10 Excellent
"Bright, clean and comfortable."
Gloria 1-night trip
Posted 3 days ago
Hampton Inn Long Island/Islandia

Find out more about Shirley

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

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?

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.