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Shirley Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Shirley vacation rentals

A modern kitchen with a stainless steel refrigerator, a large island with bar stools, and pendant lighting.

1. Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
9.6 out of 10, Exceptional, (5 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is ￥47,986
￥88,248 total
includes taxes & fees
Sep 30 - Oct 1
Modern Vacation home. Close to The Hamptons
A dining area with a table set for four, large windows, and a ceiling fan.

2. 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, (24 reviews)
"Great property, wonderful communication with owner. Would stay here again"
United States
Robert L.
The price is ￥31,010
￥94,956 total
includes taxes & fees
Oct 20 - Oct 21
3 Story Beach Waterview, 3 KING bed, golf putting green!
A compact hotel room with a bed, a sofa, a desk with a chair, a TV, and a small kitchenette.

3. South Shore Studio in Mastic

South Shore Studio in Mastic
Mastic
10.0 out of 10, Exceptional, (7 reviews)
"Really nice and great price! Would stay again. "
United States
Philip P.
The price is ￥21,233
￥35,044 total
includes taxes & fees
Oct 13 - Oct 14
South Shore Studio in Mastic
A room with a closed door, a potted plant, a small table with a sign, and a wall with a decorative sign.

4. Cozy king suite with kitchen and dining area.

Cozy king suite with kitchen and dining area.
Coram
9.4 out of 10, Exceptional, (8 reviews)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is ￥27,524
￥40,434 total
includes taxes & fees
Oct 1 - Oct 2
Cozy king suite with kitchen and dining area.
A hot tub with two chairs, a pergola, and a wooden deck.

5. Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Mastic
10.0 out of 10, Exceptional, (33 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is ￥102,232
￥255,162 total
includes taxes & fees
Oct 22 - Oct 23
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
A living room with a sofa, armchairs, a coffee table, and a rug.

6. Peaceful 3BR Garden Cottage Long Island Escape

Peaceful 3BR Garden Cottage Long Island Escape
Coram
10.0 out of 10, Exceptional, (1 review)
"Excellent host and peaceful getaway. I highly recommend!"
United States
Greg M.
The price is ￥32,566
￥78,356 total
includes taxes & fees
Sep 30 - Oct 1
Peaceful 3BR Garden Cottage Long Island Escape
A covered outdoor seating area with a white door, a 'No Smoking' sign, and string lights.

7. The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
9.8 out of 10, Exceptional, (9 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is ￥17,836
￥51,107 total
includes taxes & fees
Oct 5 - Oct 6
The Royal Suite - Ronkonkoma
An outdoor patio area with a grill, seating, and string lights.

8. Private Apartment on River Ave. close to main st

Private Apartment on River Ave. close to main st
Patchogue
9.6 out of 10, Exceptional, (8 reviews)
"Nice little property. Perfect for what we needed. Host was great."
United States
A H.
The price is ￥25,186
￥50,538 total
includes taxes & fees
Oct 20 - Oct 21
Private Apartment on River Ave. close to main st
A compact kitchen with dark cabinets, stainless appliances, and a tiled floor.

9. Private 1 bedroom apt in a quiet neighborhood, close to all!

Private 1 bedroom apt in a quiet neighborhood, close to all!
Centereach
9.6 out of 10, Exceptional, (29 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 ￥22,648
￥38,456 total
includes taxes & fees
Oct 5 - Oct 6
Private 1 bedroom apt in a quiet neighborhood, close to all!
A bedroom with a bed, a nightstand, a mirror, and a window with curtains.

10. 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
9.4 out of 10, Exceptional, (53 reviews)
"This stay was very clean and easy. The check-in process was efficient. Thank you, I would definitely book again for a short stay!"
United States
Jaelyn
The price is ￥15,571
￥25,879 total
includes taxes & fees
Oct 1 - Oct 2
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
A living room with a sofa, a coffee table, a TV mounted on the wall, and a window with a view of houses outside.

11. Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Rocky Point
10.0 out of 10, Exceptional, (28 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 ￥36,834
￥74,636 total
includes taxes & fees
Oct 6 - Oct 7
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Roger’s Beach

12. Prime location, walk to all, cozy cottage WHB

Prime location, walk to all, cozy cottage WHB
Westhampton Beach
10.0 out of 10, Exceptional, (3 reviews)
"Erica was very communicative and helpful. Very cozy with a great location."
United States
Chris J.
The price is ￥55,048
￥95,958 total
includes taxes & fees
Oct 2 - Oct 3
Prime location, walk to all, cozy cottage WHB
A white shelving unit with decorative items, including a mixtape box, two golden bird figurines, and three glass vases.

13. Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
10.0 out of 10, Exceptional, (1 review)
"Very clean. Easy to get to. Listing as described. Bed and furniture are nice and comfy. Only thing I would add is a broom and dust pain and some Clorox wipes so guest can keep it neat. 5 stars! Very nice host. "
United States
Samantha
The price is ￥18,118
￥44,079 total
includes taxes & fees
Oct 21 - Oct 22
Sundown Escape-South Shore Long Island
A wooden deck with a white railing, a stone pathway, and a white fence in the background.

14. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is ￥30,146
￥50,013 total
includes taxes & fees
Oct 5 - Oct 6
Spacious 3BR Family Home Near Everything
Property grounds

15. Walk to Beach 2BR Near Dining & Shopping

Walk to Beach 2BR Near Dining & Shopping
Rocky Point
7.2 out of 10, Good, (35 reviews)
"Was a decent place. I was only there 1 night. Communication could be better. So could accommodating check in but overall Good"
United States
Patrick H.
The price is ￥24,772
￥50,047 total
includes taxes & fees
Sep 30 - Oct 1
Walk to Beach 2BR Near Dining & Shopping
A modern living room with a grey sofa, a wooden coffee table, a flat-screen TV mounted on the wall, and a ceiling light fixture.

16. Peaceful private 2-bedroom house in Bayport. Amazing location!

Peaceful private 2-bedroom house in Bayport. Amazing location!
Bayport
8.8 out of 10, Excellent, (8 reviews)
"He’s an excellent hosts and his place is well worth it."
United States
Rowena V.
The price is ￥40,342
￥49,686 total
includes taxes & fees
Oct 5 - Oct 6
Peaceful private 2-bedroom house in Bayport. Amazing location!
A living room with a brown sofa, a glass coffee table with decorative items, and a kitchen in the background with wooden cabinets and a black refrigerator.

17. Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
8.0 out of 10, Very good, (11 reviews)
"The place was great. It was clean and spacious, and located on a quiet street. It was also accessible to all the major roads. The host was very accommodating. Very pleased with it all and would highly recommend! "
United Kingdom
Selective Travel M.
The price is ￥17,694
￥50,764 total
includes taxes & fees
Oct 7 - Oct 8
Spacious one Bedroom Apt with private entrance
A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

18. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (6 reviews)
"The host was very welcoming and the house was very clean"
United States
James W.
The price is ￥23,073
￥47,926 total
includes taxes & fees
Oct 6 - Oct 7
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
A living room with a blue door, a white shelf, a grey sofa with patterned cushions, and a small table with a decorative item.

19. Bright & Comfortable Home in the Heart of It All

Bright & Comfortable Home in the Heart of It All
Central Islip
8.8 out of 10, Excellent, (3 reviews)
"My stay was amazing! The place was bigger in person than i expected, which was such a pleasant surprise. The house was spotless and very clean, making me feel comfortable from the moment I arrived. The host was incredibly helpful, responsive, and made the entire experience smooth and stress-free. I enjoyed my stay and would absolutely book this home again. Highly recommend to anyone looking for a clean, spacious, and welcoming place to stay!"
United States
Tatiana J.
The price is ￥27,941
￥74,872 total
includes taxes & fees
Sep 30 - Oct 1
Bright & Comfortable Home in the Heart of It All
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

20. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ￥22,019
￥254,466 total
includes taxes & fees
Oct 4 - Oct 5
Jacuzzi year-round - Villa Luz Private Home
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

Courtyard by Marriott Long Island Islip/Courthouse Complex

Courtyard by Marriott Long Island Islip/Courthouse Complex

10/10 Excellent
"Very clean and great parking"
Adriana 1-night trip
Posted 3 hours ago
Courtyard by Marriott Long Island Islip/Courthouse Complex

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!

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?

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly: This vacation home rental near Shirley offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Shirley?

With 12 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 Wertheim National Wildlife Refuge and Lasorda Legacy Park.

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.