Shirley Vacation Rentals

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In two weeks
Jan 16 - Jan 18
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In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Shirley vacation rentals

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

Vacation Home in Shirley

3 Story Beach Waterview, 3 KING bed, golf putting green!
10.0 out of 10, Exceptional, (22)
"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 ￥27,919
￥96,048 total
includes taxes & fees
Jan 4 - Jan 5, 2026
3 Story Beach Waterview, 3 KING bed, golf putting green!
Terrace/patio
South Shore Studio in Mastic

Apartment in Mastic

South Shore Studio in Mastic
2.0 star property
10.0 out of 10, Exceptional, (2)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is ￥16,845
￥29,940 total
includes taxes & fees
Jan 1 - Jan 2, 2026
South Shore Studio in Mastic
Terrace/patio
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Vacation Home in Hampon Bays

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
9.6 out of 10, Exceptional, (22)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ￥15,441
￥198,331 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Apartment in Kings Park

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
2.0 star property
10.0 out of 10, Exceptional, (16)
"Overall, a great crash pad. Hosts were great with communication and convenience. Location was convenient, clean, and comfortable. "
United States
Erika K.
The price is ￥19,378
￥28,377 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
2 bedrooms, WiFi, bed sheets
Cozy 2 bedroom retreat in long island

Apartment in Central Islip

Cozy 2 bedroom retreat in long island
2.0 star property
8.8 out of 10, Excellent, (3)
"Apt was clean and comfortable. Beds were comfortable. Area was nice. Owner communication was good. Only drawback is the plumbing situation was not advertised in the listing. Iif you are comfortable using a bidet and not flushing paper, this apt is perfect. "
United States
Deborah R.
The price is ￥16,845
￥41,519 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy 2 bedroom retreat in long island
Terrace/patio
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Vacation Home in Hampton Bays

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
9.6 out of 10, Exceptional, (14)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is ￥23,396
￥198,513 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Fridge, microwave, oven, stovetop
Spacious one Bedroom Apt with private entrance

Apartment in Centereach

Spacious one Bedroom Apt with private entrance
7.8 out of 10, Good, (10)
"I answered this. Safe and Quit."
United States
John
The price is ￥17,547
￥53,546 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Spacious one Bedroom Apt with private entrance
Oven, stovetop, dishwasher
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Vacation Home in Calverton

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
2.0 star property
8.6 out of 10, Excellent, (8)
"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 ￥48,156
￥103,666 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Terrace/patio
Immaculate Waterfront 2 bedroom!

Vacation Home in Hampton Bays

Immaculate Waterfront 2 bedroom!
10.0 out of 10, Exceptional, (5)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is ￥50,690
￥100,862 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Immaculate Waterfront 2 bedroom!
Fridge, microwave, oven, stovetop
Private 1 bedroom apt in a quiet neighborhood, close to all!

Apartment in Centereach

Private 1 bedroom apt in a quiet neighborhood, close to all!
9.6 out of 10, Exceptional, (26)
"It was the perfect landing pad for a family reunion. We hope to stay there again next year."
United States
Amanda
The price is ￥23,583
￥40,130 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Private 1 bedroom apt in a quiet neighborhood, close to all!
Microwave, oven, stovetop, coffee/tea maker
Peaceful private 2-bedroom house in Bayport.Amazing location!

Vacation Home in Bayport

Peaceful private 2-bedroom house in Bayport.Amazing location!
2.0 star property
10.0 out of 10, Exceptional, (1)
"Patrick is a fantastic host. Super accommodating and attentive! Clean and organized home, comfy bed too!"
United States
Emily D.
The price is ￥27,295
￥34,752 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Peaceful private 2-bedroom house in Bayport.Amazing location!
Property grounds
Walk to Beach 2BR Near Dining & Shopping

Apartment in Rocky Point

Walk to Beach 2BR Near Dining & Shopping
6.8 out of 10, (26)
"Well kept. Small yet comfortable."
United States
Aimee W.
The price is ￥11,932
￥35,017 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Walk to Beach 2BR Near Dining & Shopping
Smart TV, fireplace, video games, stereo
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

Cottage in Center Moriches

East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
10.0 out of 10, Exceptional, (110)
"Amazing stay! Everything was super clean and beautiful "
United States
Liannys P.
The price is ￥46,011
￥92,482 total
includes taxes & fees
Jan 11 - Jan 12, 2026
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
Fridge, microwave, oven, stovetop
Cozy Country Cottage #4

Cottage in Miller Place

Cozy Country Cottage #4
10.0 out of 10, Exceptional, (15)
"Lovely cottage with great host! All was wonderful!! very happy with our 17 day vacation!"
United States
Laurita S.
The price is ￥23,396
￥50,252 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Cozy Country Cottage #4
Terrace/patio
Fabulous 1-bedroom, 1 bathroom Hotel inspired Room in Ronkonkoma

Apartment in Ronkonkoma

Fabulous 1-bedroom, 1 bathroom Hotel inspired Room in Ronkonkoma
2.0 star property
The price is ￥11,854
￥21,565 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Fabulous 1-bedroom, 1 bathroom Hotel inspired Room in Ronkonkoma
Exterior detail
Cozy king suite with kitchen and dining area.

Apartment in Coram

Cozy king suite with kitchen and dining area.
9.4 out of 10, Exceptional, (6)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is ￥27,295
￥41,165 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Cozy king suite with kitchen and dining area.
Fridge, microwave, oven, stovetop
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Vacation Home in Rocky Point

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
10.0 out of 10, Exceptional, (24)
"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 ￥45,092
￥86,577 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
1 bedroom, iron/ironing board, free WiFi, bed sheets
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Vacation Home in Brentwood

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
9.4 out of 10, Exceptional, (36)
"Very convenient location for where I needed to be. Perfect room to stay for a night "
United States
Sophie B.
The price is ￥15,441
￥25,663 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Oven, dishwasher
Cozy and Modern 2-bedroom apartment in lovely Yaphank

Apartment in Yaphank

Cozy and Modern 2-bedroom apartment in lovely Yaphank
2.0 star property
The price is ￥25,267
￥63,617 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cozy and Modern 2-bedroom apartment in lovely Yaphank
2 bedrooms, iron/ironing board, WiFi, bed sheets
Stylish 2BR House Near Stony Brook University and shopping, fully renovated

Vacation Home in Stony Brook

Stylish 2BR House Near Stony Brook University and shopping, fully renovated
2.0 star property
10.0 out of 10, Exceptional, (1)
"perfect place"
New Zealand
Akaki G.
The price is ￥52,464
￥105,202 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Stylish 2BR House Near Stony Brook University and shopping, fully renovated
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

Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

10/10 Excellent
"Great Breakfast. Enjoyed the coffee and tea area. Room was clean.Great set up on the room. Lots of places to put your items. "
Rochelle 2-night trip
Posted 22 hours ago
Holiday Inn Express Hauppauge-Long Island

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 16 Expedia vacation rentals, you're sure to find just the right place for your Shirley stay.

What can I see and do in Shirley?

Carmans River and Great South Bay 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.