Shirley Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday 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 HK$2,211
HK$4,384 total
includes taxes & fees
25 Nov - 26 Nov
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)
"The place was very well sized and in a lovely location by the beach. Eddie was extremely responsive to all of our questions through out our stay. Would highly recommend!"
United States
Matt H.
The price is HK$1,393
HK$4,855 total
includes taxes & fees
9 Dec - 10 Dec
3 Story Beach Waterview, 3 KING bed, golf putting green!
Fridge, microwave, oven, stovetop
Tranquil Stay

Tranquil Stay

Shirley
8.4 out of 10, Very good, (9)
"Great stay with family to see a couple of our son's shows at the Gateway Theatre. Thank you Andre for be a great host...!!!"
United States
Tony W.
Tranquil Stay
Interior
Cozy Country Cottage #3

Cozy Country Cottage #3

Miller Place
10.0 out of 10, Exceptional, (29)
"Fantastic stay! "
United States
Michael V.
The price is HK$1,168
HK$2,534 total
includes taxes & fees
30 Nov - 1 Dec
Cozy Country Cottage #3
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, (12)
"IF I COULD COULD 10 STARS I WOULD, APARTMENT WAS CLEAN , EVERYTHING WORKED PROPERLY, WAS A PLEASURE"
United States
Thomas
The price is HK$946
HK$1,392 total
includes taxes & fees
4 Dec - 5 Dec
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
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, (2)
"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 HK$747
HK$1,974 total
includes taxes & fees
25 Nov - 26 Nov
Cozy 2 bedroom retreat in long island
Full-sized 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 HK$2,174
HK$7,154 total
includes taxes & fees
25 Nov - 26 Nov
LUXURY BAY SHORE HOME
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)
"My family and I thoroughly enjoyed our stay! The house is very spacious and the outdoor area/pool are beautiful. Check-in was a breeze and the host was very friendly and responsive to all our questions about the home as well as offering wonderful suggestions for restaurants and beaches in the area. Would definitely recommend for a family vacation!"
United States
livinann
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Property grounds
Walk to Beach 2BR Near Dining & Shopping

Walk to Beach 2BR Near Dining & Shopping

Rocky Point
6.6 out of 10, (25)
"Great location, great host, and nice rental especially for the price! Everything went smoothly and we will be returning next year."
United States
Joshua W.
The price is HK$630
HK$1,823 total
includes taxes & fees
25 Nov - 26 Nov
Walk to Beach 2BR Near Dining & Shopping
Property grounds
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)
"The location is superb, can’t do much better! Towards the end of the main strip for privacy but still right near the action that you come to Ocean Beach for. The rental was clean and stocked with essentials upon our arrival (definitely a life-saver) with the onsite washer/dryer a bonus!As for the property owner, I’m happy to report that this one is a pleasure… congenial, accommodating and professional from the start of the reservation process and onward.We are looking forward to returning next...
United States
Amy B.
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!
Oven, stovetop, dishwasher
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
Calverton
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 HK$2,403
HK$5,173 total
includes taxes & fees
1 Dec - 2 Dec
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Smart TV, fireplace, books
Serenity Haven: Cozy 2-Bedroom Home with Spacious Living & Big Backyard

Serenity Haven: Cozy 2-Bedroom Home with Spacious Living & Big Backyard

Coram
9.4 out of 10, Exceptional, (6)
"Great first time doing Vrbo great experience would do again "
United States
Rodrigo M.
Serenity Haven: Cozy 2-Bedroom Home with Spacious Living & Big Backyard
Smart TV, DVD player, books
1856 Trading House w/ walk to water

1856 Trading House w/ walk to water

Mt Sinai
9.6 out of 10, Exceptional, (52)
"The place was really unique! We liked the charm, it was clean and exactly as pictured and described. Super close to Port Jefferson ms a beautiful area to visit! "
United States
Stephanie S.
1856 Trading House w/ walk to water
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, (143)
"Large house and deck with plenty of room Beautiful view of bay Not easy to get from deck to water because of boulders "
United States
Robert H.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Private kitchen
4-bedroom house in awesome Brookhaven with AC

4-bedroom house in awesome Brookhaven with AC

Brookhaven
4-bedroom house in awesome Brookhaven with AC
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)
"Cute space - great communication - would come back again! "
United States
Cathy N.
One Bedroom Apt. in Ocean Bay Park with Rooftop Deck
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)
"Great Hamptons break with family. We had an amazing time with great pool, tennis, firepit and beautiful house. Very relaxing and close to fantastic beaches and nice ice cream spots and beach bars."
United Kingdom
Jack T.
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Smart TV, books
fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc

fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc

Islip
9.8 out of 10, Exceptional, (21)
"Worked well for our visit."
United States
Mark G.
fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc
Pool
10 Bedroom Hampton House with a regulation size Pickleball court

10 Bedroom Hampton House with a regulation size Pickleball court

Hampton Bays
10.0 out of 10, Exceptional, (32)
"Wonderful place to stay, close and convenient to restaurants/bars. Very comfortable and cool space with games and eclectic decorations "
United States
Chris M.
10 Bedroom Hampton House with a regulation size Pickleball court
Smart TV, fireplace, video games, stereo
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

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

Center Moriches
10.0 out of 10, Exceptional, (109)
"Amazing stay! Everything was super clean and beautiful "
United States
Liannys P.
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
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

Jake's 58 Casino Hotel - Adult Only

Jake's 58 Casino Hotel - Adult Only

10/10 Excellent
"Great security and staff"
Victor 2-night trip
Posted 14 hours ago
Jake's 58 Casino Hotel - Adult Only

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:

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

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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 18 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.