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Shirley Vacation Rentals

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Vacation Rentals in Shirley

Modern Vacation home. Close to The Hamptons

Shirley
10.0 out of 10, Exceptional, (3)
"good time"
United States
Roy T.
$476 nightly
The price is $544
Nov 20 - Nov 21
Total with taxes and fees
Modern Vacation home. Close to The Hamptons

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

Shirley
10.0 out of 10, Exceptional, (21)
"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.
$543 nightly
The price is $620
Nov 19 - Nov 20
Total with taxes and fees
3 Story Beach Waterview, 3 KING bed, golf putting green!

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

LUXURY BAY SHORE HOME

2.0 star property
Bay Shore
2.0 out of 10, (1)
$804 nightly
The price is $919
Nov 19 - Nov 20
Total with taxes and fees
LUXURY BAY SHORE HOME

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.
$222 nightly
The price is $254
Nov 19 - Nov 20
Total with taxes and fees
Cozy 2 bedroom retreat in long island

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
$157 nightly
The price is $179
Nov 19 - Nov 20
Total with taxes and fees
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Brentwood
9.6 out of 10, Exceptional, (34)
"Very convenient location for where I needed to be. Perfect room to stay for a night "
United States
Sophie B.
$144 nightly
The price is $165
Nov 19 - Nov 20
Total with taxes and fees
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Cozy Country Cottage #3

Miller Place
10.0 out of 10, Exceptional, (29)
"Fantastic stay! "
United States
Michael V.
$286 nightly
The price is $327
Nov 29 - Nov 30
Total with taxes and fees
Cozy Country Cottage #3

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.
$205 nightly
The price is $234
Nov 25 - Nov 26
Total with taxes and fees
Walk to Beach 2BR Near Dining & Shopping

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Centereach
10.0 out of 10, Exceptional, (44)
"Great experience and stay!"
United States
Annie P.
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

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

Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

Jamesport
10.0 out of 10, Exceptional, (8)
"The is great!!! Very convenient location and plenty to do."
United States
Jose G.
Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

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

Hampton Bays
9.6 out of 10, Exceptional, (143)
"Perfect property to hangout and stay entertained for hours"
United States
Ryder I.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

Ocean Bay Park
9.0 out of 10, Wonderful, (32)
"Great location, cute property. My third time staying there. The experience would be meaningfully enhanced with some updated furnishings and cookware - especially the sofa in the living room and the furniture on the upstairs deck. Regarding cookware - a frying pan and spatula would be nice!"
United States
Will M.
One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

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

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

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

Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs

Sound Beach
9.6 out of 10, Exceptional, (105)
"With two levels of living space overlooking the Long Island Sound it was the perfect space and backdrop for all the prep and merriment for our daughter’s wedding at Giorgio’s on Saturday. I also totally enjoyed relaxing and unwinding the deck on Sunday evening with a spectacular sunset!"
United States
Julie M.
Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs

1856 Trading House w/ walk to water

Mt Sinai
9.6 out of 10, Exceptional, (52)
"We were on LI for my husband’s 1 year memorial. The place was exactly what we needed. "
United States
Georgia M.
1856 Trading House w/ walk to water

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!
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

Find out more about Shirley

Everything you need to know about Shirley vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shirley vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shirley vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shirley vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shirley. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Shirley in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $165 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Shirley rentals

At Expedia, we put the best Shirley vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Shirley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shirley vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shirley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 18 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 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.