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Shirley Holiday Rentals

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Holiday Rentals in Shirley

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

10.0 out of 10, Exceptional, (15)
"We stayed on Long Island for 4 nights to coach a Perfect Game Baseball Tournament. This property was spacious enough to host my wife and I along with 4 other coaches (6 adults total). We were also able to bring our two jack russells with us. We had a great time, and look forward to staying here again."
The price is AU$861
includes taxes & fees
7 Jan - 8 Jan 2025
3 Story Beach Waterview, 3 KING bed, golf putting green!

Gorgeous private Hamptons house with pool and volleyball court

8.4 out of 10, Very good, (17)
"Enjoyed this house in a great location. It was perfect for attending a family wedding!"
Gorgeous private Hamptons house with pool and volleyball court

Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

10.0 out of 10, Exceptional, (33)
"The house was perfect, a home away from home located in a nice quiet area, with stores and restaurants close by. House was clean, spacious and stocked with the essentials. The kids loved the pool and the ping pong table. Thank you Val for the perfect weekend, hope to see you next Summer!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.

8.8 out of 10, Excellent, (9)
"Clean, spacious home with an amazing pool in a quiet neighborhood. If you're looking for a quiet getaway a good choice!"
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.

Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach

9.8 out of 10, Exceptional, (64)
"The house was exactly as advertised, the water views were beautiful! Easy access to the North Fork of Long Island."
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach

5 bedroom Private Family Get Away w/ Heated Pool

10.0 out of 10, Exceptional, (13)
"We were a group age 3 to 75! The house was clean, well stocked and things for everyone’s interest. Our host, Carrie, was kind and responsive. It will be a beautiful memory of spending time with our children and grandchildren. "
5 bedroom Private Family Get Away w/ Heated Pool

Fall in the🌅beautiful sunsets

10.0 out of 10, Exceptional, (24)
"Margaret is just wonderful. We felt like we were staying at a dear family member’s home. Stayed in her very private upstairs suite and it was perfect for me, my wife and our pup. He had a blast running around the yard, meeting the chickens going to the bay beach etc. We had the best time! Thank you Margaret!!"
Fall in the🌅beautiful sunsets

A Quiet Place in the Hamptons

9.8 out of 10, Exceptional, (34)
"We had a very nice time. The house was exactly what we needed and was close to everything. "
A Quiet Place in the Hamptons

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

9.4 out of 10, Exceptional, (19)
"I really enjoyed my stay. It was convenient and exceeded my expectations. When I am in town again I will definitely book again."
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

10.0 out of 10, Exceptional, (167)
"Group of 6 women getting together. Beautiful spacious home. We all had our own bedrooms. Having 4.5 baths was great. Plenty of space for all of us. Host was excellent and had great recommendations. Quick ride to the beautiful beach. "
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

Beachfront Romance: Rustic Home w/ Private Beach

9.2 out of 10, Wonderful, (46)
"We were looking for a small and private beach house getaway for the weekend and found this hidden gem. Our property manager, Debbie, made herself available throughout our stay to answer all of our questions. Everything needed for our comfort weekend was provided. We strongly recommend this place for those who are looking to get away from the hustle and bustle of city life. We will be returning! "
Beachfront Romance: Rustic Home w/ Private Beach

Summer getaway

9.2 out of 10, Wonderful, (10)
"Overall, we had a terrific time at the house. Thank-you so much Andres for sharing your home with us. Getting there, checking in, all simple and easy. House was very well stocked. There was plenty of room for the eight of us. The beds were all comfortable. The deck was delightful. A couple of minor things that we had happen, or noticed that might want to be addressed. Given the house is controlled by Alexa, some detailed instructions as to how to work with "her" might be a good idea for...
Summer getaway

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

9.6 out of 10, Exceptional, (20)
"This apartment was perfect for me. I was in town for a Stony Brook parents weekend and was in close proximity to everything I needed. Comfy bed, very clean, private, and I liked having my coffee out on my patio in the mornings. Great communication from the owner as well. A+ all around!"
The price is AU$379
includes taxes & fees
22 Dec - 23 Dec
Private 1 bedroom apt in a quiet neighborhood, close to all!

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

8.2 out of 10, Very good, (44)
"This house was very nice, as pictured or better. Clean, no issues checking in or out. Wagon was there as promised, more bikes than promised, lots of beach towels and chairs provided. The house had two wonderful outdoor second story decks with great views of the water and the ferry dock. Location was perfect, so convenient to ferry and market. Two things not great. Although it had an AC unit in every bedroom that all worked fine which made ground floor cool and comfortable, the main living...
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets

10.0 out of 10, Exceptional, (79)
"Second time staying here, great house right on the water. Owners are extremely responsive and helpful"
Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets

Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private

10.0 out of 10, Exceptional, (74)
"What a great home base for my family during Thanksgiving week! This house is everything it says it is and more. I seriously felt like I was a guest visiting family for the week. Too many awesome accommodations to list. The view out of the back windows, the bright coastal vibe, the home/audio setup, the huge/clean hot tub, the insanely awesome master bathrom!! What a neat house! Thanks, Joe for making our trip to the area a memorable one!"
Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private

Charming Hampton Bays Home 5 Mi to Cooper’s Beach

9.6 out of 10, Exceptional, (9)
"my family and i grew up coming to hampton bays - and while myself and my parents have moved away - a family wedding brought us back to the area and we were so happy to stay local in this perfect home. it felt great to be back in the old neighborhood and not have to be cramped at my brothers home just a short 5 minute drive away. i hope we can stay again during our next trip!"
Charming Hampton Bays Home 5 Mi to Cooper’s Beach

Charming home close to beach with fast WiFi & washer/dryer - dog-friendly

7.6 out of 10, Good, (9)
"It was as cute as it looked on-line and gave us a great space for hanging out and enjoying each other's company. That said, I would recommend that you rent this with loved ones as privacy is limited because of the indoor design. With no insulation or dry wall every noise is heard throughout the house! Other nice surprises: new AC units (very quiet), very comfortable beds, and an outdoor shower with good light. The street is very quiet. I was surprised that basic kitchen supplies weren't included...
Charming home close to beach with fast WiFi & washer/dryer - dog-friendly

Dog-friendly home just blocks from the bay with deck & private hot tub

8.0 out of 10, Very good, (24)
"We loved the location, but the home was loaded with spiders, most appliances did not work (dishwasher did not work, blender, toaster oven, the stove top only half worked) - plus the pots were scratched (and with Teflon not useable) The shower door was broken and would not close, the toilet paper roll holder had no dowel to hold roll, toilet seat very loose, door frames were chipped and dirty, hold in wall next the bed in room with bunkbeds, laundry closet had missing doors. "
Dog-friendly home just blocks from the bay with deck & private hot tub

Large Home with Ocean Views, Fireplace, and Gas Grill - Dogs Welcome

6.2 out of 10, (14)
"We all had an amazing time. Convenience to the beach was a bonus. Spectacular views of the ocean n the bay. Plenty of space , screen doors were annoying ( but I also live on the beach and understand how beat up everything gets). Would definitely rent this house again."
Large Home with Ocean Views, Fireplace, and Gas Grill - Dogs Welcome
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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Other types of properties in Shirley you may be interested in

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

10.0 out of 10, Exceptional, (15)
"We stayed on Long Island for 4 nights to coach a Perfect Game Baseball Tournament. This property was spacious enough to host my wife and I along with 4 other coaches (6 adults total). We were also able to bring our two jack russells with us. We had a great time, and look forward to staying here again."
The price is AU$861
includes taxes & fees
7 Jan - 8 Jan 2025
3 Story Beach Waterview, 3 KING bed, golf putting green!

Hyatt Regency Long Island

3.5 star property
8.0 out of 10, Very good, (1001)
"We were in town briefly to attend a family function. The staff were helpful and competent. Our room itself was comfortable and clean - the pillows could probably use some refreshing as they all seemed like the life had been squished out of them already. Check-in/out was quick and easy; the bar area was nice and the staff there were lovely. Didn't get to check out other amenities like pool or fitness area. "
The price is AU$227
includes taxes & fees
24 Dec - 25 Dec
Hyatt Regency Long Island

Hampton Inn Long Island-Brookhaven

2.5 star property
8.6 out of 10, Excellent, (1008)
"Convenient location, teasonable price, friendly staff, decent breakfast. $15/night for parking is a little much!"
The price is AU$190
includes taxes & fees
22 Dec - 23 Dec
Hampton Inn Long Island-Brookhaven
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.

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?

Gorgeous private Hamptons house with pool and volleyball court: This holiday home rental outside of Shirley offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a fridge, an oven and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a pool table.

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?

Carmans River and Great South Bay 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.