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Shirley Holiday Rentals

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Holiday Rentals in Shirley

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

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

9.8 out of 10, Exceptional, (19)
"Great costal location on Long Island. Eddie is a rockstar and took great care of us. Very unique architecture with lots of cool angles. Awesome family gettaway...!"
The price is HK$1,407
HK$4,893 total
includes taxes & fees
26 Aug - 27 Aug
3 Story Beach Waterview, 3 KING bed, golf putting green!
Relaxing Smith Point Beach House on private canal
Outdoor dining

Relaxing Smith Point Beach House on private canal

9.6 out of 10, Exceptional, (58)
"Great location, so close to the beach! We very much enjoyed our time at the property, had everything we could need. The hosts were amazing!"
Relaxing Smith Point Beach House on private canal
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
1 bedroom, iron/ironing board, free WiFi, bed sheets

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

9.4 out of 10, Exceptional, (23)
"its small but very nice for a short stay would recommend."
The price is HK$774
HK$1,286 total
includes taxes & fees
25 Aug - 26 Aug
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.
Beach

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

10.0 out of 10, Exceptional, (2)
"Friendly host, very good location and a simple check-in process. Few minutes drive to the beach. "
The price is HK$2,075
HK$2,862 total
includes taxes & fees
2 Sept - 3 Sept
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.
Newly Renovated Luxury Beach House Ocean Bay Park
Outdoor dining

Newly Renovated Luxury Beach House Ocean Bay Park

10.0 out of 10, Exceptional, (66)
"Very nice place for a family to stay"
The price is HK$5,620
HK$10,144 total
includes taxes & fees
1 Sept - 2 Sept
Newly Renovated Luxury Beach House Ocean Bay Park
10 Bedroom Hampton House with a regulation size Pickleball court
Pool

10 Bedroom Hampton House with a regulation size Pickleball court

9.8 out of 10, Exceptional, (30)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball court
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
Fridge, microwave, oven, stovetop

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (33)
"We had a amazing stay and plan to come back next July again"
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.
Fridge, microwave, oven, stovetop

East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.

10.0 out of 10, Exceptional, (96)
"Great indoor and outdoor spaces to hang out. Took SUP on the water - so nice and calm. "
The price is HK$2,306
HK$4,715 total
includes taxes & fees
1 Sept - 2 Sept
East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
Private kitchen

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

5.0 out of 10, (2)
"Overall clean space and super easy check in/out. Location is on a quiet street/neighborhood which is nice. Not full a/c in rooms but had two floor fans; was hot in summertime but manageable for a short stay. Had a nice deadbolt on door to lock it. Awkward entrance as you go through the back of the house and all the way around the property, but it isn't terrible. A bit of a dead zone for Verizon but T-mobile was OK; Wi-Fi was available which was needed. Good for easy overnight stay and cheaper...
The price is HK$1,219
HK$1,795 total
includes taxes & fees
31 Aug - 1 Sept
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters
Outdoor pool, a heated pool

Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters

10.0 out of 10, Exceptional, (57)
"From the moment we booked this trip we knew we were in for a treat. Windows on the Sea did not disappoint! From the early communication with our hosts and their thoughtful check-ins leading up to our trip, this was the best experience we could ask for. We highly recommend staying here!"
Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Outdoor pool, a heated pool

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

9.4 out of 10, Exceptional, (71)
"Wonderful time in a wonderful property. Megan the property owner was so very helpful."
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Beautiful historic home in Stony Brook!
Interior

Beautiful historic home in Stony Brook!

2.0 star property
8.2 out of 10, Very good, (12)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Terrace/patio

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

9.6 out of 10, Exceptional, (133)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Spacious Home Located Close to Stony Brook!
Property grounds

Spacious Home Located Close to Stony Brook!

6.8 out of 10, (18)
"Great stay great people great costumer care definitely reccomend"
Spacious Home Located Close to Stony Brook!
Hamptons Retreat
Terrace/patio

Hamptons Retreat

Hamptons Retreat
NEW 7 Bedrm House-Pool, Swim-Up Bar, Grill, Pool Table, Fitness and play room
Outdoor pool, a heated pool

NEW 7 Bedrm House-Pool, Swim-Up Bar, Grill, Pool Table, Fitness and play room

9.2 out of 10, Wonderful, (14)
"Beautiful property! Well stocked with essentials and perfect for our group with and age range o16 - 83"
NEW 7 Bedrm House-Pool, Swim-Up Bar, Grill, Pool Table, Fitness and play room
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Oven, stovetop, dishwasher

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
9.0 out of 10, Wonderful, (4)
"Large open first floor for a large family stay. Great back patio with a nice view of the river. Don't miss the morning swans. "
The price is HK$3,900
HK$7,134 total
includes taxes & fees
26 Aug - 27 Aug
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park
Beach

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park
Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach
Fridge, microwave, stovetop, coffee/tea maker

Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach

10.0 out of 10, Exceptional, (2)
"Everything was as pictured, and the whole place was very clean. It was a perfect stay for us, and we will come again soon!"
The price is HK$598
HK$1,308 total
includes taxes & fees
3 Sept - 4 Sept
Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach
Stunning Bayfront Views
Interior

Stunning Bayfront Views

9.8 out of 10, Exceptional, (36)
"House was exactly as described, excellent host and definitely went the extra mile to ensure we had a great stay. Cannot beat this location!"
Stunning Bayfront Views
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

Hampton Inn Long Island/Islandia

Hampton Inn Long Island/Islandia

10/10 Excellent
"Our stay was very nice."
Lori 1-night trip
Posted 10 hours ago
Hampton Inn Long Island/Islandia

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?

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. : This holiday home rental outside of Shirley has air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

How many holiday rentals are there in Shirley?

With 17 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.