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Shirley Vacation Rentals

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Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
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In three months
Dec 19 - Dec 21

Vacation Rentals in Shirley

Modern Vacation home. Close to The Hamptons
Fridge, microwave, oven, stovetop

Modern Vacation home. Close to The Hamptons

10.0 out of 10, Exceptional, (3)
"good time"
The price is ￥49,705
￥94,193 total
includes taxes & fees
Sep 30 - Oct 1
Modern Vacation home. Close to The Hamptons
3 Story Beach Waterview, 3 KING bed, golf putting green!
Property grounds

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

10.0 out of 10, Exceptional, (21)
"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 ￥22,274
￥87,446 total
includes taxes & fees
Sep 29 - Sep 30
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
Spacious Home Located Close to Stony Brook!
Property grounds

Spacious Home Located Close to Stony Brook!

7.0 out of 10, Good, (20)
"Great stay great people great costumer care definitely reccomend"
The price is ￥46,955
￥105,226 total
includes taxes & fees
Oct 10 - Oct 11
Spacious Home Located Close to Stony Brook!
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, (29)
"its small but very nice for a short stay would recommend."
The price is ￥14,800
￥24,598 total
includes taxes & fees
Sep 29 - Sep 30
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 ￥35,653
￥49,445 total
includes taxes & fees
Oct 6 - Oct 7
“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, (71)
"Very nice place for a family to stay"
The price is ￥94,044
￥175,420 total
includes taxes & fees
Sep 29 - Sep 30
Newly Renovated Luxury Beach House Ocean Bay Park
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Outdoor pool, a heated pool

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

10.0 out of 10, Exceptional, (190)
"Had a lovely relaxing time with family and friends. Very convenient and great size."
The price is ￥66,598
￥122,374 total
includes taxes & fees
Oct 2 - Oct 3
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
East End Cottage Retreat - Dock, Fireplace, Beaches, Wineries & More!
Smart TV, fireplace, video games, stereo

East End Cottage Retreat - Dock, Fireplace, Beaches, Wineries & More!

10.0 out of 10, Exceptional, (98)
"Great indoor and outdoor spaces to hang out. Took SUP on the water - so nice and calm. "
The price is ￥32,140
￥76,172 total
includes taxes & fees
Oct 28 - Oct 29
East End Cottage Retreat - Dock, Fireplace, Beaches, Wineries & More!
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
10 Bedroom Hampton House with a regulation size Pickleball court
Pool

10 Bedroom Hampton House with a regulation size Pickleball court

10.0 out of 10, Exceptional, (32)
"Cannot say enough good things. Unique, sprawling, beautiful property with more than enough room for a large group. Endless entertainment, great pool, walking distance from a few bars and restaurants. Great communication and accommodation from our host. Would recommend and rent again."
10 Bedroom Hampton House with a regulation size Pickleball court
Walk to Beach 2BR Near Dining & Shopping
Property grounds

Walk to Beach 2BR Near Dining & Shopping

6.6 out of 10, (20)
"The beach is private and you need to be a Brookhaven resident to be admitted. This is not specified anywhere on the listing. Communication about this with the owner via app was rather poor. "
The price is ￥16,818
￥41,249 total
includes taxes & fees
Sep 29 - Sep 30
Walk to Beach 2BR Near Dining & Shopping
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
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
8.4 out of 10, Very Good, (7)
"prefect experience! The house is clean and well decorated with a large organized yard. Many parking spaces. "
The price is ￥74,596
￥136,294 total
includes taxes & fees
Sep 29 - Sep 30
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
Microwave, oven, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (39)
"Great place to stay. It was prefect for our family of six. We really enjoyed the stay and would stay there again. It was very clean and organized."
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
Beautiful historic home in Stony Brook!
Interior

Beautiful historic home in Stony Brook!

2.0 star property
8.4 out of 10, Very Good, (15)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!
Large 6-Bedroom 3-BR Waterfront Hamptons House, your own Private Beach in Front.
TV, fireplace

Large 6-Bedroom 3-BR Waterfront Hamptons House, your own Private Beach in Front.

The price is ￥83,116
￥439,961 total
includes taxes & fees
Sep 29 - Sep 30
Large 6-Bedroom 3-BR Waterfront Hamptons House, your own Private Beach in Front.
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!
Fridge, microwave, oven, stovetop

OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!

9.0 out of 10, Wonderful, (53)
"Has a very nice stay."
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!
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, (136)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Stunning Bayfront Views
Interior

Stunning Bayfront Views

9.8 out of 10, Exceptional, (37)
"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

Comfort Inn Medford - Long Island

Comfort Inn Medford - Long Island

10/10 Excellent
"Stay for Ryder Cup. Clean, quiet, comfortable. "
Sharon 2-night trip
Posted 9 hours ago
Comfort Inn Medford - Long Island

Find out more about Shirley

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

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 19 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.