Photo by AnnMarie Guli Photography

Holiday Rentals in Shirley

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Holiday Rentals in Shirley

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

10.0 out of 10, Exceptional, (17)
"This place was clean and comfortable, just what we needed."
The price is €580
includes taxes & fees
3 Jun - 4 Jun
3 Story Beach Waterview, 3 KING bed, golf putting green!

Modern Vacation home. Close to The Hamptons

10.0 out of 10, Exceptional, (2)
"good time"
The price is €646
includes taxes & fees
4 Jun - 5 Jun
Modern Vacation home. Close to The Hamptons

Meets Modern Comfort in This 3-Bedroom Long Island Sound Retreat

Meets Modern Comfort in This 3-Bedroom Long Island Sound Retreat

Quiet Bayside cottage. 10 minutes to beach, 15 minutes to shopping.

8.4 out of 10, Very good, (11)
"Wonderful location, love the brine scented air & cattails. Perfect location for us to easily visit family. Really enjoyed the relaxing weekend. Will definitely try to stay there again. "
The price is €172
includes taxes & fees
26 May - 27 May
Quiet Bayside cottage. 10 minutes to beach, 15 minutes to shopping.

2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment

8.8 out of 10, Excellent, (26)
"Clean and efficient, full kitchen and an extra 2nd bathroom come with the outside shower! 1 block to spectacular Ocean beaches, about a mile walk (or bicycle ride) to Ocean Beach. In this town Ocean Bay Park there are several restaurants, a grocery store/deli and marina. A short walk from the ferry."
2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment

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

The price is €208
includes taxes & fees
26 May - 27 May
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

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

10.0 out of 10, Exceptional, (86)
"Property was a great home base for a weekend getaway. Location and accommodations were great."
The price is €651
includes taxes & fees
27 May - 28 May
East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.

1856 Trading House close to water

9.4 out of 10, Exceptional, (15)
"We loved the location. It was very convenient being close to Port Jefferson and Cedar Beach"
1856 Trading House close to water

Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

10.0 out of 10, Exceptional, (79)
"A gorgeous and peaceful setting for a wonderful week with family. Thank you so much for a fantastic stay - and looking forward to visiting again in the future."
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

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

8.0 out of 10, Very good, (24)
"We had a great stay here! The pictures accurately portrayed the house and there was plenty of space and a really nice outdoor space. There is a wagon at the ferry we weren't made aware of and a lock on the bikes with no code provided. Very much a bare bones house. Kitchen was adequately stocked. The stove only had one working burner. Felt the property was well priced. Would definitely come back!"
Dog-friendly home just blocks from the bay with deck & private hot tub

10 Bedroom Hampton House with a regulation size Pickleball

10.0 out of 10, Exceptional, (25)
"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

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

8.2 out of 10, Very good, (44)
"This house was in the perfect location as it was close to the ferry terminal and a short walk to ocean beach."
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

10.0 out of 10, Exceptional, (7)
"Robert was an amazing host..We had an incredible New Year’s Eve…We are already planning our next trip back… "
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

LUXURY BAY SHORE HOME

2.0 star property
The price is €1,337
includes taxes & fees
25 May - 26 May
LUXURY BAY SHORE HOME

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

7.6 out of 10, Good, (9)
"Great 4-day visit to Ocean Bay Park- this Geller-designed house was minutes from ferry, beach and market and easy walking/biking distance frome and Ocean Beach. Beds were comfy, grill and WiFi worked well (downstairs) and house was fun design, with decks on both floors. Before staying again, I’d ask if they had fixed the lights in MBR and LR, the shower for MBR and the low-performing fridge."
Charming home close to beach with fast WiFi & washer/dryer - dog-friendly

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

10.0 out of 10, Exceptional, (176)
"We had a wonderful stay. The house was great and check in and check out were both easy. We definition would love to stay again."
The price is €1,055
includes taxes & fees
30 May - 31 May
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Walk to Beach 2BR Near Dining & Shopping

6.6 out of 10, (13)
"a little hard to find: hint, look for the address on the garbage cans, because the addresses get a bit wonky further down the block, but this is a lovely spot on the north shore if all you're looking for is a clean bed on a quiet street, and the two bedrooms are so much better for friends or families than would be two rooms in the hotel by the highway -- oh, and there's a nice bagel place just north of the Starbucks on the corner of 25A"
The price is €300
includes taxes & fees
11 Jun - 12 Jun
Walk to Beach 2BR Near Dining & Shopping

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

10.0 out of 10, Exceptional, (12)
"Perfect , clean , well decorated and great location for a stay on the south shore of Long Island . Close to Robert Moses beach and easy access to highways ."
fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc

Designer beach cottage & studio with bikes, outdoor shower, deck - walk to beach

9.2 out of 10, Wonderful, (20)
"This house was perfect for our weekend gathering with our adult children!! The house was very comfortable & had everything we needed for a great weekend!"
Designer beach cottage & studio with bikes, outdoor shower, deck - walk to beach

Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

9.4 out of 10, Exceptional, (36)
"Lovely cottage beautifully decorated, close to restaurants, farm stands, and food stores. A least a 15 to 20 minute walk to the beach."
The price is €482
includes taxes & fees
28 May - 29 May
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
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.
Save an average of 15% on thousands of hotels when you're signed in

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, (17)
"This place was clean and comfortable, just what we needed."
The price is €580
includes taxes & fees
3 Jun - 4 Jun
3 Story Beach Waterview, 3 KING bed, golf putting green!

Hyatt Regency Long Island

4.0 star property
8.4 out of 10, Very good, (1007)
"Loved this place, was super clean and the atmosphere was great."
The price is €150
includes taxes & fees
27 May - 28 May
Hyatt Regency Long Island

Hampton Inn Long Island-Brookhaven

2.5 star property
8.8 out of 10, Excellent, (1088)
"Great stay"
The price is €108
includes taxes & fees
27 May - 28 May
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?

3 Story Beach Waterview, 3 KING bed, golf putting green!: This highly rated holiday home rental in Shirley is located near the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Shirley?

With 14 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.