Bay Shore Holiday Rentals

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Holiday Rentals in Bay Shore

The President Mansion Luxurious 7BR Family Retreat

9.6 out of 10, Exceptional, (4)
"I booked this property for my in-laws to stay at for the weekend of my wedding. There was plenty of space for all the adults and the kids to stay comfortably. The host was helpful, attentive, and accommodating. I would happily stay here again in the future. "
The President Mansion Luxurious 7BR Family Retreat

1 bedroom 1 bath private entrance

9.0 out of 10, Wonderful, (16)
"Place was very clean and well maintained. Host was extremely helpful and communicative! 10/10 would recommend "
The price is AU$309
includes taxes & fees
29 Nov - 30 Nov
1 bedroom 1 bath private entrance

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

8.8 out of 10, Excellent, (26)
"This property is steps away from the ferry, steps away from the beach and steps away from food, drinks and music. We had a great time. Cassie greeted us and made sure we had everything we needed!!!! She also went out of her way to make my daughters 21st birthday special. Highly recommend this property."
2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment

One Bedroom Apt. in Ocean Bay Park with deck & gas grill

9.4 out of 10, Exceptional, (36)
"Property is cozy and quaint just large enough for two people.The wifi code in the email and posted in the property were different. We expected a call back from the property manager but never got it. The weather was fantastic."
One Bedroom Apt. in Ocean Bay Park with deck & gas grill

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

10.0 out of 10, Exceptional, (56)
"The hosts Anthony and Whittney are nothing short of fabulous! They were very gracious and very responsive to all my questions. The house was in a great location being so close to the ocean and it was very clean and easy to navigate with the touch of an iPad. The heated pool was perfect for my family to gather and play. I highly recommend this home to anyone looking for a fun, relaxing stay on Fire Island. "
Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters

Fair Harbor Living - Barefoot Beach Getaway

8.8 out of 10, Excellent, (13)
"This Fair Harbor cottage is on a great block with dune grass all around. The central rooms and screened porch are charming, vintage Fire Island, boho-surf style. The tiny kitchen is not easy to work in, and very disorganized, so you’ve got to put ideas of cooking like you’re used to aside and get into beach shack mode. This place calls for you to relax your expectations. It’s not very well maintained, there are traces of past renters everywhere, including trash, and debris so we did quite a bit...
Fair Harbor Living - Barefoot Beach Getaway

Dog-Friendly Condo with High-Speed WiFi, Outdoor Shower, Gas Grill, Beach Access

7.6 out of 10, Good, (15)
"Our stay was really wonderful. A true beach getaway. The place had everything we needed, was comfortable, spacious. A few minor things arised but the management communicated right away and our vacation time was not effected. Overall, our experience was great."
Dog-Friendly Condo with High-Speed WiFi, Outdoor Shower, Gas Grill, Beach Access

One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

8.8 out of 10, Excellent, (26)
"Wonderful 2nd time staying at this location. Easy walk to the beach and great restaurants in ocean bay park. Biggest issue was not having anyone to text with questions. At other properties we have stayed we could contact the owners- Vacasa didn’t allow for this here. When the codes given to us didn’t unlock the bicycles we needed, it took a long time to get a hold of someone and the people who texted back gave generic answers and couldn’t help. They gave us the same code we had already received....
One Bedroom Apt. in Ocean Bay Park with Rooftop Deck

Charming oceanfront home w/ stunning views & wraparound deck - steps from beach

9.6 out of 10, Exceptional, (9)
"Loved it, will book again!"
Charming oceanfront home w/ stunning views & wraparound deck - steps from beach

Waterfront Cottage cute and cozy

9.4 out of 10, Exceptional, (93)
"It was excellent "
The price is AU$399
includes taxes & fees
2 Dec - 3 Dec
Waterfront Cottage cute and cozy

Peaceful Gathering Modern Kitchen & Living space

7.8 out of 10, Good, (13)
"For some reason he thought I canceled my reservation. When I got nervous that I hadn't recieved any check in information I messaged him. He did message me right back and apologized for the misunderstanding. I asked when we would get the access information and I didn't get a response. After a few hours I had to call VRBO because I was about to catch my flight. I had family that would be arriving before myself. I wanted to be sure they could get in , To be clear they would be there after...
Peaceful Gathering Modern Kitchen & Living space

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (52)
"The captain cottage was exactly what Mom and I wanted! Beautiful views of the bay,super easy five minute walk to the main street of Cold Spring Harbor, adorable house with everything you need, and Kim was on top of it every time we neededhelp. Thank you so much for hosting us and cannot wait to be back!"
The price is AU$672
includes taxes & fees
10 Dec - 11 Dec
Captain's Cottage - Cold Spring Harbor Water Views

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

Waterfront Home magnificent view!

9.4 out of 10, Exceptional, (118)
"Cozy property with stunning views. Yes, it is older but it worked for our needs since my family and I was out of the house for most of the stay. Very close to grocery and other stores for essential needs. Good location!"
The price is AU$487
includes taxes & fees
25 Nov - 26 Nov
Waterfront Home magnificent view!

Luxuriously Comfortable Suite

9.0 out of 10, Wonderful, (21)
"very easy check in"
The price is AU$388
includes taxes & fees
25 Nov - 26 Nov
Luxuriously Comfortable Suite

Cheerful 2-Bedroom Home With On Premises Parking

8.4 out of 10, Very good, (7)
"Everything was very good and just as stated in the listing. Clean and comfortable. "
Cheerful 2-Bedroom Home With On Premises Parking

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

10.0 out of 10, Exceptional, (22)
"Nice place—modernized and spacious! Perfect for families/friends weekend with separate basement suite! "
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Beautiful Beach House with Large Swimming Pool in Ocean Beach

10.0 out of 10, Exceptional, (34)
"Wonderful vacation! House has everything you need and the location is perfect. Hosts are quick to respond to any questions. Would definitely stay here again!"
Beautiful Beach House with Large Swimming Pool in Ocean Beach

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$364
includes taxes & fees
25 Nov - 26 Nov
Private 1 bedroom apt in a quiet neighborhood, close to all!

Luxurious NYC Retreat / Central Location / Wi-Fi

7.8 out of 10, Good, (8)
"Nice place to stay with family for relaxing with all amenities like fridge, oven, TV etc"
The price is AU$341
includes taxes & fees
1 Dec - 2 Dec
Luxurious NYC Retreat / Central Location / Wi-Fi
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 Bay Shore you may be interested in

The President Mansion Luxurious 7BR Family Retreat

9.6 out of 10, Exceptional, (4)
"I booked this property for my in-laws to stay at for the weekend of my wedding. There was plenty of space for all the adults and the kids to stay comfortably. The host was helpful, attentive, and accommodating. I would happily stay here again in the future. "
The President Mansion Luxurious 7BR Family Retreat

1 bedroom 1 bath private entrance

9.0 out of 10, Wonderful, (16)
"Place was very clean and well maintained. Host was extremely helpful and communicative! 10/10 would recommend "
The price is AU$309
includes taxes & fees
29 Nov - 30 Nov
1 bedroom 1 bath private entrance

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

8.8 out of 10, Excellent, (26)
"This property is steps away from the ferry, steps away from the beach and steps away from food, drinks and music. We had a great time. Cassie greeted us and made sure we had everything we needed!!!! She also went out of her way to make my daughters 21st birthday special. Highly recommend this property."
2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Bay Shore?

Yes, there are holiday rentals in Bay Shore close to Bay Shore Mini Golf, or you can select a more secluded option if you're looking for a relaxing stay. Bay Shore is known for its beaches.

What are some of the best holiday rentals that Bay Shore has to offer?

The President Mansion Luxurious 7BR Family Retreat : This highly rated holiday home rental in Bay Shore offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Another good choice for your trip to Bay Shore is Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters.

How many holiday rentals are there in Bay Shore?

With 88 Expedia holiday rentals, you're guaranteed to find just the right place for your Bay Shore stay.

What’s there to see and do in Bay Shore?

Cultural attractions include Bay Shore Historical Society and YMCA Boulton Center for the Performing Arts, whereas Robert Moses Beach and Robert Moses State Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Fair Harbor Ferry Terminal and Fire Island Lighthouse.

What’s a holiday rental in Bay Shore like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Bay Shore. Holiday rentals offer extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family gatherings.