Family-friendly holiday rentals in Shirley

We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!

This house was the perfect place to enjoy a peaceful stay with our three young daughters. The grounds were in beautiful bloom during our time which made all of the outdoor time even more enjoyable. From the large yard, to the hot tub and the fire pit we enjoyed staying at the property as much as exploring the area. I appreciated the well equipped kitchen and the high quality bedding. Would love to return during the summer when the pool is open and the patios were all ready for the warm weather.

Victoria's place was wonderful! It was spacious and comfortable and gave our family plenty of room to spread out and enjoy our visit. Victoria was a very responsive host and made check in and check out stress free and easy! There was ample parking for our cars and the house was private - it was the "house behind the house" so we weren't subject to busy traffic noise on the street. (Got a little confusing for DoorDash drivers but we worked it out :D). I will book this same place next time I am up for an extended weekend with the family. Highly recommend!

We had a great time in David and Claires beautiful house in Bellport. Such a nice place and perfekt location for daily trips by the coast with stops on the way out to the Hamptons. Or a daytrip to the city, close enough. Nice and quiet location, the house is very cosy and a lot of space for a bigger family or perfect for family reunion. We loved the ping pong table and other activitites as the pool, jacuzzi and the outdoors. If the weather had been better we would have used the facilities outside more for sure. We would love to come back to the house again. David and Claire are excellent hosts, very helpful and quick at responding.

Fantastic absolutely amazing experience. Jaime was beyond great when it came to professionalism and kindness and responsiveness. Super clean beautiful apartment didn’t miss a trick when it came to anything you might need. This was a top-notch experience. Amazing customer service, beautiful location. Beautiful pool and spa overlooking the ocean We will definitely be back.

This was a great find for a long weekend! It was perfect for our dog as the front- and backyards are fenced in. Wonderful kitchen, great pool and close to town which made for a perfect stay. Cindy gives good recommendations on restaurants and activities and is very responsive if you have any questions.

We enjoyed a lovely stay in the beautiful home. Josh was easy to reach and flexible with our requests.

Hi, we had a great stay with plenty of space for all of us. We all loved the fresh flowers on the living room table. The roses were a beautiful touch! The place was very clean to which my mother-in-law said it at least 4 times a day! LOL The bedrooms were set up so neatly when we arrived (very impressive). The kitchen had all the necessary utensils we needed and more. Great weekend! Thank you.

Beautiful space both inside and outside. Location connected to the animal farm and bakery was so charming. Location was perfect for the family reunion nearby. Easy parking. Clear communication made the stay seamless.

I had a very nice stay at the Rex. It is dog friendly and very clean. Although my space was private, there are other rentals nearby and it had a camp like feel. I would stay there again if need be.

The house was clean, well-decorated, had all the things we needed, and private, with a long wooded lot leading down to the bay. We women friends were totally comfortable there. When we couldn’t find the entrance to the driveway off the main road, she stayed on the phone & directed us until we found it. Excellent choice!

Had an amazing stay with my business partner. Farms around the area and proximity to multiple Hampton towns was ideal(5 mins from Southampton). Great stay, 10/10 recommend.

Jason was a great host. Very responsive to any questions we had while staying on Shelter Island. The location is great - easy walk from the North Ferry and central to great restaurants. Airbnb was exactly as pictured. Would definitely stay again! Thanks again Jason!

I stayed at Mary's rental with my sister's family including a 4yo and 6yo, as well as my 72yo mother and the house was a perfect fit! The downstairs bedroom and full bath were perfect for mom to avoid the steep stairs, and the house was well equipped with a ton of kids books and some toys. Proximity to town was the highlight, we were easily able to walk with the kids which was perfect since the weekend was too chilly for the beach. Mary was responsive if needed but the house is well stocked and easy to navigate so we felt at home right away. I will absolutely be renting from Mary again!

We were greeted by walking through the gate to the backyard in a rhododendron bush in full bloom. It was absolutely gorgeous. Everything from walking in the door to the Airbnb apartment to settling into the very comfortable bedding we had a really lovely stay, and I would definitely return for future trips. Michael helped us find a beach that didn’t require a local sticker that was perfect!

We love staying at George’s place, it feels just like home away from home for us. We’ve visited this property several times over the years, most recently with our son who’s now old enough to fully enjoy the yard on his own. He had a fantastic time playing outside, talking to the deer and rabbits that came to visit. We even saw some turkey vultures! Overall a solid place to stay and it’s become somewhat of a family tradition. Thank you George!

Marta could not have been more accommodating! She was responsive and provided everything we needed. She even went the extra mile and insta cart-ed garbage bags and paper towels when we ran out. She could not have been a kinder host! We had the best weekend and would HIGHLY recommend staying at Marta’s place! We will definitely be back!

Everything was perfect for our girls weekend. This is the 3rd time we’ve used Laurie’s house and there’s obviously a reason we keep coming back. Can’t wait to go again.

Wendy’s house is immaculate, tastefully decorated, very spacious and extremely comfortable. Her instructions were clear and her responsiveness immediate. We would absolutely consider staying there again.

Great place and location with a very nice backyard for relaxing, swimming and grilling. We had an excellent stay and Jean Francois was very responsive to some questions from our end. Highly recommended.

Jeff's place has a lot of character and is spacious. The setting is excellent, near the water, with Satterly Landing right down the road. We enjoyed our stay.

Yvonne's place is wonderful, we spent six days there on a family vacation to celebrate a graduation and it was a perfect spot for a crowd. The description and pictures are spot on (maybe even better) and the place is very well maintained. The weather was not great - so we landed up staying in more than we anticipated and this was a great spot for that. The kitchen is well stocked, having a barbecue really helped, and the large windows and skylights kept us connected to the outside. Yvonne was also highly responsive in case we needed anything. Highly recommend.

John was a perfect host! Friendly, responsive and made us feel welcome. I took my 9 year old son and we had a great time fishing off the dock and kayaking. The kitchenette is lacking if you want to cook any meals but it didn’t matter in our case. Absolutely beautiful location!

Ed was a great, communicative host, and the place was cozy for four of us during a week-long work trip!