Kid-friendly holiday rentals in Shelter Island Heights

The property is well located in a very private setting with a large yard, and had space to comfortably accommodate our party of six adults, two children, and two infants. The home is well furnished, nicely decorated, immaculate, and very child friendly. Chelsea was a great host and provided helpful recommendations before and during our visit. Overall, our family group had a wonderful time during our four-night visit to Westhampton.

Ed was great at communicating, house was everything we could have asked for. Would definitely book again!

Paula was a very responsive host. She made checking in easy. The house itself was beautiful and very clean. Plenty of space inside and outside. My favorite part of the house was the separate guest house and the hot tub which was very easy to use. Highly recommend this host and house! Thank you Paula!

The place was perfect for our getaway weekend! The house is super spacious, very clean and has everything one may need to enjoy your stay. The host was friendly, accommodating and always available to answer any questions we may had. Will absolutely recommend this place

Gloria was a very amenable host the place worked out great for us and our two dogs and we were able to entertain a few friends and cook an amazing dinner

Very nice setup for two couples, a baby, and a dog - could spread out with bedrooms and full bathrooms on each floor. Comfortable space with amenities you'd want while traveling with a dog and a baby (fenced in yard, laundry, etc). Very walkable to all the shops & restaurants in town, and easy drives to wineries & breweries. The only drawback was that it was close to a fire station and the sirens woke the baby from a nap.

We had an amazing stay at Alissa and Danny’s house! The location is perfect—convenient to everything we needed, yet peaceful and relaxing. The house is carefully designed with families in mind, especially with kids. It has everything you could possibly need for young children, from toys to safety features, making it so easy to enjoy our time there. We were so impressed that we’ve already booked again for our next trip! Highly recommend for any family looking for a comfortable, family-friendly! Mine Gur

We enjoyed our stay at your cozy beach house. Rosemary set up the place with everything we needed.

We enjoyed the weekend at the the mystic getaway, the apartment is clean and comfy! We located the Denison Homestead and took a beautiful trail hike even though it was cold and windy. We had a great dinner at SnP and comedy night at Mohegan Sun. We hope to return in the summer!

There are a lot a reasons to use Airbnb, and one is that you can stay in the most interesting places. That's the reason to stay at the Ludington mansion. Incredible property. If you have any interest in history or architecture, this is your place. We stayed in the 3rd floor suite; of course, it's not a good choice if you can't manage the stairs, but since that was not a problem for us, we loved it. The space was as described: full of character and immaculately clean (if not always new). It was nice having two full baths. The next-door church bells didn't bother us. I can't think of anything we needed that wasn't there. We appreciated the host's suggestion for where to have dinner and were not disappointed. We ended the evening by streaming the (admittedly cheesy) Hallmark Christmas movie filmed on the property and spotting furnishings that were in our suite. We wished we could have stayed longer instead of just over-nighting while on the drive from Maine to NC.

We rented the apartment to visit with our grown kids for our Christmas vacation. The kitchen had everything I needed to cook a small brunch for them to snack on. The fenced in area, for our dog, was perfectly secure and separate from the main yard which I appreciate. Lee and Kelly were both very friendly and responsive but also gave us privacy as well. The pricing of the unit was very competitive for this area. Our dog can bark a bit when we couldn't bring him out with us so I hope he didn't disturb them too much. We never heard any loud noise from there house so for an above garage apartment, I thought that was great!

Our 3 time staying at Amanda’s home. Beautiful and spacious within walking distance to village. Looking forward to coming back next year!

Had an absolutely wonderful stay! Location is perfect and Jaime was incredibly friendly throughout!! He let me know that they had everything we would need.. but as a self-described obsessive packer I didnt listen. He wasn't kiding! They had beach chairs, umbrellas, and everything else you need for the perfect beach day. I brought an entire wagon of stuff and used one bag. It really is an awesome little find!!

Wonderful host and place to stay. Always enjoyed staying there

This was our second stay at Nick's, and it did not disappoint. The apartment is exactly as pictured, with all the amenities needed to feel like a home away from home! When I encountered an issue that required me to request a policy change, Nick responded quickly and was very helpful. We will be back.

My husband and I thoroughly enjoyed our stay in Sag Harbor at Whaling Captain Pierson's Apartment TOO! The apartment was absolutely beautiful and the surroundings were gorgeous. My husband and I are a lover of old / historic homes and antiques, and if you are too - this is a great place for you. We stayed in Sag Harbor for our anniversary weekend and Paris made us feel right at home, and went as far as to leave us a wonderful gift to help us celebrate. Would highly recommend to others! We hope to be back.

Camila was a great host, very responsive and always helpful. The apartment was clean, tidy and cosy and made us feel at home very quickly. Location was good, walkable distance to New Haven Green and its surroundings. All in all, we enjoyed our stay very much and would recommend Camila’s place to anyone planing to spend some time in New Haven.

We rented the entire property for a wedding party and it was perfect. Very clean, beautifully furnished, and you can't beat the location in Mystic. Walkable to downtown and local restaurants. The hosts communicated well and we had no issues! Would highly recommend this location!

Lovely stay in greenport! Short drive from major north fork activities. Can imagine its even better during the busy season!

This place was perfect! It looks exactly like the pictures and was perfectly clean inside. Doug was always responsive for any questions we had. We couldn’t have asked for a better place to spend the weekend. Would definitely come back and stay again

We really enjoyed staying at Lynn’s place! Very clean and had a great view of the ocean from the deck. Lynn was very responsive and made the experience seamless. We would definitely stay with Lynn again.

Overall relaxing stay and trip to Greenport. Sherri is very communicative and her instructions and listing is clear and accurate. The condo is well decorated and clean and has everything you need for a nice weekend. One thing to note- we were aware check in is between 3 and 5 pm based on the listing (wound up being around 4) but it would be nice for it to be earlier. Still 5 stars though!

We really enjoyed our stay. The unit was just enough space for my husband and I and our two daughters. Having a kitchen to prepare quick breakfasts in the morning before heading out for the day and having the pool and beach in the late afternoons gave us everything we needed to start and end busy days at the Hamptons Classic or visiting family. We are hopeful to visit again!

Incredible stay at #19 The Bridge the whole 3rd floor with two comfy family inviting areas to hang out and enjoy, large tv in every space, 4 great bedrooms with new mattress so comfy, luggage holder and greeted with fresh towels in every bedroom and great sound machines, chargers and ceiling fans in each bedroom. Bathroom one with jet tub, shower and bidet, beautiful tile and clean! Kitchen had all the plates, glasses and utensils, pots and pans needed and an awesome coffee station we enjoyed cooking breakfast every morning and then enjoyed at the family table large enough for 10-people if needed and a high chair provided for our grand baby! Rooftop outside table was great for enjoying the gorgeous view of beautiful Old Colony Beach! Short block walk to private Old Colony Beach made for an amazing family vacation! We can’t wait to come back and make this an annual stay. Thank you Peter for making #19 our new vacation spot.