
Family-friendly holiday rentals in Long Island Sound
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Top-rated family-friendly rentals in Long Island Sound
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for Long Island Sound family-friendly rentals
Family-friendly home rentals with a hot tub

Waterfront cottage overhanging the water!
We thoroughly enjoyed our time at the cottage. It was so very peaceful and we loved being literally right around n the water! Slept amazingly well and the cottage was just lovely! Robert was also a great host. 5 stars all around and we hope to return again!

Your Zen Retreat
We had an event nearby and Brian’s place was a great base for us. Lovely and peaceful neighborhood. Brian was super responsive and reached out to us when the house was ready(before the official check-in time). Would def recommend to anyone!

Relaxing Spa Retreat~Gorgeous View~Walk to Village
Ami’s place was great! Stayed for my birthday and was surprised with a delicious tres leche cake upon my arrival! The view was incredible, amenities were amazing, overall it was everything I hoped for and more. Thanks Ami!

(°) The Wandering Peacock (°)
Abigail is an incredible host. She is super accommodating and communicative. She is the sweetest and her home is incredible. This place is definitely worth it. Beautiful space and a wonderful experience.

Cozy Mountainside Suite - Minutes from Beacon
My fiancé and I stayed at Lambs hill to celebrate our anniversary. We had the most wonderful time. The views are breathtaking. The wrap around deck with jacuzzi and hammock made our stay calming and serene. I loved seeing the horses and donkeys throughout the day. They made the experience even more special and unique. Charlotte was super responsive and accommodating. We took cabs to Main Street at night for dinner and drinks and it was so close and convenient. I left my heart in lambs hill and can’t wait to return one day.

Clove Schoolhouse on Mohonk Preserve
We had a nice time staying. It has a Well stocked kitchen. It is near to grocery and shopping in Stone Ridge. It has Great fireflies at night and a good view of the sunset.

Hampton's Haven
Esther is hands down one of the finest hosts we have had, and her house is beautiful and was spotless upon arrival and everything worked from pool to hot tub to grill etc... Area is very quiet. great place to relax with a mature group of friends or with your family. Esther was always responsive. Me and my crew have been renting houses for over three decades (Way before AirBnB). Esther is at the top of the list hands down. Thank you for everything. Will 1000% be back. ANd you shuld rent there too. You will not be disappointed.

Catskills cabin over waterfall w/ views & hot tub
It is clear Adam and Chrissy take care of this place like their own home. I cannot emphasize enough how wonderful this place is. Perfectly equipped, yet doesn’t feel cluttered. Cozy, tasteful, full of wonderful little details, clear instructions and good vibes overall. Location is amazing and perfect for days of reflection / retreat in the mountains. Has all you need in the kitchen, plenty of books, board games, movies, records, even Atari and an AMAZING outdoor spa. Best of all is the water stream running below: natural forest + running water sounds - not even headspace can give you this to perfection. Outdoor seating area also lovely. I felt at home from beginning to end. Hosts incredibly responsive and helpful. Can’t wait to return !
Family- and pet-friendly home rentals

Dave's Milk Barn
We loved our stay at this beautiful, charming, and peaceful barn. The space was cozy and thoughtfully designed—perfect for a relaxing staycation. The property itself is beautiful, and it’s just a short drive to great hikes, bike trails, restaurants, and breweries. A truly lovely spot to unwind and explore. Thank you for such a wonderful experience!

Winston's Place - Woodland Cozy Catskills Cabin
Such a peaceful, rustic cabin—just what we needed to unplug and relax. It was clean, cozy, and surrounded by nature, yet close to plenty of fun things to do in the area. We’d definitely stay again!

Whaling Captain Pierson's Cottage
This was my second time staying in Paris' cottage and it was just as charming and lovely as the first time. The cottage is set back from the road, nestled in a charming neighborhood. It's a very comfortable, quiet and peaceful place with a beautiful view and privacy. The center of Sag Harbor - with shops, restaurants and a sweet movie theater - are all walking distance from the cottage! Thank you for another great stay, Paris!

Victorian Haven
We had such a lovely weekend staying in this cozy cabin. The views of the river and ridge from the yard were beautiful and calming. We were able to have a late check out with ease! Definitely will be back to stay again!

Charm + location. Walk to beach, town, & harbor.
Jeanne's place was perfect for my trip to Guilford. Excellent location, close to the Green and to the water, quiet, peaceful. The house had everything I needed and more, Jeanne was super responsive and kind, and the bed was comfortable.

Charming Fairfield Beach 3BR Cottage By The Sea
We enjoyed our stay! Such easy access to the beach was so convenient. You’re definitely better off venturing out after high tide to enjoy the most amount of beach and there are a lot of shells that make being barefoot challenging. We did arrive after major storms which could have contributed to that. The house was spotless with everything you need to be comfortable! We did not utilize the outdoor space but definitely would have if the weather was drier! Definitely would stay here again.

"Cabinessence" on Greenwood Lake, 60 mi from NYC
“Cabinesse” host (s), clearly care about their cabin and their guest. The cabin is sparkly clean and comfortable. The lake views are beautiful. The host is responsive and very helpful. We followed some suggestions from the guest book, such as a visit to Warwick, Bellvale Farms Creamery for amazing ice cream and Appalachian Pochuck Boardwalk Trail. We also tried the Bellvale Market (everything made there; amazing food) and hiked the Sterling Lake Loop (4.2 miles). Amazing unplug! Highly recommended.

Byrdcliffe Artist Studio (27.1-1-70)
Fantastic place, very private, very peaceful! Couldn’t be any happier staying there for a couple of days with my dog.
Family-friendly home rentals with a pool

Casino Wine Down House
Beautiful, relaxing, clean Airbnb. Had an issue with the shower, which can happen anywhere, Mk was super responsive and came over quickly. Loved loved loved our stay here. Didn’t use the swimming pool due to weather but the screened deck with the Fire Pit and the superb game room saved the day. Thank you for hosting us will be back

Private Oasis W/Stunning Vinyard and Pool Views
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!

Escape to a Restored New England Antique Milk Barn
My girlfriend and I had a great stay here. The place was cozy, well-equipped, and perfect for a relaxing getaway. The outdoor area was the true highlight — from the spacious patio to the beautifully maintained landscaping, the property felt peaceful and private. There’s also a pool that looked amazing, even though we couldn’t enjoy it due to the weather. We had some trouble during check-in after a delayed flight and arrived around midnight, but the property owners were just a phone call away and quickly helped us get settled, which we really appreciated. Overall, it was a great experience and we’d absolutely recommend this spot to anyone looking for a quiet, scenic place to unwind.

Spacious Studio Apartment- near SBU
Gabby’s apartment is exactly as described. It is in a great location. Very close to Stoney Brook Village. We enjoyed walking to get our morning coffee. The apartment was very well stocked and spotless. Gabby thought of everything we could have possibly needed. We hope to be back next year!

Modern East Hampton Home w/ Heated Saltwater Pool
Beautiful home, very clean, spacious and comfortable to stay with the family. We used the grill on multiple occasions and it was easy to use. The fire pitt was also enjoyable. The kitchen was well stocked, would bring own source of caffeine if you’re picky with your coffee though. Stephen, the host was very responsive and easy to reach when asked questions. The one thing I would recommend is to check in with the host if the pool is available to use prior to booking. Overall a great experience, would stay with them again.

Garden Level Suite with Beautiful Pool
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

Montauk Oceanview with Fireplace (2)
Loved the stay! Exactly what we thought it was - extremely convenient and cozy. Plenty of beaches to walk to and the food options were plentiful. Would definitely stay again.

Beach House Feel - newly renovated backyard Oasis
Christine's place was nice and clean! We especially loved the fire pit and the pool. Upon arrival of the AirBNB Christine was waiting to meet us and show us around. This was something that was new to me in my AirBNB experience, but it was honestly so nice and so was she! Christine let me know that I could communicate with her for anything that was needed and asked for recommendations to make her place better. This place was so well-equipped, close to everything and it comfortably fit me and my 6 other friends! I would definitely book again with Christine.
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