Family-friendly holiday rentals in Long Island Sound

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Long Island Sound family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Cottage in Ledyard
4.88 out of 5 average rating, 207 reviews

Waterfront cottage overhanging the water!

JenRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Wading River
4.96 out of 5 average rating, 505 reviews

Your Zen Retreat

ChrisRating, 5 stars1 week ago
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!
Top guest favourite
Flat in New Paltz
4.97 out of 5 average rating, 544 reviews

Relaxing Spa Retreat~Gorgeous View~Walk to Village

LacieRating, 5 stars1 month ago
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!
Guest favourite
Farm stay in Kent
4.87 out of 5 average rating, 319 reviews

(°) The Wandering Peacock (°)

MikaylaRating, 5 stars3 days ago
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.
Guest favourite
Guest house in Beacon
4.94 out of 5 average rating, 400 reviews

Cozy Mountainside Suite - Minutes from Beacon

AnthonyRating, 5 stars1 week ago
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.
Guest favourite
Home in High Falls
4.96 out of 5 average rating, 218 reviews

Clove Schoolhouse on Mohonk Preserve

PaulRating, 5 stars4 days ago
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.
Guest favourite
Home in Westhampton Beach
4.93 out of 5 average rating, 149 reviews

Hampton's Haven

DavidRating, 5 stars2 weeks ago
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.
Guest favourite
Cabin in Wurtsboro
4.93 out of 5 average rating, 101 reviews

Catskills cabin over waterfall w/ views & hot tub

Ana PaulaRating, 5 stars3 weeks ago
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

Guest favourite
Farm stay in High Falls
4.87 out of 5 average rating, 945 reviews

Dave's Milk Barn

ClaraRating, 5 stars3 weeks ago
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!
Top guest favourite
Cabin in Boiceville
4.98 out of 5 average rating, 509 reviews

Winston's Place - Woodland Cozy Catskills Cabin

SherryRating, 5 stars2 weeks ago
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!
Guest favourite
Flat in Sag Harbor
4.94 out of 5 average rating, 155 reviews

Whaling Captain Pierson's Cottage

JennyRating, 5 stars2 days ago
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!
Top guest favourite
Home in New Paltz
4.97 out of 5 average rating, 752 reviews

Victorian Haven

LaurenRating, 5 stars1 week ago
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!
Guest favourite
Cottage in Guilford
4.93 out of 5 average rating, 273 reviews

Charm + location. Walk to beach, town, & harbor.

MaryRating, 5 stars2 weeks ago
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.
Top guest favourite
Cottage in Fairfield
4.98 out of 5 average rating, 120 reviews

Charming Fairfield Beach 3BR Cottage By The Sea

BriannaRating, 5 stars10 months ago
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.
Guest favourite
Cabin in Greenwood Lake
4.96 out of 5 average rating, 428 reviews

"Cabinessence" on Greenwood Lake, 60 mi from NYC

Maire Rating, 5 stars1 month ago
“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.
Top guest favourite
Cabin in Woodstock
4.94 out of 5 average rating, 740 reviews

Byrdcliffe Artist Studio (27.1-1-70)

ThiagoRating, 5 stars1 week ago
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

Guest favourite
Home in Montville
4.92 out of 5 average rating, 273 reviews

Casino Wine Down House

EsperanzaRating, 5 stars1 week ago
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
Top guest favourite
Home in Cutchogue
4.97 out of 5 average rating, 206 reviews

Private Oasis W/Stunning Vinyard and Pool Views

RebeccaRating, 5 stars1 month ago
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!
Top guest favourite
Barn in Bethel
4.98 out of 5 average rating, 237 reviews

Escape to a Restored New England Antique Milk Barn

GavinRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Stony Brook
4.93 out of 5 average rating, 535 reviews

Spacious Studio Apartment- near SBU

ElizabethRating, 5 stars2 weeks ago
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!
Superhost
Home in East Hampton
4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

MariaRating, 5 stars4 weeks ago
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.
Top guest favourite
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars3 months ago
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!
Guest favourite
Bungalow in Montauk
4.91 out of 5 average rating, 619 reviews

Montauk Oceanview with Fireplace (2)

AdrienneRating, 5 stars3 weeks ago
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.
Top guest favourite
Home in Hampton Bays
4.98 out of 5 average rating, 128 reviews

Beach House Feel - newly renovated backyard Oasis

JessRating, 5 stars4 days ago
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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