Family-friendly holiday rentals in Long Island

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Long Island family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favourite
Home in Woolwich
5 out of 5 average rating, 43 reviews

Amazing view, eagles, hot tub, 1 mi walk from Bath

GregoryRating, 5 stars3 weeks ago
Sometimes photos just don't do the real thing justice, and this is the case with this property. The property and the views are truly spectacular! The home is huge and has everything you could ever need to live for a week or more. The porch, especially the screened in portion are magnificent and the hot tub was a perfect way to finish up a great day. We had so many plans to adventure out, but found ourselves wanting to stay and enjoy the pristine yard or just sit on the porch and enjoy each others company, we didn't want or need to leave. Having coffee and watching eagles fly by over the river was truly spectacular. Judy is one of the nicest, easiest hosts we have had the pleasure to work with and truly appreciates your patronage. And Hugh's journal on all things Graywood is a lifesaver. Not only would we return again, but we look forward to it.
Top guest favourite
Home in Portland
4.97 out of 5 average rating, 224 reviews

Stunning & Spacious 6BR Waterfront House + Hot Tub

PeterRating, 5 stars2 weeks ago
The house was perfect for our group of 12. It was spacious and well-cared for. While not located in downtown Portland, it was just minutes away by car. There was ample parking in the driveway and on the street. Meghan was a very responsive and flexible host. We had a great time.
Top guest favourite
Flat in Falmouth
4.91 out of 5 average rating, 200 reviews

Falmouth 3br near Town landing

EllenRating, 5 stars2 weeks ago
David and Valle’s house is welcoming, and it was just right for our family get-together. The kitchen is very well set up for cooking, and the counter is both beautiful and a great place for gathering and conversation. There are many lovely touches in the house. We appreciated the yard and gardens, and our dog loved the walking trail. The location is peaceful but just a few minutes from Portland. David communicated well and offered helpful ideas for our visit.
Guest favourite
Treehouse in Georgetown
4.97 out of 5 average rating, 341 reviews

Tree Dwelling with Water Views & Cedar Hot Tub (2)

JustinRating, 5 stars3 weeks ago
Beautiful spot to stay at, we didn’t get so lucky with how weather panned out but it didn’t take away from the experience we had. Would recommend to anyone!
Superhost
Home in Conway
4.84 out of 5 average rating, 241 reviews

Best backyard in N Conway w/ hot tub, game room...

KatherineRating, 5 stars4 months ago
We spent a lovely few days at this property enjoying the winter weather at its finest. The house is close to everything but still felt private and cozy. A great choice for families!
Guest favourite
Flat in Topsham
4.87 out of 5 average rating, 552 reviews

Cozy hot tub haven

ColeRating, 5 stars1 week ago
Nice stay, nice host, lots of recommendations in binder for things to do. Nice hot tub. Cozy place and location. DQ right across the street.
Guest favourite
Home in Conway
4.87 out of 5 average rating, 130 reviews

Hot tub with country setting, close to village.

HarrisonRating, 5 stars3 months ago
House was as listed, great location in a beautiful area. Plenty of amenities and host was helpful and responsive leading up to and during my stay.
Superhost
Home in Harrison
4.9 out of 5 average rating, 308 reviews

Riverfront Luxury in the woods, Million $ Views.

KristieRating, 5 stars2 weeks ago
Jon’s cabin is a beautiful place to get away from it all. Very comfortable and well designed. We had everything we needed to cook and hole up for a few days. If you decide to drive to the lake, I would recommend 4WD. We had a truck but were not aware of how soft the ground was and ended up needing to be towed out. Still highly recommend! Enjoy your stay!

Family- and pet-friendly home rentals

Guest favourite
Flat in East End
4.87 out of 5 average rating, 1,036 reviews

Private Hill Top Apartment/w One Car Driveway

AmyRating, 5 stars1 week ago
This was a perfect stay for our 2 days in Portland. We could walk everywhere from the apartment. There were plenty of options for restaurants nearby.
Guest favourite
Cabin in Dresden
4.95 out of 5 average rating, 186 reviews

McKeen's Riverside Retreat

KathleenRating, 5 stars1 month ago
We have stayed at Jackies place twice now and enjoyed it just as much this time as the last. Even though it rained for two days the house is plenty big enough to spread out. We had to change our reservation days twice because of circumstances and Jackie was very accomidating..
Guest favourite
Flat in Lisbon falls
4.94 out of 5 average rating, 468 reviews

Charming Victorian farmhouse 1880's bedrooms-2

MollyRating, 5 stars4 days ago
Marcia’s place was exactly what we needed for the week. Convenient location in town with several walkable dining options. So happy we chose Marcia’s place for our vacation.
Superhost
Townhouse in West End
4.81 out of 5 average rating, 622 reviews

1200 sq ft | West End Gem | Steps from Old Port

AshleyRating, 5 stars1 week ago
We enjoyed our stay at Jason’s place. It is a quiet neighborhood and a comfortable place to rest your head after exploring the city.
Guest favourite
Home in Bath
4.91 out of 5 average rating, 345 reviews

Gorgeous Studio on the Kennebec

AlexandraRating, 5 stars1 week ago
Easy 5 stars! Phillip was kind, proactive and responsive. The space, while quaint and simple, was clean, had all the essentials and, it was perfect for a week visiting my grandparents/ working remote! Not to mention my dogs loved being a half mile from the Bath dog park. Highly recommend if you’re looking for a Maine mid-coast getaway!
Guest favourite
Cabin in Boothbay
4.95 out of 5 average rating, 446 reviews

Simple Boothbay Log Cabin on Water

TorreyRating, 5 stars6 days ago
Elia's cabin is magical. What a beautiful and peaceful place. We had everything we needed, but be sure to bring bug spray.
Superhost
Flat in Brunswick
4.75 out of 5 average rating, 256 reviews

King Size Bed - Little House On Lincoln Street

BobbieRating, 5 stars2 weeks ago
Had a relaxing stay this past weekend. The apartment had all that I needed and was close to great restaurants. As always, Spencer was a fantastic host. I would stay here again.
Guest favourite
Home in Phippsburg
4.93 out of 5 average rating, 269 reviews

Classic Maine, Modern Comfort

AnnRating, 5 stars4 days ago
We did not want to leave this home! It was stunning and had everything we could possibly need. Close to the beach. Spinney’s restaurant was right up the road. It was quiet and peaceful. It was good for the soul. We will definitely be back!

Family-friendly home rentals with a pool

Superhost
Cottage in Poland
4.61 out of 5 average rating, 18 reviews

Lake Beach House at Poland Spring Resort

Erin Rating, 5 stars10 months ago
Our stay at the beach house was great! You couldn't be closer to the water! So much fun kayaking, floating and swimming in the lake! House is much better than the pictures do it justice. For a 2 bedroom house its very big and spacious, beds were extremely comfortable. The no wifi was a little bit of a downer but there were plenty of board games to play. There is some street noise but not bad at all. Would most definitely recommend if you are looking for waterfront property. The access to the resort pool was a plus too for the kiddos!
Top guest favourite
Apartment in Old Orchard Beach
5 out of 5 average rating, 15 reviews

LUXURY OCEANFRONT CONDO Best Location on the beach

JennyRating, 5 stars11 months ago
This place had everything we needed. The view was spectacular! We really enjoyed seeing fireworks from the deck. The home was very clean, kitchen fully stocked. We loved hearing live music each day and night. So much walkable fun for the kids. We had a wonderful stay!
Guest favourite
Apartment in Wells
4.85 out of 5 average rating, 188 reviews

Two-Bedroom Condo on the Wells/Ogunquit town-line

SusanRating, 5 stars2 weeks ago
Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones
Superhost
Cottage in Wells
4.88 out of 5 average rating, 42 reviews

Beach Dreaming

ArtemRating, 5 stars8 months ago
A nice private cottage in a quiet community that was super handy for us to stay until we secured our house in New England. Everything is in place for comfortable living. We lived there for a month long and the hosts were always responsible.
Guest favourite
Flat in Falmouth
4.97 out of 5 average rating, 95 reviews

Poolside Suite-Gateway to Portland

DavidRating, 5 stars4 days ago
Maryann was a wonderful host and Maine is a wonderful state to visit. We couldn't have been happier with the place!
Apartment in Wells
4.95 out of 5 average rating, 41 reviews

Chic 1 bedroom condo only 1 Mile from Wells Beach!

MaxineRating, 5 stars9 months ago
We had an excellent weekend at Christopher’s condo in Wells! The place was exactly as described and Christopher was incredibly responsive and accommodating! The pool and the hotub were also great!
Guest favourite
Home in Portland
5 out of 5 average rating, 11 reviews

The Hill's on Buttonwood

DanielRating, 5 stars7 months ago
Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown
Chalet in Frye Island
4.76 out of 5 average rating, 87 reviews

Cabin in Paradise

ChiaraRating, 5 stars9 months ago
My family and I had a awesome time enjoyed the quiet and relaxing days. Michael was very helpful and very quick responses to any questions we had.The cabin was very nice it felt like home was very comfortable slept very well. Everything about the cabin and the island was well worth going looking forward to going again in the future.

Quick stats about holiday rentals that are family-friendly in Long Island

  • Total rentals

    50 properties

  • Nightly prices starting at

    $102 SGD before taxes and fees

  • Total number of reviews

    1.6K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 properties include access to wifi

Destinations to explore