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Family-friendly holiday rentals in Long Island

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Long Island

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.
Cottage in Brunswick
5 out of 5 average rating, 203 reviews

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Top guest favourite
A wooden deck leads to the entrance of the yurt, featuring two green Adirondack chairs flanking the doors. The surroundings are wooded, with a carpet of forest floor visible and trees providing a natural backdrop.
Yurt in Chebeague Island
4.98 out of 5 average rating, 172 reviews

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking: fridge, stovetop, sink, water, firepit & firewood. Outdoor shower. WiFi . Heater for cool spring nights. Ferry options on Casco Bay Lines or CTC Ferry. Host provides transport to/from ferry to the yurt.

Top guest favourite
The exterior of the guest cottage is presented, featuring a white facade with dual garage-style doors. Brightly colored flower boxes adorn the front, adding a vibrant touch. The sunny sky and surrounding greenery contribute to a welcoming atmosphere.
Guest house in Cumberland
4.96 out of 5 average rating, 136 reviews

Cozy & Convenient Cumberland Guest Cottage

Make yourself at home in this quaint, private guest cottage, perfectly nestled halfway between Portland and Freeport. This detached guest cottage makes a perfect overnight spot as you make your way up the coast, or a home base as you explore Portland, Freeport and the whole breathtaking Casco Bay area. With a kitchenette, bedroom and living area, the cottage is ideal for solo travelers, couples, or a pair of friends looking for a comfortable home base while they explore southern Maine.

Top guest favourite
A bright yellow studio space features a comfortable queen bed with light bedding. Two windows allow natural light, adorned with patterned curtains. A small dining table and chairs are positioned near the bed, complemented by a plush green loveseat and decorative wall art.
Guest suite in Back Cove
4.97 out of 5 average rating, 274 reviews

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

Top guest favourite
The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.
Cabin in Freeport
5 out of 5 average rating, 102 reviews

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Top guest favourite
The modern tiny home features a sleek exterior with horizontal siding and a dark roof. Two chairs are positioned on the covered entryway, accompanied by a small table adorned with a pot of flowers. Lush green grass surrounds the home, complemented by a newly paved pathway.
Tiny home in Scarborough
4.98 out of 5 average rating, 109 reviews

Cozy Tiny Home | Fireplace • 9 Miles to Portland

This unique cottage has a style all its own. Discover modern comfort in our brand-new suburban tiny home located in The Downs in Scarborough, ME! This stylish space offers all-new amenities and a cozy atmosphere. Ideal for solo travelers or couples, but can accommodate up to four guests. Enjoy a private escape while being ~9 miles from Portland and ~6 miles from the beach. Experience efficient living without compromising on luxury. Book now for a fresh, contemporary getaway!

Top guest favourite
A spacious bedroom features a large, neatly made bed with a soft blanket, complemented by two bedside lamps. Natural light filters through large windows covered by wooden blinds. A vibrant red area rug adds warmth to the polished flooring. A small plant stands next to the bed.
Flat in Ferry Village
4.96 out of 5 average rating, 380 reviews

Studio Apt w/Parking, 7 Mins to Old Port: Dirigo

A beautiful, private studio with kitchenette and luxury bathroom in the heart of So. Portland. Although not on Portland peninsula, the Old Port is just an 7 min drive away. The apartment is five minutes to Willard Beach and 15 minutes to Scarborough beaches. Also in the building is the Second Rodeo Cafe, which serves coffee, breakfast and lunch. Enjoy our new seasonal back patio. The coffee shop is closed Wed. We are owner-operated. Lic#2764

Top guest favourite
An elevated queen bed is showcased with a white comforter and a decorative pillow. Natural light filters through a large window above, accompanied by small potted plants. A wooden staircase leads to a different area, enhancing the studio's overall spacious feel.
Guest suite in Ferry Village
5 out of 5 average rating, 293 reviews

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer, and cozy couch for lounging.

Guest favourite
A studio apartment is presented with a queen size bed adorned with a muted blanket. A cozy sitting area includes a light grey sofa, while a small dining table with chairs occupies a portion of the space. A bookshelf is visible, enhancing storage and decor.
Flat in Downtown Portland
4.9 out of 5 average rating, 440 reviews

Central-Local Studio in Vibrant Portland, Maine!

Spacious and private studio apartment, with sitting area, queen size bed, table and chairs for dinning, kitchen and full bathroom. Newly updated appliances in a well maintained building. Wood floors lend charm, while modern decor makes for a contemporary feel. This comfortable space is perfect to come back to after exploring the surrounding neighborhood. The Studio is steps away from Portland's best restaurants, shops, nightlife and more!

Top guest favourite
A welcoming living area features a light gray sectional sofa adorned with various textured pillows. A wooden coffee table sits on a neutral rug, accompanied by a dark, upholstered chair. Natural light filters through the two windows, complementing the space's relaxed ambiance.
Flat in West End
4.98 out of 5 average rating, 201 reviews

Downtown Historical Victorian 2 BR APT

The West End is one of Portland's most historical districts. The house is within walking distance of Long Fellow Square, and the Western Promenade. It is a great home base while exploring. From its rich history rooted in the Victorian era, to its parks and restaurants, Portland's West End is consistently ranked as a favorite local hotspot. New reno located on a popular street in a neighborhood filled with historic homes.

Guest favourite
A bright living room features neutral-colored walls and hardwood flooring. Comfortable seating options include a dark gray couch and armchair, complemented by a patterned area rug. A flat-screen TV is mounted on the wall, and large windows allow natural light to fill the space.
Flat in East End
4.86 out of 5 average rating, 231 reviews

Oceanside Modern Victorian 2BR- East End/ Downtown

Classic New England style home, recently renovated and updated with modern amenities. A stone's throw from Portland's best public park, The Eastern Promenade. The Promenade boasts beautiful ocean views, a public beach, basketball & tennis courts & large playground. The neighborhood offers great restaurants and coffee shops. The Old Port and the rest of Downtown Portland is a 10 minute walk or 4 minute Uber ride away.

Top guest favourite
A cozy living room features a leather couch adorned with vibrant red pillows and a soft blue throw. A wooden coffee table sits in front, accompanied by a designer easy chair. Natural light filters through large windows, illuminating the space.
Guest suite in South Portland
4.92 out of 5 average rating, 290 reviews

Top of the Hill So Po In Law

Lovely In law apartment in desirable Meeting House Hill area of South Portland .We were recently the hottest real estate market in the country .Conveniently located , 10 minutes to Portland , and on the doorstep of local beaches, State parks , restaurants ,unique boutique shops ,amazing bakeries and coffee , lunch and antiquing .All you need for a home away from home . Your going to love this neighborhood !

Popular amenities for Long Island family-friendly rentals

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

  • Total holiday rentals

    Explore 50 holiday rentals in Long Island

  • Nightly prices starting at

    Long Island holiday rentals start at £111 per night before taxes and fees

  • Verified guest reviews

    Over 1,500 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 of Long Island holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Long Island rentals

  • 4.9 Average rating

    Long Island stays are highly rated by guests – averaging 4.9 out of 5!