
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.

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.

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.

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.

Sopo Abode
Welcome to your garden oasis. Your home away from home. This elegantly styled garden level apartment in South Portland's crown jewel neighborhood, Sylvan Sites, is spacious, calm, and inviting. Have a sit in your private sauna, and take in the abundant birdsong of the neighborhood from your private back patio while you sip your morning coffee. Just down the road (5 minutes) to downtown Portland, Willard Beach, or Knightville, and 10-15 minutes to Scarborough and Cape Elizabeth beaches.

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!

Peaks Island Master Bedroom Suite
Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

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!

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

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!

Gorgeous Studio 2 Blocks from Eastern Prom!
Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

Oceanside Open Concept 2BR- East End/ Downtown
Classic New England style home, recently renovated and updated with modern amenities. A stone's throw from the best public space in all of Portland, the Eastern Promenade. The Promenade boasts beautiful ocean views, food trucks, a public beach, basketball & tennis courts & large playground. The neighborhood offers great restaurants and coffee shops. The Old Port and rest of downtown is a 10 minute walk or 4 minute Uber ride away.

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
Family-friendly home rentals with a hot tub

Luxury Home w/HOT TUB & Fire Pit

Modern Treehouse w/Water Views+Cedar Hot Tub

Welcome to our BoHo Treehouse!

Beautiful West End studio, hot tub, free parking

Historic Schoolhouse c1866 / Sauna + Hot Tub + Gym

HotTub+Firepit/5 min to DockSquare, Dining, Beach

Loft Apartment on Tree-Lined Street in Falmouth

Tiny house near the beach!
Family- and pet-friendly home rentals

Bright, clean, private cottage near Higgins Beach!

Winter Dates: Cozy and Peaceful Island Getaway

Beautiful Kettle Cove Apt Steps to Beaches

Cozy 2 Bedroom Apartment Close to Portland

Waterfront Private Apartment only 5 min to LLBean!

Private Guesthouse in the Woods

Apartment Walking Distance to Willard Beach

Bright and cozy Munjoy Hill neighborhood apartment
Family-friendly home rentals with a pool

Resort-like 2 bed/1 bath - seasonal pool/hot tub

Attitash Retreat

AttitashResort! 1-flr, studio, secure check-in

Family friendly + Mountain Views @amountainplace

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Poolside Suite-Gateway to Portland

An Amazing Mountain Getaway!

Steep Falls Escape, river & falls just steps away
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!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Island of Montreal Holiday rentals
- Jersey City Holiday rentals
- Rentals with a fireplace Long Island
- House rentals Long Island
- Rentals with outdoor seating Long Island
- Rentals with beach access Long Island
- Rentals with a washing machine and dryer Long Island
- Pet-friendly rentals Long Island
- Waterfront rentals Long Island
- Cottage rentals Long Island
- Rentals with a patio Long Island
- Family-friendly rentals Cumberland County
- Family-friendly rentals Maine
- Family-friendly rentals United States
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Scarborough Beach
- Long Sands Beach
- York Harbor Beach
- Popham Beach, Phippsburg
- Popham Beach State Park
- Pemaquid Beach
- King Pine Ski Area
- Short Sands Beach
- Willard Beach
- East End Beach
- Gooch's Beach
- Pemaquid Point Lighthouse
- Cape Neddick Beach
- Funtown Splashtown USA
- Coastal Maine Botanical Gardens
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Palace Playland
- Footbridge Beach
- Pleasant Mountain Ski Area
- Maine Maritime Museum




