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
The spacious loft is highlighted by 16-foot ceilings and multiple skylights. A queen bed is positioned near a cozy seating area, complemented by a wooden dining table. Eye-catching artwork adorns the walls, and natural light fills the room through large windows.
Loft in Falmouth
4.95 out of 5 average rating, 662 reviews

Loft Apartment on Tree-Lined Street in Falmouth

Staying in this huge second floor loft (32'x25’), you will find a quiet oasis in the treetops. The 16' ceilings and stylish decor provide sanctuary after a busy day of sight seeing. We offer a queen bed and two twins. You are surprisingly close to Portland's restaurants and shops, well located for day trips up and down the Maine coast. Start the day with a self-brewed local coffee. Relax at the end of the day streaming your favorite entertainment on a 55" 4K-HD TV paired with a Sony sound bar. Soak in the secluded backyard HOT TUB, OPEN YEAR ROUND, with a pool available in the summer. The loft is bright and airy given its 16 foot cathedral ceilings, four sky lights and five large windows. Each window has room darkening blinds and full curtains that can darken the room for an afternoon nap. It is accessed through a private entrance up a wide stairwell in the stand alone garage. An In-Suite thermostat allows you to control a comfortable room temperature. The newly renovated space is equipped with queen bed and a twin trundle bed, which pulls out a second twin bed (sleeps two). The beds are fitted with 100% cotton sheets. The living room lounge area has a 55" 4K Ultra UHD flat screen TV equipped with a Roku streaming device. Spectrum TV streaming app provides the broadcast networks, as well as ESPN, TNT, AMC, Bravo and others. Bring your log-in ID to access your favorites programming, such as NETFLIX, HBO-Go, HULU and SlingTV. A Blu-ray/DVD player is available upon request. (There are 3 redbox locations within 2 miles.) The full bath has a shower stall (no tub). Plush towels and premium soap, shampoo and conditioner are provided. Enjoy use of backyard hot tub year round and in ground pool during summer season. Children are welcome. The loft is stocked with books and board games. There is a baby gate available. We are happy to assist you in making plans to see the area. Please ask us if you need recommendations to things to do during your stay. While you will have your own private space and free standing four walls, we will generally be nearby and available. The setting of this property is a long and winding street with large, open lots and eye-catching homes. Stroll to the mouth of the Presumpscot River, which empties into Casco Bay. Dine and shop in the heart of the Old Port, only 14 minutes away. There are no bus lines close to the house. One could manage navigating the area via Uber if not driving a car. The loft has an efficiency kitchen with toaster oven, mini fridge, coffee maker, electric tea kettle, two burner hot-plate, pans, utensils, plates and silverware. We keep the loft stocked with Wicked Joe Sumatra blend. Wicked Joe is a local family-owned company committed to producing exceptional coffees using sustainable business practices from crop to cup. Additional large beach towels provided for hot tub and pool use. We can connect you with local area shops for surf board, stand-up paddle board and bike rentals. We have plenty of ideas on restaurants, shops and points of interest which we are happy to share. Local area magazines and tourist information available in the loft.

Guest favourite
A cozy sitting area features a blue couch, a comfortable chair, and a footrest, all arranged around a coffee table. A potted plant adds a touch of greenery, while natural light streams through a window. Nearby, a small television is set on a media unit.
Apartment in South Hiram
4.93 out of 5 average rating, 156 reviews

Private, Cozy, Deep Soaking Tub

Escape to this quiet space and deep soak your mind in the meditation room or relax your body with the deep soaking tub and recharge after a long day. The whole 3rd floor is yours. A private sitting room, meditation area and food prep area (there is no kitchen), bedroom and bath with deep soaking tub are ready for your arrival. This is a 3rd story walk up. Parking is right in front of the house and a keypad lock. Easy access in and out. AirBnB insists there is golf at my location. There is not.

Top Guest favourite
A charming yellow cottage is shown from the exterior, featuring a covered porch adorned with wicker seating. Green ferns and lush grass surround the home, which is framed by trees showcasing fall foliage.
Home in Peaks Island
4.87 out of 5 average rating, 181 reviews

Winter Dates: Cozy and Peaceful Island Getaway

*Quiet and Peaceful *Easy Portland Access *Sparkling Bathroom Remote Downeast island experience just two hours from Boston ... Renovated home in the tranquil Tolman Heights section of Peaks (the island’s highest point) offers a modern kitchen and sparkling new bathroom. Sleeps 6-plus comfortably in bedrooms all equipped with ceiling fans. Spacious home is a short stroll to the Back Shore, with its dramatic views of Casco Bay and the open ocean. Great biking, hiking, swimming, and kayaking.

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, 198 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 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, 270 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 living area features a modern couch in navy with light-colored cushions, complemented by a cozy chair. A flat-screen TV is mounted on a light wood cabinet. Natural light enters through a skylight, enhancing the serene ambiance of the space.
Apartment in Oakdale
4.9 out of 5 average rating, 104 reviews

Centrally Located Urban Abode

Centrally located in Portland, just steps away from USM, Back Bay, Bird & Co., Rose Foods, and other Oakdale gems. This apartment features personal touches and is stylishly furnished with attention to detail. Located on a quiet street in the Oakdale neighborhood, it is one of the best locations - as you can walk everywhere. It is a short Lyft or Uber to the famous Old Port. Feel the charm of a quiet neighborhood while also being close to city center. License #: STHR-006692-2025

Guest favourite
A bright living area features a yellow loveseat, a gray circular chair, and a glass coffee table on a woven rug. A vibrant accent wall with colorful patterns adds a lively touch. A potted plant and a lamp complete the cozy ambiance.
Apartment in Knightville
4.94 out of 5 average rating, 134 reviews

Sunny Spot with Private Parking

This cozy, 1 bedroom apartment is located in the peaceful neighborhood of Knightville. The Portland Peninsula, which includes the historic Old Port and the downtown arts district, is less than a 10-minute drive across the bridge. The perfect spot for a couple or a fun friend getaway! Several excellent dining spots, coffee shops, and markets are all within walking distance from the house. Bike rentals are 2 blocks away! The local beach is a 5-minute drive /10-minute bike ride.

Top Guest favourite
A bright hallway leads into the living space, featuring light wood flooring and white walls. A dining area is seen to the left with a small table and chair, while decorative elements, including potted plants and books, add character to the space.
Apartment in Peaks Island
4.99 out of 5 average rating, 202 reviews

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.

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, 102 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
Apartment in Cape Elizabeth
4.98 out of 5 average rating, 124 reviews

Beautiful Kettle Cove Apt Steps to Beaches

Enjoy some of the Portland area’s finest destinations year-round. This sunny, 1 BR ground floor apt in Cape Elizabeth has seasonal water views and is nestled between Kettle Cove, Crescent Beach, and Two Lights State Parks. Fields, forests and ponds are a stroll away while downtown Portland is an easy 15-minute drive. The apartment is a great base to explore Southern Maine from and an equally great location to chill out and soak in coastal Maine’s restorative water and air.

Top Guest favourite
A compact sleeping area features a queen-sized bed with a decorative white throw. Flanking the bed are two bedside tables, each topped with a lamp. Neutral-colored walls and soft lighting create a calm and inviting ambiance.
Apartment in Windham
4.98 out of 5 average rating, 176 reviews

The Roost - lovely one bedroom efficiency unit

Staying at the Roost means you will be 15 minutes to the ocean, the airport and to the Old Port; 10 minutes to nearby lakes and rivers; 5 minutes to everything downtown Westbrook has to offer, including many restaurants, parks, live music venues, shopping and a movie theater: what you are looking for is nearby! Kick back and relax in this calm, stylish space with a queen-sized bed, kitchenette, dining/work area, excellent wifi, a full bathroom and a big yard.

Top Guest favourite
A cozy cabin interior features warm wooden walls and flooring. Twinkling string lights adorn the ceiling, creating a soft glow. A comfortable armchair is positioned beside a small lamp, with a spacious bed visible in the background, framed by large windows allowing natural light.
Cabin in Lovell
4.97 out of 5 average rating, 395 reviews

Secluded, cozy cabin nestled in the Maine woods

Kick back and relax in this calm, stylish space with a semi-remote cabin experience while keeping the gentle daily living comforts. Right at the edge of the White Mountain National Forest in one direction and in the other direction, a short five minute drive to Kezar Lake this secluded cabin has it all for the nature lover in you! Close to local favorite trailheads for hiking and mountain biking as well having nearby ski mountains and snowmobile trails.

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 $154 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,530 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Long Island holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Long Island rentals

  • 4.9 Average rating

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

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