Family-friendly vacation rentals in Bailey Island

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Bailey Island

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

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Top guest favorite

The exterior of a three-story house is presented, featuring a modern porch with steps leading to a dark front door. Flanked by lush greenery and vibrant orange flowers, the property is highlighted by tall windows that allow natural light indoors.

Apartment in Portland

4.96 out of 5 average rating, 556 reviews

Peaceful Oasis on Munjoy Hill -1st flr/3BR+parking

Spacious, light-filled 3 Bedroom/1 bath 1st-floor apartment with tasteful art, contemporary furnishings, + a well-appointed kitchen. Fantastic location! -A 5-minute walk to the Eastern Promenade with its food trucks, beach & scenic trails -Nearby are bakeries, cafes, world-class restaurants and popular breweries -Relax in the serene garden w/ outdoor seating -A 15-minute walk takes you to the Old Port. Discover the best of Portland, then return to A Peaceful Oasis, a place to truly call home.

Top guest favorite

A well-maintained backyard garden features a stone fire pit surrounded by seating. Flower beds with various plants provide color and texture. A wooden swing set and a shed are visible in the background, with a stone path leading through the grassy area.

Home in South Portland

4.91 out of 5 average rating, 116 reviews

Cottage style home 2 blocks from the beach!

Comfortable Cottage style home with 3 bedrooms, private baths. Many amenities. Two living areas for everyone's comfort, a beautiful kitchen, a large private outdoor patio with multiple seating, a fire pit and a gas grill. Backyard is partially shared. We are close to the Portland nightlife, airport, shopping, restaurants and family-friendly activities. We are in a community that offers biking , running routes, parks and History. Warm, welcoming home. In law attached with private entrance.

Guest favorite

A two-story home is situated on a grassy area adorned with colorful chairs, contrasting with a vibrant patch of blooming flowers. A spacious deck extends from the house, and an American flag gently waves in the breeze. Tall trees provide a natural backdrop.

Home in Buxton

4.88 out of 5 average rating, 126 reviews

Charming 4 bedroom lake front, with private beach

Will not consider less than weekly rentals for July and August and the last week in June.The house sits 80 ft off the lake. It has over 150 ft of lake shore and own private beach. We supply several kayaks paddle boards canoes and tubes . You will be required to sign a waiver to use them and you Must wear lifejackets .The home is located down a private gravel road .We are only 20 miles from the city of Portland, Old Orchard beach, Lake Sebago. Come explore and relax. 2 hours from Boston

Top guest favorite

The exterior of a multi-level beach house is visible, featuring a spacious deck with railings and steps leading to the sandy area by the water. The house is painted white with green accents, and tall windows allow for natural light to enter. A brick chimney is located at one end.

Home in Wells

4.97 out of 5 average rating, 108 reviews

Family Beach House, Wells Beach, Maine

Family Beach House on the Harbor/River of Wells Beach. House Sleeps 8 adults, plus 3 - 4 children. Full kitchen, 4 bedrooms plus Sleeping Loft, 3 baths, Dining Room, large deck, patio, laundry, outdoor shower, fire pit. Private access back beach. Bring your kayaks, paddle boards, surf boards, or boat. Water behind house at High Tide. Approx. 100 yard walk across Atlantic Ave to beach. Parking for 5 cars Max. Optional in-law apartment available, sleeps 5, for $115 per night/$800 per week

Top guest favorite

An airy upstairs room features a large skylight, allowing natural light to fill the space. A yoga mat is positioned on the carpet alongside a soft red bean bag, two green blocks, and a small yellow toy truck. A wooden table sits to the right, complemented by a potted plant.

Apartment in Falmouth

4.9 out of 5 average rating, 194 reviews

Falmouth 3br near Town landing

Enjoy the rocky coast of Maine with lobster rolls on Town Landing pier. Watch the Lobster fishers work and buy fresh lobster right off the boat. With Portland Maine’s iconic Foodie city with artisan brewers and fun dining and night life just down the road. (6.6 miles) Our classic New England Cape home is the perfect place to meet family and cook and eat around the counter in our amateur chef’s kitchen. Crack some fresh Lobster from Shaws on Rt One they are happy to cook them for you.

Guest favorite

An open living area features exposed wooden beams and dark wood flooring. A circular dining table with four purple upholstered chairs is positioned beside a comfortable sectional sofa. Soft lighting illuminates the space, with large windows allowing natural light to fill the room.

Home in Kennebunkport

4.86 out of 5 average rating, 175 reviews

Kennebunkport House - Walk to Dock Square!

Guests are sure to enjoy a memorable vacation in this fully furnished, 5 bedroom/5 bath house, which can comfortably sleep up to 12 people. With two kitchens, an open concept dining room with farm style table, and 600+ square foot deck, this house is perfect for families and large groups. Located near the beach and within walking distance to Dock Square, guests can enjoy an afternoon of fun activities and later watch the sunset from the deck or spend time around the fire pit at night.

Guest favorite

A large two-story white house is depicted, featuring multiple gabled roofs and blue accent doors. Surrounding trees provide shade, and a driveway is visible leading to a side parking area. The property is situated on a quiet road with ample outdoor space.

Townhouse in Kennebunkport

4.94 out of 5 average rating, 167 reviews

Great get away spot,historic home in Kennebunkport

Located 1.8 mi-dock square, 2.6 mi- Colony Beach, .7 mi -Cape Arundel Golf Course. Plenty of onsite parking, beach pass provided for Kbunk Beaches, a large back yard for fun and relaxation. Just on the outside of town in a country setting. Comfortable setting for relaxation. This is a daily reservation from Oct.1st-June. I love to make sure my guests have as much fun as they can while they are visiting and will help out in anyway possible. No dogs of any kind are allowed

Top guest favorite

The exterior view shows a spacious lawn bordered by a wooded backdrop, featuring a mix of rustic wooden and modern structures. A yellow volleyball net is set up on one side, with large rocks and a gravel driveway visible in the scene.

Guest suite in Kennebunkport

4.99 out of 5 average rating, 206 reviews

Get back to nature in this new woodsy retreat.

Perfect for "leaf peeping". Beautiful 2nd floor two bedroom apartment with great light, nestled in the woods. Listen to the owls at night and wake to the birds chirping. Comfortably sleeps 5 in two queen beds and a twin XL bunk. Easy access to Goose Rocks Beach as well as Smith Preserve conservation trails for biking, hiking, trail running, snow shoeing and cross-country skiing. Located 6 miles from the center of Kennebunkport and 3 1/2 miles from Cape Porpoise.

Guest favorite

A modern kitchen features sleek cabinetry and a granite countertop, with appliances and cookware neatly arranged. A color-coordinated backsplash adds depth to the design. In the background, a living area is visible, furnished with comfortable seating and a smart TV on the wall.

Home in Kennebunk

4.95 out of 5 average rating, 151 reviews

Quiet cozy cottage close to restaurants, beach

Winter-wonderland, close to skiing and a walk from great dining. In the summer, enjoy the quiet backyard or walk to the beach! No need to find parking, my place is 3/10 of a mile from downtown Kennebunkport and 7/10 of a mile to Gooch's Beach. You will love my place because of the kitchen, the coziness, and the location. My place is good for couples. It has a tempurpedic king-sized bed and a queen sized pull out bed in the living room.

Superhost

A spacious dining room features a large glass table surrounded by six dark wooden chairs. Natural light floods in through multiple large windows, illuminating the patterned area rug beneath. A side table holds decorative items, and a chalkboard wall adds a unique touch.

Apartment in Portland

4.83 out of 5 average rating, 139 reviews

Fall in LOVE With PORTLAND, MAINE

Portland and its surrounding areas is a FOODIE's paradise. Our comfortable home is perfect for Family or Friends to enjoy Portland's charm. Approx 3 miles from Portland Jetport and 90 miles from Boston Logan airport. Walk to downtown or the Old Port on the waterfront. The surrounding areas offer fine beaches and beautiful scenic towns guaranteed to make you want to come back and visit this best kept secret again!

Guest favorite

The exterior of a cedar home is highlighted, surrounded by lush greenery and trees. The structure features large windows and a spacious deck, showcasing a distinct A-frame design. A stone pathway leads to the entrance, enhancing accessibility to the outdoor space.

Home in Kennebunk

4.91 out of 5 average rating, 111 reviews

A Great Space in a Great Place

This Lindal Cedar Home overlooks the tidal marsh. Walking distance to beach and Kennebunkport. Second story duplex with master bedroom loft. Complete kitchen. Children's play park, pitch and putt golf, kayak and bike rentals, bakery, restaurants, market, antiquing, whale watching, Shipyard brewery and retail shopping; all within walking distance. Owners on site.

Guest favorite

The exterior of the cozy rental home is seen blanketed in snow, showcasing its blue siding and white roof. The large front porch is prominent, while snowflakes gently fall, creating a serene winter landscape with trees in the background.

Home in Bethel

4.96 out of 5 average rating, 116 reviews

Sunday River Bethel Village ! Walk to Restaurants

2 Bdrm, 1 Bth, Cozy Rental located in Bethel Village. 400 yds from The Bethel Inn. Walk to Bethel Village Restaurants & Shops. Home is in residential area with plowed sidewalks and well lit street. Ideal for a mature quiet couple or similar who are into skiing / enjoying the Bethel area and respectful of the property and neighbors. small dog ok, no cats.

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What guests are saying

Old Orchard Beach House

4.94 out of 5 average rating, 88 reviews8 months ago

Perfect location for a family vacation. The extras in the shed such as beach toys, tumbling mats, and wagons to carry beach gear made all the difference. Our group consisted 6 adults and 3 children ages 5 and under. There was plenty of room for everyone and the kids were never bored. The fenced in yard and deck were perfect for relaxing.

Home in Old Orchard Beach

What guests are saying

Waterfront House with Pier

4.89 out of 5 average rating, 18 reviews6 months ago

Awesome place! If you've always wanted to stay in a 5-star AirBnB, this is it. Spotlessly clean, great surroundings, private and very welcoming. Everything was perfect, in great condition and exactly like the listing. We don't give out 5-star ratings very often so you can bet this one is genuine. Very highly recommended.

Home in Kennebunkport

What guests are saying

Quiet Ocean View Cottage

4.85 out of 5 average rating, 59 reviews6 months ago

Very nice rustic cabin, convenient location to Brunswick. Our stay was in mid-October, and we knew there was no heat, only space heaters - unfortunately got into the low 30s at night and we were very cold. Grateful for the many blankets! The two beds are not full twins, more like 24” beds; it was ok for our small teenager. Well water. Nice location and would go back in warmer weather! Very responsive host.

Home in Brunswick

What guests are saying

The "Happy Hen House" cottage in lakes region

4.7 out of 5 average rating, 67 reviews6 months ago

As Mainer living across the country, it is always nice to come. Unfortunately this trip was to attend my Mom's funeral. Pam's home was the right level of closeness to the rest of my family to make visiting easy. The place was the peaceful retreat I needed to visit with myself. Five minutes to most things a person living out of a suitcase could need. Also less then 5 minutes walk puts one at the boat launch for personal watercraft. A great place to sit for a few. The amenities were plentiful at the house and the character was Maine charming. Pam was wonderful and easy to communicate with at all stages. I will be back in the future. Matt

Home in Windham

What guests are saying

Peaceful Lakeside Maine Retreat

4.92 out of 5 average rating, 118 reviews4 months ago

The home was in a beautiful location and it was so peaceful to wake up and look out over the water. The beds were comfortable and there was lots of space for our group to hang out. The host was very accommodating and answered all our questions quickly. Highly recommend!

Cottage in Standish

What guests are saying

15A -5 Min Walk to Beach&Pier. Quaint Cottage

4.92 out of 5 average rating, 59 reviews8 months ago

This was the perfect place for our beach vacation. VERY quick walk to the beach and town and the perfect amount of space for our family. The place was clean and Jeanette always responded quickly if there was an issue. We had a great stay and would definitely stay again in the future!!

Cottage in Old Orchard Beach