Family-friendly vacation rentals in Wiscasset

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Wiscasset

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 East End

4.96 out of 5 average rating, 557 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.

Superhost

Apartment in Damariscotta

4.85 out of 5 average rating, 102 reviews

Cottrill House on Damariscotta River #2

A convenient and newly renovated apartment. Enjoy the mid-coast in down town Damariscotta Maine. Private entrance, two bedrooms, private bathroom, living room, kitchen. NO CLEANING FEE! Private back yard with views over the Damariscotta River. Walk to unique restaurants and shops. Rent a kayak or a paddle board across the street and enjoy the beautiful views of the Damariscotta River. Only, 25 minutes away from Pemaquid Point and Beach. 32 miles to Popham Beach and Reid State Park. No smoking!

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.

Superhost

A playground structure is situated on sandy terrain, featuring a slide, climbing structures, and various play areas. The background reveals a view of the beach and water, complemented by distant greenery and a calm sky.

Apartment in South Portland

4.79 out of 5 average rating, 192 reviews

Bay Windows at Willard Beach, 3 BR, 1 BA

Perfect home base for your visit. One block from Willard Beach and next to Scratch Bakery. Beautiful, sunny, 3 BR, sleeps five. Comfortable Tempur-Pedic beds (queen, full, twin), AC, fully stocked kitchen, 42" flat screen TV with Netflix, Wi-Fi. Off-street parking for 2 vehicles and complimentary laundry in the basement. Perfect Willard Beach plug & play vacation only 10-minute drive to Portland, 5 to Fort Williams, and restaurants within walking distance. Family friendly neighborhood.

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.

Superhost

The kitchen features modern cabinetry and stainless-steel appliances, with an open layout leading to a dining area. A wooden table with four chairs is positioned near a window, allowing natural light to fill the space. Slate tile flooring provides a stylish element.

Home in Portland

4.89 out of 5 average rating, 151 reviews

Great Modern Space and House

Beautiful house, updated and renovated by the owners. Very nice, quiet and friendly neighborhood on a dead end street. Clean, simple and modern home. Natural light in every space. Nice Bathrooms and updated Ikea kitchen. Open space in living room, very nice fence yard to watch from the living room and for kids to play. Wood and tile floors on the first floor. Carpet only on the bedrooms in the second floor. A lot of Storage and closets to make your stay very comfortable.

Guest favorite

The bathroom features a well-lit space with a modern sink and a shower area. A turquoise shower curtain contrasts with the beige tiles, while a toilet is conveniently positioned nearby. Fresh towels and toiletries are neatly arranged for guest use.

Cottage in Standish

4.92 out of 5 average rating, 118 reviews

Peaceful Lakeside Maine Retreat

Beautiful and peaceful lakeside retreat in Maine. With plenty of space for you and your family or friends to spread out and relax, this fully updated home has all of the features you'll need to enjoy your vacation on the water. Or get away from it all while working remotely using our reliable WiFi. Only half an hour from Portland's lighthouses and exceptional seafood and craft beer. Just two hours from Boston, come and experience Maine - "the way life should be!"

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 East End

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!

Top guest favorite

An open kitchen and dining area features a rustic wooden table surrounded by metal chairs. The modern kitchen is equipped with new appliances and dark blue cabinetry. Natural light fills the space, highlighting the wood-look tile flooring and charming wall accents.

Apartment in Waterville

5 out of 5 average rating, 113 reviews

Sweet Retreat: 3 BDR Stylish Home Mins To Colby

This spacious home of approximately 1,200 square feet is just 1.1 miles from I-95 and located on the ground floor of a charming, two family home completely renovated and tastefully furnished in 2020. Here the “modern design” and “charming rustic feel” mix perfectly. BONUS: Guests have access to the backyard! The private yard boasts a patio set, fire pit, garden, fence and trees along the property line.

Superhost

A single-story mobile home is set among trees, featuring a light yellow exterior with maroon shutters. A small porch is positioned at the front, while flower beds with blooming plants and a stone border enhance the well-maintained yard.

Home in Paris

4.92 out of 5 average rating, 146 reviews

Just a get away!!

My place is close to great views - for fall time - half hour to ski area's -oxford casino 7 miles away - hour drive to Mt Washington or Portland - Plenty of hiking area's- Oxford plains speed way 3 miles - , restaurants and dining . Read all { House Rules } it's under things to know, on the bottom left, before making reservation - Thank You

Guest favorite

Home in Phippsburg

4.93 out of 5 average rating, 262 reviews

Classic Maine, Modern Comfort

NOTE: Summer Bookings are 7 Days from Saturday-Saturday and tend to fill up by February/March or sooner. All the comforts of home while you're away from home. Come enjoy a newly built beach house (2008) just short walk from beautiful Popham Beach - one of Maine's most beautiful and expansive beaches, one hour north of Portland, Maine.

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Cottage in Old Orchard Beach

4.94 out of 5 average rating, 109 reviews

Newly renovated beach cottage in Old OrchardBeach

My place is close to The Pier , great views, restaurants and dining, the beach, family-friendly activities, nightlife. You’ll love my place because of the kitchen, the coziness, the high ceilings, and the location. My place is good for couples, solo adventurers, business travelers, and families (with kids).

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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

Rustic, cozy cabin on Sebago Lake. A hidden gem.

4.93 out of 5 average rating, 154 reviews6 months ago

Came for the Fall colors; left in love with the place! Small but delightful. Cluttered in the most fantastical way. Nestled in paradise. Bonnie is so nice and friendly! Pay attention to the fact that the toilet is not attached to house. Short walk to privet and very clean!

Cabin in Raymond

What guests are saying

Charming, Family-Friendly Historical In Town Home

4.98 out of 5 average rating, 108 reviews4 months ago

This was the perfect rental for our family of 4 for the thanksgiving holiday. The home had everything we needed and wanted, great location within walking distance of so many great places in Rockland, and was clean and comfortable. Alicia went out of her way to provide recommendations for our stay! This is probably the best Airbnb we’ve stayed at and the most helpful host we’ve encountered. Highly recommend and thank you to Alicia and family for making our week so enjoyable while spending time with our kids on their college break.

Home in Rockland

What guests are saying

Classic Maine Cottage - dock, sauna & kayaks

4.89 out of 5 average rating, 153 reviews5 months ago

The property is as advertised. It’s perched on a rocky shoreline with a nice wraparound deck that enables you to enjoy the water views and stars at night. The dock was removed due to end of season so actual water access was not feasible given the tidal schedule. This property does not disappoint. It’s location is ideal for exploring (driving) the region or not going anywhere. I would not hesitate to book this cottage again.

Cottage in Harpswell

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