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Family-friendly vacation rentals in Waterboro

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Waterboro

  • Total vacation rentals

    Explore 30 vacation rentals in Waterboro

  • Nightly prices starting at

    Waterboro vacation rentals start at G$27,193 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,080 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Waterboro vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Waterboro rentals

  • 4.9 Average rating

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

Top-rated family-friendly rentals in Waterboro

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

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Top guest favorite
A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.
Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

4.91 out of 5 average rating, 604 reviews
Top guest favorite
A modern two-story home is set amidst a wooded area, featuring a spacious outdoor seating arrangement with a picnic table and various chairs. A fire pit and grill are present, with the soft glow of twilight highlighting the inviting exterior.
Cottage in Acton

Eclectic Lakefront Cottage on Great East Lake

Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!

4.99 out of 5 average rating, 187 reviews
Top guest favorite
Place to stay in Shapleigh

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

Stay at our one-room Schoolhouse c1866. Winner of Maine Homes Small Space Design Award 2023 and consistently top 1-5% of Airbnb homes for exceptional hospitality, comfort, cleanliness & quintessential romantic New England vibes. The Schoolhouse is 1 of 3 homes on our family's resort-like retreat, Camp Tall Pines: Featuring tennis/pool/gym/sauna, 1000-feet of frontage along the private 80-acre Shapleigh pond (boat/swim/fish), and nestled amongst a majestic 50-acre forest of tall pine trees.

5.0 out of 5 average rating, 145 reviews
Top guest favorite
The studio apartment features a queen size bed with a striped duvet and two large leather chairs. A wooden desk is positioned near a window, while the warm wooden floor adds to the inviting feel of the space.
Apartment in Wakefield

Clean, quaint studio apartment on small farm

Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

4.98 out of 5 average rating, 128 reviews
Top guest favorite
Home in Limerick

Lakefront Getaway

Looking for a quiet peaceful getaway? Our Maine post and beam home is set on 7 acres of lake front. Great getaway to enjoy marshmallows and a roaring fire, kayaking, canoeing, swimming, boating or enjoy a great movie. For downhill skiers proximity to King Pine, Sunday River, Shawnee Peak and Black Mountain. Cross country and snow shoeing on property and on the lake. If you have a snow mobile- great trails available. Finally, great shopping in nearby North Conway at the outlets.

4.93 out of 5 average rating, 150 reviews
Top guest favorite
Treehouse in Pownal

The Copper Fox Treehouse

Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse

4.99 out of 5 average rating, 199 reviews
Guest favorite
A wooden dock extends into a calm lake, reflecting the clear blue sky. Lush greenery lines the shore, complementing the serene water's surface. Fluffy white clouds drift overhead, creating a peaceful outdoor setting.
Home in Limerick

Sokokis Lake House

The perfect place for friends & family getaways. The boat dock & fire pit are perfect for relaxing. It has everything you want: fully stocked kitchen, linens, towels, grill, dock, stand up paddle board, kayaks, life jackets, games, books wifi, cable, smart tvs, free parking & many more amenities. 2 hours from Boston 45 min to Portland, Lake Winnipesaukee, Old Orchard Beach, Sebago. Snowmobiling & lake in the back yard! Groceries, restaurants, & general store all within 1/2 mile.

4.89 out of 5 average rating, 133 reviews
Top guest favorite
The Birch Ledge Guest House is a two-story structure nestled among trees, featuring a rustic exterior with a metal roof. A small patio with two chairs is positioned at the entrance, and a staircase leads to the loft area. Lush greenery surrounds the home.
Home in Hollis

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

4.99 out of 5 average rating, 510 reviews
Top guest favorite
Home in Wakefield

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!

Experience ultimate relaxation with over 100 feet of sandy lakeside beach frontage, nestled among serene pine trees. This spacious lake house features: Open concept main floor 3 levels (3100 sq ft) for privacy Family & dog friendly Hot tub, kayaks, beach, game room, firepit & more! Ideal for large families wanting to share a vacation without compromising on privacy. Enjoy year-round activities and create lasting memories. Get 10% OFF for weekly or longer stays!

4.98 out of 5 average rating, 210 reviews
Top guest favorite
The lakefront property is nestled among trees, showcasing a charming house with large windows and a deck. A private dock extends into the calm water, providing space for seating. A sandy beach area leads to the water's edge, creating a serene natural setting.
Home in Limerick

Waterfront, Wood stove & Private beach, Solo Stove

Welcome to the Luna Lake House, your very own lakefront retreat! Just 2 hrs from Boston and 1 hour from Portland, this is the perfect getaway. You get the entire house to yourself! This 1,810 sq ft house has 100 ft of private waterfront, a wood burning stove, private dock (June-October) and outdoor bonfire pit for your enjoyment. With incredible sunset views and it’s amazing location, you will make lasting memories in this one of a kind experience.

5.0 out of 5 average rating, 142 reviews
Top guest favorite
A relaxing outdoor area is shown, featuring several seating options around a fire pit. Two cabins can be seen, with one situated on a hill and the other by the water. A sun umbrella provides shade, surrounded by trees and nature.
Chalet in Standish

Blueberry Hill

Beautiful property located on Watchic Lake in Standish Maine. Clear clean spring fed lake. 25 minutes to Portland with access to shopping, restaurants and entertainment. 45 minutes to North Conway New Hampshire. Where you wil find plenty of shopping, restaurants and winter skiing. Property includes use of Main Chalet home year round and two additional cabins each sleeping 4 are available from May-Oct. Great for extended families and friends.

4.96 out of 5 average rating, 263 reviews
Top guest favorite
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

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for couples, small families, or a getaway with friends, our signature A-frame features soaring ceilings, oversized windows, a cozy gas fireplace, and thoughtfully designed interiors. • This cozy 1,100-square-foot space sleeps four in two bedrooms—one King and one Queen—with a shared bathroom. • 7 minutes to downtown Freeport. • Proud to be ranked in the top 1% of eligible homes and recognized as a Guest Favorite on Airbnb.

5.0 out of 5 average rating, 155 reviews

Popular amenities for Waterboro family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
Home in Shapleigh

Lakehouse/HottubFirePit/2pvtdocks/SUPs/YAKs/LgYard

4.96 out of 5 average rating, 191 reviews
Top guest favorite
An aerial view captures the modern cabin surrounded by lush greenery, featuring warm string lights illuminating the outdoor area. A hot tub is positioned near a cozy seating arrangement, with a gravel path visible leading away from the cabin.
Cabin in Kennebunk

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

4.96 out of 5 average rating, 229 reviews
Top guest favorite
Cabin in Norway

Secluded Cabin: Mountain View, Hot Tub + Fireplace

5.0 out of 5 average rating, 106 reviews
Guest favorite
Cabin in Sanford

Log Home on 8 Acres. Campfire and Jacuzzi. PETS

4.9 out of 5 average rating, 122 reviews
Top guest favorite
Home in Saco

Oceanfront Escape • Walk to Beach • Sleeps 14

4.98 out of 5 average rating, 175 reviews
Guest favorite
Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

4.98 out of 5 average rating, 200 reviews
Top guest favorite
A spacious living area features a large sectional sofa adorned with patterned throw pillows. A wooden coffee table sits nearby, complementing the light wood flooring. Natural light fills the room through large windows, with a mounted television and decorative wall art enhancing the modern aesthetic.
Home in Old Orchard Beach

Luxury Home w/HOT TUB & Fire Pit

4.96 out of 5 average rating, 237 reviews
Guest favorite
A hot tub sits on a wooden deck, overlooking a serene lakeside view. Lush greenery surrounds the area, with clear blue skies overhead and a sandy beach visible in the background. The relaxing setting invites peaceful outdoor enjoyment.
Home in Wakefield

Lake Front Log Cabin · Hot Tub · Arcade · Fire Pit

4.82 out of 5 average rating, 119 reviews

Family- and pet-friendly home rentals

Top guest favorite
A spacious living area features a large sectional sofa adorned with decorative pillows. A mural of mountains and a lake provides a scenic backdrop. Natural light fills the room through a large window with sheer curtains, complemented by light wooden flooring and a textured area rug.
Cottage in Wakefield

Lake View Cottage / Fenced in Yard / Pet Friendly

4.93 out of 5 average rating, 229 reviews
Top guest favorite
An aerial view displays a colonial home surrounded by vibrant autumn foliage, set on an expansive lawn. The nearby Kennebunk River curves through the landscape, bordered by trees. The property includes a serene setting with open spaces and distant houses visible among the greenery.
Home in Arundel

Classic, calm river view & centrally located home

4.96 out of 5 average rating, 112 reviews
Top guest favorite
A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.
Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

4.96 out of 5 average rating, 179 reviews
Top guest favorite
A rustic white barn with a grey roof is nestled within a field of tall grasses and wildflowers. Autumn foliage in shades of red and gold decorates the surrounding trees, offering a tranquil rural landscape. A separate red cottage is visible in close proximity.
Guesthouse in Denmark

Red Shed Cottage at Pickett Hill Farm

4.96 out of 5 average rating, 105 reviews
Top guest favorite
A warm and inviting living area showcases a stone fireplace framed by soft lighting. Two plush armchairs are positioned near a wooden coffee table. A cozy sofa adorned with a colorful blanket complements the wooden beams and walls, creating a tranquil atmosphere.
Cabin in Conway

The Conscious Cabin | Getaways + Retreats

4.96 out of 5 average rating, 201 reviews
Top guest favorite
A multi-level cabin constructed from wood blends seamlessly into the surrounding greenery. A spacious deck extends from the second floor, offering shaded seating under an umbrella. Stairs lead down to the ground level, where a welcoming entrance is accessible amidst the natural landscape.
Cabin in Kennebunk

CHowder Cabin Dog Oasis Fenced Yard

4.95 out of 5 average rating, 221 reviews
Top guest favorite
The exterior of Valley View Farm is presented, featuring a charming white house with a sloped roof. A welcoming sign stands at the entrance, surrounded by colorful blooming flowers and greenery, with a gravel path leading up to the home under a bright blue sky.
Home in Freedom

Farmhouse Retreat, Dog Friendly w/ view & deck

4.96 out of 5 average rating, 101 reviews
Superhost
A view from water level shows a bright blue kayak in the foreground, with a forest of tall green trees surrounding a cabin in the background. The cabin features multiple windows that reflect the natural light and scenery.
Cottage in Parsonsfield

RiverPine Retreat - Clean & Bright Waterfront Home

4.84 out of 5 average rating, 196 reviews

Family-friendly home rentals with a pool

Guest favorite
The modern cabin features a sleek design surrounded by lush greenery. Soft bistro lights create a warm glow, illuminating the outdoor seating area with two Adirondack chairs. The deck can be seen in the background, enhancing the inviting atmosphere of the natural setting.
Cabin in Freeport

Romantic hideaway cabin w/ access to spa - 26

4.96 out of 5 average rating, 125 reviews
Guest favorite
The large, historical home features a spacious outdoor deck adorned with string lights, creating a soft glow during twilight. The manicured lawn is visible in the foreground, while the house showcases a combination of large windows, highlighting the inviting interior ambiance.
Home in Falmouth

Large Historic 7 Bedroom home with Pool & Hot Tub

4.88 out of 5 average rating, 119 reviews
Top guest favorite
An aerial view of the property displays a spacious yard with a well-maintained in-ground saltwater pool surrounded by wooden decking. A barrel sauna and fire pit are positioned nearby, complemented by manicured greenery and tall coniferous trees in the background.
Home in Meredith

1840 Meredith Farmhouse w/ outdoor Sauna & Pool

5.0 out of 5 average rating, 102 reviews
Top guest favorite
A bright kitchen area features modern white cabinetry and a spacious countertop. Barstools with woven seats are positioned at the counter. Natural light floods in through a nearby door, illuminating the polished wooden floor and light blue walls.
Cottage in Wells

Cozy Cottage with Ocean Views, Wells Maine

4.95 out of 5 average rating, 180 reviews
Guest favorite
A welcoming living area features warm wood flooring and natural light from multiple windows. Comfortable seating includes a sofa and chairs arranged around a central table. A ceiling fan provides gentle airflow, while double French doors lead to an outdoor space.
Guest suite in Standish

Steep Falls Escape, river & falls just steps away

4.92 out of 5 average rating, 125 reviews
Top guest favorite
A spacious living area features a large sectional sofa with cozy cushions, complemented by a wooden coffee table. A spiral staircase ascends to the upper level. Light flows through windows, illuminating the warm tones of the carpet and walls. A stone fireplace adds a focal point.
Apartment in Bartlett

Stunning 2BR with Mountain Views | Nordic Village

4.99 out of 5 average rating, 168 reviews
Top guest favorite
A spacious suite is showcased with large windows allowing natural light. A comfortable couch faces a marble-topped coffee table, and a custom-built king bed is nestled against a natural pine headboard. The decor reflects minimalism, offering a peaceful setting for relaxation.
Apartment in Portland

Luxury Retreat In Back Cove | 10 Min to Downtown

5.0 out of 5 average rating, 116 reviews
Guest favorite
A grassy area features seating made up of Adirondack chairs and a patio table set, facing a row of cottages with large windows. The clear sky above is dotted with clouds, complementing the peaceful surroundings.
Cottage in Wells

Wells Maine Home with a View

4.93 out of 5 average rating, 213 reviews

When is the best time to visit Waterboro?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$50,202 GYDG$49,992 GYDG$46,855 GYDG$42,462 GYDG$52,293 GYDG$68,818 GYDG$75,302 GYDG$73,211 GYDG$59,196 GYDG$56,477 GYDG$55,431 GYDG$50,202 GYD
Avg. temp-4°C-3°C1°C7°C13°C18°C21°C21°C16°C10°C4°C-1°C

Destinations to explore