Family-friendly vacation rentals in Waterboro

4.91 out of 5 average rating, 604 reviews

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.

FamilyIndoor spacesView

4.99 out of 5 average rating, 187 reviews

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!

KitchenIndoor spacesBathroom

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.

Indoor spacesKitchenGetting around

5.0 out of 5 average rating, 145 reviews

4.98 out of 5 average rating, 128 reviews

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.

Indoor spacesKitchenView

4.93 out of 5 average rating, 150 reviews

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.

FamilyIndoor spacesAir conditioning

4.99 out of 5 average rating, 199 reviews

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

FamilyIndoor spacesSkiing

4.97 out of 5 average rating, 189 reviews

Cottage in Buxton

Peaceful Cottage on Maine Flower Farm

Maine’s Peaceful Escape Nestled next door to Ferris Farm, our family-run flower farm, this charming cottage offers a private place to rest and recharge. Enjoy slow, coffee-filled mornings, quiet walks, and cozy evenings by the fire pit. Use the cottage as your home base to explore nearby beaches (30 minutes) or head into Portland (35 minutes) for breweries, coffee shops, and great dining. Perfect for a couple retreat, solo escape, or remote work getaway, with dedicated workspace.

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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.

4.89 out of 5 average rating, 133 reviews

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.

Indoor spacesFamilyOutdoor spaces

4.99 out of 5 average rating, 510 reviews

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.

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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.

5.0 out of 5 average rating, 142 reviews

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.

FamilyIndoor spacesGetting around

4.96 out of 5 average rating, 263 reviews

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.

Indoor spacesKitchenAccess

5.0 out of 5 average rating, 157 reviews

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.

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Popular amenities for Waterboro family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 137 reviews

The lodge-style home stands amid tall trees, showcasing a modern dark exterior. A gravel driveway leads to the house, which features a welcoming front entrance. The surrounding landscape is dotted with seasonal foliage, providing a serene setting.

Home in Standish

Beautiful Home w-Hot Tub & Pond access

KitchenFamilySkiing

4.98 out of 5 average rating, 210 reviews

Home in Wakefield

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

Indoor spacesFamilyHospitality

4.96 out of 5 average rating, 191 reviews

Home in Shapleigh

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

Indoor spacesKitchenRiver

4.96 out of 5 average rating, 229 reviews

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

FamilyKitchenWifi

5.0 out of 5 average rating, 107 reviews

Cabin in Norway

Secluded Cabin: Mountain View, Hot Tub + Fireplace

KitchenIndoor spacesBeach

4.9 out of 5 average rating, 122 reviews

Cabin in Sanford

Log Home on 8 Acres. Campfire and Jacuzzi. PETS

FamilyIndoor spacesAir conditioning

4.98 out of 5 average rating, 175 reviews

Home in Saco

Oceanfront Escape • Walk to Beach • Sleeps 14

KitchenFamilyPets

4.98 out of 5 average rating, 200 reviews

Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

FamilyKitchenWifi

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 179 reviews

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!

Indoor spacesKitchenBreakfast

4.96 out of 5 average rating, 112 reviews

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

Indoor spacesKitchenSleep quality

4.96 out of 5 average rating, 105 reviews

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

FamilyKitchenGrill

4.96 out of 5 average rating, 201 reviews

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

FamilyIndoor spacesCheck-in

4.95 out of 5 average rating, 221 reviews

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

KitchenIndoor spacesCheckout

5.0 out of 5 average rating, 39 reviews

The cabin is situated amidst tall trees and greenery, featuring a charming gabled roof and a screened-in porch that extends across the front. Stairs lead to the main entrance, while a gravel pathway and a spacious yard enhance the serene wooden setting.

Cabin in Limerick

Cozy Cabin @ Lake Arrowhead, Movie Screen, Dogs OK

Indoor spacesFamilyAccuracy

5.0 out of 5 average rating, 71 reviews

The exterior of the home is showcased at dusk, featuring large windows that reflect warm light. The two-story structure is framed by trees, with a deck visible on the upper level and stairs leading down to the ground. A serene natural setting surrounds the property.

Home in Shapleigh

Extraordinary Lakefront Retreat with Private Beach

Indoor spacesFamilyBeach

5.0 out of 5 average rating, 16 reviews

5 Acre Lakefront Getaway

KitchenIndoor spacesAccuracy

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 105 reviews

A heated pool is set within a stone patio, surrounded by lush greenery. Two lounge chairs are positioned nearby, while modern heating units stand along the patio's edge. The pool's clear water reflects the surrounding area, offering a serene outdoor retreat.

Home in Ogunquit

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

FamilyKitchenLayout

4.96 out of 5 average rating, 125 reviews

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

Indoor spacesKitchenCleanliness

4.9 out of 5 average rating, 120 reviews

Condo in Wells

Starfish Condo Wells Beach

FamilyKitchenCleanliness

4.95 out of 5 average rating, 180 reviews

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

Indoor spacesFamilyAccess

5.0 out of 5 average rating, 102 reviews

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

FamilyIndoor spacesCheck-in

5.0 out of 5 average rating, 116 reviews

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

Indoor spacesKitchenAmenities

4.92 out of 5 average rating, 125 reviews

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

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