Family-friendly holiday rentals in Kennebunkport

5 out of 5 average rating, 309 reviews

A modern cabin with an A-frame shape is illuminated by warm lights, surrounded by tall trees. In front, a fire pit with wooden chairs invites gatherings, while a hot tub and sauna are visible nearby, contributing to the outdoor relaxation space.

Cabin in South Berwick

Romantic A-Frame cabin in the woods

Stay at Hidden Pines Cabins. Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

An aerial view showcases the lush greenery of the property, framed by the coastline and tranquil waters of Cape Porpoise. The landscape reveals homes, docks, and boats dotting the cove, all under a bright sky with scattered clouds.

4.98 out of 5 average rating, 141 reviews

Luxurious 5 bedroom on the ocean, w/ dock & kayaks

Historic 1735 home on a spacious one-acre property overlooking the ocean. Enjoy swimming from the dock in Cape Porpoise’s protected cove. Two kayaks provided for exploring the lighthouse & picnicking on nearby islands. Stroll past picturesque lobster boats to the town pier, where restaurants serve fresh local lobster & drinks. Walk to morning coffee, pastries, a local grocery store, athe renowned Nunan’s Lobster Hut. Just two miles from Kennebunkport and a nine-minute drive to Goose Rocks Beach.

4.91 out of 5 average rating, 593 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.

5 out of 5 average rating, 134 reviews

A spacious studio apartment features an open layout with a fully equipped kitchen, illuminated by pendant lights above the island. A cozy living area showcases a plush couch and decorative plants, while large windows provide natural light and views of the surrounding area.

Apartment in Kennebunk

Lower Village Lofts •North• Steps to Dock Square

The Lower Village Lofts *North* is a newly renovated large studio apartment located in the heart of the action - just steps from Dock Square (downtown Kennebunkport) and 1/2 mile to the beach! This unit features a brand new fully equipped kitchen, all new designer and higher end furnishings, and a custom built-in room divider complete with an electric fireplace, armoire, and 50" smart TV. The bedroom area has a new king bed with luxurious bedding, black out shades, and an additional smart TV.

4.98 out of 5 average rating, 363 reviews

A spacious living area features a large, white, slipcovered sectional sofa adorned with decorative pillows. A light wooden coffee table sits in the center, highlighted by a small potted plant. Artwork adorns the walls, and soft lighting creates a bright, inviting atmosphere.

Home in Kennebunk

★"Life~at~Sea"★I mi to beach★W/D★Park★2 full baths

• Open floor plan/first floor bedroom+full bath • Fully stocked kitchen with coffee & tea bar • Peaceful neighborhood close to Dock Square & less than 1 mile to KBK Beaches • Shaded back+side yard/patio/grill/outdoor shower • Netflix+Sling+Hulu+HBO+Amazon Video+4 TVs • 1 car garage parking+driveway parking for 2-3 cars • washer+dryer+towels+bed linens provided • board games, pack N plays x 2 • 2 KBK beach passes+boogie boards+beach towels+chairs

4.96 out of 5 average rating, 246 reviews

The tiny home is set in a snowy wooded area, with its natural wood exterior complementing the surrounding environment. A fire pit and seating area are visible in front, surrounded by a blanket of snow, indicating a tranquil retreat in winter.

Tiny home in Biddeford

Tiny house near the beach!

Enjoy a wooded retreat just minutes from Maine's stunning Fortune's Rocks beach. This newly constructed tiny home welcomes you for a memorable stay near the coast. We strive to offer a thoughtful balance between modern amenities and a natural setting. This space is perfect for two guests, with a maximum of four who are comfortable sharing tiny accommodations. We are pet friendly for an additional fee - one dog maximum per reservation.

5 out of 5 average rating, 106 reviews

Home in Kittery

Seacoast Escape with a View

Enjoy the peace and tranquility of staying in Kittery Maine’s exclusive waterfront area. • Walk to downtown Portsmouth • Visit Fort McClary • Hike Cutts Island Trail • Visit Crescent and Seapoint beaches • Shop and dine in Kittery’s Wallingford Square, downtown Portsmouth, and the Kittery Outlets. Everything is within fifteen minutes away! See our other home and awesome reviews: airbnb.com/h/pepperrellparadise

4.88 out of 5 average rating, 140 reviews

A sandy beach stretches into the distance, visible from a coastal property. The exterior features a light-colored shingle design, with a covered porch offering seating. Green shrubbery lines the foreground, creating a natural border against the ocean backdrop and clear blue sky.

Home in Wells

Drakes Island Beach Front Breathtaking Property !

Ocean views from Kennebunkport to Cape Neddick and a gorgeous half mile sandy beach right outside your door! Watch the sunrise and the sunset over the sandy Drakes Island shores. Enjoy daily walks on the beach or take a walk on the peaceful trails nearby alongside the Rachel Carson Wildlife Refuge & Laudholm Farm, and go to town for restaurants, arcades and more fun. It doesn’t get better than this !

A charming cape-style house is framed by a well-maintained garden, with lush green grass and vibrant shrubbery. The light blue front door is complemented by white shutters on the windows. A wooden picket fence lines the yard, providing a welcoming boundary.

4.93 out of 5 average rating, 195 reviews

Seaglass Cottage

Three bedroom antique cape located perfectly between Dock Square, Cape Porpoise, and the ocean! Close to everything Kennebunkport has to offer including renowned Cape Arundel golf course yet still have your privacy with the large backyard and deck. 2 bedrooms with Queen beds and 1 bedroom with two single beds. Plenty of parking, washer/dryer, large backyard, fire pit, and much more!

4.95 out of 5 average rating, 213 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

🐾 Dog Welcoming Cabin with Fully Fenced Yard Escape to a peaceful, cozy cabin tucked away in the woods — the perfect balance of private seclusion and close proximity to town. Kick your feet up on the deck, breathe in the pine, listen to the birds and frogs, or take a gentle stroll down Bufflehead Cove Lane. Walk quietly and you may spot a heron or egret on the pond!

4.96 out of 5 average rating, 208 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

Follow us on IG @anchorunwind. Escape to a hidden gem nestled in the heart of the Kennebunkport area, where modern comfort meets nature's serenity. Our cabin offers an unforgettable vacation experience. ✭"...A must stay location. The host’s were very helpful and genuine..." ✭"...We’ve travelled all around the world and this is in our top 3 Airbnbs we’ve stayed in."

Guest suite in Kennebunkport

A cozy seating area features a light-colored couch adorned with decorative pillows, positioned near a fireplace. A glass coffee table sits in front, displaying wine glasses and a bottle. Built-in shelves showcase books and decorative items, enhancing the welcoming ambiance.

4.99 out of 5 average rating, 213 reviews

No. 48 *Cozy Getaway* King Bed I Tub I Fireplace

We’re Bill and Jen Adams and we welcome you to No. 48 in Kennebunkport, Maine! No. 48 is a cozy guest suite located above the garage of our 1900 farmhouse in Cape Porpoise East. Enter the breezeway from your reserved parking space, and access your private getaway with your own key code.

Popular amenities for Kennebunkport family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.92 out of 5 average rating, 183 reviews

The exterior of a modern A-frame cabin features a sleek black facade and a large glass wall, nestled among tall trees. Soft light emits from within, illuminating the inviting bedding visible through the glass. A rustic, natural setting surrounds the cabin.

Cabin in Freeport

Cozy, romantic cabin overlooking a stream - 25

4.92 out of 5 average rating, 129 reviews

A cozy kitchen area features a gray countertop and green cabinetry. Three barstools are positioned at the counter. Lush plants adorn the sloping ceiling, accompanied by a small dining table and vibrant flower arrangements. A comfortable seating area with decorative pillows completes the space.

Apartment in Saco

Welcome to our BoHo Treehouse! Beaches/Portland

4.81 out of 5 average rating, 160 reviews

Home in Kennebunk

Cape | Hot Tub · Golf Simulator · Arcade

4.98 out of 5 average rating, 190 reviews

The cabin exterior is showcased with large glass walls, allowing natural light to fill the interior. A wooden deck is lined with outdoor lights, leading to a hot tub. Surrounded by trees, the peaceful setting is visible, creating a serene outdoor atmosphere.

Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

4.91 out of 5 average rating, 102 reviews

A cozy bedroom features a comfortable queen bed covered with white linens, complemented by a decorative pillow. Natural light filters through the window treatment, illuminating the warm yellow walls. A compact kitchenette area, complete with a microwave and Keurig, is positioned adjacent to the entry door.

Guest suite in Kennebunk

Glamour meets Country Suite in Heart of Kennebunk

4.91 out of 5 average rating, 109 reviews

Condo in Wells

Starfish Condo Wells Beach

Place to stay in Shapleigh

5 out of 5 average rating, 133 reviews

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

4.95 out of 5 average rating, 172 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

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 150 reviews

An open floor plan is showcased, featuring a cozy futon couch with decorative pillows. A wooden staircase leads to the loft, while large windows allow natural light to illuminate the space. Basic kitchen supplies are visible on the wooden countertop.

Cabin in Standish

THE LILLIPAD.Off-grid A frame. Sebago lake region!

4.95 out of 5 average rating, 513 reviews

A beverage sits on a small table beside a glass bottle filled with sticks. The view through a window reveals the sandy beach and calming ocean waves, with a colorful sunset casting soft hues in the sky. An American flag is partially visible in the background.

Cottage in Saco

Deja Blue Guesthouse

Apartment in Kennebunkport

The exterior of a two-story building is displayed, featuring a gray facade with white trim. A wooden deck wraps around the second floor, providing multiple seating options. Stairs lead to the upper deck, where a satellite dish is visible. The clear blue sky complements the autumn foliage.

4.99 out of 5 average rating, 108 reviews

#2Marsh Views, Cozy quiet spot on river&preserve

5 out of 5 average rating, 109 reviews

A rustic log cabin is set against a backdrop of greenery, featuring a stone chimney and a spacious covered porch. The exterior showcases a natural wood finish, complemented by a red roof. A gravel path leads up to the porch, inviting guests to relax outdoors.

Cabin in Wakefield

Riverside Log Cabin Sanbornville NH

4.94 out of 5 average rating, 279 reviews

A yurt is set against a wooded backdrop, surrounded by trees. A wooden deck features a seating area and an umbrella, providing shade. Access to the deck is facilitated by a small ramp, ensuring easy entry.

Yurt in Lyman

Fire Fly Yurts on Funky Bow Lane

4.95 out of 5 average rating, 164 reviews

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

Quiet cozy cottage close to restaurants, beach

4.95 out of 5 average rating, 102 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

A charming yellow house features white trim and black shutters, complemented by a large American flag adorning the front. Lush greenery surrounds the entry, with a neat pathway leading to the porch, where a shaded seating area is visible.

4.94 out of 5 average rating, 115 reviews

Historic Kennebunkport home .3 mile to Dock Square

Family-friendly home rentals with a pool

Apartment in Kennebunkport

The living area features a modern design with a spacious gray sectional sofa and a sleek wooden coffee table. Soft lighting is provided by two standing lamps flanking the couch. A large window and glass doors allow natural light to fill the space, enhancing the cozy atmosphere.

5 out of 5 average rating, 43 reviews

Maine Coastal Village Getaway

4.93 out of 5 average rating, 135 reviews

The outdoor area features a circular pool surrounded by reclining lounge chairs with blue and white stripes. A stone patio is adorned with a wooden table and chairs, while lush greenery and flowering shrubs frame the scene under a clear blue sky.

Guest suite in Portland

Resort-like 2 bed/1 bath - seasonal pool/hot tub

4.96 out of 5 average rating, 168 reviews

A private pool area features a colorful inflatable parrot floating in clear water. Surrounding the pool are several lounge chairs arranged for relaxation. Lush trees provide shade, and a fence ensures privacy for the space, which is brightly illuminated by natural sunlight.

Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

4.88 out of 5 average rating, 111 reviews

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

4.96 out of 5 average rating, 121 reviews

Condo in Wells

Steps to Wells Beach + Pool | Coastal Retreat

4.93 out of 5 average rating, 213 reviews

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

A classic beach house is situated amidst lush greenery, featuring a charming wraparound porch. The two-story structure is accentuated by large windows and a balcony above. A clear blue sky complements the inviting landscape, creating a serene setting just steps from the beach.

4.98 out of 5 average rating, 56 reviews

Lovely Beach house in GRB - Heated pool!