Family-friendly holiday rentals in Kennebunkport

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.

4.97 out of 5 average rating, 151 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.

FamilyKitchenNearby

5.0 out of 5 average rating, 105 reviews

An inviting entryway is presented under a large, sloping roof supported by exposed wooden beams. Comfortable seating is arranged on the porch, with decorative pumpkins placed on the ground. Pathways made of stones lead to the entrance, surrounded by a tranquil natural setting.

Cottage in Biddeford

Secluded Coastal Home & Cottage 3 Minutes to Beach

Escape to Thistle Pond Cottage, a peaceful coastal retreat in southern Maine. Nestled on 2 acres with pond views, lush gardens, and local wildlife, it’s minutes from beaches and Portland. Every stay begins with homemade bread from our kitchen and thoughtful, locally sourced welcome accompaniments. Weather and seasonal permitting, guests may occasionally savor a host-prepared wood-fired pizza made with fresh garden ingredients. Cozy, bright, and full of garden-to-table charm and seasonal delight.

FamilyKitchenCondition

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, 120 reviews

Historic Kennebunkport home .3 mile to Dock Square

Under 10 min walk to Dock Square, 2 min walk to Kennebunk River. Luxury linens, Casper pillows, SandCloud towels, Malin + Goetz toiletries, well-appointed kitchen and beach chairs included in your stay. 2 bikes & 2 kayaks available. Walk to Colony Beach, bike to Kennebunk Beach. 2 min walk to Perkins Park on the River, steps down to water for launching kayaks. Dock Square is a vacationer’s dream. Stroll along Ocean Ave on the water or grill fresh seafood on the cozy porch. 420 friendly outside

KitchenFamilyParks

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 spacesBiking

Guest suite in Kennebunkport

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.

4.99 out of 5 average rating, 271 reviews

Get back to nature in this new woodsy retreat.

K-port License: STR-2100303 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.

KitchenIndoor spacesComfort

5.0 out of 5 average rating, 112 reviews

Apartment in Kennebunk

Lower Village Lofts •South• Steps to Dock Square

The Lower Village Lofts *South* is a newly renovated large studio apartment located in the heart of the action - just steps from Dock Square (downtown Kennebunkport) and a half 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, and 50" smart TV. The bedroom area has a new queen bed with luxurious bedding, black out shades, and an additional smart TV.

KitchenIndoor spacesCheckout

4.95 out of 5 average rating, 111 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

We are happy to share with you our coastal, colonial home set on eight acres along the Kennebunk River. Enjoy our quaint, warm home just 5 min to the beach and 3 minutes to Cape Arundel Golf Club. Our 4 bdrm, 2.5 bathroom suits short or long term stays. The location is ideal: 6 min from Kennebunkport, 15 min from Biddeford, and 30 min from Portland or Portsmouth! We hope to make you feel at home with the morning birds chirping and the calmness of the river just in back of the property.

Indoor spacesFamilyCheck-in

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.

4.97 out of 5 average rating, 374 reviews

★"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

KitchenIndoor spacesHiking

An aerial view shows a classic multi-story home positioned near the beach, surrounded by lush greenery. The coastline is visible, along with gentle waves and neighboring houses, highlighting the inviting ocean setting.

4.94 out of 5 average rating, 117 reviews

Ocean/Beach Unique Views: THE New England !

QUIET NEIGHBORHOOD, WELCOME TO FAMILIES! GAS FIREPLACE ! Classic architectural details all sited on an enviable ocean/beach location. An alluring home, lovingly maintained for 110 years, encompasses the true understated elegance of the era in which it was created. Amidst the 3,500 sq ft+, find 6 gracious bedrooms accented by 4 and a half baths, updated granite kitchen, pantry, glassed in front porch with mesmerizing views of the ever-changing sea.

FamilyKitchenLaundry

A brick pizza oven features two uncooked pizzas placed on its floor, surrounded by a lively fire. The oven's interior shows a warm glow from the flames, highlighting the rustic brickwork and setting a welcoming tone for cooking.

4.92 out of 5 average rating, 250 reviews

Unique Home w/ Pizza Oven, Minutes from the Beach

Enjoy a cozy and relaxing stay in a beautiful Maine family home just minutes from Goose Rocks Beach. The house sits at the end of a long dirt driveway in an incredibly quiet location. It’s hard to believe a home with this much privacy is just 3/4 of a mile from serene Goose Rocks Beach! The space is perfect for a romantic getaway, families with kids, large groups and of course, your four-legged friends.

FamilyKitchenCheck-in

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.

4.94 out of 5 average rating, 203 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!

KitchenFamilyDecor

4.95 out of 5 average rating, 220 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!

KitchenIndoor spacesBathroom

Popular amenities for Kennebunkport family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 188 reviews

The exterior of a private entrance features a charming blue door framed by natural wood shingles. Flowering plants and greenery line the pathway, enhancing the inviting atmosphere. A trellis with climbing vines is visible beside the door, contributing to the tranquil setting.

Apartment in Kennebunk

Birch Sea

Indoor spacesFamilyNearby

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

FamilyIndoor spacesBackyard

4.98 out of 5 average rating, 143 reviews

CozyKennebunkEscape|Nearbeaches|HottubLgPatio&Yard

Indoor spacesFamilyCleanliness

4.8 out of 5 average rating, 172 reviews

Cape | Hot Tub · Golf Simulator · Arcade

FamilyKitchenHospitality

4.95 out of 5 average rating, 179 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 spacesFamilyAccuracy

4.97 out of 5 average rating, 262 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!

KitchenIndoor spacesCondition

Home in Old Orchard Beach

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.

4.96 out of 5 average rating, 235 reviews

Luxury Home w/HOT TUB & Fire Pit

Indoor spacesFamilyAir conditioning

Place to stay in Shapleigh

5.0 out of 5 average rating, 144 reviews

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

FamilyKitchenBackyard

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 292 reviews

A charming home is surrounded by vibrant autumn foliage and a carpet of fallen leaves. The inviting exterior features a garage and large windows, while a colorful tree adds warmth to the scene. A playful atmosphere is enhanced by nearby decorations.

Guest suite in Kennebunk

The Nest! VERY CLEAN! Near downtown! Self check-in

FamilyKitchenComfort

Superhost

A spacious bedroom features a large bed with neutral bedding, flanked by two windows fitted with leafy green curtains. A decorative mirror and bedside lamps on wooden tables complement the modern design. Natural light illuminates the room, creating a serene atmosphere.

4.9 out of 5 average rating, 145 reviews

Bungalow Wharf - Lower Village and 1 mile to beach

Indoor spacesKitchenBiking

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, 122 reviews

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

Indoor spacesKitchenTV

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.

4.95 out of 5 average rating, 170 reviews

Quiet cozy cottage close to restaurants, beach

Indoor spacesFamilyBarbecue

Guesthouse in Old Orchard Beach

4.91 out of 5 average rating, 226 reviews

Adorable 2 bedroom cabin only 50ft from Beach no.7

KitchenIndoor spacesCheckout

4.87 out of 5 average rating, 240 reviews

Cottage in Harpswell

Quaint & Peaceful Designer's Oceanfront Cottage

FamilyKitchenLayout

4.97 out of 5 average rating, 116 reviews

A modern interior of a camper features a bright seating area with a fold-down table surrounded by two built-in benches. Light wood flooring complements the stylish white cabinetry, while a cozy reclining chair rests nearby, enhancing the overall inviting space.

Campervan/RV in Wells

Private, Bright, Cozy, and Close to Beaches

KitchenFamilyAmenities

4.97 out of 5 average rating, 198 reviews

Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

FamilyIndoor spacesView

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 108 reviews

The living area features a plush gray sofa and an armchair beside a large area rug. Natural light filters through a skylight, illuminating the space. A coffee table sits at the center, accompanied by two lamps and a faux fireplace, creating a cozy ambiance.

Condo in Ogunquit

Newly designed one-bedroom condo- heart of OGT

Indoor spacesFamilyValue

4.96 out of 5 average rating, 178 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 spacesKitchenComfort

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 spacesFamilyNearby

4.9 out of 5 average rating, 118 reviews

Condo in Wells

Starfish Condo Wells Beach

FamilyKitchenWi-Fi

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

Indoor spacesFamilyValue

4.95 out of 5 average rating, 702 reviews

The spacious loft is highlighted by 16-foot ceilings and multiple skylights. A queen bed is positioned near a cozy seating area, complemented by a wooden dining table. Eye-catching artwork adorns the walls, and natural light fills the room through large windows.

Loft in Falmouth

Loft Apartment on Tree-Lined Street in Falmouth

FamilyIndoor spacesHospitality

4.93 out of 5 average rating, 147 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

KitchenFamilyTV