Family-friendly holiday rentals in Kennebunkport

5.0 out of 5 average rating, 107 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.

4.94 out of 5 average rating, 121 reviews

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.

Home in Kennebunkport

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

4.92 out of 5 average rating, 132 reviews

A hobbit house is nestled among lush green trees, with a sloping earth-covered roof adorned with grass and ferns. The rounded front features a large window framed in white, complemented by a natural stone border, emphasizing the home's connection with its woodland surroundings.

Earthen home in Sanford

Luxury Year-round Hobbit House w/ private hot tub

Fern Hollow 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.

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.

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.

4.99 out of 5 average rating, 272 reviews

5.0 out of 5 average rating, 148 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.

5.0 out of 5 average rating, 249 reviews

A modern beach house is positioned along a serene shoreline, featuring large windows that reflect the colorful sunset. The exterior showcases a blend of natural materials and white accents, with a deck that offers expansive ocean views. Rocky shores frame the property, enhancing the coastal setting.

Home in Saco

Oceanfront w/ Stunning views and Private Deck☀️🏖

Welcome to the Beach House on the Rocks, your very own oceanfront retreat! This beautiful, 1350 sq ft house is nestled right next to the ocean. With panoramic views and the ocean just steps away, you won’t forget this one of a kind experience. Tucked away in the hidden gem of Camp Ellis, you’ll enjoy a lively beach scene in the summer and a tranquil retreat in the off season. Just a short trip away to Old Orchard Beach and 30 min to Portland you’ll never be in need of fun activities.

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

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.

4.98 out of 5 average rating, 123 reviews

A cozy living area features a plush blue-and-white patterned chair, positioned next to a modern fireplace. A wall-mounted television is displayed above a wooden mantel. The open kitchen area can be seen in the background, with stylish bar stools and kitchen shelving.

Cottage in Kennebunkport

Charming Designer Cottage on Marsh

Cozy renovated Cottage w/ stunning marsh views is short walk to beautiful Goose Rocks Beach. No need to pack gear, cottage comes equipped w/ 2 kayaks, 2 bikes/helmets & beach buggy. Stroll to general store for morning coffee, walk on beach or head out and explore the Kennebunks & Cape Porpoise. Our community offers world class dinning, boutique shopping , entertainment and beautiful hiking trails all close by. At days end kick back & relax by the fire pit...”The way life should be”

4.99 out of 5 average rating, 294 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

**Please note: As of Summer 2026, Airbnb has shifted its service fee from guests to hosts. My rates & fees have been adjusted to reflect this change, not to increase my profit. The total ending cost to guests remains the same as before. :) Welcome to The Nest! We offer a beautiful private studio suite in Kennebunk, Maine! We are half a mile from downtown Kennebunk Village and less than 15 minutes to Kennebunkport and local beaches! A keyless entry makes check-in a breeze!

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, 375 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

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.

4.94 out of 5 average rating, 204 reviews

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.

Home in Kennebunkport

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!

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

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

Place to stay in Shapleigh

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

5.0 out of 5 average rating, 145 reviews

4.97 out of 5 average rating, 263 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!

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.

Luxury Home w/HOT TUB & Fire Pit

4.96 out of 5 average rating, 237 reviews

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

5.0 out of 5 average rating, 326 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

4.8 out of 5 average rating, 172 reviews

Cape | Hot Tub · Golf Simulator · Arcade

4.99 out of 5 average rating, 393 reviews

An open space features a vaulted wooden ceiling with beams and skylights. A cozy seating area includes a brown sofa and a modern coffee table. A wood stove adds warmth, while a well-equipped kitchen with dark green cabinets is visible in the background.

Tiny home in Freeport

Cozy Rock Cabin #thewaylifeshouldbe

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 250 reviews

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.

Home in Kennebunkport

Unique Home w/ Pizza Oven, Minutes from the Beach

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

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.

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

4.99 out of 5 average rating, 123 reviews

4.96 out of 5 average rating, 235 reviews

A view from the staircase leads to an open kitchen and dining area, featuring light-colored cabinetry and stainless steel appliances. Natural light floods the space through a nearby entryway, while wooden banisters and wide pine flooring add warmth to the contemporary loft.

Loft in Kennebunk

Swanky Loft! Dock Square,Over 1000 5 Star Reviews!

Guesthouse in Old Orchard Beach

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

4.9 out of 5 average rating, 229 reviews

4.97 out of 5 average rating, 167 reviews

Apartment in Biddeford

Sunny Cottage

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

Apartment in Kennebunkport

Feel at Home at Annette’s – A Coastal Retreat

4.98 out of 5 average rating, 48 reviews

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 109 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

4.98 out of 5 average rating, 200 reviews

Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

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

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

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!

4.9 out of 5 average rating, 120 reviews

Condo in Wells

Starfish Condo Wells Beach

4.88 out of 5 average rating, 119 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