Family-friendly vacation rentals in Kennebunkport

4.99 out of 5 average rating, 173 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

This new, very private apartment attached to our home is in a quiet and picturesque environment minutes away from Dock Square. It's great for couples, solo adventurers and families with one child. If you are seeking to spend the day at one of the beautiful Kennebunk beaches they are just minutes away. We are committed to environmental sustainability and the apartment is powered by solar energy. A new outdoor hot tub was recently installed in February, 2024! We look forward to your visit!

4.96 out of 5 average rating, 212 reviews

A charming two-story house is framed by vibrant yellow flowers. The white exterior features large windows that glow warmly, highlighting the inviting entrance. A manicured lawn leads to a driveway with decorative plants flanking the path, contributing to a welcoming atmosphere.

Home in Arundel

NewBuilt/HotTub/Great Location-4 min Kennebunkport

Follow us on IG @anchorunwind. Welcome to Mama Bear's House! Perfect girlfriends' getaway or to celebrate a special someone. Sit back and relax in our brand new and fully equipped stylish home just 5 minutes away from Kennebunkport's Dock Square. Spend time reading and sipping a fresh grounded coffee on our cozy egg chair, looking in our peaceful backyard while the sunset closes another memorable chapter of your vacation. Enjoy the firepit with hot cocoa and s'mores or fall for a cornhole game!

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, 254 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.

Place to stay in Shapleigh

5 out of 5 average rating, 113 reviews

Historic Schoolhouse c1866 / Sauna + Hot Tub + Gym

Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond, gym and tennis court.

5 out of 5 average rating, 119 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 out of 5 average rating, 216 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.

4.95 out of 5 average rating, 101 reviews

A cozy living area features two patterned armchairs and a neutral-colored sofa, creating a welcoming seating arrangement. A light-colored coffee table is centered on an area rug, with decorative items and reading materials arranged on it. Natural light enters through the window, enhancing the space.

Farm stay in Kennebunk

1760 Morrill Farm House-5 Minutes to Kennebunkport

Welcome to the 1760 Morrill Farm House, your idyllic sanctuary for your iconic Vacationland experience. Just a 5 minute drive to Kennebunk and Kennebunkport villages, Mother’s, Middle and Gooch’s beaches. Free beach pass provided. PLEASE NOTE: This unique space has very low ceilings and may not accommodate people over 6 feet tall comfortably. PLEASE NOTE: Unit 2 only has one designated parking spot. Any extra cars in your party must park on the side of the road next to the bushes.

4.82 out of 5 average rating, 123 reviews

Apartment in Kennebunk

Farmhouse Retreat Downstairs | Walk to Downtown

Experience the charm of our beautifully renovated 1870 farmhouse, a spacious, main level Kennebunk vacation 1BDR, offering comfort and relaxation, just a 5-minute walk from downtown!! Enjoy easy access to local coffee shops, restaurants, the farmers market and popular Garden Street Bowling Alley. Ideal Need more space? Check out our profile to book the full-house rental, perfect for up to 8 guests. Your perfect Maine stay awaits! Beach Parking Permit for Kennebunk Beaches included!!

Farm stay in Kennebunkport

The barn house features a rustic design with large, welcoming doors framed by vibrant greenery and colorful flower beds. Two red chairs are positioned invitingly on a pebble pathway leading to the entrance. A soft pink and purple sky complements the charming exterior.

4.92 out of 5 average rating, 130 reviews

Farmhouse Experience in a Beachside Community

2025 Summer Rentals: 7 night min requirement (Friday Check-in) / Inquire for alternative dates. Enjoy being equidistant between Dock Square and Cape Porpoise, where you be immersed in a world of top chefs, fine wines, beautiful homes, acclaimed artists, and the quintessential oceanfront charm of Kennebunkport. Relax in this inspired barn house restored design with modern touches in a farm to table community. Weather the storm with our newly installed generator.

Guest suite in Kennebunkport

A polished tray is displayed with two glasses and a can of Cranberry Island cocktail, complemented by a small vase of white flowers. The arrangement evokes a welcoming ambiance, signaling a thoughtful touch for guests.

4.98 out of 5 average rating, 171 reviews

Cape Porpoise Private Guest Suite with King Bed

Come relax in the guest suite of our new modern farmhouse, 1 mile from Cape Porpoise's village town centre in Kennebunkport. Enjoy a private entrance and outdoor seating space/ fire pit overlooking a wooded lot. The 1000 sq. ft. space is bright and roomy. It has a king-sized bed with tv, kitchenette, office area and a 50 inch smart tv in the comfy living room. Walk outside our home and find 27 miles of interconnecting conservation land trails.

4.97 out of 5 average rating, 183 reviews

A bright sunroom features large windows offering natural light and views of the surrounding landscape. Comfortable seating includes a light blue couch with decorative pillows and two woven chairs. A small wooden coffee table sits in the center, complemented by a lamp on a dark side table.

Home in Kennebunk

350 Steps to Gooch’s Beach! Water Views

Ideal location 350 steps to beautiful Gooch’s beach. Easy walk or short drive to Kennebunkport's Dock Square with shops and restaurants. This is the upper floor of a 2 floor, 2 unit building. Sunny and cheerful w/open floor plan, gas fireplace, and large back deck. WiFi and live streaming tv are included. Outdoor shower. Beach chairs/towels provided. Walk to beach & town. 7 day minimum, Saturday check in/check out July through August 2026.

4.96 out of 5 average rating, 219 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.

Popular amenities for Kennebunkport family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 203 reviews

Luxury Home w/HOT TUB & Fire Pit

4.98 out of 5 average rating, 189 reviews

A spacious sitting area is visible from the entrance, featuring a contemporary sofa and a grand piano. Natural light floods the room through large windows, with artwork adorning the walls and decorative elements placed thoughtfully on shelves.

Guest suite in Freeport

Solar Suite surrounded by Nature

4.98 out of 5 average rating, 302 reviews

Guesthouse in Alton

Vineyard Terrace - Modern & Beautiful

4.87 out of 5 average rating, 283 reviews

A rustic cabin is nestled among lush greenery, showcasing a stone patio with comfortable seating around a firepit. The outdoor area is surrounded by trees, enhancing the tranquil atmosphere, and features stepping stones leading to the entrance of the cabin.

Guesthouse in York

Cozy Cabin with hot tub, walk to beach, rock cove

4.99 out of 5 average rating, 340 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

4.95 out of 5 average rating, 166 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 out of 5 average rating, 120 reviews

A contemporary cabin retreat is nestled among tall trees, softly illuminated by warm outdoor lights. A wooden deck with steps leads to a welcoming entrance. A separate sauna structure is visible, surrounded by snow-covered ground, providing a serene atmosphere in a tranquil forest setting.

Home in South Berwick

Romantic Mirror cabin in the woods

4.9 out of 5 average rating, 296 reviews

A charming coastal home is showcased with light-colored siding and a bright blue front door. Surrounding greenery includes tall trees and manicured shrubs. The property is set back from a grassy area, adding to its inviting curb appeal.

Home in Falmouth

Amazing Bay View Home with Hot Tub

Family- and pet-friendly home rentals

Vacation home in Old Orchard Beach

4.71 out of 5 average rating, 211 reviews

Beautiful one bedroom cabin only 50 ft from beach4

4.97 out of 5 average rating, 253 reviews

A cozy cottage is surrounded by lush trees and greenery. Two blue chairs are placed outside near the entrance, with a small table between them. A gas grill is positioned nearby, creating a welcoming space for outdoor relaxation and dining.

Cottage in Scarborough

Bright, clean, private cottage near Higgins 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.

4.99 out of 5 average rating, 106 reviews

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

4.94 out of 5 average rating, 485 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~Guest Beach House

Guest suite in Ferry Village

A serene beach scene is captured, featuring a gentle shoreline with soft sand. Small boats are anchored in the calm water, while a lush green landscape forms the backdrop under a partly cloudy sky. Sunlight reflects off the waves, creating a sparkling effect.

4.92 out of 5 average rating, 399 reviews

Apartment Walking Distance to Willard Beach

4.94 out of 5 average rating, 108 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

4.91 out of 5 average rating, 132 reviews

A traditional two-story cottage features shingle siding and a gabled roof. The front entrance is framed by three large windows, with a set of steps leading to a well-maintained lawn surrounded by shrubs and flowers. A blue sky with scattered clouds provides a bright backdrop.

Cottage in Cape Neddick

Cozy Cottage by the Sea

Cottage in Old Orchard Beach

The open-concept living area features a modern kitchen with a breakfast bar and a wooden countertop. A cozy seating area includes a sofa with decorative pillows, a wooden coffee table, and soft lighting from lamps, creating a relaxed environment with warm tones.

4.94 out of 5 average rating, 315 reviews

#4 Vintage Cottage walk to the beach and Pier!

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 334 reviews

A cozy lounge area features a green patterned armchair and a sofa adorned with pillows. Natural light filters through the large windows, illuminating a potted plant on a side table and a soft area rug beneath. Light curtains frame the scene, creating a warm ambiance.

Apartment in Rosemont

Tower Suite w/ Hot Tub, W/D, & Parking

4.99 out of 5 average rating, 361 reviews

A bright sitting room features large windows that invite natural light and offer views of the harbor. A round table with two chairs occupies the space, alongside a built-in seating area with cushions. A door leads to an outdoor deck, enhancing indoor-outdoor connectivity.

Guest suite in West End

Sunny West End Guest Suite w/Harbor Views and Pool

4.86 out of 5 average rating, 214 reviews

The kitchen features modern cabinetry with a light grey finish and granite countertops. Stainless steel appliances include a refrigerator, dishwasher, oven, and microwave. A window allows natural light to illuminate the space, and oak flooring runs throughout, providing a warm atmosphere.

Condo in Wells

Two-Bedroom Condo on the Wells/Ogunquit town-line

4.89 out of 5 average rating, 298 reviews

A spacious room features a large bed with plush bedding against a warm-toned wall. A relaxing jetted tub is positioned beside it, with soft lighting provided by bedside lamps. A window allows natural light to enter, enhancing the overall calm and comfortable ambiance.

Apartment in Bartlett

Attitash Retreat

Townhouse in North Conway

The open kitchen features modern stainless steel appliances, including a refrigerator and stove. A spacious island with Quartz countertops provides seating for four, complemented by white bar stools. The dining area is visible, showcasing a dining table set for six, with natural light flowing in from nearby windows.

4.97 out of 5 average rating, 373 reviews

Family friendly + Mountain Views @amountainplace

4.97 out of 5 average rating, 153 reviews

A charming cottage features light blue siding and white trim, complemented by a small porch with railing. Surrounding trees provide shade, while a picnic table and grill are positioned in the grassy yard. Stone landscaping offers a natural backdrop to the cottage.

Cottage in York

Tiny house living close to Ogunquit center!

4.81 out of 5 average rating, 106 reviews

A warm living and dining area features a wooden dining table surrounded by five chairs, a stone fireplace, and a comfortable seating arrangement with a brown sofa. Large windows allow ample natural light, complemented by a rustic chandelier overhead.

Condo in Conway

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