Pet-friendly holiday rentals in Kennebunk

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.

4.93 out of 5 average rating, 107 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

4.83 out of 5 average rating, 163 reviews

An expansive in-ground pool is surrounded by a spacious wooden deck, featuring comfortable lounge chairs. The house, with gray siding, is visible in the background, flanked by trees that provide privacy. Soft clouds pass overhead, contributing to a tranquil outdoor setting.

Home in Kennebunk

Kennebunk/Kennebunkport Beach House w/Pool!

Perfect home for hosting and entertaining! Private in-ground pool, 600+ sq. ft. sprawling deck, large yard, and close proximity to beaches, restaurants, and shopping. Brand new renovations throughout! Amenities and features include: Newly renovated top to bottom 2 beautiful kitchens w/ granite, stainless steel appliances In-ground pool and 600 sq. ft. wrap-around deck Spacious 2 acre yard One mile from the beach Walking distance to Kennebunk Lower Village/Kennebunkport Dock Square Pet friendly!

Place to stay in Shapleigh

5 out of 5 average rating, 111 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.

Hotel room in Downtown Portland

A modern living area features a comfortable gray sofa draped with a soft throw. A wooden coffee table sits on a patterned rug, accompanied by a small black side table. A wall-mounted television is positioned against a light-colored wall, with large windows showcasing a view of brick buildings.

4.93 out of 5 average rating, 220 reviews

Luxury One Bedroom Loft in Portland’s Old Port

Immerse yourself in the culture of the Old Port at your luxury loft. A top choice for travelers, The Docent's Collection was most recently awarded Condé Nast Readers' Choice (2025) and Tripadvisor Travelers' Choice (2025). Enjoy this spacious open-concept floor plan featuring a full-sized kitchen and bedrooms with soft luxurious linens and cozy pillows for your comfort. Admire the tapestry of a curated collection of local artists and enjoy five-star service from our local hospitality team.

4.92 out of 5 average rating, 257 reviews

A light-filled living area features a comfortable beige sofa and a vibrant blue rug. A round dining table with blue chairs is positioned by the bay window, allowing natural light to enhance the cheerful atmosphere. A framed artwork adds a touch of character to the space.

Apartment in Kennebunk

Prime Dock Square Location! Walk Everywhere!

Welcome to Kennebunk Coastal Suites. (Cove Side Suite unit 3) Best location! 2 minute walk to Dock Sq ONSITE PARKING FOR 1 CAR Dozens of Shops, restaurants, and music surrounds you and all your senses! This is the perfect place for your Maine vacation. We painstakingly renovated this 1880’s charmer into 5 charming apartments complete with all your necessities including a washer/dryer. There are many houses for rent in the Kennebunks but none as convenient as this Kport charm

4.93 out of 5 average rating, 134 reviews

A cozy studio space features a double size bed dressed in a red coverlet and accented with colorful throw pillows. A small wood stove is positioned near the bed, with a television mounted on the wall opposite. Natural light filters through windows adorned with lace curtains.

Tiny home in Wells

COZY&RELAXING Studio-Home, Wells ME 3.5 mi 2beach

Get away from the chaos of everyday life & relax in this studio-style home, nestled by nature. Located just 3.5 mi. from Wells Beach, this peaceful space is just far enough away to make for a wonderful place to call your own. Relax by the glow of a campfire after a sunny day at the beach. Kick off your shoes, enjoy your favorite cold drink & a burger on the grill! Unwind & listen to natures "symphony" ~ the wind in the trees, the crickets, the owls, the frogs ~ truly delightful!

Cottage in Old Orchard Beach

A cozy living area is presented with a gray sofa and a vibrant orange chair, alongside a small black, patterned table. Brightly colored wall art enhances the surroundings, while a TV is mounted on the wall. Natural light enters through glass doors leading to a fenced backyard.

4.94 out of 5 average rating, 387 reviews

#2 Walk to the beach Vintage Cottage.

3 night Min. stay 6/1 to Labor day. Cottage #2 is a classic one-bedroom with soothing beach colors and well-appointed with comfortable furnishings and updated finishes. It is outfitted with vintage and modern decor mixed in. The cottage has a fully stocked kitchen with pots and pans and utensils for those times when you may just want to stay in and cook. Private fenced backyard with a gas grill, table and chairs. Just a short 5-minute walk, to the beach. Yes we allow pets.

4.93 out of 5 average rating, 103 reviews

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.

Home in Kennebunk

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.

4.95 out of 5 average rating, 163 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

Winter-wonderland, close to skiing and a walk from great dining. In the summer, enjoy the quiet backyard or walk to the beach! No need to find parking, my place is 3/10 of a mile from downtown Kennebunkport and 7/10 of a mile to Gooch's Beach. You will love my place because of the kitchen, the coziness, and the location. My place is good for couples. It has a tempurpedic king-sized bed and a queen sized pull out bed in the living room.

4.96 out of 5 average rating, 155 reviews

A stylish bathroom is showcased with wooden paneling, featuring a deep claw-foot tub and a round shower enclosure. Modern fixtures, a circular mirror, and decorative plants provide a fresh ambiance. A wooden bath tray rests on the tub, enhancing functionality and comfort.

Cabin in Newfield

The NEST Haven awaits you.

You found your ultimate relaxation spot, sandy beaches on Rock Haven Lake (only 800' from your front door) infrared Sauna (accessible through the secret door) , 3 person hot tub, outdoor (seasonal) shower, luscious king seize bed, 6' TIPI daybed, firepit, outdoor tipi swing, a balcony and deck to enjoy the peaceful neighborhood. Round shower and deep claw foot soaker tub. Enjoy, relax and let your soul ponder.

4.97 out of 5 average rating, 435 reviews

A serene snowfall blankets the landscape, with a quaint house visible in the background. The house features a front porch and is surrounded by tall trees. A smooth, snowy path leads up to the entrance, highlighting the peaceful, winter setting.

Home in Lebanon

Beautiful, Peaceful, Maine Getaway House

Kick back and relax in this beautiful Maine getaway. Romantic, Quiet, country setting. Pet friendly. Big yard and trails for you and your pets to roam. Outdoor seating w/hammock. Minutes away from boat launching area to rent party boats, kayaks and paddle boats. Winter sports on Milton 3 ponds close by. Seasonal fruit picking right in town. Skydive New England. Fall leaf peeping. Extended stays welcome

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, 193 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!

Popular amenities for Kennebunk pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.93 out of 5 average rating, 136 reviews

A red post and beam house is nestled among trees, featuring multiple windows and a sloped roof. A wooden deck extends from the entrance, leading to a gently sloping yard surrounded by lush greenery. Sunlight filters through the leaves overhead.

Home in Limerick

Lakefront Getaway

Home in Old Orchard Beach

A charming cottage exterior showcases fresh landscaping and a well-maintained lawn. A welcoming porch features a small entryway, while flowering plants and shrubs add greenery. The surrounding white fence provides privacy, and the sky is clear with scattered clouds.

5 out of 5 average rating, 30 reviews

Robin’s Retreat

Superhost

4.57 out of 5 average rating, 7 reviews

Walk to Dock Square- Quiet neighborhood!

A newly renovated colonial house features a light grey exterior with black shutters and a welcoming front porch. An American flag hangs from the porch, adding a touch of character. A well-maintained garden with greenery surrounds the foundation, enhancing the quaint appearance.

5 out of 5 average rating, 85 reviews

Cozy updated colonial, 5 minute walk to town!

4.94 out of 5 average rating, 593 reviews

A bright living room is filled with natural light from two large windows. A soft blue sectional sofa, accentuated by coordinating pillows, faces a round coffee table. A vibrant piece of wall art and potted plants enhance the space. A comfortable armchair is situated in the corner.

Home in Portsmouth

Private Sunny Apartment in hip Portsmouth West End

4.88 out of 5 average rating, 146 reviews

A quaint turquoise house is surrounded by a spacious lawn, with a winding path leading to the entrance. Large windows provide natural light, while a chimney adds a traditional touch. Lush greenery and colorful flowers are visible around the exterior.

Home in Cape Neddick

Rocky Acres at York Beach

5 out of 5 average rating, 108 reviews

A modern blue house is nestled within lush greenery, featuring multiple large windows and a rooftop deck with an umbrella. The tranquil marshland, dotted with tall grasses, stretches into the distance under a sky filled with soft clouds.

Home in Salisbury

Pirates Hideaway - Sanctuary on the Marsh

5 out of 5 average rating, 103 reviews

A modern kitchen features dark stone countertops and antique-style cabinetry. A large island with seating is positioned at the center, complemented by stylish bar stools. High-end appliances are visible, and a window allows natural light to brighten the space.

Home in Greenland

Newly Restored 1850’s farm house 3 bedroom 2 bath

Pet-friendly home rentals with a pool

4.91 out of 5 average rating, 110 reviews

A spacious two-story building is featured, characterized by green siding and a brown roof. Large windows create a bright appearance, while a front staircase leads to the main entrance. Surrounding pine trees and a plaque at the entrance enhance the natural setting.

Condo in Bartlett

White Mountains Hiking Dogs Storyland Family

Home in Old Orchard Beach

A clear blue swimming pool is featured at the center, surrounded by lounge chairs on the sunbaked concrete deck. A fenced area and trees in the background provide a natural setting, with additional homes visible nearby, creating a welcoming community atmosphere.

4.92 out of 5 average rating, 13 reviews

Family Fun with Community Pool

4.97 out of 5 average rating, 58 reviews

A spacious bedroom is presented, featuring a dark wooden bed frame with a light-colored bedding set. Two nightstands with lamps are positioned on either side. Natural light enters through three windows, complementing the warm tones of the wooden floor and subtle wall color.

Home in Kittery

Fantastic Kittery Home with Pool

Superhost

A modern kitchen is equipped with stainless steel appliances, including an oven, microwave, and dishwasher. White cabinetry provides ample storage, complemented by a stylish backsplash. A small area rug adds a touch of warmth, while soft lighting illuminates the workspace.

Apartment in Bartlett

4.79 out of 5 average rating, 132 reviews

Ski, snowboard, skate, hike, clubhouse and more

4.86 out of 5 average rating, 123 reviews

A spacious living area features warm wood paneling and a cozy wooden fireplace. Comfortable seating is arranged around a coffee table, and large glass doors allow natural light to fill the room, leading to the scenic outdoors. A ladder provides access to the loft area.

Chalet in Bridgton

Charming Chalet 3 min to SKIING & PVT beach access

Apartment in North Conway

4.9 out of 5 average rating, 127 reviews

Main Street for 6!

4.87 out of 5 average rating, 166 reviews

A collage showcases the winter season. The top left displays a group enjoying snowmobiling on a snowy landscape. The top right captures expansive ski trails across a mountain range. The bottom left features a heated indoor pool surrounded by lounge chairs, while the bottom right highlights a game room equipped with pool and arcade tables.

Condo in Bartlett

Spacious Condo-Attitash Ski-Storyland-Saco & More!

Superhost

A hot tub filled with bubbling water overlooks a serene landscape of rolling green hills and distant mountains. The sky is lightly clouded, and the surrounding trees frame the view, creating a peaceful atmosphere for relaxation.

Apartment in North Conway

4.79 out of 5 average rating, 131 reviews

The 1785 Suite, Amazing Views, Walk to River

Private, pet-friendly home rentals

4.92 out of 5 average rating, 25 reviews

A view of the tranquil outdoor space includes a flag gently waving in the breeze, framed by colorful trees. The foreground features a BBQ area with lobster-themed placemats, while the background reveals a serene landscape leading down to the water.

Guest suite in York

Seaside Retreat on Cape Neddick Beach

5 out of 5 average rating, 16 reviews

A quaint tiny house is positioned beside a serene marsh area, where various birds are observed wading in shallow waters. Lush greenery surrounds the home, and the calm landscape extends toward the horizon, indicating a peaceful setting.

Guesthouse in Wells

Dream Catcher at the beach

4.91 out of 5 average rating, 78 reviews

A lakeside view features a charming house framed by lush trees, with wooden decking and patio space visible. A swimming platform can be seen off shore, accompanied by a couple of colorful chairs. The water reflects the surrounding greenery and the structure, creating a serene ambiance.

Guest suite in Lyman

Studio, listen to the loons at Bunganut Lakefront

4.92 out of 5 average rating, 97 reviews

A two-story farmhouse-style cabin is situated amidst autumn foliage, showcasing a spacious front porch with steps leading to the entryway. The surrounding yard features a well-maintained lawn and a gravel path, creating an inviting outdoor space.

Cabin in Wells

Relaxing Coastal Escape Near Beaches with Hot Tub

4.92 out of 5 average rating, 71 reviews

The front exterior of the house is showcased, featuring a welcoming red door and a wide staircase leading to the entry. The landscaped yard includes a stone patio area, surrounded by greenery and neatly arranged stones, contributing to the inviting presence of the home.

Home in Ogunquit

Cozy cape in the Heart of Ogunquit Center

4.92 out of 5 average rating, 63 reviews

The modern kitchen is equipped with white cabinetry and stainless steel appliances, including an oven and microwave. A stylish countertop is complemented by a vase of fresh flowers, and natural light floods in from the adjacent room, enhancing the inviting ambiance.

Condo in Kennebunk

Gorgeous Coastal Getaway

4.99 out of 5 average rating, 70 reviews

A cozy den area features a comfortable sofa and a matching armchair. A ceiling fan provides airflow. A granite-topped table sits centrally, with a table lamp casting warm light. A wall art piece adds character, and wooden flooring complements the space.

Guest suite in Arundel

Rustic and cozy one bedroom