House holiday rentals in Kennebunkport

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

4.96 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!

A comfortable living area features a dark sofa adorned with cushions, accompanied by a red recliner. A wooden coffee table sits at the center, displaying a brochure. Large windows dressed in sheer curtains allow natural light to illuminate the space.

4.98 out of 5 average rating, 125 reviews

DriftRose, Bestlocation/AC/Beachpass/patio/grill

This home belonged to my grandmother and has loads of personality. It has been recently updated while still preserving its charm. Fast internet, new AC, all the necessities in the kitchen, new bedding, and a relaxing outdoor space! The location is perfect. Walk to the best the area has to offer or spend the day just 1 mile away at the beach (parking pass included) or unwind and relax on the deck or patio and enjoy a gorgeous view of the Drift Roses when in season. Cheers to making memories!

5 out of 5 average rating, 214 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.

4.99 out of 5 average rating, 150 reviews

A modern coastal home featuring a light grey shingle exterior and a contrasting dark roof. The entrance showcases a well-defined porch with elegant lanterns and large windows, while a driveway leads to a two-car garage. Lush greenery surrounds the property, enhancing the seaside setting.

Home in Cape Neddick

Luxurious Oceanfront Property

Welcome to The Luxurious, where a unique boat feeling awaits you. Completely remodeled with high-end finishing, an elevator accesses all three levels. An open floor concept invites the ocean breeze and offers unique views. A modern fitness room, a year-round hot tub and firepit will enhance your stay. After a day at the beach, enjoy the sunset from the house and walk to the Nubble Light House to savor Maine's famous blueberry ice cream and pie ! Fishing dock not available at the moment.

The exterior of a two-story wooden house is surrounded by lush greenery, showcasing a large wraparound deck with outdoor seating. A pathway leads to the entrance, with soft light spilling from the windows at dusk, creating an inviting atmosphere in the natural setting.

4.87 out of 5 average rating, 197 reviews

Kennebunkport House - Walk to Dock Square!

Guests are sure to enjoy a memorable vacation in this fully furnished, 5 bedroom/5 bath house, which can comfortably sleep up to 12 people. With two kitchens, an open concept dining room with farm style table, and 600+ square foot deck, this house is perfect for families and large groups. Located near the beach and within walking distance to Dock Square, guests can enjoy an afternoon of fun activities and later watch the sunset from the deck or spend time around the fire pit at night.

4.81 out of 5 average rating, 130 reviews

Farmhouse Retreat Upstairs | Walk to Downtown|

Experience the charm of our beautifully renovated 1870 farmhouse, a spacious upper unit Kennebunk vacation rental, 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 for a cozy, convenient getaway. Need more space? Check out our profile to book the full-house rental, perfect for up to 8 guests. Beach Parking Permit for Kennebunk Beaches included!!

5 out of 5 average rating, 169 reviews

A welcoming living area showcases a large screen displaying Netflix. Two brown armchairs with throw pillows are positioned beside a modern coffee table. A cozy fireplace adds warmth, while soft gray and blue tones create a relaxing atmosphere. Natural light filters through the windows.

Home in Kittery Point

A water view slice of heaven at Pepperrell Cove

Enjoy the peace and tranquility of staying in Kittery Point Maine’s exclusive Pepperrell Cove area. • Walk three minutes to dinner at one of three amazing waterfront restaurants • Enjoy a private chartered boat ride from across the street • Rent kayaks • 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!

4.93 out of 5 average rating, 256 reviews

The exterior entrance of the property features a paved pathway leading to a dark blue front door, flanked by two windows. A small bench is positioned nearby, and an American flag is displayed on the ground. Lush greenery surrounds the area.

Home in Wells

3-Bed | 2-Bedroom | Hot Tub | Close To Beach

If you've never stayed in Wells before, make your first stay at the oldest established property in Wells, dating back to 1604, but updated for today's modern needs with wifi, streaming, jacuzzi, grill, outdoor furniture, and hammock all within a short drive to Wells beach in a peaceful neighborhood on a dead end street. Let the Webhannet Falls and River lull you to sleep as they flow through the backyard and see the foundation of the historic gristmill and sawmill.

4.99 out of 5 average rating, 467 reviews

The Birch Ledge Guest House is a two-story structure nestled among trees, featuring a rustic exterior with a metal roof. A small patio with two chairs is positioned at the entrance, and a staircase leads to the loft area. Lush greenery surrounds the home.

Home in Hollis

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

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, 352 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

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.

4.97 out of 5 average rating, 183 reviews

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.

Popular amenities for Kennebunkport house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a 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

Home in Old Orchard Beach

A serene community pool is surrounded by a spacious deck with lounge chairs for relaxation. Tall trees in the background provide a natural setting, while neighboring homes are visible, enhancing the sense of community.

4.96 out of 5 average rating, 106 reviews

Faith Lane with community pool

Home in Old Orchard Beach

5 out of 5 average rating, 54 reviews

Our Beach House Getaway

4.93 out of 5 average rating, 239 reviews

A spacious living room features a large sectional couch and an accent chair, both positioned on a patterned area rug. A wall-mounted TV is visible, with light streaming through the windows, highlighting the natural wood flooring and airy design.

Home in Derry

Sanctum by the Lake

4.96 out of 5 average rating, 153 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 North Deering

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

4.83 out of 5 average rating, 117 reviews

A two-story home is presented, featuring a yellow exterior and dark blue shutters. A welcoming front porch is adorned with decorative elements. Lush green grass and various shrubs frame the entrance, while a driveway leads to a garage on the left side.

Home in Deering Center

There's No Place Like Home

4.91 out of 5 average rating, 11 reviews

A spacious living room features a large sectional sofa with colorful accent pillows. A wooden coffee table sits in the center. Natural light fills the space through multiple windows, while a spiral staircase leads to an upper level. A mounted television is positioned above the fireplace.

Home in Arundel

Spectacular 3 Bed Resort Cottage

4.87 out of 5 average rating, 117 reviews

A modern kitchen is highlighted by warm wooden cabinets and sleek granite countertops. Stainless steel appliances, including a microwave and stove, are on display. A mirrored wall reflects the natural light coming through nearby windows, enhancing the spaciousness of the area.

Home in Bartlett

Bear Brook House

Weekly house rentals

A modern kitchen is displayed, featuring a large central island with a light countertop and stylish pendant lighting. Large windows provide views of the surrounding greenery, while a cozy sitting area with a fireplace is seen in the background, complemented by natural light.

5 out of 5 average rating, 15 reviews

Stunning Dock Sq Waterfront Home

5 out of 5 average rating, 12 reviews

Home in Wells

Coastal Maine Cottage

5 out of 5 average rating, 37 reviews

An aerial view captures the coastal neighborhood, showcasing the home with beach access. Nearby residences are visible, alongside a street leading to the ocean. The sky displays a blend of blue hues and soft clouds, while the calming presence of the sea lies in the background.

Home in Wells

Happy Days at Wells Beach

4.91 out of 5 average rating, 11 reviews

Coastal Maine Retreat ~ 1 Mile to BEACH! Outdoor T

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.

4.95 out of 5 average rating, 93 reviews

Classic, calm river view & centrally located home

4.97 out of 5 average rating, 59 reviews

A dining space features a large wooden table paired with four chairs, set on a decorative area rug. A bright green wall provides a cheerful backdrop, complemented by a charming fireplace. Natural light enters through an adjacent window, enhancing the inviting atmosphere.

Home in West End

Sweet Home Near Food & Old Port

A tranquil view of a calm waterway, reflecting the sky and surrounding landscape. A small white boat is anchored nearby, and a charming oceanfront cottage is visible in the distance. Soft hues of blue and green create a peaceful atmosphere.

4.93 out of 5 average rating, 29 reviews

Ocean Front Cottage in Cape Porpoise Kennebunkport

The exterior of a coastal cottage is shown, featuring a cozy patio area with two wicker chairs and a small table. A large red umbrella provides shade, while a charcoal grill is positioned nearby. Lush greenery surrounds the cottage, and soft outdoor lighting enhances the evening ambiance.

5 out of 5 average rating, 39 reviews

The Cottage at Kennebunk!

Private house rentals

5 out of 5 average rating, 20 reviews

Home in Biddeford

Bluebell Cottage Beach Vacation

The exterior of the cottage is depicted, featuring light-colored siding and a welcoming front porch. Two Adirondack chairs are positioned in the foreground, accompanied by a small ornamental plant. A mature tree provides shade, while the surrounding greenery adds to the charm of the setting.

5 out of 5 average rating, 27 reviews

Kennebunk Cottage

A welcoming two-story cottage features a gray exterior with white trim and a cozy front porch. Lush greenery surrounds the home, while a manicured lawn invites outdoor relaxation. A decorative well stands near the entrance, set against a backdrop of trees for added privacy.

5 out of 5 average rating, 25 reviews

Sailor'sCottage-Walk to DockSq, Deck,2 BeachPasses

The outdoor space is highlighted by well-maintained garden beds featuring a variety of flowers and plants. A wooden playset with a slide stands in the background, while a spacious home with multiple stories is visible, surrounded by lush greenery.

4.97 out of 5 average rating, 78 reviews

Family-Friendly Retreat in Cape Porpoise

4.93 out of 5 average rating, 15 reviews

A wooden deck overlooks the tranquil bay, featuring a seating area with wicker chairs and a round table. Nearby, a grill is positioned alongside umbrellas offering shade. The view captures water and greenery under a clear sky, creating a peaceful outdoor setting.

Home in Saco

Beach front home with deck and balcony

5 out of 5 average rating, 11 reviews

New Cozy Coastal Escape, near beach!

5 out of 5 average rating, 6 reviews

Saltaire at Goose Rocks Beach-Outdoor Shower/BBQ

A spacious beachfront home is presented with a distinct gabled roof and shingle siding. The front porch features multiple chairs and is lined with potted plants. An American flag is displayed prominently. Large glass windows allow for ample natural light, offering views of the surrounding landscape.