Holiday rentals in Kennebunkport

4.94 out of 5 average rating, 174 reviews

Cabin in Kennebunk

C-Howder Cabin Dog Oasis Fenced Yard

Don’t forget your dogs! Enjoy the peacefulness of this cozy tranquil cabin tucked away in the woods. The cabin has the best of both worlds; private & secluded, while being close to town. Kick your feet up on the deck. Breathe in the pine, listen to the birds & frogs. Or take a lovely stroll down Bufflehead Cove Lane, walk quietly you may see a heron or egret on the pond. Left at Port Rd. & continue down to Western Ave. Lots of stairs. Driveway very steep, requires 4-wheel drive in winter.

4.99 out of 5 average rating, 148 reviews

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!

4.98 out of 5 average rating, 336 reviews

Flat in Arundel

Cape Arundel Cottage 1 mile to downtown KPT

Tastefully appointed 1 bedroom apartment one mile from desirable Dock Square, Kennebunkport. This apartment features Panoramic views of the famous Cape Arundel Golf Course and Goff's Brook Tidal River. Private, secluded back deck with dining and lounge areas, Cozy furnishings throughout, King sized bed with memory foam topper, Fully Equipped Kitchen, and more! At Cape Arundel Cottage, guest experience is our highest priority! *See “other things to note” for additional important information.*

4.96 out of 5 average rating, 155 reviews

Guest suite in Saco

Suite LunaSea

Be our guests and enjoy this dreamy, romantic little getaway and all that Saco and surrounding areas have to offer! Direct access to the River Walk. Short 5 minute walk to downtown Saco, Amtrak station, and 10 minute walk to downtown Biddeford. Visit our amazing shops, breweries, restaurants and cafes! Bayview Beach 3 miles OOB Pier 4.4 miles Private entrance and deck with outside fireplace. Hosts, Melissa and Doug, are quiet and considerate early risers with 2 friendly pups

5 out of 5 average rating, 204 reviews

Cabin in South Berwick

Romantic A-Frame cabin in the woods

Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Farm stay in Kennebunkport

4.96 out of 5 average rating, 114 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.

4.99 out of 5 average rating, 428 reviews

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.

4.96 out of 5 average rating, 210 reviews

Dock Square Pied-A-Terre Loft Beachy Vibes!

The Sail Loft Unit is a brand new (since 2018) 2nd floor 1 bedroom, 1 full bathroom Suite. Our Property has 5 apartments and we are proud to say we have over 1000 5 Star Reviews!! Discover the delightful town of Kennebunk and enjoy your ideal seaside retreat in our snug 1-bedroom holiday house. Situated just a short walk from the vibrant Dock Square, you'll be immersed in the heart of the local community, with easy to all beaches and attractions!

Guest suite in Cape Porpoise

4.99 out of 5 average rating, 137 reviews

Cape Porpoise Private Guest Suite with King Bed

Come relax in the guest suite of our new modern farmhouse, one 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.

Guest house in Kennebunk Beach

4.93 out of 5 average rating, 262 reviews

Intimate Ocean View Cottage Near the Mousam River

A newly renovated 700+ sqft one-bedroom, two story cottage, with a beautiful ocean view, is less than one mile from Parson’s Beach. The Mousam River access is less than ¼ of a mile away. A cozy Maine living space with a private backyard and fire pit for your enjoyment. Interested in biking or walking trails? We are less than 500' to the bridal path that can take you to nearby Mother’s Beach or into downtown Kennebunk.

4.87 out of 5 average rating, 119 reviews

Home in Wells

Drakes Island Beach Front Breathtaking Property !

Ocean views from Kennebunkport to Cape Neddick and a gorgeous half mile sandy beach right outside your door! Watch the sunrise and the sunset over the sandy Drakes Island shores. Enjoy daily walks on the beach or take a walk on the peaceful trails nearby alongside the Rachel Carson Wildlife Refuge & Laudholm Farm, and go to town for restaurants, arcades and more fun. It doesn’t get better than this !

4.83 out of 5 average rating, 315 reviews

Flat in Wells

The Crow's Nest

This is a one bedroom unit with its own private bathroom close to Wells Beach, and Route 1 Shopping, restaurants , etc. High-speed WiFi, AC/Heat, comfy queen sized bed, mini fridge, microwave, table with 2 chairs, ceiling fan, first aid kit, iron, and blow dryer. I don't do long term rentals for the summer but please message me if you'd like to do a long term rental from October to May.

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Kennebunkport holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Kennebunkport

4.99 out of 5 average rating, 67 reviews

Cottage in Cape Porpoise

Luxury KPort Cottage w/ private water access

KristinRating, 5 stars8 months ago

The perfect place to unwind and relax after a day spent exploring Kennebunkport! The cottage was super cozy, bed was comfortable and the hosts provided everything needed for an enjoyable stay! We would definitely stay here again. Thanks Dionne and Tim for sharing your lovely home!😊 Kristin & Kevin Dodson

4.96 out of 5 average rating, 78 reviews

Guest suite in Kennebunk

Beautiful PRIVATE Oasis - On the River's Edge

AmyRating, 5 stars3 days ago

Perfect spot in Kennebunk! Host was great and the suite was very clean and everything needed for a relaxing and enjoyable stay. Walkable to many things including new bookstore, restaurants, coffee and farmers market. Place was quiet and lovely. The backyard looking down to the river is quite beautiful. I will return!

Guest suite in Kennebunkport

4.99 out of 5 average rating, 139 reviews

Stylish Private Guest Suite

AlexandraRating, 5 stars2 weeks ago

Great experience! Lauren's place was exactly as described, right next to downtown. It was cozy and clean! I would recommend staying at Lauren's.

5 out of 5 average rating, 10 reviews

Flat in Kennebunkport

Bass Cove Point Guest Apartment

JeniferRating, 5 stars3 days ago

So happy we stayed here! What a beautiful, newly renovated place. It was immaculately clean and thoughtfully put together. The location couldn’t be better — right on the money. Highly recommend!

5 out of 5 average rating, 49 reviews

Guest house in Arundel

Kennebunkport - 1 mile to Dock Sq - Brookside

AnnRating, 5 stars1 week ago

We loved the Bungalow, it was just right for 2 people. We enjoyed sitting on the back deck and watch the Brook, it was beautiful by day and the sound of the Brook at night was peaceful. The birds were just lovely too, all kinds. We also would watch the Brook go to high tide and then low tide. The Bungalow had everything we needed, even a washer and dryer if needed. We definitely would like to stay again on our next getaway. 😁

Cabin in York

5 out of 5 average rating, 3 reviews

NEW! York Cabin - Near Ogunquit

MichaelRating, 5 stars2 weeks ago

Me and my growing family had a wonderful stay at the property. Great privacy, beautiful wooded lot surrounded by nature for or son to explore. Conveniently located and easy access made our action pack schedule feel like we were a local! Very well appointed home, great beds and toilets that are something to write home about. We cannot wait to be back! Great communication with the host, which made all arrangements simple and effortless. Home design is thoughtful and purposeful, ensuring management of the little ones easy because of a suburb layout and control of staircases with lockable doors. Cannot wait to be back!

4.81 out of 5 average rating, 375 reviews

Excellent Location

LisaRating, 5 stars1 week ago

John was very friendly and made our stay easy and enjoyable. The location was great, 20 minute walk down to the beach and just a few minutes away from several restaurants and shops. It was a good location to explore further north and south too as we loved all the little towns in each direction.