Holiday rentals with outdoor seating in Kennebunkport

4.91 out of 5 average rating, 122 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.

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

Enjoy this 2nd floor getaway in this totally quiet & cozy spot with beautiful sunrises and awesome views off the back deck. Close to beaches and town but far enough away to be secluded from the hecticness. Lots of nature trails very close by. Roads have bike/ walking lanes. Many fresh seafood restaurants & eateries close by. Kayaks & bikes for use are available. Free parking on site. Enjoy a complimentary bottle of wine when you visit. **(Waivers must be signed for kayak & bike usage)

4.95 out of 5 average rating, 102 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.

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.

4.93 out of 5 average rating, 138 reviews

Farmhouse Experience in a Beachside Community

2026 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.

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.

4.98 out of 5 average rating, 361 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

5 out of 5 average rating, 137 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

Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

4.96 out of 5 average rating, 244 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.

5 out of 5 average rating, 106 reviews

Home in Kittery

Seacoast Escape with a View

Enjoy the peace and tranquility of staying in Kittery Maine’s exclusive waterfront area. • Walk to downtown Portsmouth • 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! See our other home and awesome reviews: airbnb.com/h/pepperrellparadise

4.88 out of 5 average rating, 139 reviews

A sandy beach stretches into the distance, visible from a coastal property. The exterior features a light-colored shingle design, with a covered porch offering seating. Green shrubbery lines the foreground, creating a natural border against the ocean backdrop and clear blue sky.

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 !

4.93 out of 5 average rating, 194 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!

4.95 out of 5 average rating, 212 reviews

A multi-level cabin constructed from wood blends seamlessly into the surrounding greenery. A spacious deck extends from the second floor, offering shaded seating under an umbrella. Stairs lead down to the ground level, where a welcoming entrance is accessible amidst the natural landscape.

Cabin in Kennebunk

CHowder Cabin Dog Oasis Fenced Yard

🐾 Dog Welcoming Cabin with Fully Fenced Yard Escape to a peaceful, cozy cabin tucked away in the woods — the perfect balance of private seclusion and close proximity to town. Kick your feet up on the deck, breathe in the pine, listen to the birds and frogs, or take a gentle stroll down Bufflehead Cove Lane. Walk quietly and you may spot a heron or egret on the pond!

4.97 out of 5 average rating, 233 reviews

The cabin is illuminated warmly at dusk, featuring a hot tub in the backyard. Outdoor seating arrangements with four chairs are positioned around a fire pit, set against a backdrop of trees, creating a serene and inviting atmosphere.

Cabin in Kennebunk

HotTub/5min to K-port, Pet friendly, @anchorunwind

Follow us on IG @anchorunwind. Escape to a hidden gem nestled in the heart of the Kennebunkport area, where modern comfort meets nature's serenity. Our cabin offers an unforgettable vacation experience. ✭"...A must stay location. The host’s were very helpful and genuine..." ✭"...We’ve travelled all around the world and this is in our top 3 Airbnbs we’ve stayed in."

Popular amenities for Kennebunkport outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

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, 221 reviews

Luxury Home w/HOT TUB & Fire Pit

4.88 out of 5 average rating, 100 reviews

A warm and inviting living area features a wood-burning fireplace set against a stone wall. A spacious, light-colored couch faces the fire, complemented by a round ottoman and a wooden coffee table. Large windows allow natural light to fill the space, showcasing surrounding greenery.

Home in Intervale

As Unique as they come!

4.98 out of 5 average rating, 189 reviews

The cabin exterior is showcased with large glass walls, allowing natural light to fill the interior. A wooden deck is lined with outdoor lights, leading to a hot tub. Surrounded by trees, the peaceful setting is visible, creating a serene outdoor atmosphere.

Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

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, 185 reviews

350 Steps to Gooch’s Beach! Water Views

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, 164 reviews

Quiet cozy cottage close to restaurants, beach

Superhost

4.79 out of 5 average rating, 138 reviews

Farmhouse Retreat Upstairs | Walk to Downtown|

4.94 out of 5 average rating, 114 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

4.98 out of 5 average rating, 377 reviews

A cozy living room features a white-brick fireplace, with a functional gas flame. Stylish furniture includes a patterned armchair and a soft couch, complemented by a light-colored striped wooden floor. Large windows allow natural light and offer views of the surrounding area.

Home in Rye

*Beachfront* Vintage Coastal Cottage - Relaxation

Apartment rentals with outdoor seating

4.8 out of 5 average rating, 161 reviews

A charming farmhouse apartment is visible, featuring white siding and multiple windows. A blue front door is situated near a mailbox on a well-maintained lawn with green grass and small shrubs. The surrounding area includes trees, offering a natural ambiance.

Apartment in Kennebunk

Kennebunk Landing: The way life should be!

4.88 out of 5 average rating, 128 reviews

A light-filled living area features a comfortable grey sofa and natural wood coffee table. A textural area rug complements the space, while a vibrant aqua and white patterned wall adds visual interest. Nearby, a dining table with woven pendant lighting offers an inviting space for meals.

Apartment in Ogunquit

Twenty Shore - 2 Ocean Suite

4.92 out of 5 average rating, 127 reviews

A cozy kitchen area features a gray countertop and green cabinetry. Three barstools are positioned at the counter. Lush plants adorn the sloping ceiling, accompanied by a small dining table and vibrant flower arrangements. A comfortable seating area with decorative pillows completes the space.

Apartment in Saco

Welcome to our BoHo Treehouse! Beaches/Portland

4.99 out of 5 average rating, 185 reviews

A well-appointed bedroom features a spacious bed dressed in soft white linens and a decorative pillow. Natural light filters through the large windows, framed by patterned curtains. A small lamp and a decorative plant highlight the bedside, contributing to a calming atmosphere.

Apartment in Kennebunk

Sea Road Suite

4.97 out of 5 average rating, 196 reviews

A cozy living space features light blue walls and a sloped ceiling. A gray sofa is centered on a neutral area rug, with a wooden coffee table in front. Natural light floods in from a window above, providing a bright ambiance complemented by a floor lamp.

Apartment in York

Cute 1-Bedroom apartment in the woods by the sea

4.92 out of 5 average rating, 486 reviews

A cozy bedroom features a spacious bed adorned with plush pillows. Natural light enters through a skylight and a nearby window, illuminating the soft carpeting. A bedside table holds a lamp, while a small ottoman offers additional seating or storage.

Apartment in Scarborough

Beach retreat - bright, cozy, clean, private!

Apartment in Old Orchard Beach

A spacious room features a comfortable seating area with a sofa and a coffee table. A kitchenette is visible, equipped with essential appliances. The sleeping area includes a king bed, while an ensuite bathroom can be seen in the background, ensuring convenient amenities.

4.9 out of 5 average rating, 124 reviews

160 East by the sea #5 Steps to the beach

4.98 out of 5 average rating, 291 reviews

Apartment in Kittery

Goose Point Getaway (a boutique AirBnB experience)

Condo rentals with outdoor seating

Superhost

A bright living area features two dark leather sofas and a patterned area rug. Natural light enters through large windows adorned with sheer curtains. A coffee table is positioned in the center, and a piece of wall art enhances the space. A plant and floor lamp provide additional warmth.

Condo in Portland

4.94 out of 5 average rating, 147 reviews

Penthouse, Walk To The Old Port & The Beach!

Condo in Old Orchard Beach

4.75 out of 5 average rating, 151 reviews

Attractive 1 bedroom cabin only 50 ft from beach#1

5 out of 5 average rating, 106 reviews

Condo in Intervale

Spectacular Mountain Views, at Eagle Ridge !

Superhost

A cozy living area features wooden beams and paneling, with a comfortable sofa and an ottoman. Natural light enters through the windows, highlighting decorative shelves and a compact kitchen area. A small table and lamp add functionality to the space.

Condo in Scarborough

4.95 out of 5 average rating, 304 reviews

Comfy condo with loft by the beach!

4.96 out of 5 average rating, 121 reviews

Condo in Wells

Steps to Wells Beach + Pool | Coastal Retreat

4.98 out of 5 average rating, 120 reviews

The open layout features a dining area with a rustic table and comfortable seating for six. A cozy sectional sofa is positioned near a door leading to the outdoor patio. Soft lighting and decorative elements create a welcoming and homey environment.

Condo in Conway

3 bd / 2 bth, SLOPE SIDE at Cranmore! Unit#1104

4.95 out of 5 average rating, 221 reviews

A cozy living area features a brown leather sofa and two woven armchairs flanking a wooden coffee table. Light flows in through two large windows with sheer curtains, creating a bright, inviting space. A decorative rug adds warmth to the floor.

Condo in South Portland

Rustic Willard Beach condo ten mins from Old Port!