Vacation rentals with a kayak in Kennebunk

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Top-rated kayak rentals in Kennebunk

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Guest favorite

Home in Naples

4.99 out of 5 average rating, 151 reviews

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Top guest favorite

Two kayaks, one yellow and one blue, are positioned side by side on a calm riverbank. The surface of the water reflects the overcast sky and surrounding trees, creating a serene scene perfect for outdoor activities.

Cottage in Buxton

4.97 out of 5 average rating, 157 reviews

Peaceful Cottage on Maine Flower Farm

Overlooking the gardens at Ferris Farm, our family-owned specialty cut flower farm, this charming cottage offers a peaceful retreat to relax and reconnect with nature. Take in garden views, sip coffee on the deck, wander through the flowers, kayak the river, and end your day with a cozy bonfire under the stars. Use the cottage as your home base to explore beaches, or head into Portland for breweries, coffee shops, and great dining. Perfect for a solo retreat, romantic escape, or work getaway.

Top guest favorite

Two kayaks are positioned on the grassy shore, facing a serene cove surrounded by trees and charming houses. A wooden dock extends into the water, where boats can be seen. Bright blue skies and scattered clouds enhance the tranquil atmosphere.

Home in Kennebunkport

4.98 out of 5 average rating, 107 reviews

Luxurious 5 bedroom on the ocean, w/ dock & kayaks

Historic 1735 home on a spacious one-acre property overlooking the ocean. Enjoy swimming from the dock in Cape Porpoise’s protected cove. Two kayaks provided for exploring the lighthouse & picnicking on nearby islands. Stroll past picturesque lobster boats to the town pier, where restaurants serve fresh local lobster & drinks. Walk to morning coffee, pastries, a local grocery store, athe renowned Nunan’s Lobster Hut. Just two miles from Kennebunkport and a nine-minute drive to Goose Rocks Beach.

Guest favorite

A wooden dock extends into the calm waters of Littlefield Pond, surrounded by lush greenery. The still surface of the water reflects the blue sky and trees, creating a serene atmosphere. Delicate plants can be seen in the water near the dock, enhancing the natural beauty.

Treehouse in Sanford

4.9 out of 5 average rating, 543 reviews

Luxury Year-round Treehouse with private hot tub

The Canopy 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.

Top guest favorite

A serene waterfront view is captured during sunset, showcasing vibrant hues reflecting on calm water. A wooden deck is shown in the foreground, complemented by lush grasses and trees. The distant dock is visible, enhancing the tranquil lakeside atmosphere.

Guest suite in Dover

4.88 out of 5 average rating, 233 reviews

Lovely Waterfront Suite, New Hampshire Seacoast

Great location to enjoy the New Hampshire Seacoast. Just a few minutes to Portsmouth and Durham, perfect romantic getaway, or convenient spot to visit your student at the University of New Hampshire. Wonderful one bedroom suite, private patio. Enjoy the waterfront deck, have your breakfast or cocktail there. This is place is truly magical. You will enjoy how special it is. Close and convenient spot on the New Hampshire Maine boarder. New this summer an outdoor KITCHEN! Everything you’ll need

Guest favorite

A lakefront chalet is framed by lush trees, featuring a spacious deck with seating and a view of the water. A kayak rests on the sandy shore, leading to a clear lake that reflects the surrounding greenery and the home's inviting design.

Cabin in Barnstead

4.95 out of 5 average rating, 242 reviews

Scenic Lake and Ski Chalet: Hot Tub & Dreamy Views

This romantic & family friendly lakefront chalet comes with a private beach, hot tub, camp fire, and stunning views. It’s a serene home base to explore everything the Lakes Region has to offer. Mid Apr-Oct we also provide kayaks and paddle board. Enjoy the beach, swim, kayak, bike, fish, hike, or explore quintessential New England towns and food scene. Or simply dine with a view and play board games. We have poured our hearts into making this place romantic yet practical for families. Enjoy!

Guest favorite

A bright, open kitchen and living area is designed with large windows allowing natural light. A central island with chairs offers space for dining or socializing. A comfortable seating area is visible, complemented by warm wood accents and serene artwork on the walls.

Cottage in Lyman

4.84 out of 5 average rating, 110 reviews

RK North : All season Waterfront cottage with dock

Waterfront get away !You will love the cottage in any season - right on the pond! Enjoy a private dock, swimming and floating right at your door. Relax at the fireplace under twinkle lights , enjoy birdwatching, hiking and swimming during your stay. Lots of ATV and snowmobile trails near by. A close drive to Kennebunkport where your find beach’s , shops and restaurants galore. The cottage has 2 kayaks and a canoe for use during your stay. There are 2 Smart TVs for streaming. Shows and DVD

Guest favorite

A warm and inviting living area showcases a stone fireplace framed by soft lighting. Two plush armchairs are positioned near a wooden coffee table. A cozy sofa adorned with a colorful blanket complements the wooden beams and walls, creating a tranquil atmosphere.

Cabin in Conway

4.95 out of 5 average rating, 171 reviews

The Conscious Cabin

Your cozy, mountain retreat awaits. Settle by the fire in this thoughtfully renovated log cabin, located in the heart of the White Mountains & less than 10 minutes from downtown North Conway's local shops, restaurants & adventures. Just 5 minutes from hiking Mt. Chocorua, paddling Lake Chocorua & exploring the scenic Kancamagus Highway. Featuring a bedroom, loft, full bathroom, kitchen, tea/coffee bar, fireplace, outdoor shower, firepit & more. Bask in the restorative magic of cabin living.

Top guest favorite

The studio apartment features a queen size bed with a striped duvet and two large leather chairs. A wooden desk is positioned near a window, while the warm wooden floor adds to the inviting feel of the space.

Apartment in Wakefield

4.98 out of 5 average rating, 102 reviews

Clean, quaint studio apartment on small farm

Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

Top guest favorite

An aerial view captures the cottage's location near a winding marsh, surrounded by lush greenery. The nearby stream flows gently, with a cluster of cottages visible along the road. The setting suggests tranquility and proximity to nature's beauty.

Cottage in Kennebunkport

4.98 out of 5 average rating, 111 reviews

Charming Designer Cottage on Marsh

Cozy renovated Cottage w/ stunning marsh views is short walk to beautiful Goose Rocks Beach. No need to pack gear, cottage comes equipped w/ 2 kayaks, 2 bikes/helmets & beach buggy. Stroll to general store for morning coffee, walk on beach or head out and explore the Kennebunks & Cape Porpoise. Our community offers world class dinning, boutique shopping , entertainment and beautiful hiking trails all close by. At days end kick back & relax by the fire pit...”The way life should be”

Top guest favorite

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

4.99 out of 5 average rating, 452 reviews

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.

Top guest favorite

A compact sleeping area features a queen-sized bed with a decorative white throw. Flanking the bed are two bedside tables, each topped with a lamp. Neutral-colored walls and soft lighting create a calm and inviting ambiance.

Apartment in Windham

4.99 out of 5 average rating, 165 reviews

The Roost - lovely one bedroom efficiency unit

Staying at the Roost means you will be 15 minutes to the ocean, the airport and to the Old Port; 10 minutes to nearby lakes and rivers; 5 minutes to everything downtown Westbrook has to offer, including many restaurants, parks, live music venues, shopping and a movie theater: what you are looking for is nearby! Kick back and relax in this calm, stylish space with a queen-sized bed, kitchenette, dining/work area, excellent wifi, a full bathroom and a big yard.