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Vacation rentals with a kayak in Durham Region

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Durham Region

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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A spacious backyard features a well-maintained lawn with red Adirondack chairs arranged around a stone fire pit. A wooden playground set with a slide and climbing structure is visible, alongside a large cottage with multiple levels and large windows that reflect the sky.

Cottage in Ennismore

4.89 out of 5 average rating, 120 reviews

Luxury Modern Cottage Best Sunrises with Hot Tub

*4 SEASONS COTTAGE*Newly built custom luxury cottage, with brand new beds, mattress, furniture and furnishings. Cottage right on the lake , great fishing right off the dock, amazing boating, east exposure provides the best sunrises right from master bedroom, bon fires lake side, all bedding, linen and towels provided, all life jackets provided, tankless BBQ, ice fishing is available in winter, large hottub, pool table, ping pong, enjoy the canoe, kayaks and SUP. Quarry Golf Club is 5 mins away.

Top guest favorite

A charming cabin is nestled among tall evergreen trees, surrounded by well-maintained landscaping. Stone steps lead to the entrance, illuminated softly by exterior lights. The lush green lawn flows gently, creating a serene outdoor setting.

Cabin in Whitchurch-Stouffville

4.99 out of 5 average rating, 114 reviews

Lakefront getaway for two on Musselman's Lake

An amazing getaway space for two and your dog on beautiful Musselman's Lake, close to Toronto but feels like you're in the Muskokas. This rustic designer one-bedroom cabin is the original attached cottage that our house grew from. Sit at the dock or on your patio to watch the spectacular sunsets. Have a coffee in the backyard and watch the sunrise over 160 acres of trails out your back door. This is your retreat with high-speed internet, full-size kitchen & dining area to enjoy cottage life.

The exterior of the waterfront home is shown, featuring large windows and a spacious upper deck with multiple lounge chairs. A stone pathway leads to the entrance, surrounded by well-maintained green grass and trees, providing a serene backdrop as evening light begins to illuminate the structure.

Cottage in Trent Lakes

4.98 out of 5 average rating, 104 reviews

Lux - 5 Bdrm - Waterfront, Hot Tub, Game Room+Plus

Direct waterfront cottage is perfect for multi family getaway. Situated directly on 160 ft of waterfront on Buckhorn Lake with endless fun. Boasting a hot tub, 30 foot upper deck with glass rail that lights up BLUE at night, beach volleyball, beach area for little ones, master bdrm walkout to deck & breathtaking water views from EVERY bedroom! For the kids and adults alike there is a ping pong table, foosball, pool table, poker table, pac-man arcade, 4 kayaks, 2 SUP, and paddleboat to enjoy!

A wooden deck features a rectangular glass-top table surrounded by four folding chairs. Lush greenery provides privacy, with a serene lake view and sunset reflected in the water. The space invites relaxation and outdoor enjoyment.

Guest suite in Port Perry

4.88 out of 5 average rating, 230 reviews

Sunset Haven

Cozy suite, this location provides the very best of the outdoors for cottaging enthusiasts 45 minutes from the GTA. Found on the outskirts of Port Perry near the Blue Heron Casino and on the shores of Lake Scugog, you will find great fishing, swimming, and boating at your doorstep. Also great lounging on the deck/dock! The casino is 5 min drive and the town of Port Perry with its good restaurants and shopping is 10 min car ride or take your boat! Unfortunately, no pets are allowed by guests.

The image showcases a scenic waterfront view featuring a private dock extending toward a charming cottage. Vibrant red chairs are positioned on the lawn, surrounded by lush greenery. The calm water reflects the blue sky, creating a serene atmosphere for relaxation.

Cottage in Georgina

4.96 out of 5 average rating, 116 reviews

Resort-Style Luxury Waterfront Cottage

Experience luxury at our 5-star, Superhost-rated waterfront cottage on Lake Simcoe, just 80 KM from Toronto! A guest favorite, it offers breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters, and enjoy the patio, BBQ, bar, lounge, kayaking, and fishing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for the perfect blend of relaxation and adventure!

A lakefront cottage is set on a grassy area beside the water, featuring a wooden dock extending toward the lake. The exterior shows a welcoming porch and surrounding trees provide shade. Stone borders accentuate the shoreline, creating a natural beach-like atmosphere.

Cabin in Nestleton Station

4.91 out of 5 average rating, 157 reviews

Cozy, Quirky and Modern Lakefront Cottage

Welcome to the Scugog Sugar Shack! Just 70 mins away from Toronto, escape to enjoy picturesque sunsets at this cozy lakefront cottage nestled under the largest collection of mature sugar maples on Scugog Point. This 2 bedroom open concept 1940s cottage has been updated with all the creature comforts while staying true to its quirky roots. With private access to Lake Scugog, known for fishing, kayaking, paddle boarding and swimming, bask in the sun all day & sit by a fire under the stars.

A modern kitchen is showcased with sleek white cabinetry and contrasting dark hexagonal tiles. A large refrigerator and kitchen counter space are visible, along with a coffee maker and wall clock. Natural light enters through a window, illuminating the contemporary design.

Apartment in Port Perry

4.96 out of 5 average rating, 112 reviews

Romantic & Cozy Countryside luxury loft with views

Romance in the Country. Getaway from the hustle with your sweetheart, to play, rest/work stay-cation. Newly built, full kitchen, bath/laundry/EV charger. Great trails, theatre, shopping in quaint downtown Port Perry, boating, golfing, equestrian farm, museums, & amazing 5 star restaurnts in Port Perry. Enjoy the pond on the property & lots of places to enjoy peace & quiet together! Ask about our Chef and Pontoon experiences. 1 hr from TO, 8 min to Port Perry. We have 2 rms queen loft/king.

An aerial view of the cottage situated near the Upper Buckhorn Lake is presented. The property is surrounded by lush trees, with a private dock extending into the water. Nearby, a well-maintained lawn features a circular firepit area and neatly arranged trees.

Cottage in Curve Lake

4.84 out of 5 average rating, 147 reviews

Luxury Log Cottage With Hot Tub And Sauna($)

Luxury Year around log Cottage, located up on the beautiful Upper Buckhorn Lake. This one of a kind property is only 1.5 hrs. from GTA. Enjoy paddle board, canoeing, waterfront, hot tub, firepit, BBQ, fishing, cozy fire place, free WIFI, AC, Fully equipped high end kitchen, private dock, quiet treed neighborhood, all the amenities for an outstanding getaway! 10 minutes drive to Buckhorn Centre. Near to Golf Courses, shopping and dining and hiking. Wood stove Sauna available upon request($).

Top guest favorite

Home in Nestleton Station

4.99 out of 5 average rating, 135 reviews

Retreat 82

Located just a little over an hour from Toronto, this cozy and unique lakefront cottage is the perfect place for a relaxing couples getaway. Offering private access to Lake Scugog with an oversized dock for you to take advantage of water activities, enjoy your morning coffee and watch some of the best sunsets on the lake. The cottage sits only 15 min. from the quaint town of Port Perry where you can go to enjoy its brewery, incredible cuisine, farmers markets, and picturesque Main Street.

A hot tub is positioned on a patio, providing views of the serene lake and distant horizon. Red outdoor chairs surround a firepit, while an umbrella offers shade nearby. The scene is framed by lush greenery and a stony beachfront, enhancing the tranquil setting.

Cottage in Bowmanville

4.9 out of 5 average rating, 172 reviews

“Lakeside Dreams”: All season HotTub w/lake views

Escape to our stunning lakefront family cottage! Enjoy breathtaking views, modern comforts, and the serenity of cottage life. With a private beach, firepit, BBQ, and covered patio, relaxation is guaranteed. Explore the nearby conservation area's trails or cast your line at the fishing creek, just a short walk away. A public beach is 5 min walk. Indulge in the perfect blend of nature and convenience. Book your stay now and create unforgettable memories in our charming cottage retreat!

A wooden dock extends into a calm lake, reflecting fluffy white clouds and blue skies. Lush greenery is visible along the shoreline, creating a serene natural backdrop.

Cottage in Kawartha Lakes

4.93 out of 5 average rating, 135 reviews

Ke's Rustic Retreat in Kawartha Lakes

WELCOME TO KE’S PLACE! This rustic, private, 4 season, lakefront cottage on Pigeon Lake features 3 bedrooms, 3 full/double sized beds, large bright living room with sleeper sectional, newly renovated kitchen, updated bathroom, private dock, indoor fireplace, enclosed patio room, outdoor fire pit, and large yard for games and more. Located approximately 1.5 hours from Toronto, this cottage is the perfect place for families and friends to escape the hustle and bustle, relax and unwind.

A serene view is presented through large glass windows, showcasing a snowy landscape at dusk. The soft colors of the sunset reflect over the lake, with trees lining the horizon. A cozy chair is positioned on the porch, inviting relaxation amidst the tranquil setting.

Cottage in Brechin

4.92 out of 5 average rating, 107 reviews

Cottage on Lake Simcoe Amazing lake Views

Lakefront 3-bedroom cottage on Lake Simcoe – perfect for families! . Please note You can see the lake from living room. Features a fully equipped kitchen and two 3-piece washrooms .Enjoy stunning lake views, BBQ, fishing, and crystal-clear shallow water safe for swimming (weather permitting). Apple picking in Fall and icing fishing in winter! Water access and beach area are shared with a few friendly neighbors. Fast starlink internet! Owner Allergic issue ,so please NO PET allowed.

Vacation rentals for every style

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Popular amenities for Durham Region kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

The exterior of a lakeside cottage is shown, featuring a large wooden deck and a covered seating area. Surrounding foliage includes tall trees reflected in the water, which mirrors the clear blue sky. Direct access to the shoreline enhances its tranquil setting.

Home in Peterborough

4.93 out of 5 average rating, 43 reviews

Kawartha Lakes , Chemong lake front property

A fire pit area is surrounded by multiple Muskoka chairs, with a vibrant fire burning in the center. The expansive lawn is meticulously landscaped, framed by lush greenery and a view of the lake house's covered porch, illuminated by soft evening light.

Home in Georgina

5 out of 5 average rating, 12 reviews

Royal Beach Lake House & Spa w/ Hot Tub & Sauna

An aerial view captures a stunning lakeside property featuring a spacious deck, a swimming pool, and a private dock. Surrounded by lush greenery, the retreat offers outdoor seating areas and kayaks, inviting relaxation and outdoor activities in a serene environment.

Home in Peterborough

4.94 out of 5 average rating, 33 reviews

Lakeside Retreat - Pool+GolfSim+HotTub+Sauna+Gym

Home in Kawartha Lakes

5 out of 5 average rating, 3 reviews

Floating Dreams

A circular stone patio is positioned near the water, featuring a dining table surrounded by chairs. A barbecue grill and a propane tank are nearby. The tranquil lake and a dock with boats can be seen in the background, framed by lush greenery.

Home in Little Britain

4.95 out of 5 average rating, 20 reviews

Luxurious waterfront paradise on lake Scugog

Top guest favorite

A serene exterior view of a modern home features a spacious deck with red umbrellas, inviting outdoor seating. Lush green grass surrounds the property, while trees provide a natural backdrop. The architecture showcases angular roofs and multiple windows, creating a welcoming atmosphere.

Home in Uxbridge

5 out of 5 average rating, 31 reviews

Udora house on the river!

A spacious living area features a large dining table surrounded by wooden chairs. A cozy sectional sofa is positioned in front of a 120-inch 4K projector, displaying a streaming service menu. Natural light pours in through multiple large windows, creating a bright atmosphere.

Home in Bowmanville

4.88 out of 5 average rating, 86 reviews

Axe-Throwing, Private Beach, Hot Tub & Home Cinema

A spacious living area features vaulted wood-clad ceilings and large windows that allow ample natural light. Blue sofas are arranged around a wooden coffee table, while a small dining space is visible in the background. A subtle area rug adds texture to the floor.

Home in Beaverton

4.87 out of 5 average rating, 38 reviews

Unique Lake Simcoe Boathouse Cottage-3BDRM/2WR

Cottage rentals with a kayak

A modern living area features a contemporary gray sofa positioned near large windows that offer scenic views of the water. A round glass coffee table sits on a textured rug, and colorful accent pillows enhance the seating area. Natural light fills the space.

Cottage in Bowmanville

4.75 out of 5 average rating, 4 reviews

Lake Front Escape - Hot tub!

Cottage in Peterborough

5 out of 5 average rating, 38 reviews

Enjoy your getaway at Cedar Hill Lakehouse

Cottage in Caesarea

5 out of 5 average rating, 24 reviews

Lakefront Cottage Weeklong Stay Over Xmas or NYE

Top guest favorite

Cottage in Lakefield

4.99 out of 5 average rating, 72 reviews

Luxury Waterfront Cottage (5,000 sqft w/ Hot Tub)

A cozy corner is depicted with a uniquely designed chair featuring a woven seat and warm cushions. A small table holds a book and a beverage. A wooden sign displayed on the wall contributes to a cottage theme, while a view of greenery is visible through the window.

Cottage in Little Britain

4.91 out of 5 average rating, 32 reviews

Cozy All-Season Lakeside Cottage with Sauna

The cottage features a rustic exterior with a stone chimney and large windows, inviting natural light. Below, red Adirondack chairs are arranged around a fire pit, creating a cozy outdoor gathering space. Lush greenery surrounds the seating area, enhancing the lakeside setting.

Cottage in Kawartha Lakes

5 out of 5 average rating, 4 reviews

*The Loon Street Lodge ! * A Lakefront Cottage !

Cottage in Port Perry

4.9 out of 5 average rating, 31 reviews

Luxury Lakefront Cottage

Top guest favorite

A welcoming deck extends from the cottage, featuring a comfortable wicker chair adorned with a colorful cushion. A picnic table is visible alongside a fire pit, with Adirondack chairs arranged near the water's edge, framed by tall trees and a scenic lake view.

Cottage in Kawartha Lakes

4.94 out of 5 average rating, 32 reviews

Dreamy 2BR Cottage on point, surrounded by water

Cabin rentals with a kayak

A cozy cottage exterior is depicted, featuring white siding with black trim. A wooden deck leads to the entrance, bordered by well-maintained grass. Flanking the pathway are two shrubs and a decorative lamp post holding a flower basket, enhancing the welcoming charm of the property.

Cabin in Beaverton

4.88 out of 5 average rating, 57 reviews

Thorah Centennial park Lake Simcoe Beaverton Ont

A red cabin is surrounded by green trees and grass, featuring a spacious deck with multiple chairs. A fire pit made of stones is placed on the lawn, providing a cozy outdoor gathering spot. Natural light bathes the area under a clear blue sky.

Cabin in Uxbridge

4.95 out of 5 average rating, 22 reviews

Cabin by the Lake

A green bicycle sculpture with colorful flower spokes and a 'welcome' sign is positioned in the foreground. In the background, a two-story cottage with cream-colored siding and red roof accents is visible. The surrounding area includes landscaped grass and a paved driveway.

Cabin in Kawartha Lakes

4.45 out of 5 average rating, 11 reviews

R & R Hideaway

A wooden dock adorned with red Adirondack chairs and a parasol offers a tranquil outdoor space overlooking still water, reflecting lush greenery and the cottage in the background. Tall grasses frame the area, providing a natural border along the peaceful lakeside.

Cabin in Uxbridge

New place to stay

Margaret's Luxury Lake Cottage

A serene outdoor view of a green lawn leading to the water's edge, featuring a wooden dock extending into the calm lake. A stone fire pit is situated on the grass, surrounded by seating. The cottage is visible with large windows reflecting the natural surroundings.

Cabin in Kawartha Lakes

4.71 out of 5 average rating, 177 reviews

Cute Rustic Balsam Lakefront Cottage 4 Season

A charming cottage is nestled among trees, featuring a spacious deck with outdoor seating and shaded areas. Two paddle boards are secured against the cottage, highlighting easy access to water activities. Lush green grass surrounds the structure, adding to the inviting outdoor space.

Cabin in Kawartha Lakes

4.67 out of 5 average rating, 6 reviews

The Cedar Cottage

A warm wooden cabin is illuminated by soft outdoor lighting, surrounded by tall trees. A small porch with steps leads to the entrance, while a gravel area in front adds to the rustic charm. The setting evokes a serene atmosphere in a natural landscape.

Cabin in Beaverton

4.95 out of 5 average rating, 39 reviews

Riverside Cabin Getaway

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