Holiday rentals with a kayak in Greater Toronto and Hamilton Area

Find and book unique kayak rentals on Airbnb

Top-rated Accommodation with a Kayak in Greater Toronto and Hamilton Area

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Top Guest favourite
The chalet’s exterior features large, triangular windows that allow natural light to fill the interior. A spacious deck extends from the building, surrounded by lush green grass. A hot tub is positioned nearby, offering an inviting spot for relaxation.
Chalet in Peterborough
4.96 out of 5 average rating, 105 reviews

Stunning Waterfront Chalet

Stunning Waterfront Chalet. Excellent for releasing the stresses of everyday life. Put your feet up on the deck or dock and relax your body in the hot tub. For the extra hot days the water is refreshing and weed free. The cottage has two A/C units to keep you cool on the hottest days. The floating island is great for the kids to swim to and have hours of fun splashing in the water or great for tanning. Lots of water toys to play with and be entertained and explore. Sea Doos on site for rent also

Top Guest favourite
The exterior of the guest house features a wrap-around composite deck with glass railing, overlooking the direct waterfront views of Lake Ontario. The structure is surrounded by lush greenery and is complemented by large windows allowing natural light into the living space.
Guesthouse in Lincoln
4.96 out of 5 average rating, 321 reviews

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS JULY 9-11 (2 nights/3 days) JULY 16-18 (2 nights/3 days) JULY 25-31 AUG Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include orchards and the Lake.

Top Guest favourite
A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.
Condo in Innisfil
5 out of 5 average rating, 219 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

Top Guest favourite
An outdoor stone wall shower is positioned next to a wooden deck, leading to a private pond. The deck features a covered area with dining furniture. Lush greenery surrounds the space, and sunlight illuminates the scene under a clear blue sky.
Shipping container in Clarington
4.98 out of 5 average rating, 111 reviews

Rustic Ridge

Rustic Ridge Tiny Cabin - Cozy Escape on Private Pond **Cabin will have to be winterized when temperature drops meaning no running water and outdoor shower, jugs of water will be supplied to rinse after sauna, bottled water in dispenser also provided.*** Welcome to Rustic Ridge Tiny Cabin, a unique shipping container retreat on the back of our property. Nestled by a private pond with a fountain, this serene cabin is the perfect escape for nature lovers and those looking to unwind in comfort.

Guest favourite
Cottage in Georgina
4.9 out of 5 average rating, 201 reviews

Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking

Bright and airy waterfront cottage in one of Lake Simcoe’s most desirable areas. The open-concept layout and unique lot design offer stunning lake views from almost every room. Enjoy custom furnishings, stylish decor, and a fully equipped kitchen—perfect for relaxing getaways or extended stays. Whether you're here for a peaceful retreat or lakeside fun, this cottage provides comfort, beauty, and convenience in a serene upscale setting. Ask us about fun activities that Lake Simcoe offers.

Top Guest favourite
A fire pit with flames is situated near the water's edge, surrounded by smooth stones. An Adirondack chair is positioned to face the lake, offering a view of the serene water and a colorful sunset in the background.
Guest suite in Port Perry
4.89 out of 5 average rating, 273 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.

Guest favourite
Cottage in Georgina
4.95 out of 5 average rating, 131 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!

Guest favourite
An aerial view captures the waterfront trailer set against lush greenery, with a private deck featuring seating arrangements. Nearby, two kayaks await by the water, and a fire pit is surrounded by logs. The tranquil lake reflects the surrounding foliage.
Tiny home in Acton
4.86 out of 5 average rating, 141 reviews

Lakefront 1 bedroom tiny home

Reconnect with nature at this unforgettable escape. Enjoy a wonderful stay in our lovely waterfront trailer located on Breezes Trailer park. It is a private quiet trailer park with 15 acres of nature and private access to Fairy Lake (Acton). Trailer is suitable for couple or small family. It is suited to people looking to relax and enjoy the scenery, explore the lake on kayak, exercise and explore on water bikes, fishing in the lake, enjoy some outdoor movies or campfire or under the stars.

Guest favourite
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
4.92 out of 5 average rating, 205 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.

Guest favourite
A serene view of Alder Lake is captured, featuring a wooden dock with red Adirondack chairs. Lush greenery frames the scene, including a large, weeping willow tree. Kayaks are visible along the shoreline, with calm waters reflecting the bright blue sky and scattered clouds.
Cottage in New Dundee
4.89 out of 5 average rating, 141 reviews

Cosy Lakefront Cottage

Enjoy 150 feet of lakefront just outside the city limits. This fully remodeled cottage has fun for all to enjoy. There are kayaks, a canoe and a paddle boat for those that live on the water. We also have floaties if you just want to lounge and relax by the water. In the winter months you can also bring your ice skates and enjoy skating on the lake and then coming inside for a hot drink by the propane fireplace. The 800 square feet of deck overlooks the water for all your needs.

Top Guest favourite
A vintage boxcar exterior is framed by trees, with string lights adding a warm glow. A private hot tub situated nearby invites relaxation, while a barbecue grill is positioned on the patio. A light dusting of snow covers the ground, complementing the natural surroundings.
Tiny home in Utopia
4.95 out of 5 average rating, 125 reviews

Boho Vintage Box Car Utopia

Escape to a one-of-a-kind retreat in a beautifully renovated 2-bedroom vintage boxcar with a private hot tub. High speed internet available for entertainment or a work vacation. Located on Rustic Roots Farm & Eco-Retreat just 1 hr north of Toronto. Explore 64 acres of trails, relax by the spring-fed pond, enjoy bonfires, or fish along the winding Nottawasaga River. With organic gardens, wildlife, and birdwatching all around, it’s the perfect place to slow down and reconnect.

Top Guest favourite
A communal outdoor space is presented, featuring wooden cabins with green roofs surrounded by tall trees. In the foreground, Adirondack chairs are arranged around a fire pit, with a hammock and a barbecue grill nearby, all set on a gravel surface.
Tiny home in Kimberley
4.99 out of 5 average rating, 147 reviews

Boho Beaver Cabin 1 with saltwater hot tub & sauna

So close, yet so far. Only 2 hours north of Toronto, 15 minutes to the base of Blue Mountain. This 108 square foot of "adorable" offers a four-season experience with a communal salt water hot tub and sauna. A river runs through it, the majestic Beaver River! This charming, boho inspired tiny cabin for two is nestled on an 80 acre property surrounded by farm fields, wildflowers, and ancient woodlands Check out our social media for more information and photos at: @BohoBeaver

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