Holiday rentals with a kayak in York

Find and book unique kayak rentals on Airbnb

Top-rated Accommodation with a Kayak in York

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

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Top Guest favourite

Two black Muskoka chairs are positioned on a wooden dock, facing a serene lake. The sky is filled with soft clouds, casting gentle reflections on the water's surface, creating a peaceful atmosphere for relaxation.

Home in Gilford

5.0 out of 5 average rating, 49 reviews

Blu Lake House | Waterfront May/June Special

Enjoy a peaceful two-story waterfront cottage with beach access. The perfect escape! Located an hour from Toronto. This cottage includes pedal boat, kayak, paddle board, inflatable rafts, volleyball net, basketball net, and swings facing lake view. Unwind with Netflix, or enjoy the game room, which includes a pool table, foosball, hockey, basketball, and Xbox 360. Local attractions such as the Gateway Casino, Cooks Bay Marina, Indy Go-Kart, Tanger Outlet, Local Eateries, Farmer Markets and more.

LocationOutdoor spacesCleanliness

Guest favourite

Cottage in Georgina

4.9 out of 5 average rating, 211 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.

Outdoor spacesValuePets

Guest favourite

An open-concept living space features modern furnishings and sleek cabinetry. A spacious grey sofa and an accent chair are set around a coffee table. The kitchen area includes stainless steel appliances and a breakfast bar with four stools, creating a warm and functional atmosphere.

Condo in Innisfil

4.85 out of 5 average rating, 188 reviews

Marina view at Friday Harbour 2bd/2bth Pool option

This Black Cherry model condo is the most sought after layout at Friday harbour, featuring a spacious-well-designed kitchen, living room and balcony area with two bedrooms and two bathrooms ideal for families, couples, or solo travellers. Enjoy comfortable sleeping with a king bed in the master bedroom also featuring an ensuite bath and walking closet, and a Queen bed in the second bedroom. Enjoy a view of the beautiful landscaped courtyard out to the marina while lounging or eating outside.

ValueLocationHospitality

Guest favourite

A serene backyard view showcases a well-maintained lawn bordered by diverse greenery and a calm river. Several seating areas, including white chairs and a shaded gazebo, provide relaxation spots. A swimming pool is visible, reflecting the clear blue sky above, creating a peaceful outdoor setting.

Home in East Gwillimbury

4.98 out of 5 average rating, 62 reviews

Private river access with pool, canoes, kayak

Welcome to our cozy and peaceful cottage-like getaway near Toronto and with modern conveniences close by - ideal for young families or small groups. Guests enjoy exclusive use of the spacious 2nd floor with separate entry, like a fully stocked private apartment (see below for details). Please note: - Owners live on the 1st floor with a friendly dog (separate entrance for guest). - no A/C in living/dining area, but ceiling and industrial fans provided; each bedroom has a portable A/C unit

ValueOutdoor spacesFamily

Top Guest favourite

Cottage in Innisfil

4.86 out of 5 average rating, 266 reviews

3BR on Lake Simcoe | Gorgeous Views 1hr From City

Escape the city and unwind at our peaceful three-bedroom lakefront cottage on Lake Simcoe, just one hour north of Toronto. With 129 feet of private waterfront, expansive lake views, and shallow swimmable shoreline, it’s the perfect year-round getaway for families, couples, or friends looking to relax and reconnect. 🌅 Stunning sunrise lake views 🏖️ 129 ft of private waterfront 🏊 Shallow, swimmable shoreline 🔥 Cozy all-season retreat 🌲 Quiet and peaceful setting 🚗 Just 1 hour from Toronto

ValueOutdoor spacesLayout

Top Guest favourite

A serene outdoor space is featured, illuminated by soft lights under a night sky. A patio area hosts a seating arrangement, surrounded by lush greenery and a fire pit. The water is visible in the background, enhancing the tranquil setting.

Cottage in Beaverton

4.99 out of 5 average rating, 85 reviews

Private Waterfront Cottage at Lake Simcoe

Luxurious and spacious private waterfront cottage at Lake Simcoe. Enjoy stunning lake and sunset views. An hour from Toronto, this newly renovated cottage offers a fully equipped kitchen, 5 bedrooms, 3 bathrooms, and a spacious dining and living area. Additionally, beautiful outdoor patio, BBQ grill and private fireplace, perfect for relaxing with friends and family. This cottage offers easy access to a private waterfront to enjoy water based activities such as swimming, boating, and fishing.

Outdoor spacesLocationHospitality

Guest favourite

Home in Georgina

4.9 out of 5 average rating, 49 reviews

Sunset Harmony on Cook’s Bay

🌅 SUNSET HARMONY | Cook's Bay Waterfront Retreat One of the last chances to enjoy summer on beautiful Cook's Bay! Escape to our 4.88★ waterfront retreat for families and groups. 🏡 Main House + Private Studio (exclusive use) ✔ 4 bedrooms • 3 bathrooms • 2 kitchens ✔ NEW private dock with lake access & swimming steps ✔ Year-round hot tub & wood-fired sauna ✔ Kayaks, paddle boards & paddle boat ✔ Spacious pergola deck with west-facing sunsets Relax, reconnect, and create unforgettable memories.

Outdoor spacesLocationKitchen

Guest favourite

Cottage in Georgina

4.96 out of 5 average rating, 138 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!

LocationValueBackyard

Superhost

The living room features large windows, offering a view of the lake. A spacious dark sofa is arranged around a coffee table, complemented by a side table with a lamp. Light-colored walls and wooden floors enhance the bright and open atmosphere.

Bungalow in Georgina

4.81 out of 5 average rating, 127 reviews

Lake Simcoe Retreat

Holiday retreat on Lake Simcoe with Sunset view. Front bedrooms and kitchen facing the river and Living room, Dining room, other rooms and open kitchen facing the Lake. You can enjoy the views from every part of the house. Totally renovated interior. High speed internet, a work space, Close to many world class family activities including Fishing, Hunting, Ice Fishing, Snowmobiling. Conveniently located an hour from Toronto, closest small town 5 minutes drive and Sutton town 12 minutes drive.

ValueOutdoor spacesBackyard

Guest favourite

Condo in Innisfil

4.92 out of 5 average rating, 236 reviews

The Friday Flat | Sunny Escape by the Marina

Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake Come experience the ultimate waterfront getaway at Friday Harbour

Outdoor spacesLocationPool

Superhost

A wooden dock extends over a serene pond, featuring two red Adirondack chairs positioned facing the water. Surrounding trees are visible in the background, reflecting gently on the calm surface of the pond under a clear blue sky.

Cottage in Uxbridge

4.81 out of 5 average rating, 118 reviews

Cozy Hobby Farm Cottage in Uxbridge

*4 SEASONS COTTAGE*Stunning cottage retreat at Uxbridge,where you can enjoy the perfect balance of tranquility and entertainment.Our 4-bedroom cottage sleeps up to 12 guests, it's the ideal location for families or groups of friends looking to unwind and make lasting memories. You can also take advantage of our BBQ space,you can grill up mouthwatering burgers and steaks while taking in the fresh country air.The barn is not part of the rental and there are no animals inside or in property.

Outdoor spacesLocationKitchen

Top Guest favourite

Condo in Innisfil

4.96 out of 5 average rating, 178 reviews

Upscale Spa w/ Hot Tub-Private Sauna-Penthouse

Welcome to our most Dramatic & Romantic Penthouse Spa Getaway Suite! Reconnect with your loved one or celebrate that special milestone in our professionally designed to play with all your senses spa suite, this escape will leave you feeling refreshed and rejuvenated! Cozy up to any of 3 fire elements and then cleanse and detox in your own private in-suite Infrared Sauna! Cook up a gourmet meal in our fully equipped chef's dream kitchen and year round Weber BBQ for grilling!

Outdoor spacesLocationCheck-in