Vacation rentals with a kayak in Oro-Medonte

4.9 out of 5 average rating, 218 reviews

Cottage in Georgina

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.

4.95 out of 5 average rating, 181 reviews

A spacious hot tub overlooks the Severn River, surrounded by greenery. Chairs are positioned nearby on the grassy lawn, providing a relaxing space to enjoy the water views and sunshine. The calming river scene features boats gently cruising by, enhancing the outdoor experience.

Cottage in Severn Bridge

CARL in Muskoka: Waterfront Cottage with Hot Tub

Enjoy your own piece of Muskoka in this beautiful waterfront cottage! Only 90 minutes from Toronto nestled away on a private road along the Severn River sits CARL. Not a man... but a way of life. The Cottage and River Life! CARL is your retreat from the city, perfect for getting out in nature and experiencing everything life on the water has to offer. Whether you enjoy swimming, kayaking, great fishing or just relaxing on the dock or in the hot tub taking in the views... we've got you covered.

4.84 out of 5 average rating, 191 reviews

The cottage is situated on a well-maintained lawn, framed by trees, with a spacious deck accessible via a stone pathway. Colorful kayaks and a paddle boat are visible by the water, and the sky displays a warm sunset with varying shades of orange and purple.

Cottage in Waubaushene

Waterfront Paradise on the Georgian Bay

This beautiful cottage of 2950sqft faces a breathtaking view of the Georgian Bay with over 105ft of lakefront. During the summer, this cottage is perfect for ATV and bike trails, wateractivities and fishing. The cottage includes kayaks and a paddle board for the guests to enjoy. During the winter, the cottage is ideal for ice fishing and is only a 13 minute drive to Mount St. Louis skiing. Under 10 minute driving distance to beaches, Tim Horton’s, LCBO, gas station, ice cream parlour and more.

4.96 out of 5 average rating, 183 reviews

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

Cottage in Tiny

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

4.96 out of 5 average rating, 145 reviews

Cottage in Georgina

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!

4.97 out of 5 average rating, 176 reviews

A cozy living area features two armchairs and a comfortable sofa, arranged around a central coffee table. Large windows allow natural light to illuminate the space, showcasing views of the surrounding woods. A television and a stylish lamp enhance the room's functionality.

Cottage in Washago

Relax at The Rock: Muskoka Waterfront Cottage

Enjoy fishing, swimming and paddling 22km of the green and black rivers. Paddleboat, canoe, 2 kayaks, and a SUP provided. Take the short 5 minute stroll into town for ice cream or fresh baked treats. Lay out on the elevated deck or in the screened in porch with a good book. End your evening at the riverfront firepit. Nearby day adventures include hiking, golfing, parks, beaches, breweries, casino rama, and downhill skiing at Mount St Louis Moonstone and Horseshoe Valley (30 minute drive).

4.98 out of 5 average rating, 156 reviews

A tranquil lakeside view displays a spacious cottage with large windows, reflecting on the calm water. Surrounding trees and a clear blue sky add to the serene atmosphere, inviting relaxation and enjoyment of the natural beauty.

Cottage in Georgian Bay

Muskoka Stunning Cottage On Little Lake

Surrounded by Little Lake, this gem provides a relaxing getaway with amazing water views. Spend your days peacefully rowing on the lake or having a picnic on the private beach, and your nights settling by a crackling fire. The home itself is plenty spacious for unwinding and getting a good night's sleep, views all-inclusive. Explore Port Severn Park right next door and play around in the public beach and splash pad. For more adventure, hike the beautiful Georgian Bay Islands National Park.

4.93 out of 5 average rating, 242 reviews

Condo in Innisfil

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

4.85 out of 5 average rating, 113 reviews

A hot tub is situated under a wooden gazebo, featuring railings and a ceiling adorned with decorative elements. Sunlight illuminates the scene, highlighting the inviting water surface. A view of the snowy landscape and frozen lake extends in the background, enhancing the serene atmosphere.

Home in Elmvale

Ski, Swim, Soak, Boat & Golf

Renovated 2 storey cottage overlooking beautiful Orr Lake. Ski at Mt. St. Louis Moonstone or Horseshoe Valley. Both 13 minutes away. A heated swimming pool in the summer and a hot tub all year. Canoeing, kayaking, paddle boarding or golfing across the street. Fully equipped kitchen. Livingroom includes an overhead projector, plus as a second floor Family room with a Wet Bar. 5 bedrooms, 7 beds, & 3 Baths. Max occupancy: 10 adults or 12 including children under 13. Parking for 5 cars.

4.96 out of 5 average rating, 188 reviews

Condo in Innisfil

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!

4.96 out of 5 average rating, 140 reviews

Tiny home in Utopia

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.

4.91 out of 5 average rating, 304 reviews

Cottage in Georgina

Lakefront | Private Dock, Sandy Beach & Hot Tub

Lake Simcoe waterfront cottage with a rare shallow sandy-bottom shoreline, private dock, and hot tub. Enjoy swimming, kayaking, paddleboarding, fishing, BBQs, fire pit evenings, and breathtaking sunsets. Perfect for family vacations, holiday getaways, and groups near Toronto, just minutes from Hwy 404. Features 6 bedrooms, 4 bathrooms, a fully equipped kitchen, and spacious indoor and outdoor areas. Private, peaceful, and ideal for year-round Lake Simcoe getaways.

Popular amenities for Oro-Medonte kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.92 out of 5 average rating, 125 reviews

A hot tub is positioned beneath a covered patio, offering views of the waterfront. The clear water of the hot tub contrasts with the lush green surroundings and the calm blue of the lake in the distance. Sunlight filters through the patio overhead.

Home in Port Mcnicoll

Breathtaking 5 bedroom Waterfront Home W/ Hot Tub!

4.94 out of 5 average rating, 112 reviews

A well-maintained front yard features lush green grass, framed by trees. The entrance of the home is highlighted by a gray facade and a distinctive yellow accent above the doorway. Well-kept shrubs are positioned on either side of the path leading to the entrance.

Home in Wasaga Beach

Relaxing fall getaway / games room

4.84 out of 5 average rating, 51 reviews

The cottage exterior is illuminated at dusk, showcasing its modern design. Large windows reveal the open-concept interior, while a spacious deck offers seating options. The surrounding landscape features a manicured lawn and trees in the background, enhancing the serene lakeside setting.

Home in Orillia

[Casa Luna] Chic Lakehouse | BBQ | HotTub | LakeViews

4.95 out of 5 average rating, 41 reviews

A sandy beach stretches out towards calm waters, complemented by a small dock and an island visible in the distance. Red and gray Adirondack chairs are setup in a semicircle on the beach, inviting relaxation under a clear blue sky dotted with clouds.

Home in Victoria Harbour

Welcoming Waterfront Cottage

4.78 out of 5 average rating, 41 reviews

An outdoor firepit is surrounded by stone, with flames flickering invitingly. Adjacent, a wooden Adirondack chair faces a serene lake, reflecting warm sunset hues. A charming playhouse stands nearby, nestled among mature trees, creating a peaceful lakeside setting.

Home in Orillia

Couchiching Lake Retreat - Sauna! Near Downtown!

4.9 out of 5 average rating, 58 reviews

Home in Georgina

Sunset Harmony on Cook’s Bay

4.94 out of 5 average rating, 36 reviews

Home in Severn Bridge

New Built Modern Luxury Cottage

4.89 out of 5 average rating, 9 reviews

Home in Gravenhurst

Winterized Muskoka Lakefront w Sandy Entrance

Cottage rentals with a kayak

4.93 out of 5 average rating, 180 reviews

Cottage in Gravenhurst

Marrakahshe Retreat | Luxury Sauna, Beach & Yurt

4.97 out of 5 average rating, 116 reviews

A stone patio leads to a sandy beach, featuring a seating area with red chairs overlooking Georgian Bay. The calm water is visible in the background, framed by trees and large rocks, with yellow kayaks positioned along the shore.

Cottage in Tiny

Beautiful Beachfront Cottage.

4.96 out of 5 average rating, 134 reviews

A unique wooden sauna, shaped like a barrel, is placed on a grassy area by the lake. Above, a clear night sky is filled with bright stars, providing a serene backdrop. Nearby, lounge chairs are arranged on the lawn, with trees lining the water’s edge.

Cottage in Coldwater

Cottage on the Rocks - with Hot Tub and Sauna!

4.97 out of 5 average rating, 258 reviews

A serene waterfront view is presented from a deck, showcasing calm water surrounded by lush green trees. Comfortable seating arrangements are visible, creating a perfect spot for relaxation while enjoying the natural landscape.

Cottage in Torrance

Beautiful Nine Mile Lake

4.92 out of 5 average rating, 141 reviews

A spacious cottage is set against a lush green backdrop, featuring a distinct barrel sauna nearby. A manicured lawn hosts a small putting green with flags, alongside several lounge chairs. The architecture blends modern and natural elements, creating an inviting outdoor environment.

Cottage in Washago

Waterfront Cottage sauna/golf/kayaks/beach/games

4.98 out of 5 average rating, 200 reviews

A charming cottage sits by a serene waterfront, surrounded by lush trees. The sandy beach leads to calm water, with lounging spaces and two docks visible. Muskoka chairs are positioned on the lawn, inviting relaxation amid nature. The cottage's structure offers multiple outdoor seating options.

Cottage in Washago

Mistywood Cottage

4.95 out of 5 average rating, 146 reviews

A wooden dock extends over calm waters, framed by lush forests and rocky shores. Two adirondack chairs face the sunset, inviting a moment of connection. Vibrant hues of orange and purple fill the sky, reflecting gently on the water's surface.

Cottage in Gravenhurst

Private & Modern Muskoka Lakefront Cottage w/ WiFi

4.88 out of 5 average rating, 168 reviews

A spacious lake house exterior is set against a cloudy sky, featuring large windows that allow natural light to enter. The surrounding yard is adorned with fallen leaves, while a deck with outdoor furniture and a hot tub enhances the outdoor space.

Cottage in Innisfil

Spacious family cottage 45 mins from GTA!

Cabin rentals with a kayak

4.89 out of 5 average rating, 358 reviews

A queen-sized bed is surrounded by a delicate canopy, with colorful patterned pillows adding a touch of charm. Soft morning light filters through two windows, illuminating the wooden floor and a bedside table with a lamp and small plant. A leafy plant hangs near the window.

Cabin in Gravenhurst

Forest Cabin 90 steps to the beach

4.96 out of 5 average rating, 52 reviews

A bright and airy living area features large windows revealing serene lake views. A comfortable light-colored sofa faces a wooden coffee table, complemented by a woven ottoman. Soft curtains frame the windows, while a small dining table and a potted plant add a touch of warmth.

Cabin in Elmvale

The White Cottage with infinity views

4.89 out of 5 average rating, 76 reviews

A serene waterfront view features a sandy beach area with calm waters, a wooden dock extending into the lake, and kayaks resting nearby. Lush greenery surrounds the cabin, enhancing the natural scenery and providing a peaceful setting for relaxation.

Cabin in Severn Bridge

Oak Cabin on Sparrow Lake

Cabin in Township Of Brock

Lake view house

4.71 out of 5 average rating, 24 reviews

5.0 out of 5 average rating, 9 reviews

A cottage is set amidst tall trees, featuring a wooden deck and steps leading to the water. Outdoor seating includes red chairs on the lawn and around a fire pit, creating a welcoming environment for relaxation and gatherings.

Cabin in Muskoka Lakes

Luxury Cottage with Hot Tub

5.0 out of 5 average rating, 38 reviews

Cabin in Severn

Muskoka Escape with Hot Tub, Waterfront & Firepit

4.95 out of 5 average rating, 58 reviews

A wooden dock extends into calm waters, leading to a seating area with several red Adirondack chairs and an umbrella. A boat is moored alongside, surrounded by lush green trees that frame the serene lake view.

Cabin in Muskoka

Charming Muskoka cottage, amazing views!