Vacation rentals with a kayak in Oro-Medonte

A covered patio area features a hot tub alongside a glass-topped table with comfortable seating. The peaceful lakeside view showcases expansive green space and a row of chairs positioned along the shore, framed by trees lining the property.

4.96 out of 5 average rating, 106 reviews

Sunset Shores Lakehouse- Hot Tub, Wet Bar & Games

Welcome to Sunset Shores Lakehouse! Nestled in a tranquil bay on the shores of Lake Simcoe, this spacious family lake house is the perfect escape in all 4 seasons with many indoor and outdoor activities to enjoy! This peaceful waterfront retreat boasts 4 bedrooms + Wet Bar + Patio Oasis with lakeside Fire Pit + 6 person Hot Tub overlooking the lake and spectacular daily sunsets and sunrises you wont want to miss! Only 1 hour from Toronto and close to many Georgina attractions and adventures!

LocationOutdoor spacesWifi

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.

ValueLocationBathroom

4.96 out of 5 average rating, 144 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!

LocationOutdoor spacesLaundry

4.96 out of 5 average rating, 182 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.

ValueLocationSkiing

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).

LocationOutdoor spacesLayout

4.97 out of 5 average rating, 110 reviews

A dock extends over calm waters, featuring two red Adirondack chairs facing the horizon. The sky above is clear, with soft clouds drifting in the distance. A ladder is positioned at one end of the dock, providing easy access to the lake.

Bungalow in Hawkestone

Water front Cottage Lake Simcoe Sauna Hot Tub

The lake Simcoe region is a favourite year round holiday destination with any area events and attraction. This is family waterfront cottage with a beautiful spacious open concept kitchen,dining & living room. Another separated of the house room with pool table,sauna, TV& 2 sofa beds. (4 sofa beds all in total). Perfect place to enjoy the sunshine, sky nearby Horseshoe Valley or MT.St. Louise. 2 minutes walk to boat lounge, 7 minutes walk to the park with a beautiful beach and playground

ValueOutdoor spacesAir conditioning

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.

LocationOutdoor spacesFamily

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

LocationOutdoor spacesFamily

4.85 out of 5 average rating, 112 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.

ValueLocationLayout

4.93 out of 5 average rating, 179 reviews

Cottage in Gravenhurst

Marrakahshe Retreat | Luxury Sauna, Beach & Yurt

Welcome to Marrakahshe Retreat: A curated lakeside experience & sauna under 2-hours from Toronto. With 230 feet of private lakefront, southwestern exposure, stunning views and eclectic high-end decor, this exquisite Muskoka retreat is the perfect place to relax, unwind, and immerse yourself in nature. Enjoy the pristine beauty of Kahshe Lake and the Canadian Shield, along with your very own 50 ft. walk-in sandy beach, glamping yurt, dock, sauna, fire pits, home theatre and more.

ValueOutdoor spacesGrill

4.91 out of 5 average rating, 303 reviews

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.

Outdoor spacesLocationCleanliness

4.97 out of 5 average rating, 115 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.

Township of Tiny License Number: STRTT-2026-110 Enjoy our all-season paradise only 1.5 hours north of Toronto! In summer, enjoy the sandy beach waterfront with incredible views of Georgian Bay with the Town of Penetanguishene, and all its historic charm, only 20 minutes away! In winter, enjoy all the area has to offer with incredible OFSC groomed snowmobile trails and amazing ski resorts less than an hour away! *Contract to be sent and signed prior to stay.

Outdoor spacesValueView

Popular amenities for Oro-Medonte kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.88 out of 5 average rating, 113 reviews

A hot tub is set under wooden beams, providing a calming retreat. It overlooks a grassy area leading to the waterfront, where bright red Muskoka chairs are positioned. Steps lead up to the deck, enhancing outdoor accessibility and views.

Home in Victoria Harbour

Modern Waterfront Home on Georgian Bay w/ Hot Tub!

LocationOutdoor spacesIndoor spaces

4.94 out of 5 average rating, 111 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

ValueOutdoor spacesCheckout

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

LocationOutdoor spacesView

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!

LocationOutdoor spacesBathroom

4.84 out of 5 average rating, 50 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

Outdoor spacesLocationCheckout

4.89 out of 5 average rating, 54 reviews

Home in Georgina

Sunset Harmony on Cook’s Bay

ValueLocationComfort

4.94 out of 5 average rating, 36 reviews

An aerial view showcases the retreat's surroundings, featuring a landscape of lush greenery with a private lake in the background. The property, set in a residential area, includes several houses and a clear path leading to the water's edge, emphasizing the peaceful environment.

Home in Georgina

5 bdrm home with pool and private lakefront

LocationOutdoor spacesIndoor spaces

5.0 out of 5 average rating, 38 reviews

Two pairs of players are engaged in a game of pickleball on a well-maintained court surrounded by trees. The court has a bright green surface with nets dividing the play area. Sunlight filters through the foliage, creating a lively atmosphere.

Home in Innisfil

Luxury home with pickleball!

LocationOutdoor spacesAccess

Cottage rentals with a kayak

4.9 out of 5 average rating, 217 reviews

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

Outdoor spacesLocationBiking

4.95 out of 5 average rating, 180 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

ValueOutdoor spacesQuiet

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!

LocationOutdoor spacesSkiing

4.86 out of 5 average rating, 150 reviews

The exterior of the Lake House is surrounded by lush trees, with a wide wooden dock extending into the calm waters. A patio area features multiple red Muskoka chairs, inviting relaxation by the water's edge. Soft evening light hints at the cozy ambiance of the home.

Cottage in Orillia

AMIGO LAKE HOUSE

ValueLocationWalkability

4.94 out of 5 average rating, 145 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

ValueLocationKitchen

4.92 out of 5 average rating, 140 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

LocationValueLong stay

4.97 out of 5 average rating, 199 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

Outdoor spacesValueRiver

4.93 out of 5 average rating, 129 reviews

The living area features a plush blue sofa paired with a modern coffee table, creating a comfortable seating arrangement. Large windows offer views of the lake, allowing natural light to fill the space. Simple decor elements enhance the inviting environment.

Cottage in Sebright

Private Lakefront Cottage | Fishing, Canoe & Sauna

Outdoor spacesValueKitchen

Cabin rentals with a kayak

4.8 out of 5 average rating, 131 reviews

A serene lakeside property is depicted, featuring a dark blue exterior and a welcoming wooden staircase leading to the entrance. Lush greenery surrounds the home, and a calm body of water reflects the clear sky in the background.

Cabin in Gravenhurst

Sparrow Sunset Retreat Lakefront• Hot Tub • Dock

LocationValueGrill

4.89 out of 5 average rating, 357 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

Outdoor spacesValueHiking

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

ValueOutdoor spacesAmenities

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

Outdoor spacesLocationAccess

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!

LocationValueFamily

4.82 out of 5 average rating, 67 reviews

An open indoor/outdoor porch is featured, showcasing a large dining table surrounded by chairs and string lights overhead. Comfortable seating areas are arranged around a cozy lounge space, with wooden flooring enhancing the inviting atmosphere. Large windows allow for natural light and views of the outdoors.

Cabin in Sebright

Waterfront Cabin W/ Indoor Hot Tub, 90 min to GTA

Outdoor spacesValueBeach

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

LocationOutdoor spacesAccess