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Vacation rentals with a kayak in Lake Simcoe

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Top-rated accommodations with a kayak in Lake Simcoe

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

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Guest favourite
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.
Cottage in Georgina

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!

ValueOutdoor spacesCheckout

4.96 out of 5 average rating, 108 reviews
Guest favourite
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.

LocationOutdoor spacesGrill

4.9 out of 5 average rating, 221 reviews
Top guest favourite
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.

ValueOutdoor spacesHospitality

4.95 out of 5 average rating, 187 reviews
Guest favourite
Cottage in Brechin

COTTAGE ON LAKE SIMCOE -4 BEDROOMS /2WSHRMS

Welcome to our cozy cottage in Simcoe County, just a short drive from Toronto. It's the perfect place to bring together family and friends, where laughter fills the home and nature surrounds you. Enjoy kayaking, fishing, and time on the water from your private dock just across the quiet road, then wake up to beautiful Lake Simcoe sunrises. Explore scenic trails, fire up the BBQ, paddle around the lake, and create heartwarming memories that will last a lifetime. Book your special getaway today!

LocationValueBiking

4.92 out of 5 average rating, 194 reviews
Top guest favourite
Cottage in Innisfil

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

LocationValueGrill

4.86 out of 5 average rating, 273 reviews
Top guest favourite
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!

LocationOutdoor spacesCheckout

4.96 out of 5 average rating, 146 reviews
Guest favourite
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.

Outdoor spacesValueSleep quality

4.96 out of 5 average rating, 185 reviews
Top guest favourite
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.

Outdoor spacesLocationKitchen

4.98 out of 5 average rating, 159 reviews
Top guest favourite
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).

Outdoor spacesLocationAmenities

4.97 out of 5 average rating, 181 reviews
Top guest favourite
Cottage in Georgina

Lakefront Escape | Private Dock, 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, cozy fire pit evenings, and breathtaking sunsets. Perfect for family vacations, holiday getaways, and group retreats near Toronto, just minutes from Hwy 404. Features 6 bedrooms, 4 bathrooms, a fully equipped kitchen, and spacious indoor and outdoor living areas. Private, peaceful, and ideal for year-round Lake Simcoe getaways.

ValueLocationNearby

4.92 out of 5 average rating, 306 reviews
Top guest favourite
A modern cottage is set against a backdrop of tall trees, featuring a large wraparound deck illuminated by warm lights. A fire pit sits on a granite outcrop, surrounded by outdoor chairs. The peaceful evening sky casts a calm ambiance over the scene.
Cottage in Bracebridge

Tiny Luxury Cottage with Hot Tub

This tiny luxury 2 bedroom cottage is perfect for a romantic couple or small family getaway. Nestled on 1.5 acres among majestic trees and granite outcrops, creates beautiful views from the deck with BBQ, fire pit, hot tub or massive windows throughout the cottage. Water dam and river across the road create relaxing waterfall sounds that are heard from deck or enjoy it close up from the private shoreline deck and dock. Explore the Muskoka River on the kayak, SUP or river tubes.

ValueLocationCheck-in

4.99 out of 5 average rating, 188 reviews
Superhost
Cottage in Highlands East

Tranquil Minnicock Lake | Hot Tub & Lake Front

✨ Tranquil Minnicock Lake Escape ✨ Experience the "wow" factor 15 mins from Haliburton! 🌲 This luxury retreat features a clean, shallow shoreline perfect for swimming. 🏊‍♂️ The Highlights: Wellness: Private Hot Tub & peaceful Creek sounds Water: Kayaks, Canoe & Life Jackets included Outdoors: Large Fire Pit, BBQ & Trekking Trails Included: Full Linens, Towels & Coffee Station ☕ 📡 Essentials: Wi-Fi, Washer/Dryer, TV & Sleds 🛷 STR License: STR25-00047

LocationValueCheck-in

4.91 out of 5 average rating, 371 reviews

Popular amenities for Lake Simcoe kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a kayak

Top guest favourite
The custom-built A Frame cabin is set amidst lush greenery, featuring a striking black exterior and a distinctive peaked roof. A spacious deck extends at the front, furnished with seating, and surrounded by nature for a serene environment.
Home in Bracebridge

Secluded Muskoka A-Frame | Hot Tub, Dock, Firepit

LocationValueAmenities

4.95 out of 5 average rating, 141 reviews
Guest favourite
The kitchen features dark wooden cabinetry and a spacious island with seating. A full range of stainless steel appliances are visible, including a refrigerator and stove. Ambient lighting from pendant fixtures enhances the open layout, which combines dining and kitchen areas beneath a vaulted wooden ceiling.
Home in Port Mcnicoll

Spectacular Waterfront 3 Bedroom Home!

Outdoor spacesLocationSleep quality

4.95 out of 5 average rating, 288 reviews
Top guest favourite
A modern cabin is nestled among tall trees, showcasing large floor-to-ceiling windows that invite natural light. A spacious covered porch, framed by lush greenery, features outdoor seating. The grassy area surrounding the cabin adds to the serene atmosphere of the wooded retreat.
Home in Eagle Lake

HyggeHaus—sleek snuggly secluded apres-ski cabin

LocationOutdoor spacesSleep quality

4.97 out of 5 average rating, 154 reviews
Superhost
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

LocationValueCleanliness

4.85 out of 5 average rating, 115 reviews
Top guest favourite
The calm water reflects an array of trees along the shoreline, showcasing a blend of green and vibrant autumn foliage. The sky above features soft clouds, enhancing the tranquil atmosphere of the river setting.
Home in Bracebridge

The Muskoka River Homestead

LocationValueNearby

4.92 out of 5 average rating, 254 reviews
Guest favourite
A spacious living area features large windows that provide ample natural light and views of the surrounding trees and water. A comfortable sectional sofa, a stylish leather couch, and a glass coffee table are arranged around a cozy wood stove, creating a welcoming atmosphere.
Home in Port Carling

Waterfront Boutique Cottage Getaway

ValueLocationLaundry

4.89 out of 5 average rating, 159 reviews
Top guest favourite
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

Come see the leaves change colour / games room

LocationValueLayout

4.94 out of 5 average rating, 114 reviews
Guest favourite
A warm and inviting living area features wooden walls with large windows offering ample natural light. A spacious couch and two armchairs surround a glass coffee table on a soft area rug. A dining table is visible in the background, illuminated by natural light.
Home in Buckhorn

Lakefront Log Home-Reach Out for Special Deals!

LocationOutdoor spacesCheck-in

4.9 out of 5 average rating, 120 reviews

Cottage rentals with a kayak

Top guest favourite
Cottage in Washago

Riverfront Cottage with HotTub Near Muskoka

ValueOutdoor spacesGrill

4.93 out of 5 average rating, 177 reviews
Guest favourite
A private dock extends into calm waters, leading to a lakefront house with a red roof and spacious outdoor area. Bright red chairs are arranged on the dock, surrounded by lush green trees and a rocky shoreline, providing a welcoming space for relaxation.
Cottage in Cameron

Lakefront Cottage | 2 BR, Hot Tub, Fire Pit

Outdoor spacesValueGrill

4.91 out of 5 average rating, 111 reviews
Guest favourite
A lakeside cottage is displayed from the dock, featuring a modern design with large windows and a spacious deck. The outdoor area includes a Jacuzzi surrounded by a stone border. Lush greenery frames the scene, enhancing the serene lakeside setting.
Cottage in Gilford

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

LocationValueBeach

4.83 out of 5 average rating, 147 reviews
Superhost
Cottage in Washago

Vintage Cottage Lakeview Fireplace near Muskoka

LocationValueAccuracy

4.86 out of 5 average rating, 160 reviews
Superhost
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

ValueLocationNearby

4.84 out of 5 average rating, 193 reviews
Top guest favourite
A spacious outdoor seating area features comfortable wicker chairs and a grill, surrounded by soft lighting under a canopy. The two-story home provides large windows that reflect the evening sky, and lush trees frame the property, creating a serene atmosphere.
Cottage in Trent Lakes

Lux-5 Bdrm-Waterfront+Hot Tub+Sauna+Game Rm+SUP's+

ValueOutdoor spacesGrill

4.99 out of 5 average rating, 145 reviews
Guest favourite
A spacious living room features a high wooden ceiling with a ceiling fan and large windows allowing natural light to fill the space. Comfortable seating is arranged around a central coffee table, complemented by a wood stove. Books and games are displayed on a nearby shelf.
Cottage in Kawartha Lakes

Year-Round Relaxation, a Modern Riverfront Cottage

Outdoor spacesLocationNearby

4.87 out of 5 average rating, 182 reviews
Superhost
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

FRIEND LAKE HOUSE

LocationOutdoor spacesWifi

4.86 out of 5 average rating, 152 reviews

Cabin rentals with a kayak

Top guest favourite
A handcrafted timber frame cabin is set among trees, featuring natural wood siding and large windows that invite the outdoors in. A welcoming porch is accessed by a wooden staircase, while a covered area to the side provides shelter. The surrounding forest complements the rustic design.
Cabin in Bracebridge

Secluded Lakeside Retreat - Atkins Hideaway

Outdoor spacesLocationGrill

5.0 out of 5 average rating, 297 reviews
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

Cozy, Quirky and Modern Lakefront Cottage

Outdoor spacesLocationKitchen

4.91 out of 5 average rating, 235 reviews
Guest favourite
A wooden dock extends into the lake, featuring three comfortable adirondack chairs facing the water. The cottage, surrounded by trees, glows warmly in the evening light, with a spacious deck and lush greenery enhancing the peaceful lakeside setting.
Cabin in Haliburton

LakeKabin: Lakefront, Sauna, HotTub, Arcade, Kayak

LocationOutdoor spacesSkiing

4.99 out of 5 average rating, 141 reviews
Top guest favourite
A modern cabin exterior is shown, featuring dark siding and a spacious wooden deck overlooking the lake. Outdoor seating is arranged on the deck, surrounded by lush greenery. The tranquil waters of Sandy Lake are visible just beyond the cabin's edge.
Cabin in Buckhorn

The Beautiful Sandy Lake Cabin (as seen on HGTV)

Outdoor spacesLocationLong stay

4.94 out of 5 average rating, 146 reviews
Guest favourite
A custom-built home is set amidst trees, featuring a mix of stone and siding exterior. The entryway is accented by a covered porch with white railings. A spacious driveway leads to the two-car garage, bordered by autumn leaves scattered on the ground.
Cabin in Orillia

Beautiful Vacation Home with a Large Backyard.

LocationValueTV

4.83 out of 5 average rating, 118 reviews
Top guest favourite
A rustic cabin is seen amidst a lush wooded setting, with the soft glow of the sun rising behind the trees. The entrance features steps leading up to the door, and a small structure is visible nearby. The ground is covered in grass and bare earth.
Cabin in Tory Hill

Crooked Cabin - Irondale River -Geocaching Capital

Outdoor spacesLocationAmenities

4.87 out of 5 average rating, 411 reviews
Guest favourite
A wooden dock extends over the calm waters of the lake, featuring lounge chairs positioned for relaxation. The horizon displays a subtle sunset glow, with trees lining the shore in the background, enhancing the serene lakeside experience.
Cabin in Haliburton

Retreat style cottage + wood fired sauna

Outdoor spacesValueAir conditioning

4.83 out of 5 average rating, 686 reviews
Guest favourite
A stylish living area features a tufted gray sofa adorned with decorative pillows. A round marble-top coffee table is centered on a textured rug. Recessed lighting illuminates the space, highlighting the dark wood ceiling and modern chandelier, while a mirror reflects the room's design.
Cabin in Norland

Vintage Hollywood Cabin: Hot Tub/ BBQ/Sauna/ Beach

Outdoor spacesLocationParking

4.92 out of 5 average rating, 123 reviews

Destinations to explore