Vacation rentals with a kayak in Simcoe County

4.92 out of 5 average rating, 149 reviews

Waterfront @Muskoka Pines /kayaks/bbq/firepit

Get ready to relax and recharge in this charming 4 season Muskoka waterfront cottage. All day Sun filled southern exposure. Surrounded by nature. Loon lake is a clean water Muskoka lake,great for fishing,ice fishing,skating, swimming,boating and water sports. The cottage is equipped with new central gas heating and a wood burning fire stove. There's central AC for the warm summer season. Conveniently located within a few minutes drive to the activities, shops and restaurants of Gravenhurst Wharf

4.86 out of 5 average rating, 182 reviews

Stunning 3BR Waterfront Lake Cottage Hottub&Sauna

Welcome to Cardinal Cottage! The Ultimate Winter Wonderland Getaway. Featuring outdoor Scandinavian Experience - HotTub & Sauna! 3bedrooms (6 beds), 1bath right on the water only 1.5hrs from the GTA & 10mins from Gravenhurst. Breathtaking waterfront dock views. Gather inside with our extended Dining Table, Giant U-shaped couch, 65" smartTV w/Netflix & Cable, WIFI, Stereo System, LOTS of board games & books! Offering a Private Remote Workspace. Join us for a refreshing & recharging 5-star stay!

Guest favorite

Cottage in Brechin

4.94 out of 5 average rating, 157 reviews

Spacious waterfront cottage w/ spectacular sunsets

Hi welcome to Sunset Shores Vacations on beautiful Lake Dalrymple. Enjoy the perfect vacation with the most spectacular sunsets viewable from the living room/kitchen, large upper deck, lower patio or right down at the waters edge. The fishing is great you can even catch fish off the dock. Swimming is great especially for young children cause the water is shallow off the dock. Explore the lake with the use of canoes, kayaks and paddle boat. Enjoy ice fishing, snowmobiling or a winter retreat.

4.99 out of 5 average rating, 106 reviews

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.

4.99 out of 5 average rating, 157 reviews

Cottage in Georgina

Granny's Cottage

Granny’s Cottage is located on Lake Drive East across the road from Lake Simcoe. Our private lakefront is yours to enjoy. Our lakehouse equipped with mini fridge and chairs while looking out over beautiful Lake Simcoe. Lakehouse is available late spring to early fall. This cozy cottage is newly renovated with all the comforts for a much needed getaway. Available for your use is a badminton net, 2 kayaks and a large canoe (seasonal). There is also a secure lock up for you bicycles.

4.88 out of 5 average rating, 131 reviews

Cottage in Port Severn

2 BEDRM WATERFRONT COTTAGE, CANOE, KAYAKS, WIFI

No linens provided (No Blankets, sheets pillowcases or towels). Sorry NO PETS as guests on the property and NO SMOKING indoors. The cottage is right on the water, lots of wildlife, great for bird watching, Large 4 lake system, miles of boating on Gloucester pool, then for a further adventure it is connected to Georgian bay by locks on the Trent Severn. Honey Harbor, Midland, Whites Falls and lots of provincial parks close by, great fishing, ATV and hiking trails, fish right off the dock

4.86 out of 5 average rating, 139 reviews

Muskoka Dream Cottage

Spectacular 4,200 square foot open concept custom luxury four season lakefront cottage in beautiful Gravenhurst Ontario. Great room boasts 26' high cathedral ceilings with gourmet kitchen and wood burning fireplace. The cottage boasts 3 bedrooms, 2 bathrooms upstairs. 1 bedroom and 1 bathroom on the main floor. Attached 2 bedroom bunkie is fully heated. Rental includes use of all non motorized water toys during the summer months including kayaks, paddle boards, canoe, and row boat.

Guesthouse in Gravenhurst

4.91 out of 5 average rating, 151 reviews

Waterfront Guest Cabin in Muskoka

Upscale guest cabin with brand new hot tub and WiFi deep in the heart of Muskoka. Unlimited access to a private hot tub, a dock with deep water diving, and a fireplace with night sky views. Remote cabin in nature with modern amenities and touches, accessible only by private road. Great for unplugging from social media and getting away from the city. Ideal for couples looking to relax, have campfires, and enjoy water activities such as swimming, kayaking, and paddle boating.

4.95 out of 5 average rating, 56 reviews

Home in Washago

Breathtaking RiverFrontOasis with a HOT Sauna

Beautifully renovated home with 140 feet of waterfront on Green River with cathedral ceilings, 1.5 bathrooms, 2021 kitchen with quartz counters. 3 bedroom home plus pull out couch in a semi private reading nook, as well as bunkie with queens size bunk beds for bonus sleeping quarters. Enjoy wine or mimosa on the dock while the kids play on the sandy beach. Great for kayaking, and stand up paddle boarding. Deep water perfect for fishing, bass, pickerel and muskie.

4.93 out of 5 average rating, 152 reviews

Cottage in Richmond Hill

White Oak on Wilcox-Richmond Hill Lakefront Oasis

Welcome to The White Oak on Wilcox - a lakefront oasis in the heart of Richmond Hill, perfect for an all-season getaway. Located just 30 mins from Toronto, enjoy direct access to Lake Wilcox with beautiful sunset views from the private dock. This vacation home welcomes you to a relaxing and serene lakefront experience. Surrounded by numerous activities to enjoy year-round, this is the perfect home-away-from-home! Share your memories with us @whiteoakcottageco

Guest favorite

4.93 out of 5 average rating, 125 reviews

Marrakahshe Retreat: A Curated Lakeside Experience

Welcome to Marrakahshe Retreat: A curated lakeside experience & sauna under 2-hours from Toronto. With 230 feet of private lakefront, 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.