Vacation rentals with a kayak in Simcoe County

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat

4 Seasons: Heated+A|C! You and friends/family will enjoy easy access to everything Gravenhurst has to offer from our centrally located retreat cottage. Conveniently located on Pine Lake, you will have sun-filled water views throughout the cottage. We are located directly off the main highway, easy road access and parking. The lake is perfect for swimming and water sports. Get ready to sip your morning coffee on the back porch and watch the sun rise! A perfect spot for yoga and/or meditation.

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

Luxury Waterfront Cottage Hot Tub & Amazing Sunset

Private lakefront cottage on Lake Simcoe with hot tub, stunning sunset views, and a rare shallow sandy-bottom waterfront — a unique feature rarely found on the lake. Perfect for large families and group getaways near Toronto, just minutes from Hwy 404. Enjoy swimming, kayaking, paddleboarding, fishing, BBQ, fire pit, and a private dock. Features 6 bedrooms, 4 bathrooms, a chef’s kitchen, and spacious open-concept living. Close to town, yet private, peaceful, and perfect for waterfront getaways.

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

Private & Modern Muskoka Lakefront Cottage w/ WiFi

This ultra private and modernly designed Muskoka lakefront / beachfront cottage is perfectly situated at the corner of a beautiful lake, only a 1.5h drive from the GTA and 2hs from Toronto. It borders acres of pristine Crown pine forests, has a private beach, and a luxury new dock that extends from sandy shores. It has a massive new deck and large premium Weber BBQ. New leather couch. Swim, fish, canoe, kayak, sunbathe. Modern interior. High-speed WiFi. Trails. Superhost and guest favourite.

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!

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.

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).

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.

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.

Private Lakefront Cottage | Fishing, Canoe & Sauna

Wake up to sparkling Lake Dalrymple views at our private lakefront cottage, just 1.5 hours from Toronto ☀️🌊 Swim, canoe, fish from the dock, BBQ, or relax by the water. After a lake day, enjoy the outdoor barrel sauna 🧖‍♂️ or gather by the lakeside firepit 🔥 for sunsets, s’mores, and stargazing ✨ Inside features AC, a full kitchen, Netflix, games, record player, and stunning lake views. Perfect for couples & families seeking a fun, relaxing summer escape.

Riverfront Cottage with HotTub

Escape to our beautiful family owned and loved picturesque and serene waterfront cottage and wrap around deck with HotTub. With over 140 feet of private shoreline directly on the Black River offering 3 bedrooms, 4 beds, 2 full bathrooms, gas fireplace, a/c and central heating. Perfect winter getaway for couples and families, 90 minutes from Toronto, 15 minutes to Orillia. 3 Kayaks included. Fully equipped kitchen, fire pit and BBQ.