
Holiday rentals with a kayak in Orillia
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Orillia
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

CozyPeaceful LakeCottage HotTub Canada
Cozy Lakefront Cottage located on Sparrow Lake is the idea of relaxation. Enjoy the stunning sunsets while lounging on the large deck with a beverage in hand. The loons singing in the background. Perfect to enjoy with the whole family or on a couples retreat. The area is perfect for boating, fishing, walking, and biking around the neighbourhood. A mini toboggan hill Sparrow Lake is part of the Trent-Severn Waterway and you can boat to either Georgian Bay or Lake Couchiching in a few hours

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!

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.

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.

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.

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).

Waterfront Cottage sauna/golf/kayaks/beach/games
Welcome to Hally’s Cove Riverside Retreat! A fully loaded 4-season escape on the Trent Severn River! Dock your boat with shore power ⚓, lounge in the over-the-water hammock 🌅, relax in the panoramic sauna 🧖♀️, or play in the games room 🕹️ (ping pong, basketball, air hockey plus lots more). Enjoy the 4-hole putting green ⛳, 6 kayaks 🛶, lily pad and custom landscaped Muskoka rock fire pit 🔥. Summer Bonus - Mosquito-sprayed for extra comfort! IG to see more photos: @hallys_cove

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.

The Muskoka River Chalet - The King's Den
Welcome to Muskoka River Chalet! **Please read full listing description before booking.** Relax in your fully private one-bedroom walkout apartment with private kitchen, cozy living room, featuring smart TVs and toasty fireplaces. Explore our shared outdoor spaces along 60' of waterfront. Indulge in the hot tub for relaxation. Just minutes walking to town for shopping, dining, and nightlife. Book now for a perfect blend of comfort and convenience!

Private Lakefront Escape Hot Tub | Family Friendly
Escape to our private lakefront cottage on Lake Simcoe, perfect for families, friends, and large groups looking to relax by the water. With 6 bedrooms, 4 bathrooms, and space for up to 15–16 guests, there is plenty of room to enjoy time together while still having space to spread out. Enjoy your own private sandy beach, beautiful sunset views, hot tub, kayaks, paddle boards, BBQ, firepit, games room, and large dining area for everyone to gather.

Beautiful Nine Mile Lake
Beautiful Muskoka getaway! Modern 4 season waterfront cottage! Stunning views! Located on picturesque Nine Mile Lake. Over 70% of the lake is crown land. Perfect for kayaking and canoeing to enjoy all the beauty Muskoka is known for. We have kayaks a canoe and a paddle board for you to enjoy. Plenty of sun exposure on the dock you can swim all day long. Close to hiking and snowmobile trails. May 15-Oct Minimum 6 nights with a Sunday check in.

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.
Popular amenities for kayak rentals in Orillia
House rentals with a kayak

Orillia Lakefront Home by Nature Reserve, Hot Tub

Lakefront Bungalow "Sunrise Bay" Kawartha Lakes

Cozy Lakeside Cottage on Lake Scugog

Welcoming Waterfront Cottage

River's End: Explore the river by kayak or canoe!

Couchiching Lake Retreat - Sauna! Near Downtown!

Bluewood Lake Cottage

Ski, Swim, Soak, Boat & Golf
Cottage rentals with a kayak

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

Luxury lakefront cottage escape

Beachfront on the Green River

All Season Muskoka Retreat on Sparrow Lake

Muskoka Cottage Getaway with Sauna

The Gingerbread House | Near Lake + Wedding Venues

Simcoe Sunrise - Cozy Waterfront Home in Orillia

Couchiching Lakefront Retreat Incredible location!
Cabin rentals with a kayak

Oak Cabin on Sparrow Lake

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

Waterfront Muskoka Cottage | Hot Tub, BBQ & Canoes

The White Cottage with infinity views

Beautiful Vacation Home with a Large Backyard.

Beautiful Six Mile Lake Muskoka

Misty River Cabin Private Waterfront Pet-Friendly!

Muskoka Escape with Hot Tub, Waterfront & Firepit
Quick stats about holiday rentals with a kayak in Orillia

Total holiday rentals
Explore 20 holiday rentals in Orillia

Nightly prices starting at
Orillia holiday rentals start at £44 per night before taxes and fees

Verified guest reviews
Over 870 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Orillia holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Orillia rentals

4.8 Average rating
Orillia stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
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- Rentals with a washing machine and dryer Orillia
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- Family-friendly rentals Orillia
- Cabin rentals Orillia
- Rentals with lake access Orillia
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- Rentals with a fireplace Orillia
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- Rentals with beach access Orillia
- Pet-friendly rentals Orillia
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- Rentals with a hot tub Orillia
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- Beachfront rentals Orillia
- Rentals with a kayak Simcoe County
- Rentals with a kayak Ontario
- Rentals with a kayak Canada
- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Lakeridge Ski Resort
- Osler Bluff Ski Club
- Pigeon Lake
- Devil's Glen Country Club
- Dagmar Ski Resort
- Gull Lake
- Three Mile Lake
- Georgian Bay Islands National Park
- Bigwin Island Golf Club
- Scandinave Spa Blue Mountain
- Torrance Barrens Dark Sky Conservation Area
- Taboo Muskoka Resort & Golf
- Kee To Bala
- Burl's Creek Event Grounds
- Casino Rama Resort
- Wasaga Beach Area
- Balsam Lake Provincial Park
- Menominee Lake
- Awenda Provincial Park
- Wye Marsh Wildlife Centre
- Bass Lake Provincial Park




