
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.

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

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.

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.

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).

Log Cabin on the Lake Bed and Breakfast
Log Cabin on the Lake Bed and Breakfast We provide a 1st morning continental breakfast A Lakefront getaway for couples with an amazing view. Experience tiny home living in a custom built Log Cabin. Landscaping provides privacy for all parties (owner next door) we have parking for a boat , with 2 launches within 5 min. One into Morrison Lake the other into the Trent Severn . cross country skiing, ice fishing, water skiing swimming boating. Ready to escape, our Log Cabin could be it.

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

Black River Haus - Scandi Riverfront Cabin Muskoka
Follow us on IG: @visitblackriverhaus The Black River Haus is a Scandi-inspired renovated 1970s cabin offering 3 beds + 1 bath and 140 ft riverfront near Muskoka, Ontario (20 min to Gravenhurst & Orillia). The cabin has been renovated and designed with the surrounding nature in mind, featuring a rustic living room & fireplace, fully-equipped kitchen and an outdoor patio & firepit. The Black River is 30 km long and is perfect for kayaking, canoeing and exploring.

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.

AMIGO LAKE HOUSE
Amigo Lake House, the perfect getaway for any season! Sunny South waterfront views, soak up the sun during the day and star gaze the picturesque sky over the lake at night. Start the morning with a cup of coffee and watch the sunrise over the lake, explore on the kayak/paddle boards, play games in the backyard, barbecue a savoury meal, stay warm by the fire or take dip in the hot tub.
Popular amenities for kayak rentals in Orillia
House rentals with a kayak

Lakefront Bungalow "Sunrise Bay" Kawartha Lakes

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

Couchiching Lake Retreat - Sauna! Near Downtown!

Life is Better at the Cottage

Bluewood Lake Cottage

Ski, Swim, Soak, Boat & Golf

Ice fishing Oasis-BEST Location 3BDRM/2WR

The Muskoka River Homestead
Cottage rentals with a kayak

Charming cottage on Lake Muskoka

Lakefront Escape | Hot Tub & Sauna Retreat

Cottage on the Rocks - with Hot Tub and Sauna!

1950's Romantic & Whimsical cottage on Gull River

Waterfront Paradise on the Georgian Bay

All Season Muskoka Retreat on Sparrow Lake

Kabin Tapoke | Wild Kabin | Hot tub-Sauna-Sunsets

Cottage on the lake
Cabin rentals with a kayak

Oak Cabin on Sparrow Lake

Waterfront Cottage on Severn Falls

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

The White Cottage with infinity views

Cozy Severn River Family Cottage

Beautiful Six Mile Lake Muskoka

Lakeside – Cozy Cottage Getaway

Muskoka Escape with Hot Tub, Waterfront & Firepit
When is the best time to visit Orillia?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £265 | £292 | £189 | £261 | £211 | £184 | £312 | £283 | £229 | £213 | £164 | £202 |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 12°C | 17°C | 20°C | 19°C | 15°C | 9°C | 3°C | -3°C |
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 £45 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!
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- 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
- Gull Lake
- Devil's Glen Country Club
- Pigeon Lake
- Dagmar Ski Resort
- Georgian Bay Islands National Park
- Torrance Barrens Dark Sky Conservation Area
- Scandinave Spa Blue Mountain
- Three Mile Lake
- Burl's Creek Event Grounds
- Taboo Muskoka Resort & Golf
- Wye Marsh Wildlife Centre
- Centennial Beach
- Menominee Lake
- Awenda Provincial Park
- Kee To Bala
- Wasaga Beach Area
- Casino Rama Resort
- Bass Lake Provincial Park
- Balsam Lake Provincial Park





