
Holiday rentals with a kayak in Orillia
Find and book unique kayak rentals on Airbnb
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 €77 per night before taxes and fees

Verified guest reviews
Over 980 verified reviews to help you choose

Family-friendly holiday rentals
10 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!
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

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.

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!

Waterfront Paradise on the Georgian Bay
This beautiful cottage of 2950sqft faces a breathtaking view of the Georgian Bay with over 105ft of lakefront. During the summer, this cottage is perfect for ATV and bike trails, wateractivities and fishing. The cottage includes kayaks and a paddle board for the guests to enjoy. During the winter, the cottage is ideal for ice fishing and is only a 13 minute drive to Mount St. Louis skiing. Under 10 minute driving distance to beaches, Tim Horton’s, LCBO, gas station, ice cream parlour and more.

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!

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).

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.

Lakefront | Hot Tub, Private Dock & Sandy Beach
Luxury lakefront cottage on Lake Simcoe with a rare shallow sandy-bottom shoreline, private dock, and hot tub—perfect for swimming and family fun. Enjoy breathtaking sunsets, kayaking, paddleboarding, fishing, BBQs, and a fire pit. Ideal for family vacations, holiday getaways, and group retreats near Toronto, minutes from Hwy 404. Features 6 bedrooms, 4 bathrooms, a fully equipped kitchen, and an open-concept living area. Private, peaceful, and perfect for unforgettable memories year-round.

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

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.

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.

Riverfront Cottage with HotTub Near Muskoka
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

Spectacular Waterfront 3 Bedroom Home!

Ski, Swim, Soak, Boat & Golf

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

The Muskoka River Homestead

Cozy Lakeside Cottage on Lake Scugog

2 minute walk to the beach / games room

Couchiching Lake Retreat - Sauna! Near Downtown!

[Casa Luna] Chic Lakehouse | BBQ | HotTub | LakeViews
Cottage rentals with a kayak

Ultimate Georgian Bay Vacation Getaway

Cottage on the Rocks - with Hot Tub and Sauna!

Beautiful Beachfront Cottage.

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

Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking

Private Lakefront Cottage | Fishing, Canoe & Sauna

Private & Modern Muskoka Lakefront Cottage w/ WiFi

Charming cottage on Lake Muskoka
Cabin rentals with a kayak

Forest Cabin 90 steps to the beach

Cozy, Quirky and Modern Lakefront Cottage

The Beach Cabin: Hot Tub/BBQ/ Sauna/Waterfront

Oak Cabin on Sparrow Lake

Muskoka Escape with Hot Tub, Waterfront & Firepit

Waterfront Cabin W/ Indoor Hot Tub, 90 min to GTA

Cozy Severn River Family Cottage

Charming Muskoka cottage, amazing views!
When is the best time to visit Orillia?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €306 | €338 | €218 | €217 | €285 | €264 | €360 | €326 | €264 | €246 | €189 | €233 |
| 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 |
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- Blue Mountain Village
- Wasaga Beach Area
- Torrance Barrens Dark Sky Conservation Area
- Mount St. Louis Moonstone
- Pigeon Lake
- Gull Lake
- Awenda Provincial Park
- Lakeridge Ski Resort
- Dagmar Ski Resort
- Scandinave Spa Blue Mountain
- Menominee Lake
- Casino Rama Resort
- Georgian Bay Islands National Park
- Sibbald Point Provincial Park
- Three Mile Lake
- Bass Lake Provincial Park
- Wye Marsh Wildlife Centre
- Centennial Beach
- Sunset Point Park
- Innisfil Beach Park
- Couchiching Beach Park
- Burl's Creek Event Grounds
- Kee To Bala
- Craigleith Provincial Park





