
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 €78 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
4.98 out of 5 average rating, 235 reviews
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!
5.0 out of 5 average rating, 234 reviews
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.
4.95 out of 5 average rating, 180 reviews
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.
4.84 out of 5 average rating, 191 reviews
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!
4.96 out of 5 average rating, 144 reviews
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).
4.97 out of 5 average rating, 175 reviews
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.
4.98 out of 5 average rating, 156 reviews
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
4.92 out of 5 average rating, 140 reviews
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.
4.93 out of 5 average rating, 178 reviews
Beautiful Beachfront Cottage.
Township of Tiny License Number: STRTT-2026-110 Enjoy our all-season paradise only 1.5 hours north of Toronto! In summer, enjoy the sandy beach waterfront with incredible views of Georgian Bay with the Town of Penetanguishene, and all its historic charm, only 20 minutes away! In winter, enjoy all the area has to offer with incredible OFSC groomed snowmobile trails and amazing ski resorts less than an hour away! *Contract to be sent and signed prior to stay.
4.97 out of 5 average rating, 115 reviews
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.
4.93 out of 5 average rating, 129 reviews
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.
4.93 out of 5 average rating, 175 reviewsPopular amenities for kayak rentals in Orillia
House rentals with a kayak

Spectacular Waterfront 3 Bedroom Home!
4.95 out of 5 average rating, 288 reviews
Ski, Swim, Soak, Boat & Golf
4.85 out of 5 average rating, 112 reviews
Secluded Muskoka A-Frame | Hot Tub, Dock, Firepit
4.95 out of 5 average rating, 140 reviews
The Muskoka River Homestead
4.92 out of 5 average rating, 252 reviews
Cozy Lakeside Cottage on Lake Scugog
4.93 out of 5 average rating, 141 reviews
Relaxing fall getaway / games room
4.94 out of 5 average rating, 111 reviews
Muskoka Hideaway-hot tub/private trails/wood stove
4.94 out of 5 average rating, 464 reviews
Couchiching Lake Retreat - Sauna! Near Downtown!
4.78 out of 5 average rating, 41 reviewsCottage rentals with a kayak

Ultimate Georgian Bay Vacation Getaway
4.96 out of 5 average rating, 182 reviews
Private & Modern Muskoka Lakefront Cottage w/ WiFi
4.94 out of 5 average rating, 145 reviews
Kabin Tapoke | Wild Kabin | Hot tub-Sauna-Sunsets
4.99 out of 5 average rating, 135 reviews
Tiny Luxury Cottage with Hot Tub
4.99 out of 5 average rating, 184 reviews
All Season Muskoka Retreat on Sparrow Lake
4.88 out of 5 average rating, 115 reviews
Cottage on the Rocks - with Hot Tub and Sauna!
4.96 out of 5 average rating, 134 reviews
Waterfront Muskoka Cottage on Trent-Severn River
4.75 out of 5 average rating, 111 reviews
Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking
4.9 out of 5 average rating, 217 reviewsCabin rentals with a kayak

Forest Cabin 90 steps to the beach
4.89 out of 5 average rating, 357 reviews
Cozy, Quirky and Modern Lakefront Cottage
4.92 out of 5 average rating, 224 reviews
Vintage Hollywood Cabin: Hot Tub/ BBQ/Sauna/ Beach
4.92 out of 5 average rating, 121 reviews
Oak Cabin on Sparrow Lake
4.89 out of 5 average rating, 76 reviews
Waterfront Cabin W/ Indoor Hot Tub, 90 min to GTA
4.82 out of 5 average rating, 67 reviews
Newly Renovated boathouse on Balsalm Lake
5.0 out of 5 average rating, 33 reviews
Lake view house
4.7 out of 5 average rating, 23 reviews
Luxury Cottage with Hot Tub
5.0 out of 5 average rating, 9 reviewsWhen is the best time to visit Orillia?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €309 | €342 | €220 | €220 | €288 | €268 | €364 | €330 | €268 | €249 | €192 | €236 |
| 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
- Scandinave Spa Blue Mountain
- Dagmar Ski Resort
- Menominee Lake
- Casino Rama Resort
- Georgian Bay Islands National Park
- Sibbald Point Provincial Park
- Three Mile Lake
- Bass Lake Provincial Park
- Centennial Beach
- Wye Marsh Wildlife Centre
- Sunset Point Park
- Innisfil Beach Park
- Couchiching Beach Park
- Burl's Creek Event Grounds
- Kee To Bala
- Craigleith Provincial Park





