
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.

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.

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.

Retreat 82
Located just a little over an hour from Toronto, this cozy and unique lakefront cottage is the perfect place for a relaxing couples getaway. Offering private access to Lake Scugog with an oversized dock for you to take advantage of water activities, enjoy your morning coffee and watch some of the best sunsets on the lake. The cottage sits only 15 min. from the quaint town of Port Perry where you can go to enjoy its brewery, incredible cuisine, farmers markets, and picturesque Main Street.

Tiny Luxury Cottage with Hot Tub
This tiny luxury 2 bedroom cottage with loft 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.

The Friday Flat | Sunny Escape by the Marina
Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake Come experience the ultimate waterfront getaway at Friday Harbour

Muskoka Hideaway-hot tub/private trails/wood stove
Hidden amongst the trees in the middle of Muskoka, this Hemlock log cabin boasts high ceilings and a true "cabin in the woods" feel. Its not hard to relax and unwind with a coffee in front of the fire, or go and explore along the private forest trails (1-2k of walking trails). As well, downtown Bracebridge is a convenient 10 minute drive away with all amenities. There is a veggie garden on the property and depending when you come you can pick away at it :) Pets are welcome in the home!

Cottage on Lake Simcoe Amazing lake Views
Lakefront 3-bedroom cottage on Lake Simcoe – perfect for families! . Please note You can see the lake from living room. Features a fully equipped kitchen and two 3-piece washrooms .Enjoy stunning lake views, BBQ, fishing, and crystal-clear shallow water safe for swimming (weather permitting). Apple picking in Fall and icing fishing in winter! Water access and beach area are shared with a few friendly neighbors. Fast starlink internet! Owner Allergic issue ,so please NO PET allowed.

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

Upscale Spa Getaway w/ Private Sauna
Welcome to our most Dramatic & Romantic Penthouse Spa Getaway Suite! Reconnect with your loved one or celebrate that special milestone in our professionally designed to play with all your senses spa suite, this escape will leave you feeling refreshed and rejuvenated! Cozy up to any of 3 fire elements and then cleanse and detox in your own private in-suite Infrared Sauna! Cook up a gourmet meal in our fully equipped chef's dream kitchen and year round Weber BBQ for grilling!

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!

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

Lakefront Bungalow "Sunrise Bay" Kawartha Lakes

Cozy Lakeside Cottage on Lake Scugog

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

Green River Getaway

Couchiching Lake Retreat - Sauna! Near Downtown!

[Casa Luna]Chic Lakehouse| BBQ|HotTub|LakeViews

Modern Riverfront Escape w/Sauna, Gym, Dock

Paul’s Falls
Cottage rentals with a kayak

Waterfront cottage on quiet Spence lake

Cottage on the Rocks - with Hot Tub and Sauna!

Muskoka Cottage on warm lake - 4 BR/2 BR/Hottub

Peaceful Muskoka Riverfront cottage hot tub/Games

FRIEND LAKE HOUSE

Balsam Lake fully renovated 4BR 2BA modern cottage

Forest Harbour Hideaway

Charming Lakefront Bala Cottage
Cabin rentals with a kayak

Oak Cabin on Sparrow Lake

Newly Renovated boathouse on Balsalm Lake

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

Beautiful Vacation Home with a Large Backyard.

Cozy Severn River Family Cottage

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

Charming Muskoka cottage, amazing views!

Luxury Cottage with Hot Tub
Quick stats about holiday rentals with a kayak in Orillia

Total holiday rentals
Explore 10 holiday rentals in Orillia

Nightly prices starting at
Orillia holiday rentals start at € 78 per night before taxes and fees

Verified guest reviews
Over 740 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
10 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
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Grand River Holiday rentals
- Niagara Falls Holiday rentals
- Island of Montreal Holiday rentals
- St. Catharines Holiday rentals
- Northeast Ohio Holiday rentals
- Pittsburgh Holiday rentals
- Montreal Holiday rentals
- Laurentides Holiday rentals
- Erie Canal Holiday rentals
- Rentals with outdoor seating Orillia
- Cabin rentals Orillia
- House rentals Orillia
- Family-friendly rentals Orillia
- Rentals with a patio Orillia
- Rentals with pools Orillia
- Rentals with a washing machine and dryer Orillia
- Flat rentals Orillia
- Rentals with a hot tub Orillia
- Pet-friendly rentals Orillia
- Waterfront rentals Orillia
- Rentals with a fireplace Orillia
- Cottage rentals Orillia
- Beachfront rentals Orillia
- Rentals with beach access Orillia
- Rentals with a firepit Orillia
- Rentals with lake access Orillia
- Rentals with a kayak Simcoe County
- Rentals with a kayak Ontario
- Rentals with a kayak Canada
- Blue Mountain Village
- Snow Valley Ski Resort
- Devil's Glen Country Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Gull Lake
- Rocky Crest Golf Club
- Lakeridge Ski Resort
- Angus Glen Golf Club
- Mount St. Louis Moonstone
- Port Carling Golf & Country Club
- The Georgian Peaks Club
- The Club At Bond Head
- Muskoka Lakes Golf and Country Club
- Windermere Golf & Country Club
- Muskoka Bay Resort
- Lake Joseph Golf Club
- Bigwin Island Golf Club
- Wooden Sticks Golf Club
- The Georgian Bay Club
- Georgian Bay Islands National Park
- Barrie Country Club
- Dagmar Ski Resort
- Alpine Ski Club




