Vacation rentals with a kayak in Lake Simcoe

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Lake Simcoe

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Guest favorite

Guesthouse in Algonquin Highlands

4.92 out of 5 average rating, 139 reviews

Charming mini-cottage, footsteps to water's edge

**No extra fees other than airbnb fees** Relax in a quaint, studio mini-cottage surrounded by water on 3 sides! Enjoy the freshness of spring, summer water activities & gorgeous autumn colours in cottage country. Perfect for singles/couples; peninsula location & tall windows give 270 degree lakeviews. Wifi, 1 parking space, kitchenette, 3pce bthrm, Queen bed, futon bed, satelliteTV. Private for guests: shoreline, island, dock, barbeQ, mountain bikes, hammock, firepit, canoes, kayaks, tubes.

Feb 2 – 9

G$28,748 GYD per night

Guest favorite

Condo in Innisfil

4.97 out of 5 average rating, 111 reviews

•#TheFridayFlat Luxury Poolside Retreat for Summer

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!

Sep 17 – 24

G$22,555 GYD per night

Guest favorite

Cottage in Georgina

4.98 out of 5 average rating, 132 reviews

Granny's Cottage

Granny’s Cottage is located on Lake Drive East across the road from Lake Simcoe. Our private lakefront is yours to enjoy. Our lakehouse equipped with mini fridge and chairs while looking out over beautiful Lake Simcoe. Lakehouse is available late spring to early fall. This cozy cottage is newly renovated with all the comforts for a much needed getaway. Available for your use is a badminton net, 2 kayaks and a large canoe (seasonal). There is also a secure lock up for you bicycles.

Oct 12 – 19

G$35,281 GYD per night

Guest favorite

Condo in Innisfil

4.84 out of 5 average rating, 171 reviews

Marina view at Friday Harbor 2bdm/2bth Pool option

Friday Harbour is a brand new all season resort just 1 hour and 15 minutes from Toronto. A perfect getaway without the long drive. Airbnb guests can now purchase a pass for the beach club pool! This Airbnb is an eight hundred square foot condo all newly furnished with king bed in master bedroom with ensuite bathroom, Queen bed in guest bedroom. Enjoy 65” Samsung Smart TV or sitting on the huge deck overlooking the marina and island homes. Board walk to beach, this place is amazing!

Mar 28 – Apr 4

G$19,828 GYD per night

Guest favorite

Loft in Kawartha Lakes

4.99 out of 5 average rating, 179 reviews

The Lakeland Loft/A quiet getaway/near Bobcaygeon

The Lakeland Loft is situated on a peaceful one acre property with over 200 feet of shore line and surrounded by forest and walking trails. This property is minutes from the Bobcaygeon Lock by road or boat. The loft is located on the second story of a self contained building and has a private entrance. The Loft has been totally renovated for use by guests and has everything you will need for a comfortable stay. There is a dock for guest use. A public boat launch is about 5 minutes away.

Sep 29 – Oct 6

G$30,266 GYD per night

Guest favorite

Guesthouse in Kawartha Lakes

4.92 out of 5 average rating, 247 reviews

The Loft on Sturgeon Lake

Enjoy the lakeside lifestyle on Sturgeon Lake! This beautiful custom loft features one spacious bedroom with a queen bed and large, bright windows. The suite has a private washroom with a large walk-in shower. There is a full kitchen available and living space with a pull out couch. Experience stunning sunsets over Sturgeon Lake from your private balcony or by the lake at the dockside fire pit. There is an outdoor pool that can be used when available and canoes and kayaks.

Sep 15 – 22

G$28,773 GYD per night

Guest favorite

Farm stay in Gravenhurst

4.97 out of 5 average rating, 370 reviews

Stix N Stones (Includes Light Breakfast & Kayaks)

Nestled in the woods on Walkers Point, this is a great opportunity to reconnect with nature. We promise when you leave you’ll appreciate the forest as much as the water that surrounds us. Although we are not on the water, we are a 3min drive to a semi-private beach. Kayaks & life vests included (& delivered). Snowshoes incl in winter. Light breakfast is yogurt & fruit. Short distance to renowned hiking trails, Hardy Lake Park, Sawdust City & Clearlake Brewery, Muskoka Winery.

Dec 10 – 17

G$33,760 GYD per night

Guest favorite

Guesthouse in Gravenhurst

4.92 out of 5 average rating, 121 reviews

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.

May 27 – Jun 3

G$37,932 GYD per night

Guest favorite

Yurt in Irondale

4.98 out of 5 average rating, 213 reviews

Tall Pines Nature Retreats ~ L’Orange

Experience nature while staying in a unique yurt with private hot tub. Explore a magical riverside property and observe wildlife from one of several sitting areas. Sit by a campfire and gaze at the stars. Relax in the indoor soaker tub admiring intricate hand painted artwork on the ceiling of the yurt. Paddle, swim or float in the sandy river. Your stay includes complimentary use of paddling equipment canoe, kayaks, SUP or snowshoes, seasonally available.

Oct 22 – 29

G$42,284 GYD per night

Guest favorite

Cottage in Georgina

4.9 out of 5 average rating, 239 reviews

Beach House-S/W Exposure! Hot Tub Sandy Water!

Location, Location, Location! S/W Exposure! firepit, hot tub, west-facing sunset views, fishing, swimming, boating, and nearby amenities. In winter, it transforms into a winter wonderland, perfect for ice fishing and snowmobiling. New renovated 4-seasons retreat. Less than an hour from the GTA. This lakeside haven on Prestigious Cooks Bay provides the ideal getaway. Enjoy a rejuvenating experience with a *** Don't miss out on this incredible opportunity ***

Dec 12 – 19

G$142,556 GYD per night

Guest favorite

Cottage in Torrance

4.97 out of 5 average rating, 194 reviews

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Newly renovated 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 2 Minimum 6 nights with a Sunday check in.

May 20 – 25

G$34,954 GYD per night

Guest favorite

Cottage in Kinmount

4.94 out of 5 average rating, 280 reviews

Secluded Cottage on a Private Lake

2 bedroom cedar log cottage on over 300 beautiful acres. Very private. Many walking trails to explore and enjoy. Lovely deck on the cottage and a great dock at the lake. Canoe, pedal boat, and swimming raft. All just a 2 hour drive from Toronto. We have another property at the opposite end of the private lake - all of the same wonderful outdoor activities but this time based out of a stunning log house. Check it out under other Kinmount listings!!

Jan 7 – 14

G$35,686 GYD per night