Vacation rentals with a kayak in Simcoe County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Simcoe County

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Guest favorite

Cottage in Tiny

4.97 out of 5 average rating, 74 reviews

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

Oct 16 – 23

R5,431 ZAR per night

Guest favorite

Cabin in Penetanguishene

4.83 out of 5 average rating, 18 reviews

Pet Friendly Nostalgic Cabin

Welcome to our newly built waterfront cottages - 5 Individual townhouses units : ❀Unit 2 - Old Timer ❀Stunning 270' of Gerogian Bay beach waterfront ❀Kayaks, PaddleBoard, Water Trampolines, Firepit and BBQ grill (Charcoal & Propane) Onsite ❀15mins away from Balm Beach, & close to many more amazing beaches. ❄Toboggan from the top of our property down to the frozen lake！ ❄Ice Fishing on-site (Extra fees may apply) Unit 2 features: ☑ Pet Friendly ☑ 65inch 4k TV ☑ Central Heating + AC ☑ Wifi

Mar 26 – Apr 2

R1,694 ZAR 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!

Oct 5 – 12

R2,007 ZAR 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!

Apr 15 – 22

R1,757 ZAR 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 15 – 22

R3,127 ZAR per night

Guest favorite

Cottage in Innisfil

4.99 out of 5 average rating, 121 reviews

Charming waterfront cottage on Lake Simcoe

Charming four-bedroom cottage plus Boat house conveniently located 1 hour from GTA on a private waterfront lot surrounded by mature trees with sandy bottom and clear water. The proximity of the cottage to the water is sure to please either the sun or shade lovers with multiple large decks and dock for sitting, dining and lounging. We offer hot tub, Sauna, BBQ. trampoline, bball net, paddle boat, floating mat, kayaks, canoe, paddle board, pool table, foosball. fishing gear, life jackets

Feb 19 – 26

R12,418 ZAR per night

Superhost

Cabin in Washago

4.82 out of 5 average rating, 221 reviews

The Islandview

Welcome to The Islandview! Located on the sandy shores of Lake Couchiching, this gorgeous 4 season, 2-story open concept cottage is the perfect getaway. Escape to the private sun filled deck or dock on the water. Entertain in the open concept kitchen, two large living areas, or outdoors around the fire. During the day, enjoy watching the kids swim on the beach and at night take in the breathtaking sunsets. 5min to Washago & 10min to Casino Rama. Fully equipped with everything you need!

Oct 23 – 30

R3,206 ZAR 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

R3,353 ZAR per night

Guest favorite

Cottage in Orillia

5.0 out of 5 average rating, 12 reviews

Luxury lakefront cottage escape

This one-of-a-kind lakefront retreat is tucked away at the end of a peninsula with access to Lake Simcoe on either side of the cottage. Nestled in over an acre of nature, enjoy a peaceful escape just 1.5 hrs from Toronto in this newly renovated, all-season getaway. Conveniently located in Orillia, it’s a 15-min walk to Mara Provincial Park and only a short drive to Casino Rama (11 min), Vettä Nordic Spa (33 min), Mount St. Louis (34 min), and Horseshoe Resort (33 min).

Apr 10 – 17

R5,640 ZAR per night

Guest favorite

Cabin in Washago

4.95 out of 5 average rating, 205 reviews

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 (15 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.

Sep 5 – 12

R4,940 ZAR 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 ***

Sep 24 – Oct 1

R13,254 ZAR per night

Guest favorite

Cottage in Torrance

4.97 out of 5 average rating, 195 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

R3,098 ZAR per night