Holiday rentals with a kayak in Simcoe County

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Simcoe County

Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Cottage

5 out of 5 average rating, 106 reviews

CozyPeaceful LakeCottage HotTub CheckOutOurReviews

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

Guest favourite

Cottage

5 out of 5 average rating, 110 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).

Guest favourite

Cottage

4.98 out of 5 average rating, 101 reviews

Nordic Spa- Sauna: Weekday PROMO 2nd night $350

*** AMAZING WINTER PROMO: Weekday stays: BOOK first night, and ask us to send you a promo rate for the second night @ $350 and the 3rd Night @ $250 Your own private Nordic Spa !! Wood fired hot tub + sauna and Cold Plunge ! 1 hour and 20 mins from Toronto. 75 Feet of waterfront with the cottage being 18 feet from the edge of the lake. It is an incredible property to enjoy everything Lake Simcoe has to offer in the summer and winter ! Close to Orilla, ski hills and amazing ice fishing.

Guest favourite

Apartment

4.97 out of 5 average rating, 140 reviews

#TheFridayFlat: Winter Wonderland Charming Condo

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!

Guest favourite

Apartment

5 out of 5 average rating, 116 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh, unwind and rejuvenate in your very own 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! We know you will enjoy your stay and love the outdoor elements AND the indoor ones too!

Guest favourite

Cottage

4.99 out of 5 average rating, 152 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.

Guest favourite

Chalet

4.93 out of 5 average rating, 219 reviews

Log Cabin on the Lake Bed and Breakfast

Log Cabin on the Lake Bed and Breakfast We provide a 1st morning continental breakfast A Lakefront getaway for couples with an amazing view. Experience tiny home living in a custom built Log Cabin. Landscaping provides privacy for all parties (owner next door) we have parking for a boat , with 2 launches within 5 min. One into Morrison Lake the other into the Trent Severn . cross country skiing, ice fishing, water skiing swimming boating. Ready to escape, our Log Cabin could be it.

Guest favourite

Cottage

4.95 out of 5 average rating, 129 reviews

Forest Harbour Hideaway

This cozy and quaint waterfront cottage is located in the heart of a quiet neighbourhood and overlooks beautiful Georgian Bay. There is private access to the water via dock, and a public beach a 5 minute walk away. Midland is a short 15 minute drive and offers a variety of restaurants and shops, as well as local attractions such as Sainte-Marie Among the Hurons and the Wye Marsh Wildlife Centre. Parking allows for 6 vehicles comfortably, and the wifi is excellent.

Guest favourite

Cabin

4.94 out of 5 average rating, 247 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.

Guest favourite

Cottage

4.97 out of 5 average rating, 217 reviews

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 2 Minimum 6 nights with a Sunday check in.

Guest favourite

Guest suite

4.99 out of 5 average rating, 134 reviews

Spacious Apartment Facing The Severn River

Clean, lower unit, private entrance, one bedroom apartment fronting on the Severn River (aka Black). 90 mins. north of GTA. Five min. off Hwy 11 at the village of Washago where you can find most amenities. Fair weather activities include swimming, kayaking, canoeing, fishing or just dock time. Available winter months for simple relaxing accommodation. Hosts live on the upper floor and will be available to assist but will respect your privacy.

Superhost

Cottage

4.88 out of 5 average rating, 101 reviews

Orr Lake Oasis

Sit, kick back, laugh & relax in this calm, stress-free, pet-friendly, stylish space with family and friends. Enjoy the great cottage views, games and much more. Drink your favourite drink by the hot tub or by the fire pit overlooking the lake. Take a steam in the barrel sauna just a hop away or take a walk on the local trails. Shop and dine at a tasty local restaurant 10 minutes away or drive out to the city of Midland just under 20 minutes