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Vacation rentals with a kayak in Oro-Medonte

Find and book unique kayak rentals on Airbnb

Top-rated accommodations with a kayak in Oro-Medonte

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

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Cottage in Brechin

4.93 out of 5 average rating, 119 reviews

COTTAGE ON LAKE SIMCOE -4 BEDROOMS /2WSHRMS

Welcome to our cozy cottage in Simcoe County, just a short drive from Toronto. It's the perfect spot for bringing together family and friends. Here, laughter fills the home, and nature's beauty is right outside your door. Dive into clear waters for some fun kayaking and boating, and wake up to beautiful sunrises from our private dock. Take a walk on scenic paths, enjoy outdoor BBQs, and paddle around in our kayaks. Book your special getaway today and start making heartwarming memories that last.

Jun. 6 – 13

$342 CAD per night

Guest favourite

Cottage in Brechin

4.96 out of 5 average rating, 134 reviews

Spacious waterfront cottage w/ spectacular sunsets

Hi welcome to Sunset Shores Vacations on beautiful Lake Dalrymple. Enjoy the perfect vacation with the most spectacular sunsets viewable from the living room/kitchen, large upper deck, lower patio or right down at the waters edge. The fishing is great you can even catch fish off the dock. Swimming is great especially for young children cause the water is shallow off the dock. Explore the lake with the use of canoes, kayaks and paddle boat. Enjoy ice fishing, snowmobiling or a winter retreat.

Nov. 7 – 14

$485 CAD per night

Cottage in Waubaushene

4.84 out of 5 average rating, 121 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 boat 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.

Mar. 5 – 12

$1,135 CAD per night

Cottage in Washago

4.87 out of 5 average rating, 101 reviews

Vintage Farmhouse Lakeview Cottage

Perfect getaway 1.5 hours from Toronto. Custom vintage themed private cottage across from the lake. Nestled on private wooded lot with room for your family to unwind. Spacious open concept living area with large fireplace. Vintage arcade games, foosball table, board games and yard games to enhance your family fun experience. Private deck areas for outdoor lounging/picnicking. Year round activities, kayaking, fishing, swimming (lake across road), golfing, x-country skiing. Casino 18 min.

May 11 – 18

$278 CAD per night

Guest favourite

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. 1 – 8

$163 CAD per night

Guest favourite

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!

Dec. 2 – 9

$162 CAD per night

Guest favourite

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.

Sep. 18 – 25

$257 CAD per night

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. 10 – 17

$288 CAD per night

Guest favourite

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.

Jun. 24 – Jul. 1

$268 CAD per night

Guest favourite

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).

Nov. 5 – 12

$512 CAD per night

Guest favourite

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.

Oct. 7 – 14

$432 CAD per night

Guest favourite

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 ***

Mar. 27 – Apr. 3

$1,094 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Bungalows

Intimate homes, inviting architecture

Houses

A space that's all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Oro-Medonte kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Guest favourite

Home in New Tecumseth

4.99 out of 5 average rating, 105 reviews

✦9Bedroom✦8400sqft Farm House ✦28Acres ✦1HrToronto

Apr. 15 – 22

$1,579 CAD per night

Guest favourite

Home in Barrie

4.97 out of 5 average rating, 31 reviews

Exclusive Lakefront House on Private Lake

Jul. 5 – 12

$523 CAD per night

Home in Sebright

4.83 out of 5 average rating, 82 reviews

Riverfront Cottage Escape for Stress Relief

Nov. 24 – Dec. 1

$235 CAD per night

Home in Waubaushene

4.8 out of 5 average rating, 15 reviews

Waterfront/All season/Swim/Fish/Beach/Private Dock

Oct. 24 – 31

$363 CAD per night

Guest favourite

Home in Washago

4.96 out of 5 average rating, 46 reviews

Breathtaking RiverFrontOasis with a HOT Sauna

Dec. 11 – 18

$595 CAD per night

Guest favourite

Home in Wasaga Beach

4.95 out of 5 average rating, 73 reviews

20 min from Blue Mountain -2 min walk to the beach

Nov. 2 – 9

$274 CAD per night

Guest favourite

Home in Coldwater

4.92 out of 5 average rating, 24 reviews

Cozy Waterfront Cottage (90 minutes from the GTA)

Oct. 5 – 12

$365 CAD per night

Guest favourite

Home in Elmvale

4.9 out of 5 average rating, 40 reviews

Ski, Swim, Soak, Boat & Golf

Dec. 22 – 29

$1,141 CAD per night

Cottage rentals with a kayak

Guest favourite

Cottage in Innisfil

4.99 out of 5 average rating, 121 reviews

Charming waterfront cottage on Lake Simcoe

Apr. 20 – 27

$1,070 CAD per night

Guest favourite

Cottage in Port Severn

4.97 out of 5 average rating, 111 reviews

Paradise Getaway

Jun. 17 – 24

$637 CAD per night

Guest favourite

Cottage in Washago

4.97 out of 5 average rating, 144 reviews

Mistywood Cottage

Dec. 2 – 9

$785 CAD per night

Cottage in Gravenhurst

4.85 out of 5 average rating, 137 reviews

Riverside Gravenhurst cottage. Waterfront w/ sauna

Dec. 7 – 14

$352 CAD per night

Cottage in Gravenhurst

4.83 out of 5 average rating, 115 reviews

Winter Escape Waterfront Cottage Hottub&Sauna!

Sep. 19 – 26

$612 CAD per night

Guest favourite

Cottage in Waubaushene

4.85 out of 5 average rating, 132 reviews

Georgian Bay-Trail/Run/Bike/Hike/HotTub/Sauna/Swim

Aug. 15 – 22

$883 CAD per night

Cottage in Gravenhurst

4.84 out of 5 average rating, 150 reviews

Trenanthia "Cahoots" Cottage: HotTub,Sauna,GamesRm

Jan. 6 – 13

$550 CAD per night

Guest favourite

Cottage in Keswick

4.91 out of 5 average rating, 32 reviews

Private lakefront cottage of Lake Simcoe

May 4 – 11

$325 CAD per night

Cabin rentals with a kayak

Guest favourite

Cabin in Penetanguishene

4.83 out of 5 average rating, 18 reviews

Pet Friendly Nostalgic Cabin

Feb. 1 – 8

$168 CAD per night

Guest favourite

Cabin in Brechin

4.94 out of 5 average rating, 17 reviews

Waterfront Cottage Getaway with Amazing Lake Views

Nov. 26 – Dec. 3

$245 CAD per night

Guest favourite

Cabin in Innisfil

5.0 out of 5 average rating, 15 reviews

Rustic Cozy Cabin in Innisfil

Jun. 17 – 24

$127 CAD per night

Guest favourite

Cabin in Uxbridge

5.0 out of 5 average rating, 6 reviews

Cabin by the Lake

Aug. 2 – 9

$289 CAD per night

Cabin in Port Severn

4.65 out of 5 average rating, 91 reviews

Dragonfly Cottage / Six Mile Lake / Muskoka

Jun. 29 – Jul. 6

$435 CAD per night

Guest favourite

Cabin in Sebright

5.0 out of 5 average rating, 11 reviews

90 Min to GTA Waterfront Cottage in Kawartha Lakes

Jan. 11 – 18

$372 CAD per night

Cabin in Gravenhurst

5.0 out of 5 average rating, 3 reviews

Muskoka Lake View Getaway.

Sep. 22 – 29

$567 CAD per night

Guest favourite

Cabin in Coldwater

5.0 out of 5 average rating, 5 reviews

Relax at your Severn Retreat

Jul. 14 – 21

$490 CAD per night

Quick stats about vacation rentals with a kayak in Oro-Medonte

Total rentals
210 properties
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
100 properties allow pets
Family-friendly rentals
180 properties are a good fit for families
Total number of reviews
7.9K reviews
Nightly prices starting at
$41 CAD before taxes and fees

Destinations to explore