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Vacation rentals with a kayak in Simcoe County

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Top-rated kayak rentals in Simcoe County

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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.

Oct 24 – 31

G$148,190 GYD per night

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 21 – 28

G$17,913 GYD per night

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 11 – 18

G$22,724 GYD per night

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 14 – 21

G$35,371 GYD per night

Home in Bracebridge

4.93 out of 5 average rating, 340 reviews

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!

Aug 25 – Sep 1

G$66,873 GYD 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!

May 31 – Jun 7

G$52,092 GYD per night

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

G$36,730 GYD per night

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).

Dec 13 – 20

G$63,807 GYD per night

Cabin in Washago

4.95 out of 5 average rating, 204 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.

Jul 18 – 25

G$74,303 GYD per night

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

G$142,675 GYD per night

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$35,042 GYD per night

Guest suite in Washago

4.99 out of 5 average rating, 104 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.

Jul 22 – 29

G$27,665 GYD per night

Vacation rentals for every style

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Popular amenities for Simcoe County kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in New Tecumseth

4.99 out of 5 average rating, 105 reviews

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

May 20 – 27

G$220,419 GYD per night

Home in Gravenhurst

4.82 out of 5 average rating, 302 reviews

Beautiful 6 BEDROOM Muskoka Cottage

Jun 22 – 29

G$162,562 GYD per night

Home in Collingwood

5.0 out of 5 average rating, 23 reviews

An oasis getaway near trails, lake, restaurants

May 27 – Jun 3

G$48,215 GYD per night

Home in Barrie

4.97 out of 5 average rating, 31 reviews

Exclusive Lakefront House on Private Lake

Jul 5 – 12

G$66,699 GYD per night

Home in Gravenhurst

5.0 out of 5 average rating, 25 reviews

Sunfilled cottage on the lake

Mar 28 – Apr 4

G$60,005 GYD per night

Home in Coldwater

4.92 out of 5 average rating, 24 reviews

Cozy Waterfront Cottage (90 minutes from the GTA)

May 23 – 30

G$47,652 GYD per night

Home in Elmvale

4.9 out of 5 average rating, 40 reviews

Ski, Swim, Soak, Boat & Golf

Jan 16 – 23

G$103,108 GYD per night

Home in Innisfil

5.0 out of 5 average rating, 14 reviews

Luxury home with pickleball!

Aug 12 – 19

G$97,204 GYD per night

Cottage rentals with a kayak

Cottage in Innisfil

4.99 out of 5 average rating, 120 reviews

Charming waterfront cottage on Lake Simcoe

Apr 3 – 10

G$140,487 GYD per night

Cottage in Richmond Hill

4.94 out of 5 average rating, 127 reviews

White Oak on Wilcox-Richmond Hill Lakefront Oasis

Sep 16 – 23

G$57,448 GYD per night

Cottage in Port Severn

4.97 out of 5 average rating, 111 reviews

Paradise Getaway

Jun 17 – 24

G$83,439 GYD per night

Cottage in Brechin

4.96 out of 5 average rating, 134 reviews

Spacious waterfront cottage w/ spectacular sunsets

Nov 11 – 18

G$63,344 GYD per night

Cottage in Brechin

4.93 out of 5 average rating, 118 reviews

COTTAGE ON LAKE SIMCOE -4 BEDROOMS /2WSHRMS

Jul 14 – 21

G$85,085 GYD per night

Cottage in Washago

4.97 out of 5 average rating, 144 reviews

Mistywood Cottage

Sep 29 – Oct 6

G$125,378 GYD per night

Cottage in Port Severn

4.94 out of 5 average rating, 127 reviews

Muskoka Cottage on Gibson Lake - 5 BR/3 BATHS

Feb 23 – Mar 2

G$105,419 GYD per night

Cottage in Gravenhurst

4.85 out of 5 average rating, 137 reviews

Riverside Gravenhurst cottage. Waterfront w/ sauna

Apr 2 – 9

G$52,740 GYD per night

Cabin rentals with a kayak

Cabin in Brechin

4.94 out of 5 average rating, 17 reviews

Waterfront Cottage Getaway with Amazing Lake Views

Jan 20 – 27

G$35,243 GYD per night

Cabin in Uxbridge

5.0 out of 5 average rating, 6 reviews

Cabin by the Lake

Jul 15 – 22

G$38,021 GYD per night

Cabin in Innisfil

5.0 out of 5 average rating, 15 reviews

Rustic Cozy Cabin in Innisfil

Jun 17 – 24

G$18,941 GYD per night

Cabin in Bracebridge

5.0 out of 5 average rating, 70 reviews

Cabin 1 on the Muskoka River. Firewood included !

Jan 7 – 14

G$29,519 GYD per night

Cabin in Severn Bridge

5.0 out of 5 average rating, 12 reviews

Oak Cabin on Sparrow Lake

G$16,684 GYD per night

Cabin in Gravenhurst

4.76 out of 5 average rating, 62 reviews

Reay Lake Tiny House

Nov 18 – 25

G$32,963 GYD 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

G$58,793 GYD per night

Cabin in Sebright

5.0 out of 5 average rating, 11 reviews

90 Min to GTA Waterfront Cottage in Kawartha Lakes

Oct 20 – 27

G$49,394 GYD per night

Destinations to explore