
Holiday rentals with a kayak in Simcoe County
Find and book unique kayak rentals on Airbnb
Top-rated Accommodation with a Kayak in Simcoe County
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Simcoe County kayak rentals
Holiday House Rentals with a Kayak

Blu Lake House | Waterfront June Special
Would recommend Nadia’s home to anyone visiting the area, the house is located on the lake with amazing scenery within a few seconds walking distance from the house! The house was beautiful so clean and spacious, everything was labelled and well laid out for us and Nadia was just fantastic to communicate with and super helpful with any requests we had! There was a lovely homely touch when we arrived to receive a welcome basket and a note from Nadia. I would highly recommend this property to anyone and we will for sure be back to visit during the summer months.

All season/Ski/Waterfront/Fish Modern Cottage
I have nothing but AMAZING things to say about our experience at this beautiful waterfront cottage. The pictures were beautiful but I was still blown away by the view and the overall home. Lily was an exceptional host, always super kind and responsive. My friends and I had the best time here and would absolutely recommend for anyone to book! :)

2min walk to the beach & 20 min drive to Blue Mnt
We only stayed there for one night but it was a really good experience. The house is too comfortable, it is very nice and very spacious. It has everything you need at your fingertips. The kayak and bikes are souvenirs that are in very good condition and can be put to great use if you wish. Helen is very attentive, timely and willing. She responds extremely quickly to your questions and gives you solutions for everything in a friendly and warm manner.

Beautiful 6 BEDROOM Muskoka Cottage
Our stay here was fantastic. The house is big with plenty of rooms for a big group. It was clean and orderly. There is a beautiful dock with a canoe, kayak and life jackets. Our host Fred was very kind and accommodating. I would recommend this to anyone looking a cottage getaway.

Ski, Swim, Soak, Boat & Golf
Had a great time at the cottage. Everything as pictured, beds were comfy, bathrooms clean, and lots to do including games, kayaking, paddle boarding, plunge pool, and hot tub. The lake isn’t great for swimming but we were never at a loss of things to do because of it. Wasaga is also just a drive away if you want something more lively for a night. Herb was a great host and very responsive, friendly and accommodating :)

✦9Bedroom✦8400sqft Farm House ✦28Acres ✦1HrToronto
We stayed at Cindy’s beautiful home for 3 nights. It was a family reunion with ages ranging from 75 to 4. Everyone loved the home and outdoor space. Games loft, pool table, kayaks, paddle boat, exercise room, games and puzzles were all used. We cooked all meals there. The kitchen was fully stocked with everything we needed. We all felt it was a gift that we found this home, and were able to reconnect as a family in such an ideal setting. Thank you Cindy, we have memories that will last a lifetime.

Teddy Bear Cottage
It was an absolute pleasure staying here so beautiful highly recommend:)))

Tranquility Cove Estate on Muskoka Lake Front
Lovely, spacious home with a beautiful view. I really liked how modern it was and that the living room was a big open area for our group to socialize. There was also a cute little sunroom overlooking the lake. This is the perfect cottage for a weekend getaway.
Cottages with a kayak

Waterfront Cottage in Muskoka | SAUNA | Beach
One of my favourite Airbnb cottages! The space is perfect for a family (lots of kid focused things) or for a few friends. The property is beautiful, has great amenities like the sauna and water toys. The beds are very comfy and kitchen had anything you could need. All in all this was one of the best experience I’ve had. The host was super lovely, and you can tell they’ve put a lot of thought and care into creating a great experience for their guests.

Luxury lakefront cottage escape
Cottage is totally unique being on a point with water on two sides. Architecture is modern and very comfortable. Two larger bedrooms are the same size so great to share with another couple. Views include Goffat Island and McCrae Provincial Park so lots of greenery. With the pick of two sides to paddle you can stay out of the wind. I have been coming to Lake Simcoe for over 50 years and I have never heard so many loon cries! And trumpeter swans for visuals. Firepit has great views! We had a great time.

Vintage Farmhouse Lakeview and Golfers Cottage
Great host, very responsive/helpful. House and furniture were very clean. Perfect for a family getaway.

2 BEDRM WATERFRONT COTTAGE, CANOE, KAYAKS, WIFI
Trevor's Cabin has a breathtaking view. The cabin is really nice with a full wood panel interior, lots of large water facing windows, and is very isolated. The property was spotless. Super easy to check in with clear instructions. Trevor Replied to every message within minutes. BBQ was clean and in perfect condition. outdoor picnic table and 4 Muskoka chairs. Private dock. all in all, a perfect cottage getaway location. My wife and I will definitely be back.

Waterfront Paradise on the Georgian Bay
We had an excellent stay at Steve’s cottage. Comfortable, super clean and had so many fun things to do! We really appreciated the gift basket and wine! It was enjoyed. Ty!

Spacious waterfront cottage w/ spectacular sunsets
Dave and his place were amazing! Beautiful Airbnb on the water and super spacious! The games downstairs were super fun, the nature was amazing, tons of wildlife, full kitchen amenities stocked for you to use, lots of seating etc. We had a big group and everyone was very comfortable and had so much fun! Dave was extremely nice, fast at responding, accommodating and kind! He gave us tips on fishing, supplied us with firewood and made great conversation. We came up for my birthday weekend and I had the best time! Thank you so much to Dave for our experience and we will be coming back!

Granny's Cottage
Thank you, Fran and Chris for an excellent stay! The cottage was beautiful and cozy. Your thoughtful touches made our weekend. We appreciate your responsiveness and hospitality and attention to details. Five stars!!!

The Bay View Cottage w/hot tub
Wow! What an amazing place to stay! Carm and Mary have a lovely space that they have worked to make comfortable and inviting! There were so many thoughtful touches. We enjoyed the peaceful environment, the hot tub, and the surrounding beauty of the Georgian Bay. There were plenty of things that our children enjoyed- games and ping pong and the yard. The beds were the most comfortable have stayed in all vacation. The kitchen was well stocked. The hosts were responsive and quick with recommendations. Highly, highly recommend this stay! Awenda Provincial Park and Wasaga Beach were easy drives and enjoyable.
Cabin rentals with a kayak

Oak Cabin on Sparrow Lake
The place had everything we needed—clean, peaceful, and filled with activities, especially fishing, which we really enjoyed. We were also so happy to spot river otters during our stay! Big thanks to Ash and Nicholas for being so accommodating with our inquiries. We just got home and are already wishing we could go back!

Beautiful Cottage on the water!
We had a really nice September weekend at Helen's cottage. The cottage is bright with nice big windows. The property on the river is beautiful with some lovely birch trees. We were especially happy to sit on the muskoka chairs and read our books. Very peaceful. Lots of outdoor seating options and the gazebo accessible from the kitchen or the back deck was especially appreciated. We ate most of our meals there. We were all happy with this cottage.

Reay Lake Tiny House
We stayed at Laura's cabin on our honeymoon and it was amazing! We love the outdoors and if the weather has cooperated we would have taken the kayaks out onto the lake. If your looking for a quick quiet getaway close to Gravenhurst with all the amenities of cottage county, this is your place to stay! The cabin was clean, stocked with all your kitchen essentials you will need.

The Blue Cottage
Jennifer was great. We all loved the space. Very cozy and beautiful view. Also enjoyed the kayaks and hanging at the dock. Wasaga Beach is nearby and we enjoyed spending time at the beach. There is an awesome cafe on site by the cottages which was fantastic. Overall a Greta experience. Highly recommend and would love to come back.

Gorgeous Muskokan Cottage on Six Mile Lake
My friends and I stayed at this cottage over Thanksgiving weekend and had an amazing time! The cottage was clean and had all the amenities needed. The location was beautiful, with the canoe, kayak and pedal boat being an amazing way to explore the lake. Kristian was also a great host - responded fast, gave recommendations, and was very welcoming. We would definitely recommend this place!

Lake view Blue cabin by the bay
The place was relaxing and we felt like we’re home.

90 Min to GTA Waterfront Cottage in Kawartha Lakes
We had an absolutely beautiful getaway at this waterfront Gem! The location was stunning, with some of the most breathtaking sunsets we've ever seen. Everything was clean, simple, and perfectly maintained, making our stay incredibly comfortable. Our kids felt right at home from the moment we arrived, and enjoyed all the water activities! We truly appreciate Victoria's quick response and can't wait to return!

Beautiful Six Mile Lake Muskoka
Great place, super well kept and beautiful. It has all you need for an awesome cottage experience and the perfect getaway
Destinations to explore
- Kid-friendly rentals Simcoe County
- Rentals with a fire pit Simcoe County
- Loft rentals Simcoe County
- Smoking-friendly rentals Simcoe County
- Rentals with a washing machine and dryer Simcoe County
- Chalet rentals Simcoe County
- Waterfront rentals Simcoe County
- Rentals with a fireplace Simcoe County
- Boutique hotel rentals Simcoe County
- Condo rentals Simcoe County
- Rentals with lake access Simcoe County
- Rentals with a patio Simcoe County
- Farmstay rentals Simcoe County
- Pet-friendly rentals Simcoe County
- Fitness-friendly rentals Simcoe County
- Bungalow rentals Simcoe County
- Beachfront rentals Simcoe County
- Hotel rentals Simcoe County
- Rentals with pools Simcoe County
- Villa rentals Simcoe County
- Rentals with outdoor seating Simcoe County
- Tiny house rentals Simcoe County
- Townhouse rentals Simcoe County
- Private suite rentals Simcoe County
- Rentals with a sauna Simcoe County
- Bed and breakfasts Simcoe County
- Apartment rentals Simcoe County
- Rentals with a hot tub Simcoe County
- Rentals with an EV charger Simcoe County
- Family-friendly rentals Simcoe County
- House rentals Simcoe County
- Guesthouse rentals Simcoe County
- Ski-in/ski-out rentals Simcoe County
- Cabin rentals Simcoe County
- Rentals with beach access Simcoe County
- Rentals with breakfast Simcoe County
- Cottage rentals Simcoe County
- Rentals with a kayak Ontario
- Rentals with a kayak Canada
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Blue Mountain Village
- TPC Toronto at Osprey Valley
- Port Carling Golf & Country Club
- Osler Bluff Ski Club
- Horseshoe Resort
- Devil's Glen Country Club
- Georgian Bay Islands National Park
- Beaver Valley Ski Club
- Mount St. Louis Moonstone
- Snow Valley Ski Resort
- Lake Joseph Golf Club
- Hockley Valley Resort - Golf, Spa and Ski
- Muskoka Lakes Golf and Country Club
- Angus Glen Golf Club
- Lakeridge Ski Resort
- The Georgian Peaks Club
- The Club At Bond Head
- Muskoka Bay Resort
- Caledon Country Club
- Alpine Ski Club
- Wooden Sticks Golf Club
- Dagmar Ski Resort
- National Pines Golf Club
- Barrie Country Club