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Holiday rentals with a kayak in Penetanguishene

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Penetanguishene

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

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Guest favourite
A wooden dock extends over calm waters, framed by lush forests and rocky shores. Two adirondack chairs face the sunset, inviting a moment of connection. Vibrant hues of orange and purple fill the sky, reflecting gently on the water's surface.
Cottage in Gravenhurst
4.94 out of 5 average rating, 119 reviews

Private & Modern Muskoka Lakefront Cottage w/ WiFi

This ultra private and modernly designed Muskoka lakefront / beachfront cottage is perfectly situated at the corner of a beautiful lake, only a 1.5h drive from the GTA and 2hs from Toronto. It borders acres of pristine Crown pine forests, has a private beach, and a luxury new dock that extends from sandy shores. It has a massive new deck and large premium Weber BBQ. New leather couch. Swim, fish, canoe, kayak, sunbathe. Modern interior. High-speed WiFi. Trails. Superhost and guest favourite.

Guest favourite
Cottage in Tiny
4.96 out of 5 average rating, 151 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.

Top guest favourite
A tranquil lakeside view displays a spacious cottage with large windows, reflecting on the calm water. Surrounding trees and a clear blue sky add to the serene atmosphere, inviting relaxation and enjoyment of the natural beauty.
Cottage in Georgian Bay
4.98 out of 5 average rating, 135 reviews

Muskoka Stunning Cottage On Little Lake

Surrounded by Little Lake, this gem provides a relaxing getaway with amazing water views. Spend your days peacefully rowing on the lake or having a picnic on the private beach, and your nights settling by a crackling fire. The home itself is plenty spacious for unwinding and getting a good night's sleep, views all-inclusive. Explore Port Severn Park right next door and play around in the public beach and splash pad. For more adventure, hike the beautiful Georgian Bay Islands National Park.

Top guest favourite
A handcrafted timber frame cabin is set among trees, featuring natural wood siding and large windows that invite the outdoors in. A welcoming porch is accessed by a wooden staircase, while a covered area to the side provides shelter. The surrounding forest complements the rustic design.
Cabin in Bracebridge
5 out of 5 average rating, 257 reviews

Secluded Lakeside Retreat - Atkins Hideaway

Tucked in the heart of Muskoka, this handcrafted timber frame cabin rests alongside a scenic spring-fed lake, surrounded by 8 acres of private forest. Only 10 minutes from Bracebridge, enjoy serene lake life and natural beauty while remaining close to town amenities, local shops, and eateries. Enjoy private dock relaxation, cozy cabin comforts, and outdoor fires. A Provincial Park Day Pass is included (*security deposit required) for added adventure. Come relax, recharge and reconnect.

Top guest favourite
A modern cottage is set against a backdrop of tall trees, featuring a large wraparound deck illuminated by warm lights. A fire pit sits on a granite outcrop, surrounded by outdoor chairs. The peaceful evening sky casts a calm ambiance over the scene.
Cottage in Bracebridge
4.99 out of 5 average rating, 158 reviews

Tiny Luxury Cottage with Hot Tub

This tiny luxury 2 bedroom cottage is perfect for a romantic couple or small family getaway. Nestled on 1.5 acres among majestic trees and granite outcrops, creates beautiful views from the deck with BBQ, fire pit, hot tub or massive windows throughout the cottage. Water dam and river across the road create relaxing waterfall sounds that are heard from deck or enjoy it close up from the private shoreline deck and dock. Explore the Muskoka River on the kayak, SUP or river tubes.

Top guest favourite
A peaceful dock stretches over calm waters, featuring two classic Adirondack chairs positioned to face serene natural surroundings. The still surface of the lake reflects the clear blue sky and lush greenery along the shore, creating a tranquil setting for relaxation.
Guest house in Gravenhurst
4.91 out of 5 average rating, 183 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.

Top guest favourite
A wooden dock extends over calm waters, featuring four Adirondack chairs in red and yellow. The serene lake reflects the surrounding trees and sky, with a light morning mist gently hovering above the water's surface.
Cottage in Port Carling
4.99 out of 5 average rating, 137 reviews

Gorgeous Muskoka Getaway on stunning private lake

Enjoy the perfect cozy Muskoka cottage "The Perch" on a beautiful private lake. This family and pet-friendly home is your year-round retreat. Your family will be close to everything when you stay at this centrally located place but you will feel like you are at a peaceful cottage surrounded by nature. With all of the amenities that you would need, you will find that The Perch is everything you are looking for to create memories with friends, families or a loved ones.

Top guest favourite
A stone patio leads to a sandy beach, featuring a seating area with red chairs overlooking Georgian Bay. The calm water is visible in the background, framed by trees and large rocks, with yellow kayaks positioned along the shore.
Cottage in Tiny
4.96 out of 5 average rating, 104 reviews

Beautiful Beachfront Cottage.

Township of Tiny License Number: STRTT-2026-110 Enjoy our all-season paradise only 1.5 hours north of Toronto! In summer, enjoy the sandy beach waterfront with incredible views of Georgian Bay with the Town of Penetanguishene, and all its historic charm, only 20 minutes away! In winter, enjoy all the area has to offer with incredible OFSC groomed snowmobile trails and amazing ski resorts less than an hour away! *Contract to be sent and signed prior to stay.

Top guest favourite
A hot tub is positioned on a wooden deck, surrounded by natural greenery. Nearby, a fire pit emits a warm glow, creating a cozy atmosphere. Soft outdoor lighting complements the setting, with views of the landscape visible in the background.
Flat in Bracebridge
4.98 out of 5 average rating, 409 reviews

The Muskoka River Chalet - The King's Den

Welcome to Muskoka River Chalet! **Please read full listing description before booking.** Relax in your fully private one-bedroom walkout apartment with private kitchen, cozy living room, featuring smart TVs and toasty fireplaces. Explore our shared outdoor spaces along 60' of waterfront. Indulge in the hot tub for relaxation. Just minutes walking to town for shopping, dining, and nightlife. Book now for a perfect blend of comfort and convenience!

Top guest favourite
A serene waterfront view is presented from a deck, showcasing calm water surrounded by lush green trees. Comfortable seating arrangements are visible, creating a perfect spot for relaxation while enjoying the natural landscape.
Cottage in Torrance
4.97 out of 5 average rating, 245 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 Minimum 6 nights with a Sunday check in.

Top guest favourite
A hot tub is positioned beneath a covered patio, offering views of the waterfront. The clear water of the hot tub contrasts with the lush green surroundings and the calm blue of the lake in the distance. Sunlight filters through the patio overhead.
Home in Port McNicoll
4.92 out of 5 average rating, 108 reviews

Breathtaking 5 bedroom Waterfront Home W/ Hot Tub!

Stunning five-bedroom waterfront home on Georgian Bay! Located in a quiet area with stunning views and amazing sunsets! In the summer, the lake is perfect for swimming, kayaking, paddle boarding or fishing! Just bring water shoes as there are some rocks and zebra muscles. Equipped with a hot tub overlooking the lake, this five-bedroom waterfront home is perfect for a summer or winter getaway! *Please note this cottage is Pet Free.

Guest favourite
A cozy living area features a sleek Norwegian gas fireplace, modern furniture, and large windows allowing natural light to fill the space. A wood beam ceiling enhances the room's height, while a vibrant piece of artwork adds a pop of color to the wall.
Cottage in Baysville
4.93 out of 5 average rating, 309 reviews

D O C K | NEW Modern Muskoka Waterfront 2+1 bed

Enjoy the picture-perfect sights of Muskoka only two hours from downtown Toronto. Kayak on the Muskoka river, enjoy dinner on the oversized back deck, watch sunsets & stars, and roast marshmallows by the fire. This stunning two bedroom cottage is equipped with a fully modern interior. Keep warm by the beautiful Norwegian gas fireplace in the winter; stay cool with refreshing AC in the warmer months. DOCK has it all.

Popular amenities for kayak rentals in Penetanguishene

Quick stats about holiday rentals with a kayak in Penetanguishene

  • Total holiday rentals

    Explore 20 holiday rentals in Penetanguishene

  • Nightly prices starting at

    Penetanguishene holiday rentals start at $102 SGD per night before taxes and fees

  • Verified guest reviews

    Over 740 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Penetanguishene holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Penetanguishene rentals

  • 4.8 Average rating

    Penetanguishene stays are highly rated by guests – averaging 4.8 out of 5!

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