Vacation rentals with a kayak in Penetanguishene

5 out of 5 average rating, 219 reviews

A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.

Condo in Innisfil

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private 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! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

4.95 out of 5 average rating, 275 reviews

The exterior of a custom-built log cabin is framed by trees under a clear blue sky. A spacious porch features two Adirondack chairs and a fire pit, providing a welcoming outdoor space. Natural stone accents enhance the cabin's rustic charm.

Chalet in Gravenhurst

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.

4.89 out of 5 average rating, 146 reviews

A serene lake under a bright blue sky is depicted, with reflections of fluffy clouds and surrounding trees mirrored on the water's surface. The peaceful landscape suggests a tranquil environment, populated by various wildlife and foliage along the shoreline.

Cottage in Port Severn

2 BEDRM WATERFRONT COTTAGE, CANOE, KAYAKS, WIFI

No linens provided (No Blankets, sheets pillowcases or towels). Sorry NO PETS as guests on the property and NO SMOKING indoors. The cottage is right on the water, lots of wildlife, great for bird watching, Large 4 lake system, miles of boating on Gloucester pool, then for a further adventure it is connected to Georgian bay by locks on the Trent Severn. Honey Harbor, Midland, Whites Falls and lots of provincial parks close by, great fishing, ATV and hiking trails, fish right off the dock

5 out of 5 average rating, 276 reviews

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

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.

4.86 out of 5 average rating, 105 reviews

A hot tub is situated under a wooden gazebo, featuring railings and a ceiling adorned with decorative elements. Sunlight illuminates the scene, highlighting the inviting water surface. A view of the snowy landscape and frozen lake extends in the background, enhancing the serene atmosphere.

Home in Elmvale

Ski, Swim, Soak, Boat & Golf

Renovated 2 storey cottage overlooking beautiful Orr Lake. Ski at Mt. St. Louis Moonstone or Horseshoe Valley. Both 13 minutes away. A heated swimming pool in the summer and a hot tub all year. Canoeing, kayaking, paddle boarding or golfing across the street. Fully equipped kitchen. Livingroom includes an overhead projector, plus as a second floor Family room with a Wet Bar. 5 bedrooms, 7 beds, & 3 Baths. Max occupancy: 10 adults or 12 including children under 13. Parking for 5 cars.

4.99 out of 5 average rating, 171 reviews

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

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.

4.9 out of 5 average rating, 305 reviews

Cabin in Washago

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 (20 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.

4.91 out of 5 average rating, 348 reviews

Tiny home in Bracebridge

Teremok Cabin at Zukaland | Cedar Hot Tub & Sauna

Welcome to Teremok Log Cabin at Zukaland, a unique Slavic-style tiny cabin nestled among mature pines on a scenic forested cliff in Muskoka. Enjoy peaceful woodland surroundings with easy access to a sandy beach by the Muskoka River. Guests may enhance their stay with optional add-on experiences, including breakfast in bed or our Cedar Outdoor Spa with wood-fired hot tub and sauna. As evening falls, cozy up by the warmth of a real wood stove and unwind in nature.

4.96 out of 5 average rating, 112 reviews

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

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.

4.98 out of 5 average rating, 430 reviews

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.

Apartment in Bracebridge

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!

4.97 out of 5 average rating, 253 reviews

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

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.

4.92 out of 5 average rating, 124 reviews

A wooden dock extends into calm water, featuring Adirondack chairs positioned for relaxation. Sunlight reflects off the water's surface, creating a serene atmosphere. Nearby, a small boat awaits at the bottom of the dock, framed by trees on the opposite shore.

Cottage in MacTier

Baysong Cottage, with Sauna, on Georgian Bay

Welcome to Baysong Cottage. We are right on the water, with a big dock, canoe/kayaks and sauna all yours to enjoy. This is the perfect summer getaway. Enjoy our dock for swimming and boating, our sauna for a rejuvenating spa experience, and all day south west facing sunshine. Great for boating, fishing, sailing, swimming, or just a getaway to enjoy a campfire, some board games and some time together.

Popular amenities for Penetanguishene kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.94 out of 5 average rating, 31 reviews

A sandy beach stretches out towards calm waters, complemented by a small dock and an island visible in the distance. Red and gray Adirondack chairs are setup in a semicircle on the beach, inviting relaxation under a clear blue sky dotted with clouds.

Home in Victoria Harbour

Welcoming Waterfront Cottage

4.95 out of 5 average rating, 22 reviews

An aerial view captures the serene landscape of River's End, showcasing a winding inlet river bordered by trees. The property includes a pathway leading to the water and nearby homes. The lush greenery and natural beauty of the area invite outdoor exploration.

Home in Port Severn

River's End: Explore the river by kayak or canoe!

4.98 out of 5 average rating, 111 reviews

An open game room features a polished wooden pool table at its center, surrounded by exposed timber beams and vibrant green walls. Large windows provide natural light, while a television is mounted nearby. Additional seating is available, enhancing the space's social atmosphere.

Home in Meaford

Birdsong, the perfect Blue Mountains getaway

4.76 out of 5 average rating, 34 reviews

An outdoor firepit is surrounded by stone, with flames flickering invitingly. Adjacent, a wooden Adirondack chair faces a serene lake, reflecting warm sunset hues. A charming playhouse stands nearby, nestled among mature trees, creating a peaceful lakeside setting.

Home in Orillia

Couchiching Lake Retreat - Sauna! Near Downtown!

4.79 out of 5 average rating, 39 reviews

The cottage exterior is illuminated at dusk, showcasing its modern design. Large windows reveal the open-concept interior, while a spacious deck offers seating options. The surrounding landscape features a manicured lawn and trees in the background, enhancing the serene lakeside setting.

Home in Orillia

[Casa Luna] Chic Lakehouse | BBQ | HotTub | LakeViews

4.95 out of 5 average rating, 21 reviews

A serene waterfront scene captures calm water reflecting vibrant autumn foliage. Mist gently rises from the lake's surface, while a clear blue sky is partially adorned with a soft white moon. The landscape includes various trees, creating a peaceful natural environment.

Home in Kirkfield

Life is Better at the Cottage

4.92 out of 5 average rating, 240 reviews

A two-story home is nestled among lush greenery, showcasing a well-maintained exterior. A spacious lawn is framed by trees, and a picnic table can be seen in the foreground. Bright clouds float in a predominantly blue sky, adding to the serene outdoor setting.

Home in Bracebridge

The Muskoka River Homestead

4.82 out of 5 average rating, 83 reviews

Home in Collingwood

Algonquin sunrise on private balcony pond view

Cottage rentals with a kayak

4.93 out of 5 average rating, 125 reviews

A serene view of Spence Lake is captured, showcasing its calm waters reflecting a colorful display of autumn foliage on the opposite shore. A wooden dock is visible, along with manicured green grass in the foreground, enhancing the peaceful lakeside setting.

Cottage in Bracebridge

Waterfront cottage on quiet Spence lake

4.93 out of 5 average rating, 236 reviews

A serene lake view is presented from the shore, featuring a wooden dock extending over calm waters. Two boats are anchored nearby, while the surrounding trees offer shade. Sunlight reflects on the water's surface, creating a shimmering effect across the lake.

Cottage in Bracebridge

Charming cottage on Lake Muskoka

4.94 out of 5 average rating, 133 reviews

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

Private & Modern Muskoka Lakefront Cottage w/ WiFi

4.97 out of 5 average rating, 185 reviews

A charming cottage sits by a serene waterfront, surrounded by lush trees. The sandy beach leads to calm water, with lounging spaces and two docks visible. Muskoka chairs are positioned on the lawn, inviting relaxation amid nature. The cottage's structure offers multiple outdoor seating options.

Cottage in Washago

Mistywood Cottage

4.95 out of 5 average rating, 121 reviews

A unique wooden sauna, shaped like a barrel, is placed on a grassy area by the lake. Above, a clear night sky is filled with bright stars, providing a serene backdrop. Nearby, lounge chairs are arranged on the lawn, with trees lining the water’s edge.

Cottage in Coldwater

Cottage on the Rocks - with Hot Tub and Sauna!

4.98 out of 5 average rating, 120 reviews

Cottage in Gravenhurst

Lake days last longer-Muskoka Lakeside Cottage

4.91 out of 5 average rating, 296 reviews

Cottage in Georgina

Lakefront Cottage | Sandy Shore, Hot Tub & Dock

4.95 out of 5 average rating, 170 reviews

A spacious hot tub overlooks the Severn River, surrounded by greenery. Chairs are positioned nearby on the grassy lawn, providing a relaxing space to enjoy the water views and sunshine. The calming river scene features boats gently cruising by, enhancing the outdoor experience.

Cottage in Severn Bridge

CARL in Muskoka: Waterfront Cottage with Hot Tub

Cabin rentals with a kayak

4.89 out of 5 average rating, 76 reviews

A serene waterfront view features a sandy beach area with calm waters, a wooden dock extending into the lake, and kayaks resting nearby. Lush greenery surrounds the cabin, enhancing the natural scenery and providing a peaceful setting for relaxation.

Cabin in Severn Bridge

Oak Cabin on Sparrow Lake

4.89 out of 5 average rating, 44 reviews

A wooden dock extends into calm waters, featuring two red chairs positioned for relaxation. The surrounding landscape includes lush greenery and several cottages nestled in the background, providing a serene waterfront setting.

Cabin in Elmvale

The Blue Cottage

4.81 out of 5 average rating, 254 reviews

A log cabin exterior is set among lush greenery, featuring a spacious patio area furnished with several chairs and a dining table. Soft natural light illuminates the building, highlighting its natural wood texture and proximity to landscaped flower beds.

Cabin in Kimberley

Deer Park, Cozy Cabin with Hot Tub, Amazing View

4.83 out of 5 average rating, 103 reviews

A custom-built home is set amidst trees, featuring a mix of stone and siding exterior. The entryway is accented by a covered porch with white railings. A spacious driveway leads to the two-car garage, bordered by autumn leaves scattered on the ground.

Cabin in Orillia

Beautiful Vacation Home with a Large Backyard.

4.93 out of 5 average rating, 28 reviews

A serene lakeside view captures a colorful sunrise, with hues of pink, orange, and purple reflected in the calm water. The silhouette of trees lines the horizon, creating a peaceful backdrop for a morning coffee. A small boat floats gently in the foreground.

Cabin in Port Severn

Beautiful Six Mile Lake Muskoka

4.96 out of 5 average rating, 121 reviews

The log cabin is surrounded by vibrant autumn foliage, with a large front deck and stairs leading to the entrance. The natural wood exterior is complemented by a gabled roof. Softly illuminated lanterns are positioned by the door, enhancing the inviting appearance.

Cabin in Flesherton

MapleHaven Cabin @ Lake Eugenia

4.78 out of 5 average rating, 120 reviews

A serene lakeside property is depicted, featuring a dark blue exterior and a welcoming wooden staircase leading to the entrance. Lush greenery surrounds the home, and a calm body of water reflects the clear sky in the background.

Cabin in Gravenhurst

Sparrow Sunset Retreat Lakefront• Hot Tub • Dock