Vacation rentals with a kayak in Midland

4.88 out of 5 average rating, 169 reviews

A lakeside cottage is surrounded by tall trees, with a gentle slope leading to the water. A private dock is visible, along with several outdoor chairs. The cottage's warm glow is highlighted in the evening light, offering a welcoming appearance.

Cottage in Gravenhurst

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat

4 Seasons: Heated+A|C! You and friends/family will enjoy easy access to everything Gravenhurst has to offer from our centrally located retreat cottage. Conveniently located on Pine Lake, you will have sun-filled water views throughout the cottage. We are located directly off the main highway, easy road access and parking. The lake is perfect for swimming and water sports. Get ready to sip your morning coffee on the back porch and watch the sun rise! A perfect spot for yoga and/or meditation.

4.94 out of 5 average rating, 119 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

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.

4.96 out of 5 average rating, 151 reviews

Cottage in Tiny

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.

4.98 out of 5 average rating, 136 reviews

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

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.

4.94 out of 5 average rating, 270 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.

4.85 out of 5 average rating, 147 reviews

The cottage is nestled among tall trees, surrounded by lush greenery and vibrant flowers. Soft lighting from the windows casts a warm glow, emphasizing the inviting atmosphere. Stone pathways and landscaping create a harmonious blend with the natural setting.

Cottage in Tiny

The Bay View Cottage w/hot tub

Welcome to our 4 season, 2 family cottage with Georgian Bay views and a hot tub. 3 min walk to the cutest small beach that has stunning sunsets, 12 min to Awenda Provincial Park which has great hiking, beaches, biking and winter activities. Short drive to Balm Beach. Downtown Midland has great restaurants and everything a quaint downtown has to offer. Winter has so much to offer including ice fishing, OFSC snowmobile trails, cross country skiing and much more. Max occupancy is 8 adult.

4.99 out of 5 average rating, 159 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.

4.96 out of 5 average rating, 155 reviews

Condo in Innisfil

Upscale Spa Getaway w/ Private Sauna

Welcome to our most Dramatic & Romantic Penthouse Spa Getaway Suite! Reconnect with your loved one or celebrate that special milestone in our professionally designed to play with all your senses spa suite, this escape will leave you feeling refreshed and rejuvenated! Cozy up to any of 3 fire elements and then cleanse and detox in your own private in-suite Infrared Sauna! Cook up a gourmet meal in our fully equipped chef's dream kitchen and year round Weber BBQ for grilling!

Guesthouse in Gravenhurst

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.

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.

4.96 out of 5 average rating, 104 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.

4.97 out of 5 average rating, 245 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.

4.94 out of 5 average rating, 121 reviews

The custom-built A Frame cabin is set amidst lush greenery, featuring a striking black exterior and a distinctive peaked roof. A spacious deck extends at the front, furnished with seating, and surrounded by nature for a serene environment.

Home in Bracebridge

Muskoka River Cabin

Unique, A Frame, Custom built on three acres in the Heart of Muskoka. Enjoy your own dock on a quiet section of the Muskoka River. It's a perfect place to escape the city, enjoy some peace, reconnect with yourself and the ones you love. Breathe in some fresh air, enjoy the sounds of nature and do some star gazing right from the front deck. *Please note-all guests must have a minimum of two reviews to book*

Popular amenities for Midland kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.96 out of 5 average rating, 27 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

5 out of 5 average rating, 19 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!

4.77 out of 5 average rating, 31 reviews

An open-plan living and dining area features a modern kitchen with stainless steel appliances and an island bar. A dining table with four chairs sits nearby, while a spacious living room area includes multiple seating options. Large windows allow natural light to fill the space.

Home in Victoria Harbour

6 Bdrm Lake view, Luxury, Modern Cottage w Hot Tub

4.87 out of 5 average rating, 100 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

4.96 out of 5 average rating, 23 reviews

A serene exterior of a two-story house is displayed, surrounded by tall pine trees under a twilight sky. Illuminated windows provide a soft glow, contrasting with the darkening surroundings. The entrance features a step leading to a welcoming porch area.

Home in Elmvale

Waterfront cottage in Elmvale, Orr Lake

4.91 out of 5 average rating, 235 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

5 out of 5 average rating, 12 reviews

A serene lakefront view captures gentle waters lapping against a pebbled shore. Towering trees provide shade, framing a cozy guest house and a small dock. Red Adirondack chairs sit invitingly on the green grass, with kayaks and a stand-up paddleboard resting nearby.

Home in Port McNicoll

Midland ON - Lakehouse

5 out of 5 average rating, 26 reviews

A cozy lakeside cottage is surrounded by a blanket of freshly fallen snow, with bare trees revealing their structure. A spacious deck steps down to a snow-covered yard, featuring a picnic table and a fire pit, inviting quiet winter moments.

Home in Gravenhurst

Sweet 4 bedrm Muskoka Lakefront Cottage

Cottage rentals with a kayak

4.93 out of 5 average rating, 122 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, 231 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

Cottage in Penetanguishene

A wooden staircase leads up from the sandy beach to the charming cottage nestled among lush greenery. The cottage features a distinctive gray exterior, large windows, and a spacious deck that overlooks the surrounding nature.

4.85 out of 5 average rating, 60 reviews

Georgian Bay Waterfront Cottage with Sandy Beach

4.91 out of 5 average rating, 168 reviews

A serene winter scene captures the stillness of Loon Lake, with snow-dusted trees lining the shore. The calm water reflects the cloudy sky and surrounding landscape, while a wooden dock extends into the lake, inviting peaceful moments by the water.

Cottage in Gravenhurst

Waterfront @Muskoka Pines /kayaks/bbq/firepit

4.93 out of 5 average rating, 95 reviews

A modern lake house exterior features a spacious deck with four red chairs facing the water. Lush green grass and well-maintained flower beds surround the wooden deck. Large windows allow ample natural light into the interior, enhancing the connection with the outdoor environment.

Cottage in Port Mcnicoll

Georgian Bay Waterfront Cottage HotTub King Bed

Cottage in Victoria Harbour

The exterior of the cottage showcases a charming two-story structure with a covered porch. Warm lighting illuminates the entrance, while a wooden staircase leads to the front door. Lush greenery and a stack of logs add a natural touch to the inviting atmosphere.

4.88 out of 5 average rating, 96 reviews

Forest Oasis in Tay w/Large Jacuzzi Hottub

4.92 out of 5 average rating, 109 reviews

A modern, lakefront cottage is nestled among tall pine trees, with a sloped wooden staircase leading up to its large, wraparound deck. Snow blankets the ground, and the cottage exterior is painted in shades of blue, reflecting its natural surroundings.

Cottage in Port Severn

Tree Tops on Six Mile Lake

4.95 out of 5 average rating, 111 reviews

The cottage is positioned near the water's edge, featuring a large deck with seating that overlooks the lake. Large windows reflect the serene surroundings, while a flag is visible, adding a touch of character. The natural landscape includes trees showcasing autumn colors.

Cottage in Coldwater

Cottage on the lake

Cabin rentals with a kayak

4.89 out of 5 average rating, 63 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

4.88 out of 5 average rating, 8 reviews

A wooden dock extends into a calm lake, surrounded by lush greenery. The water reflects a pastel sky during sunset, with hints of purple and pink. Trees line the shore, adding to the serene atmosphere of the location.

Cabin in Port Severn

Gorgeous Muskokan Cottage on Six Mile Lake

4.95 out of 5 average rating, 38 reviews

A bright and airy living area features large windows revealing serene lake views. A comfortable light-colored sofa faces a wooden coffee table, complemented by a woven ottoman. Soft curtains frame the windows, while a small dining table and a potted plant add a touch of warmth.

Cabin in Elmvale

The White Cottage with infinity views

4.91 out of 5 average rating, 289 reviews

The cozy living room features wooden walls and a gas stove. Natural light streams through large windows, illuminating a comfortable white sofa and a wooden coffee table. A textured rug lies beneath, complementing a minimalist aesthetic with a few decorative elements.

Cabin in Washago

Black River Haus - Scandi Riverfront Cabin Muskoka

4.81 out of 5 average rating, 96 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.

4.92 out of 5 average rating, 26 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

4.84 out of 5 average rating, 45 reviews

A spacious deck overlooks the serene waters of Spence Lake, surrounded by lush greenery. Comfortable seating is arranged around a circular table, inviting relaxation and gatherings. The bright blue sky reflects on the water, enhancing the tranquil setting.

Cabin in Bracebridge

Lovely waterfront cottage in Muskoka