Holiday rentals with a kayak in Midland

4.93 out of 5 average rating, 103 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

Escape to this exceptional modern Lake house on Georgian Bay shores. Enjoy Incredible sunsets and views while you unwind in the hot tub or around the fire. Use the Kayaks to explore the Georgian Bay shores. This home can accommodate up to 4 adult guests (one additional child) Our quite property is best suited for 1 to 2 couples or a family of 5 or less and is fully equipped so you can relax on your next summer or winter getaway. Add the waterfront Bunkie to your summer stay (see additional fee)

LocationValueDecor

5.0 out of 5 average rating, 226 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!

ValueOutdoor spacesFamily

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.

4.87 out of 5 average rating, 103 reviews

Forest Oasis in Tay w/Large Jacuzzi Hottub

Beautiful cottage situated on the most southern point of Georgian Bay in Victoria Harbour. Less then 2 hours from the GTA with full amenities including an LCBO and Foodland 5 minutes away. Take advantage of plenty outdoor activities. Enjoy a bike ride on the stunning Tay Shore Trail, swimming in the lake on a hot summer day or hit the local slopes at Mt St Louie during the winter. Regardless of your choice in activities, end the evening with a soak in the hottub. Don't forget to look for stars!

ValueOutdoor spacesHot tub

4.96 out of 5 average rating, 170 reviews

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

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.

Outdoor spacesLocationWalkability

4.85 out of 5 average rating, 186 reviews

The cottage is situated on a well-maintained lawn, framed by trees, with a spacious deck accessible via a stone pathway. Colorful kayaks and a paddle boat are visible by the water, and the sky displays a warm sunset with varying shades of orange and purple.

Cottage in Waubaushene

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.

Outdoor spacesLocationHot tub

4.98 out of 5 average rating, 150 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.

Outdoor spacesLocationCheckout

4.85 out of 5 average rating, 162 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.

ValueOutdoor spacesFamily

4.86 out of 5 average rating, 107 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.

LocationValueDecor

4.99 out of 5 average rating, 177 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.

Outdoor spacesValueRiver

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.

LocationValueQuiet

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.

Outdoor spacesLocationBackyard

4.84 out of 5 average rating, 291 reviews

Cottage in Lafontaine

Cozy Beach Cottage with Pool | Georgian Bay

Georgian Bay Beach club. Cute cottage perfect for families, couples, or anyone wanting to relax! 2 bedrooms, 1 bathroom, furnished, pool and private beach on the shores of beautiful Georgian Bay in Tiny township. Cottage is part of a 12 cottage community that shares the pool and beach area. Always super clean, professionally cleaned after every guest! Note: pool is closed October to mid May.

Outdoor spacesLocationPool

Popular amenities for Midland kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.95 out of 5 average rating, 133 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

Secluded Muskoka A-Frame | Hot Tub, Dock, Firepit

LocationOutdoor spacesPool

4.98 out of 5 average rating, 113 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

LocationValueAmenities

4.94 out of 5 average rating, 458 reviews

Home in Bracebridge

Muskoka Hideaway-hot tub/private trails/wood stove

LocationOutdoor spacesView

4.92 out of 5 average rating, 246 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

ValueLocationGetting around

4.94 out of 5 average rating, 35 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

LocationOutdoor spacesCleanliness

4.89 out of 5 average rating, 55 reviews

A common pool area is surrounded by trees and features a light blue pool with a concrete deck. Lounge chairs are arranged nearby, offering a relaxing space for guests. Fencing provides privacy while adding to the tranquil environment.

Home in Tiny

Sunset Beach House with POOL

Outdoor spacesLocationWi-Fi

4.79 out of 5 average rating, 33 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

Outdoor spacesLocationAir conditioning

5.0 out of 5 average rating, 7 reviews

Home in Severn

Architectural Lakefront House & Boathouse Muskoka

Outdoor spacesLocationSleep quality

Cottages with a kayak

4.95 out of 5 average rating, 175 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

Outdoor spacesValueParking

4.92 out of 5 average rating, 131 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

LocationValueLaundry

4.91 out of 5 average rating, 300 reviews

Cottage in Georgina

Lakefront | Hot Tub, Private Dock & Sandy Bottom

LocationValueParks

4.97 out of 5 average rating, 171 reviews

A cozy living area features two armchairs and a comfortable sofa, arranged around a central coffee table. Large windows allow natural light to illuminate the space, showcasing views of the surrounding woods. A television and a stylish lamp enhance the room's functionality.

Cottage in Washago

Relax at The Rock: Muskoka Waterfront Cottage

LocationOutdoor spacesParks

4.95 out of 5 average rating, 151 reviews

A bright and inviting living area features large windows showcasing a serene lake view. Comfortable white sofas and armchairs surround a white coffee table, creating a cozy setting. Pine wood ceilings enhance the airy atmosphere, while natural light fills the space.

Cottage in Bala

Gorgeous Lake Muskoka Cottage Amazing Views Hottub

LocationValueAccess

4.91 out of 5 average rating, 174 reviews

A wooden dock extends over the sparkling surface of Loon Lake, with two white Adirondack chairs positioned for relaxation. Tall pine trees frame the view, and the sun casts a bright glow across the water, enhancing the serene natural setting.

Cottage in Gravenhurst

Waterfront @Muskoka Pines /kayaks/bbq/firepit

Outdoor spacesValueView

4.92 out of 5 average rating, 118 reviews

A wooden dock extends over the tranquil water, featuring colorful adirondack chairs in red and aqua. The cottage is nestled among tall trees, with a spacious deck visible in the background, shaded by an umbrella. Canoes and kayaks are anchored nearby, completing the lakeside scene.

Cottage in Torrance

Muskoka Lakeside Landing

LocationOutdoor spacesCleanliness

4.95 out of 5 average rating, 150 reviews

A view of the cottage from a rocky outcrop showcases its modern design. The structure features large windows and a deck, surrounded by lush greenery. Trees with autumn foliage frame the scene, while a fenced yard provides privacy.

Cottage in Waubaushene

Forest Harbour Hideaway

LocationOutdoor spacesNearby

Cabin rentals with a kayak

4.89 out of 5 average rating, 311 reviews

Cabin in Washago

Black River Haus - Scandi Riverfront Cabin Muskoka

LocationValueHeating

4.9 out of 5 average rating, 349 reviews

A queen-sized bed is surrounded by a delicate canopy, with colorful patterned pillows adding a touch of charm. Soft morning light filters through two windows, illuminating the wooden floor and a bedside table with a lamp and small plant. A leafy plant hangs near the window.

Cabin in Gravenhurst

Forest Cabin 90 steps to the beach

Outdoor spacesValueGetting around

4.96 out of 5 average rating, 125 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

Outdoor spacesValueView

4.83 out of 5 average rating, 108 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.

ValueLocationHiking

4.99 out of 5 average rating, 74 reviews

An aerial view showcases a renovated cabin surrounded by trees, with a path leading to a bright fire pit area. Colorful adirondack chairs are arranged around the fire, while string lights create a cozy ambiance on the cabin patio, illuminated by a gentle glow.

Cabin in Bala

MCM Muskoka Cabin + Sauna + Fire Pit + Lake Access

ValueOutdoor spacesBarbecue

4.96 out of 5 average rating, 73 reviews

Cabin in Bracebridge

Misty River Cabin Private Waterfront Pet-Friendly!

Outdoor spacesLocationCheck-in

5.0 out of 5 average rating, 9 reviews

A cottage is set amidst tall trees, featuring a wooden deck and steps leading to the water. Outdoor seating includes red chairs on the lawn and around a fire pit, creating a welcoming environment for relaxation and gatherings.

Cabin in Muskoka Lakes

Luxury Cottage with Hot Tub

LocationValueQuiet