Family-friendly vacation rentals in Orillia

4.95 out of 5 average rating, 180 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

Enjoy your own piece of Muskoka in this beautiful waterfront cottage! Only 90 minutes from Toronto nestled away on a private road along the Severn River sits CARL. Not a man... but a way of life. The Cottage and River Life! CARL is your retreat from the city, perfect for getting out in nature and experiencing everything life on the water has to offer. Whether you enjoy swimming, kayaking, great fishing or just relaxing on the dock or in the hot tub taking in the views... we've got you covered.

KitchenIndoor spacesTV

4.89 out of 5 average rating, 174 reviews

A spacious living area features a comfortable sofa and a television on an entertainment unit. A dining table with chairs is positioned nearby. Large glass doors open to a fenced outdoor space with patio furniture, enhancing the bright and airy atmosphere.

Home in Orillia

Orillia TwnHse Oasis w King Bed

Have fun with the whole family at this stylish townhouse oasis. The townhouse features 3 bedrooms, 2.5 bathrooms and 4 beds. The principle bedroom has a king bed, the 2nd bedroom has a queen bed, and the third bedroom has a queen bunk bed (qn bttm, qn top). The house features a large deck with a gas bbq, outdoor dining, and lots of lounging space. Right behind the townhouse is a beautiful nature ravine with lots of trails. Come, enjoy and relax. The property offers super high speed internet.

KitchenFamilyTV

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.

4.97 out of 5 average rating, 176 reviews

Relax at The Rock: Muskoka Waterfront Cottage

Enjoy fishing, swimming and paddling 22km of the green and black rivers. Paddleboat, canoe, 2 kayaks, and a SUP provided. Take the short 5 minute stroll into town for ice cream or fresh baked treats. Lay out on the elevated deck or in the screened in porch with a good book. End your evening at the riverfront firepit. Nearby day adventures include hiking, golfing, parks, beaches, breweries, casino rama, and downhill skiing at Mount St Louis Moonstone and Horseshoe Valley (30 minute drive).

FamilyIndoor spacesBackyard

4.98 out of 5 average rating, 156 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.

FamilyIndoor spacesTV

4.83 out of 5 average rating, 320 reviews

A stone pathway leads to a fire pit surrounded by colorful Adirondack chairs in red and yellow. The view overlooks the lake, with a dock extending into the water under a clear blue sky, providing a serene setting for gatherings.

Home in Orillia

Waterfront Cottage Over-the-Water view w BBQ& Wifi

Our cottage backs directly onto lake Simcoe with a view overlooking the water reminiscent of a four season water villa bungalow. Enjoy the entire house with your family and friends and be captivated by nature's beauty as the sun sets behind the treeline across the lake. Easy access to lake Couchiching for fishing in the summer and ice fishing in the winter, 30 mins to Mount St. Louis for skiing and snowboarding, 30 mins to Vetta Nordic Spa and Casino Rama is only a 10 minute drive away!

Indoor spacesKitchenCondition

4.77 out of 5 average rating, 106 reviews

An indoor pool is framed by large windows that allow natural light to fill the space. The ceiling features wooden beams that create an airy atmosphere. Two chairs are positioned nearby, and vibrant yellow flowers are visible through an adjacent window.

Home in Orillia

Casa ~ Pool ~ Fire Pit ~ BBQ

Relax with the whole family at our peaceful forest estate. Mother nature is your only neighbour and she comes right to your doorstep to welcome you. Enjoy the peaceful serenity of the forest that surrounds you. Enjoy our pool, nearby ATV trails, and all the activities Orillia has to offer. Guest access You'll have access to the entire property. The backyard is completely private, with zero light pollution, so please enjoy the stars and the peace and calm of nature.

Indoor spacesFamilyAmenities

4.87 out of 5 average rating, 277 reviews

A bungalow with a wooden deck overlooks a well-maintained lawn, surrounded by greenery and flower beds. Large windows provide views of the outdoor space. The exterior showcases a warm wooden finish and a sloped roof, enhancing the inviting appeal of the home.

Bungalow in Orillia

Luxury, Waterfront, 4 bdrm Bungalow in Sth Muskoka

Just 1 kilometer past Webers on Hwy 11! A cozy home on the lake with all the amenities. This 4 bdrm 2 bathroom yr round bungalow sleeps 8 comfortably and is perfect for all seasons. Amenities include 2 full bathrooms, 2 full TV rooms, (1 with a double sectional) and a games room w/ Foozball. Outdoor person? Lots of Swimming, Fishing, Paddle Boat, Canoe, Reading, or a glass of wine by the water. Also just 15 mins from Casino Rama!

KitchenIndoor spacesComfort

4.86 out of 5 average rating, 150 reviews

The exterior of the Lake House is surrounded by lush trees, with a wide wooden dock extending into the calm waters. A patio area features multiple red Muskoka chairs, inviting relaxation by the water's edge. Soft evening light hints at the cozy ambiance of the home.

Cottage in Orillia

AMIGO LAKE HOUSE

Amigo Lake House, the perfect getaway for any season! Sunny South waterfront views, soak up the sun during the day and star gaze the picturesque sky over the lake at night. Start the morning with a cup of coffee and watch the sunrise over the lake, explore on the kayak/paddle boards, play games in the backyard, barbecue a savoury meal, stay warm by the fire or take dip in the hot tub.

KitchenFamilyAccess

4.93 out of 5 average rating, 111 reviews

Highland Grand Retreat Studio

Ground-level Highland Grand Retreat Studio offers elegance and comfort in Oro-Medonte’s Highland Estates. Just 20 minutes to Barrie or Orillia, enjoy skiing at Horseshoe Resort, golfing nearby, or hiking the Copeland Forest. Unwind at Vetta Spa or with on-site amenities—indoor–outdoor pool, hot tub, sauna, gym, and games room. A serene, central escape for couples or solo travellers.

Indoor spacesFamilyParking

5.0 out of 5 average rating, 117 reviews

Guesthouse in Orillia

Forest Haven Guesthouse

Forest Haven Guesthouse is a scenic countryside property surrounded by trees and private trails. Your all-season, all inclusive getaway is just minutes from downtown Orillia. Your guesthouse which includes 3 bedrooms is a completely separate unit which is attached to our home. You have a keypad entrance and a front and back deck that are just for you! Happy travels!

KitchenFamilyValue

4.88 out of 5 average rating, 112 reviews

Guest suite in Severn

Lake View Loft

This charming lakeside loft sleeps up to 4 guests, featuring one king sized bed and a pull-out sofa in the living area. The open-concept design seamlessly blends the kitchen, dining, and living spaces. Enjoy serene lake views just outside the front door. This peaceful retreat is perfect for relaxation and enjoying nature's beauty.

Indoor spacesKitchenWalkability

4.99 out of 5 average rating, 183 reviews

The exterior of the Ontario Northland Railway Caboose 122 is showcased at night, illuminated by exterior lights. The vibrant yellow and blue structure is positioned on a grassy area, with a wooden pathway leading up to it. Surrounding trees are partially visible in the background.

Train in Gravenhurst

Side Tracked in Muskoka

Welcome to Side Tracked in Muskoka, Muskoka’s premier railway-themed stay. Step back in time inside a beautifully restored Ontario Northland Railway Caboose No. 122. Thoughtfully designed, the interior pays homage to the caboose’s railway history while complementing Muskoka’s cozy cottage feel.

KitchenFamilyCleanliness

Popular amenities for Orillia family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 175 reviews

Riverfront Cottage with HotTub Near Muskoka

Indoor spacesKitchenAccuracy

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.

4.97 out of 5 average rating, 199 reviews

Mistywood Cottage

Indoor spacesFamilyHospitality

4.98 out of 5 average rating, 235 reviews

A tranquil lakeside dock is highlighted under a colorful sunset, with four chairs positioned for optimal viewing. The still water reflects the vibrant hues of the sky, creating a serene atmosphere. Lush greenery borders the scene, enhancing the natural beauty.

Cottage in Severn Bridge

CozyPeaceful LakeCottage HotTub Canada

Indoor spacesKitchenAccess

A cozy living area features a spacious sectional sofa adorned with soft pillows, complemented by a minimalist coffee table. Natural elements are highlighted by an accent wall showcasing a scenic forest mural. The nearby sleeping area includes a neatly made bed with fresh linens.

4.99 out of 5 average rating, 136 reviews

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

Indoor spacesFamilySkiing

4.84 out of 5 average rating, 191 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

FamilyKitchenNearby

4.96 out of 5 average rating, 106 reviews

A covered patio area features a hot tub alongside a glass-topped table with comfortable seating. The peaceful lakeside view showcases expansive green space and a row of chairs positioned along the shore, framed by trees lining the property.

Cottage in Georgina

Sunset Shores Lakehouse- Hot Tub, Wet Bar & Games

KitchenIndoor spacesPets

4.8 out of 5 average rating, 131 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

Indoor spacesFamilyParks

The living area features a comfortable sofa beside a stone fireplace, providing a cozy focal point. A light-toned armchair sits nearby, while a television is mounted on the wall. Natural light enters through the glass door, leading to an outdoor space.

4.8 out of 5 average rating, 194 reviews

Cozy 1-Bedroom Romantic Retreat with full Kitchen

KitchenFamilyAmenities

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 144 reviews

Cottage in Georgina

Resort-Style Luxury Waterfront Cottage

Indoor spacesFamilyCheck-in

4.75 out of 5 average rating, 496 reviews

The exterior of the studio apartment is shown, featuring a combination of white and gray siding. A modern garage door and a front door are visible, framed by a small patio area. Trees provide a natural backdrop, with Lake Simcoe glimpsed in the distance.

Cottage in Barrie

The Guesthouse on the North Shore Trail

FamilyIndoor spacesSleep quality

A spacious cottage is set against a lush green backdrop, featuring a distinct barrel sauna nearby. A manicured lawn hosts a small putting green with flags, alongside several lounge chairs. The architecture blends modern and natural elements, creating an inviting outdoor environment.

4.92 out of 5 average rating, 140 reviews

Waterfront Cottage sauna/golf/kayaks/beach/games

KitchenIndoor spacesPets

The living area features a comfortable seating arrangement, including a sofa and two armchairs. A coffee table sits centrally on a patterned rug, accompanied by a dining table set for four. A stone fireplace and a mounted TV are also visible, with large windows allowing natural light to enter.

4.9 out of 5 average rating, 107 reviews

Romantic Country Getaway

KitchenIndoor spacesShared spaces

4.91 out of 5 average rating, 292 reviews

Cottage in Innisfil

Utopia villa and spa

KitchenIndoor spacesCheck-in

4.95 out of 5 average rating, 189 reviews

A calm lake setting is depicted, featuring a wooden dock extending into the water. Several ducks swim leisurely near the dock, with lush greenery lining the opposite shore. Fluffy clouds drift across a blue sky, reflecting on the tranquil surface of the water.

Cottage in Gravenhurst

Relaxing lakehouse + pool table & private docks

KitchenIndoor spacesCondition

4.93 out of 5 average rating, 178 reviews

Cottage in Gravenhurst

Marrakahshe Retreat | Luxury Sauna, Beach & Yurt

KitchenFamilyLaundry

4.96 out of 5 average rating, 182 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

KitchenIndoor spacesNearby

Family-friendly home rentals with a pool

Dome in Bradford West Gwillimbury

Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.

Four season glamping dome under the stars

Indoor spacesKitchenTV

4.97 out of 5 average rating, 503 reviews

An open living space is displayed, featuring a comfortable sofa adorned with throw pillows. A central coffee table rests atop a patterned area rug, while a wooden dining table with seating for six is visible. The kitchen area is positioned at the back, showcasing modern appliances.

4.85 out of 5 average rating, 117 reviews

Stunning Suite in Horseshoe Valley

KitchenIndoor spacesSkiing

4.98 out of 5 average rating, 131 reviews

Condo in Innisfil

Stunning 1BR w Pool ~ Free Parking & Self Check-In

Indoor spacesKitchenHospitality

4.85 out of 5 average rating, 112 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

KitchenIndoor spacesCheckout

4.98 out of 5 average rating, 105 reviews

An aerial view of the rustic chalet reveals a warm wooden exterior complemented by brick accents. A fenced-in yard features a heated, welcoming saltwater pool. Two cars are parked in the driveway, and greenery from surrounding trees enhances the serene atmosphere.

Guesthouse in Barrie

Warm rustic luxury chalet near lake and trails

Indoor spacesKitchenSkiing

The exterior showcases a striking building with a red-and-white color scheme, surrounded by lush greenery. An indoor pool area is visible through large glass windows. An inviting fireplace is framed by stone, while a spacious dining area features a wooden table accompanied by six chairs.

4.85 out of 5 average rating, 238 reviews

2BR Horseshoe Condo · Pool · Pet‑Friendly

KitchenIndoor spacesOutdoor spaces

4.93 out of 5 average rating, 242 reviews

Condo in Innisfil

The Friday Flat | Sunny Escape by the Marina

Indoor spacesFamilyBiking

The living area features a modern design with a large flat-screen TV mounted above a stone fireplace. A cozy gray sofa is paired with a rustic coffee table and a comfortable orange armchair. Natural light enters through double glass doors leading outside.