Family-friendly holiday rentals in Georgina

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.

4.97 out of 5 average rating, 501 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Indoor spacesFamilyParks

A dining table is set with decorative blue and white dishware. In the background, a fire pit is surrounded by red chairs, with vibrant greenery and a wooden swing adding to the outdoor ambiance. A flower arrangement and candles enhance the table setting.

4.96 out of 5 average rating, 102 reviews

Greystone cottage in Innisfil

Welcome to our charming cottage in Innisfil, just a short walk from beautiful Lake Simcoe. Enjoy a spacious backyard featuring a cozy fire pit, a peaceful swing, bicycles and a BBQ area perfect for relaxing evening. You’ll find a fun game room equipped with AC, pool table, air hockey for entertainment during your stay. Conveniently located near grocery stores, Home Hardware, restaurants at Friday Harbour, and other local amenities. Come experience the beautiful atmosphere with your loved ones.

KitchenFamilyAmenities

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.

4.96 out of 5 average rating, 104 reviews

Sunset Shores Lakehouse- Hot Tub, Wet Bar & Games

Welcome to Sunset Shores Lakehouse! Nestled in a tranquil bay on the shores of Lake Simcoe, this spacious family lake house is the perfect escape in all 4 seasons with many indoor and outdoor activities to enjoy! This peaceful waterfront retreat boasts 4 bedrooms + Wet Bar + Patio Oasis with lakeside Fire Pit + 6 person Hot Tub overlooking the lake and spectacular daily sunsets and sunrises you wont want to miss! Only 1 hour from Toronto and close to many Georgina attractions and adventures!

FamilyKitchenHot tub

4.91 out of 5 average rating, 291 reviews

Utopia villa and spa

Welcome to Utopia B&B, a peaceful retreat where lasting memories are created with family and friends. Just minutes from the beach, grocery stores, gas stations, and all everyday essentials. With so much to enjoy, you may never want to leave! Spend your day savoring good food by the fireplace, relaxing in the hot tub, unwinding in the sauna, and having fun in the game room. Indulge yourself with an unforgettable stay. : No smoking or eating in the hot tub. Any violation will result $500 fine.

FamilyKitchenOutdoor spaces

4.96 out of 5 average rating, 140 reviews

Resort-Style Luxury Waterfront Cottage

Experience luxury at our 5-star, Superhost-rated waterfront cottage on Lake Simcoe, just 80 KM from Toronto! A guest favorite, it offers breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters, and enjoy the patio, BBQ, bar, lounge, kayaking, and fishing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for the perfect blend of relaxation and adventure!

FamilyIndoor spacesWi-Fi

4.91 out of 5 average rating, 301 reviews

Lakefront | Hot Tub, Private Dock & Sandy Beach

Luxury lakefront cottage on Lake Simcoe with a rare shallow sandy-bottom shoreline, private dock, and hot tub—perfect for swimming and family fun. Enjoy breathtaking sunsets, kayaking, paddleboarding, fishing, BBQs, and a fire pit. Ideal for family vacations, holiday getaways, and group retreats near Toronto, minutes from Hwy 404. Features 6 bedrooms, 4 bathrooms, a fully equipped kitchen, and an open-concept living area. Private, peaceful, and perfect for unforgettable memories year-round.

KitchenFamilyLong stay

4.81 out of 5 average rating, 128 reviews

The living room features large windows, offering a view of the lake. A spacious dark sofa is arranged around a coffee table, complemented by a side table with a lamp. Light-colored walls and wooden floors enhance the bright and open atmosphere.

Bungalow in Georgina

Lake Simcoe Retreat

Holiday retreat on Lake Simcoe with Sunset view. Front bedrooms and kitchen facing the river and Living room, Dining room, other rooms and open kitchen facing the Lake. You can enjoy the views from every part of the house. Totally renovated interior. High speed internet, a work space, Close to many world class family activities including Fishing, Hunting, Ice Fishing, Snowmobiling. Conveniently located an hour from Toronto, closest small town 5 minutes drive and Sutton town 12 minutes drive.

FamilyIndoor spacesHiking

4.93 out of 5 average rating, 192 reviews

The cabin features a cozy exterior with a textured roof and large windows, surrounded by colorful fall leaves. Outdoor furniture is positioned on the deck, and a hot tub is visible. The setting is enhanced by the backdrop of vibrant autumn foliage.

Cabin in Innisfil

Lakefront Cozy Cottage w Hot Tub!

On Lake Simcoe this cozy retreat is just an hour north of Toronto Enjoy the stunning sunrises / views and access to a variety of water activities, while the surrounding area provides ample opportunities for hiking, skiing, other outdoor pursuits with many amenities closely. Down the street from Friday Harbour, LCBO, Starbucks and restaurants 5 ⭐️ review guests welcome Honey, our golden doodle will greet and visit with you. The cabin is to be left SAME as you found it. NO generator

FamilyIndoor spacesDecor

4.98 out of 5 average rating, 362 reviews

A spacious living area features a variety of seating options, including a cozy couch and rocking chairs. Large windows allow natural light to enter, illuminating the lush indoor plants. Decorative rugs and artwork add character to the eclectic decor, creating a relaxed atmosphere.

Farm stay in Uxbridge

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

Welcome to the LOFT - A private, eclectically designed spa-inspired unique stay in the historic Webb Schoolhouse, less than an hour from Toronto. Featured in TORONTO LIFE, this private loft includes your own sauna, unique hanging bed, wood stove, kitchenette and is filled with art, and huge tropical plants as well as a projector & giant screen for epic movie nights. Relax and recharge, roam the grounds and enjoy the beautiful outdoor spaces, the permaculture farm, animals, and fire pit.

FamilyKitchenParking

4.82 out of 5 average rating, 318 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!

FamilyIndoor spacesHospitality

The exterior of the house displays a stone facade, framed by trees and greenery. A large deck extends from the structure, featuring outdoor seating and a BBQ setup. Nearby, a driveway accommodates several vehicles, with spacious lawn surrounding the property.

4.92 out of 5 average rating, 207 reviews

Pearl by Lake Simcoe - with sauna and steam room

Spacious and bright newly renovated house with access to the lake. This 2700 sqf house has a very functional and beautifully decorated living/dining area, 2 state of the art kitchens, 6 cosy bedrooms and 3 full washrooms. Huge 400 sqf deck with BBQ and heater comfortably fits a large company outside. Enjoy indoor sauna and steam room for deep relaxation. Free Wifi. Large entertainment room with Smart TV, XBox, Kinect and a foosball table provide plenty of activities inside the house.

FamilyKitchenAmenities

4.92 out of 5 average rating, 203 reviews

Dome in Zephyr

Glass Dome - Sleep Under The Stars- Free Sundays

Discover this new, stunning 22ft Glass Geodesic Dome nestled in the heart of Uxbridge. Imagine waking up surrounded by 360-degree panoramic views of the natural landscape Please note... its FULL WEEKEND STAYS ONLY - BOOK FRIDAY AND SATURDAY-SUNDAY IS FREE. This allows guests to fully enjoy their Sunday without feeling rushed to check out at 11am. Enjoy all day Sunday with option of staying the evening. 8X12 BUNKIE NOW AVAIL. SLEEPS 4 ( 2 bunk beds) $100 flat fee

Indoor spacesKitchenWalkability

Popular amenities for Georgina family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Large glass patio doors frame a scenic view of the waterfront, revealing a private deck with seating and a hot tub surrounded by trees. Sunlight casts a warm glow over the area, enhancing the sense of tranquility.

4.87 out of 5 average rating, 221 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

FamilyIndoor spacesBeach

4.96 out of 5 average rating, 206 reviews

Dome in Utopia

Glamping Dome Riverview Utopia

Indoor spacesKitchenHospitality

4.97 out of 5 average rating, 199 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

Indoor spacesKitchenView

A spacious lake house exterior is set against a cloudy sky, featuring large windows that allow natural light to enter. The surrounding yard is adorned with fallen leaves, while a deck with outdoor furniture and a hot tub enhances the outdoor space.

4.88 out of 5 average rating, 166 reviews

Spacious family cottage 45 mins from GTA!

Indoor spacesFamilyWalkability

4.94 out of 5 average rating, 248 reviews

A private hot tub is positioned on a wooden deck beneath a lattice covering, allowing for relaxed soaking. Lounge chairs are arranged nearby, and vibrant greenery and decorative flowers provide a natural backdrop. A swimming pool can be seen in the distance, enhancing the outdoor ambiance.

Home in Port Perry

Home away from home with a hot tub and pool

FamilyKitchenAir conditioning

4.86 out of 5 average rating, 124 reviews

Home in East Gwillimbury

Animal Sanctuary 10 Acres W/Trails/Sauna/Hottub

KitchenIndoor spacesDecor

Cabin in Whitchurch-Stouffville

A charming cabin is nestled among tall evergreen trees, surrounded by well-maintained landscaping. Stone steps lead to the entrance, illuminated softly by exterior lights. The lush green lawn flows gently, creating a serene outdoor setting.

4.99 out of 5 average rating, 146 reviews

Lakefront getaway for two on Musselman's Lake

FamilyKitchenBarbecue

4.98 out of 5 average rating, 160 reviews

The exterior of a modern home is highlighted at sunset, showcasing large windows that reflect warm interior lighting. A spacious backyard features green grass, a dining area under a gazebo, and a hot tub on the deck, creating an inviting outdoor space.

Home in Barrie

Waterfront Home, City/Sunset View & Steps to Beach

Indoor spacesKitchenSkiing

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 114 reviews

A spacious dining area features a large wooden table surrounded by black chairs. A clock with a white face is mounted on the wall, and natural light fills the room through large windows. A view into the living area is visible in the background.

Home in Bond Head

3BR Spacious Home - KING BED

KitchenIndoor spacesLocation

4.86 out of 5 average rating, 269 reviews

3BR on Lake Simcoe | Gorgeous Views 1hr From City

FamilyIndoor spacesDecor

4.94 out of 5 average rating, 185 reviews

Guest suite in Innisfil

Beautiful 2BR Apt | Playground + Fire Pit + BBQ

FamilyIndoor spacesHiking

4.83 out of 5 average rating, 224 reviews

The exterior of the villa is captured, showcasing a spacious driveway lined with several parked vehicles. A well-maintained garden features vibrant flower beds and neatly trimmed shrubs. The building's elegant stone façade is complemented by large front windows, with trees visible in the background.

Home in Kawartha Lakes

Luxurious Waterfront Vacation Villa Kolenchery.

FamilyKitchenBathroom

4.96 out of 5 average rating, 179 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

Indoor spacesFamilyBarbecue

4.92 out of 5 average rating, 190 reviews

Cottage in Brechin

COTTAGE ON LAKE SIMCOE -4 BEDROOMS /2WSHRMS

FamilyKitchenGetting around

4.89 out of 5 average rating, 248 reviews

A circular seating area is formed by four yellow Adirondack chairs positioned around a stone fire pit. In the background, a sandy beach leads to a wooden dock extending into the calm waters of Balsam Lake, with additional seating visible at the end of the dock.

Cottage in Kirkfield

Balsam Lake fully renovated 4BR 2BA modern cottage

FamilyKitchenBackyard

4.98 out of 5 average rating, 121 reviews

A private deck is showcased, featuring two black chairs facing a serene lake view. Lush green trees and foliage surround the area, enhancing the peaceful atmosphere. The calm water reflects the blue sky, creating an inviting spot for relaxation.

Cottage in Caesarea

Lakeside Cottage Getaway South Shore Lake Scugog

FamilyIndoor spacesGetting around

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 566 reviews

A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.

Treehouse in Port Perry

Treehouse on private, isolated forest (300 acres)

FamilyKitchenQuiet

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

FamilyIndoor spacesHospitality

4.77 out of 5 average rating, 105 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

House ~ Pool ~ Fire Pit ~ BBQ

Indoor spacesFamilyHospitality

4.93 out of 5 average rating, 124 reviews

Campervan/RV in Lisle

Givi’s Cozy Camper: Warm & Welcoming

KitchenFamilyValue

4.89 out of 5 average rating, 144 reviews

A modern living area features a spacious sectional sofa complemented by decorative pillows and a large coffee table. Natural light floods in through expansive glass windows, revealing a view of the private patio. Minimalist decor includes a geometric wall design and a stylish light fixture.

Condo in Innisfil

Exceptional 2+1 ground floor condo @Friday Harbour

Indoor spacesFamilyAir conditioning

4.86 out of 5 average rating, 102 reviews

The exterior view of the two-story house is framed by lush trees, showcasing large windows that allow natural light to filter inside. A balcony extends from the second floor, providing outdoor space. The structure features a blend of wood and siding materials.

Home in Uxbridge

The Ridge Roost - Uxbridge Township

Indoor spacesKitchenBathroom

4.84 out of 5 average rating, 296 reviews

Cottage in Lafontaine

Cozy Beach Cottage with Pool | Georgian Bay

FamilyIndoor spacesValue