Family-friendly holiday rentals in East Gwillimbury

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, 503 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...

FamilyIndoor spacesSleep quality

4.93 out of 5 average rating, 270 reviews

A cozy living area features a couch facing a 55" television, placed on a low white media console. A floor lamp provides additional lighting, while a small coffee table adds functionality. Doorways can be seen in the background, leading to other areas of the suite.

Guest suite in Newmarket

2 Bed-2Bath-Kitchen | Private | Family-Couple-Work

We have an ideal place for you regardless of work, pleasure, or family time. The recently renovated suite includes: - Separate keyless entry - 2 bedrooms with closets - Living room with 55" TV - Full kitchen with storage & dining - 2 full bathrooms (1 en suite) - 2 on-premises Parking - Laundry - WiFi & more FAST EV Charger-Check for availability ($15/charge) CENTRAL LOCATION! Steps to Upper Canada Mall, Groceries, Restaurants, Trails, Parks, Golf Course, Costco, Walmart, Highway, Go, & more

Indoor spacesKitchenValue

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, 105 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!

Indoor spacesFamilyLaundry

4.93 out of 5 average rating, 113 reviews

A well-lit living area is presented, featuring a comfortable sofa, a dining table with yellow chairs, and a modern wall-mounted television. Light enters through the glass door, which leads to the outside, while a doorway on the left offers access to a private bathroom.

Guest suite in Newmarket

5Star Cozy Modern Newmarket 1BR Main Floor Getaway

Welcome to our Cozy 1 bedroom Newmarket Retreat located near the intersection of Davis and Leslie, minutes from the 404, Davis Drive, Southlake Region Health Centre, Holland Marsh Wineries, Madisons Greenhouse, and Magna International. Our charming ground-level 1 bedroom AirBnb offers an abundance of natural light making it the perfect choice for your short or extended stay. My AirBnb is neat, tidy, and ideal for professionals, couples & commuters. 45 mins from Toronto. License #BL2026-00126

FamilyKitchenWalkability

Guest suite in East Gwillimbury

A comfortable living area features a cozy sofa with decorative pillows, positioned near a large window allowing natural light. A flat-screen TV is mounted on the wall, and a small coffee table rests on a patterned rug. A lamp and electric fireplace add to the inviting ambiance.

4.91 out of 5 average rating, 532 reviews

Stylish, Modern 2nd Floor Private Apt. Quiet Area

Located in a beautiful and quiet neighborhood, this modern apartment can make for a perfect peaceful getaway no matter the occasion. Close to Lake Simcoe, beautiful beaches for swimming & fishing, and plenty of nature trails. Highlights: Large and cozy bedroom with ample storage and work space. Beautiful open concept dining area and kitchen with everything you need. Keurig coffee, tea and some snacks provided. Comfy sofa in front of a large screen TV with Netflix. High speed internet provided.

KitchenIndoor spacesDecor

4.86 out of 5 average rating, 269 reviews

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

Escape the city and unwind at our peaceful three-bedroom lakefront cottage on Lake Simcoe, just one hour north of Toronto. With 129 feet of private waterfront, expansive lake views, and shallow swimmable shoreline, it’s the perfect year-round getaway for families, couples, or friends looking to relax and reconnect. 🌅 Stunning sunrise lake views 🏖️ 129 ft of private waterfront 🏊 Shallow, swimmable shoreline 🔥 Cozy all-season retreat 🌲 Quiet and peaceful setting 🚗 Just 1 hour from Toronto

FamilyIndoor spacesGetting around

4.96 out of 5 average rating, 143 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!

Indoor spacesFamilyEV charging

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.

Indoor spacesKitchenBackyard

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, 208 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.

FamilyIndoor spacesQuiet

4.92 out of 5 average rating, 206 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

KitchenIndoor spacesLocation

4.86 out of 5 average rating, 156 reviews

The geodesic dome features a modern white exterior, set against a backdrop of trees. A wooden deck extends from the dome, leading to a covered gazebo, with a pathway of wood chips guiding the approach. Soft sunlight filters through the branches, creating a serene atmosphere.

Dome in Uxbridge

The Bubble Glamping Dome

Escape to a luxury geodesic dome on our scenic farm, nestled at the edge of the forest. Fully equipped with heating, cooling, a private washroom, deck, and hot tub, it’s the perfect blend of comfort and nature. Explore the farm, meet our sheep, chickens, and livestock guardian dog, or hike over 100 acres of connected regional forest. Whether you’re relaxing under the stars or adventuring outdoors, this unique glamping retreat promises an unforgettable experience.

FamilyKitchenAir conditioning

4.86 out of 5 average rating, 124 reviews

Home in East Gwillimbury

Animal Sanctuary 10 Acres W/Trails/Sauna/Hottub

THE COVE suite is located at The Taiga Animal Sanctuary with 10 acres of scenic forest trails. Clean & spacious 2200 sq ft 2 bedroom basement unit with 3 queen beds and a pull out couch. Outdoor sauna, hot tub, gated outdoor vegetable garden, fire pits and BBQs our guests can enjoy, along with various trails, seating, dinning tables, lawn games and hammocks to relax in. Enjoy a walk in nature, relax in the hot tub or just hang out with our rescue animals.

Indoor spacesKitchenBeach

Popular amenities for East Gwillimbury family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

5.0 out of 5 average rating, 148 reviews

The exterior of a two-story home is displayed, featuring a brick facade and large windows. A well-maintained lawn surrounds a decorative fountain at the front. Two garage doors are visible on the left, with flower pots adorning the window ledges and entrance area.

Guest suite in Newmarket

Bed of Roses Airbnb. Hot tub! 45 mins N of Toronto

KitchenFamilyLocation

4.93 out of 5 average rating, 193 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!

FamilyIndoor spacesGetting around

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

Indoor spacesKitchenWi-Fi

4.96 out of 5 average rating, 206 reviews

Dome in Utopia

Glamping Dome Riverview Utopia

FamilyIndoor spacesOutdoor spaces

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

Indoor spacesKitchenHiking

The exterior of the cottage displays a modern architectural design with large floor-to-ceiling windows, allowing for ample natural light. A spacious wooden deck surrounds the front, featuring lush greenery and vibrant flowers, creating an inviting atmosphere for relaxation.

4.87 out of 5 average rating, 372 reviews

Crystal Beach Cottage & Spa

FamilyIndoor spacesCondition

4.87 out of 5 average rating, 173 reviews

A rustic cabin, partially visible through snow-covered trees, features a warm wooden exterior. Snow blankets the roof and surrounding ground, while sunlight filters through the branches, creating a serene winter atmosphere. A wrap-around deck is seen at the front of the cabin.

Cabin in Georgina

Romantic Cabin N the Woods just 80km from CN Tower

KitchenIndoor spacesAir conditioning

4.98 out of 5 average rating, 129 reviews

Condo in Innisfil

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

FamilyKitchenSleep quality

Family- and pet-friendly home rentals

Farm stay in Whitchurch-Stouffville

A cozy living area features two brown sofas adorned with colorful cushions. Soft lighting is provided by two lamps flanking the seating. A vibrant artwork hangs on the wall, and light-colored curtains frame the window, contributing to the welcoming atmosphere.

4.83 out of 5 average rating, 307 reviews

Orchard cottage, experience the farm in the city

Indoor spacesKitchenPets

4.88 out of 5 average rating, 100 reviews

An outdoor seating area features a circular arrangement of comfortable furniture, including a low table and spacious couches with light-colored cushions. Black wooden chairs provide additional seating. The background shows a grassy area leading to the water, with trees and a trampoline visible in the distance.

Cottage in Gilford

Lake Side Manor With Games Room

FamilyIndoor spacesOutdoor spaces

4.97 out of 5 average rating, 116 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

Indoor spacesFamilyHeating

4.98 out of 5 average rating, 364 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

FamilyIndoor spacesSolo travel

4.74 out of 5 average rating, 494 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

KitchenIndoor spacesHospitality

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, 103 reviews

Greystone cottage in Innisfil

KitchenIndoor spacesCheckout

4.94 out of 5 average rating, 187 reviews

Guest suite in Innisfil

Beautiful 2BR Apt | Playground + Fire Pit + BBQ

FamilyKitchenLayout

A two-story cottage features a light gray exterior with a white railing surrounding a spacious balcony. A large, round umbrella provides shade over outdoor seating, while vibrant greenery and floral details adorn the front yard. A dark garage door is visible beneath the balcony.

4.99 out of 5 average rating, 142 reviews

❤️ Charming Cottage/Lake View/10PPL/5BDR/3BATH

FamilyIndoor spacesParks

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 206 reviews

The exterior of a modern two-story home is displayed, featuring a brick and stone facade. A well-maintained driveway leads to a double garage with decorative doors. Bright flower pots are positioned near the entrance, while lush green landscaping surrounds the property.

Apartment in Newmarket

The Hilton BnB Adult Luxury Suite

KitchenIndoor spacesLaundry

4.92 out of 5 average rating, 219 reviews

The indoor swimming pool area features a tiled pool surrounded by natural light from large skylights. Two colorful floats are positioned on the water surface, and glass doors provide a view of the outdoors, enhancing the open and airy feel of the space.

Villa in Toronto

Toronto Vacation | ➊ The One Toronto Villa

FamilyKitchenPool

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 spacesFamilyNearby

4.9 out of 5 average rating, 143 reviews

The entrance features double doors in a dark finish, adorned with elegant seasonal wreaths. Flanking the doors are decorative wall art pieces. A small bistro table with two chairs is positioned on a stone patio, complemented by potted snake plants and decorative pumpkins.

Home in Barrie

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

FamilyKitchenCondition

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 spacesKitchenBarbecue

Guesthouse in Mississauga

A serene backyard is highlighted by a clear swimming pool surrounded by natural stone coping. Comfortable seating arrangements with dark wicker chairs and a sleek table are positioned nearby, offering a relaxing spot. Lush greenery frames the area, providing a peaceful atmosphere.

4.89 out of 5 average rating, 116 reviews

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

Indoor spacesKitchenView

4.92 out of 5 average rating, 125 reviews

Campervan/RV in Lisle

Givi’s Cozy Camper: Warm & Welcoming

KitchenIndoor spacesNearby