Family-friendly holiday rentals in Bradford West 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...

Indoor spacesFamilyTV

4.93 out of 5 average rating, 271 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

FamilyIndoor spacesComfort

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, 106 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 spacesFamilyCheckout

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, 533 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.

FamilyIndoor spacesHiking

4.95 out of 5 average rating, 290 reviews

A geodesic dome is nestled among vibrant fall foliage, showcasing a combination of green coniferous trees and orange and yellow deciduous leaves. The transparent windows of the dome reveal a glimpse of the interior, enhancing the connection to the surrounding nature.

Dome in Utopia

Off-grid Glamping Dome Nestled in the Woods

Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

FamilyIndoor spacesCheckout

4.86 out of 5 average rating, 270 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

Indoor spacesFamilyRiver

4.95 out of 5 average rating, 165 reviews

An open concept living area showcases large panel doors that fully open to the outdoor deck. Inside, a comfortable seating arrangement is visible, along with a cozy area rug and a neutral color palette. Natural light floods the space, enhancing the connection to nature.

Cottage in Mono

Hockley Riverside Cottage • Loft and Bunkie

Needing an unforgettable escape? This cozy cottage is nestled in nature along the Nottawasaga river and has large panel doors that fully open for picture worthy views & peaceful sounds of the river. A new incredible outdoor fire-pit with hanging egg chairs. A cozy indoor wood burning fireplace along with a comfy pull out couch that has a projector above for the best movie nights. Heated floors if you aren't interested in maintaining a fire, fully equipped kitchen, Wi-fi, AC and washer/dryer.

FamilyIndoor spacesNearby

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

Huge Lakefront Retreat – Perfect for Multi‑Gen Family Getaway with Private Beach, Fire Pit & Games Room, 4 King Suites (3 with dedicated ensuites) - 9 Beds in total! Enjoy 3x kayaks, canoe & paddle boat, plus a games room (ping pong, air‑hockey, foosball). Central AC, Wi‑Fi & free parking for 6 cars. Partnered with Muskoka Wake for watersports & Harbour House Kitchen for private dining or catering. Pet friendly. Book now for the ultimate lakefront vacation, just 45 min from Toronto.

KitchenFamilyCheck-in

4.94 out of 5 average rating, 187 reviews

Guest suite in Innisfil

Beautiful 2BR Apt | Playground + Fire Pit + BBQ

Stay in a modern, newly renovated 2-bedroom, 1-bath lower-level basement apartment with a private entrance in the heart of Alcona. Just 5 minutes from Innisfil Beach Park and close to Friday Harbour, Gateway Casino, and Tanger Outlets, this cozy retreat is perfect for families, friends, or business travelers. Outside, enjoy a custom-built playground designed for both little ones and big kids, plus a fire pit for evenings under the stars. Please note the backyard is a shared space.

Indoor spacesKitchenLong stay

4.91 out of 5 average rating, 302 reviews

Lakefront | Private Dock, Sandy Beach & Hot Tub

Lake Simcoe waterfront cottage with a rare shallow sandy-bottom shoreline, private dock, and hot tub. Enjoy swimming, kayaking, paddleboarding, fishing, BBQs, fire pit evenings, and breathtaking sunsets. Perfect for family vacations, holiday getaways, and groups near Toronto, just minutes from Hwy 404. Features 6 bedrooms, 4 bathrooms, a fully equipped kitchen, and spacious indoor and outdoor areas. Private, peaceful, and ideal for year-round Lake Simcoe getaways.

KitchenIndoor spacesView

4.96 out of 5 average rating, 207 reviews

Dome in Utopia

Glamping Dome Riverview Utopia

Come retreat into nature at the Riverview Glamping Dome… a 4 season getaway located on Rustic Roots Farm and Eco-retreat 1 hour north of Toronto. Whether you're looking for a romantic getaway or to come disconnect from the hustle and bustle of everyday life this geodesic dome is for you! Located on 64 sprawling acres come explore hiking trails, go fishing, relax in the hot tub, and stargaze fireside.

FamilyIndoor spacesSkiing

4.91 out of 5 average rating, 291 reviews

Utopia villa and spa

✨ Welcome to Utopia Villa & Spa — a private retreat with 3 bedrooms & 2 bathrooms, thoughtfully designed for comfort and connection. Enjoy a seasonal outdoor pool, year-round hot tub, sauna, game room, and cozy spaces for family and friends. 🏡🤍 Just 7 minutes from the beach, with a fresh seasonal look every visit. Ready for your next getaway? Book Utopia today and make memories that last! ✨

FamilyKitchenDecor

Popular amenities for Bradford West Gwillimbury family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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

FamilyKitchenSleep quality

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

KitchenIndoor spacesCondition

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, 222 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

FamilyKitchenLong stay

4.98 out of 5 average rating, 130 reviews

Condo in Innisfil

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

KitchenFamilyComfort

4.93 out of 5 average rating, 194 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 spacesComfort

4.96 out of 5 average rating, 112 reviews

Home in Barrie

Hot Tub Pool Poker Table BBQ 10 Mins To Lake Simcoe Luxury

Indoor spacesKitchenQuiet

4.83 out of 5 average rating, 144 reviews

A lakeside cottage is displayed from the dock, featuring a modern design with large windows and a spacious deck. The outdoor area includes a Jacuzzi surrounded by a stone border. Lush greenery frames the scene, enhancing the serene lakeside setting.

Cottage in Gilford

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

FamilyIndoor spacesAir conditioning

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

Indoor spacesKitchenCondition

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 144 reviews

Resort-Style Luxury Waterfront Cottage

KitchenIndoor spacesEV charging

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

KitchenFamilyNearby

4.75 out of 5 average rating, 495 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

Indoor spacesKitchenSolo travel

4.98 out of 5 average rating, 365 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

Indoor spacesKitchenDecor

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, 209 reviews

Pearl by Lake Simcoe - with sauna and steam room

Indoor spacesKitchenLayout

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

KitchenIndoor spacesWi-Fi

4.92 out of 5 average rating, 128 reviews

Campervan/RV in Lisle

Givi’s Cozy Camper: Warm & Welcoming

KitchenFamilyBackyard

4.92 out of 5 average rating, 207 reviews

Dome in Zephyr

Glass Dome - Sleep Under The Stars- Free Sundays

Indoor spacesKitchenCleanliness

Family-friendly home rentals with a pool

4.9 out of 5 average rating, 145 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

Indoor spacesKitchenLayout

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 spacesHot tub

4.95 out of 5 average rating, 356 reviews

A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.

Cabin in Mono

The Trails Retreat (Private Cabin)

FamilyKitchenCheck-in

4.95 out of 5 average rating, 109 reviews

A stone fireplace is set into a rustic wall made of various sized natural stones, providing a textured and earthy backdrop. A flat-screen TV is mounted above, and a wooden cabinet is positioned to the left, adding warmth to the living space.

Apartment in Caledon

Separate apartment with pool, on golf course.

FamilyKitchenQuiet

4.93 out of 5 average rating, 242 reviews

Condo in Innisfil

The Friday Flat | Sunny Escape by the Marina

Indoor spacesKitchenDecor

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

Indoor spacesKitchenNearby

Guesthouse in Orangeville

An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.

4.96 out of 5 average rating, 404 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

FamilyKitchenHospitality