Family-friendly vacation 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, 498 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...

KitchenFamilyTV

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

FamilyIndoor spacesWalkability

5.0 out of 5 average rating, 146 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

*Requests typically replied to within 15 mins during the day.* Private bright 2 bedroom basement (sleeps 4 & no shared areas), 45 minutes N of Toronto. We live in a safe neighbourhood, in a home which backs onto a forest. Walking distance to a train station and a very large mall. You will have two private bedrooms, your OWN bathroom and full kitchen, 3 fireplaces, internet & HOT TUB! Separate entrance. No parties. No instant booking. We screen our guests as we live upstairs with our kids.

KitchenIndoor spacesCheck-in

4.93 out of 5 average rating, 111 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

FamilyKitchenValue

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, 529 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.

Indoor spacesFamilyView

4.91 out of 5 average rating, 287 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.

KitchenFamilyBackyard

4.96 out of 5 average rating, 138 reviews

Cottage in Georgina

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 spacesKitchenCondition

4.92 out of 5 average rating, 205 reviews

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.

Cottage in Georgina

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.

Indoor spacesKitchenWalkability

Townhouse in East Gwillimbury

A modern family room features a comfortable sofa with decorative pillows and two accent chairs. A large TV is mounted above a sleek fireplace. Natural light floods the space through multiple windows, with a cozy window seat inviting relaxation.

4.93 out of 5 average rating, 27 reviews

Stylish 4BR Family Home•Near GO Transit & Highways

Welcome to our comfort & style in our private 4BR and 3.5WR East Gwillimbury home - perfect for families and groups. ✓ Entire home to yourself – full privacy ✓ 4 spacious bedrooms + 3.5 washrooms ✓ Fully equipped kitchen for preparing meals ✓ Smart TV & High-Speed Wi-Fi ✓ High-quality Linens. Comfy Beds ✓ Open-concept layout with modern décor ✓ Safe neighbourhood. Easy access to highways ✓ Minutes from Mall & Hospital Book your stay with confidence and make unforgettable memories!

Indoor spacesFamilyLocation

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

FamilyKitchenCondition

4.86 out of 5 average rating, 146 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.

Indoor spacesFamilyAmenities

4.86 out of 5 average rating, 123 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.

FamilyIndoor spacesCleanliness

Popular amenities for East Gwillimbury family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 164 reviews

Spacious family cottage 45 mins from GTA!

KitchenFamilyView

4.97 out of 5 average rating, 158 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

KitchenIndoor spacesLayout

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, 144 reviews

Lakefront getaway for two on Musselman's Lake

Indoor spacesFamilyBeach

4.83 out of 5 average rating, 142 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

FamilyKitchenLocation

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, 219 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

FamilyIndoor spacesLayout

4.93 out of 5 average rating, 191 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!

FamilyKitchenGetting around

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, 370 reviews

Crystal Beach Cottage & Spa

KitchenFamilyAmenities

4.99 out of 5 average rating, 187 reviews

The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.

Home in The Beaches

Luxury 4BR: 365 Days Open- Heated Pool & Hot Tub

KitchenFamilyPets

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 99 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

Indoor spacesFamilyValue

4.86 out of 5 average rating, 266 reviews

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

Indoor spacesKitchenAmenities

4.98 out of 5 average rating, 359 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

KitchenIndoor spacesAir conditioning

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, 305 reviews

Orchard cottage, experience the farm in the city

Indoor spacesFamilyView

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, 101 reviews

Greystone cottage in Innisfil

KitchenIndoor spacesNearby

4.94 out of 5 average rating, 182 reviews

Guest suite in Innisfil

Beautiful 2BR Apt | Playground + Fire Pit + BBQ

Indoor spacesFamilyBackyard

4.83 out of 5 average rating, 222 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.

FamilyIndoor spacesBackyard

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, 140 reviews

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

FamilyKitchenAir conditioning

Family-friendly home rentals with a pool

4.92 out of 5 average rating, 217 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

KitchenFamilyDecor

5.0 out of 5 average rating, 205 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

FamilyIndoor spacesLocation

4.96 out of 5 average rating, 178 reviews

Condo in Innisfil

Upscale Spa w/ Hot Tub-Private Sauna-Penthouse

KitchenIndoor spacesCleanliness

4.94 out of 5 average rating, 247 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

Indoor spacesFamilyGetting around

4.98 out of 5 average rating, 564 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)

FamilyKitchenCheckout

4.89 out of 5 average rating, 140 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

FamilyIndoor spacesLocation

4.96 out of 5 average rating, 103 reviews

The living area features a light-colored sofa paired with a stylish armchair, placed on a neutral-toned area rug. Large glass doors provide access to the private patio, allowing natural light to fill the space. An elegant coffee table is centered in the area, complemented by modern decor.

Condo in Innisfil

Cozy Residence with Walkout to Courtyard

FamilyIndoor spacesAccuracy