Family-friendly holiday rentals in East Gwillimbury

4.94 out of 5 average rating, 231 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

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.

4.96 out of 5 average rating, 413 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...

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.

4.92 out of 5 average rating, 479 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.

Guest suite in East Gwillimbury

A cozy seating area is featured with a dark leather recliner sofa positioned near a modern fireplace. A large TV is mounted on the wall, displaying a serene sunset over water. Lush greenery is provided by a potted plant nearby, enhancing the inviting space.

4.98 out of 5 average rating, 183 reviews

Adorable Entire Suite,Sep. Entry,1 Parking

Enjoy easy access to stores, restaurants and entertainment from this perfect location. Only 5 min. drive to GO Train & Bus Terminal with quick, convenient transport to Downtown Toronto, Canada’s Wonderland, etc. This lower level guest suite is fully equipped with own laundry, kitchenette with mini fridge, Induction 2 burner Cook Top Stove, microwave, toaster and coffee maker. Cozy Fireplace, 60” screen HD TV and Luxurious King Size Bed Safe Neighbourhood with walking trails and parks.

4.99 out of 5 average rating, 194 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.

Flat in Newmarket

The Hilton BnB Adult Luxury Suite

Experience the elegance of the Hilton BnB nestled in Newmarket’s prestigious Stonehaven Estates, just 30 minutes from downtown Toronto. This beautifully decorated open concept walkout suite in a two-story home offers unparalleled comfort and amenities for 1-2 adult guests. Indulge in dining by the fireplace during winter or unwind with a poolside BBQ in the summer amidst breathtaking grounds. The suite boasts spaciousness and a uniquely designed interior that exudes luxury at every corner.

4.98 out of 5 average rating, 244 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 in 2021, this private loft includes a 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.

4.88 out of 5 average rating, 155 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

This Romantic 1 bedroom Rustic Cabin was resurrected from the original homestead to re-invent this Cabin just for Couples! Birthdays, Anniversaries, Honeymoons & Proposals! Sleep under 2 -4’ huge Skylights watching the moon as it crosses directly overhead in the Loft Bedroom! Or simply enjoy a time away to re-connect with your loved one! Sit under stars Year Round in the modern new Hot tub after your run or walk on 200 acres of hilly trails 5kms from the cabin ( Brown Hill Tract)

4.9 out of 5 average rating, 250 reviews

A glamping dome is set amidst a lush green landscape, reflected in a serene pond featuring lily pads and blooming flowers. Towering trees provide a natural backdrop, while a wooden deck extends from the dome, enhancing the outdoor experience.

Dome in East Gwillimbury

Deerleap Glamping Dome

Located close to the city, our four-season glamping dome offers a peaceful and unique escape. In winter, the snow-covered landscape creates a magical scene, while inside, the wood pellet stove keeps the dome exceptionally warm and cozy. Nestled on 10 acres of picturesque land and a stunning pond view, Enjoy everything you need—from upscale sanitary facilities to fast Wi-Fi. Whether you’re celebrating a birthday, an anniversary, or simply seeking quiet time in nature.

4.95 out of 5 average rating, 132 reviews

A relaxing outdoor space features a circular fire pit surrounded by four red Adirondack chairs. A stack of firewood sits nearby. Behind the seating area, a glimmering glass geodesic dome is surrounded by lush greenery and open sky.

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 $100/NIGHT ( 2 bunk beds)

4.77 out of 5 average rating, 157 reviews

A well-maintained home exterior is shown, featuring a neutral brick facade and a dark garage door. Green grass and small ornamental plants are visible in the front yard, contributing to the overall neat appearance of the property.

Home in Newmarket

Cozy apartment in Newmarket

This cozy home, located at Leslie and Mulock, is within walking distance of parks, grocery stores, and restaurants. It’s a short drive to Southlake Hospital, Historic Downtown Newmarket, the GO station, and Upper Canada Mall, Walking distance to Pickering College. Guests have full access to the first floor, featuring a living room, kitchen, dining room, and a private basement apartment, with a private bathroom. Perfect for a comfortable and convenient stay.

Guest suite in New Tecumseth

A spacious living area features a sectional sofa and a wooden coffee table, complemented by a textured area rug. Natural light is provided by recessed lighting, and a white curtain elegantly separates the space. Nearby, a kitchen area with a dining table and modern appliances is visible.

4.85 out of 5 average rating, 322 reviews

Modern, Private and Luxurious!

Welcome to our bright and stylish lower level unit in a friendly new development! You'll enjoy all the comforts of home in this cozy space. Located near Base Borden, the Honda Plant and Baxter Labs. 5 mins from Nottawasaga Inn. 30 mins to skiing at Snow Valley Ski Resort, Hockley Valley Resort, and Mansfield Ski Club. Right around the corner is an awesome community park that features a summer splash pad and a great winter tobogganing hill.

4.85 out of 5 average rating, 131 reviews

A spacious open-concept suite features a comfortable sleeping area with a bed adorned with decorative pillows. A sleek black sofa is paired with a circular table, while a small plant adds a fresh touch. Soft lighting and a window enhance the inviting atmosphere.

Guest suite in Newmarket

The Quiet Retreat

Welcome to our cozy suite, your perfect private retreat. Soft beige walls and warm lighting create a comforting atmosphere in our open-concept space. Unwind in the sleeping area or kick back in the living and dining areas with a good book or work. Our separate entrance ensures complete privacy, allowing you to come and go as you please. Make yourself at home in our warm and inviting place, your home away from home. License #BL2023-00257

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

4.85 out of 5 average rating, 281 reviews

A spacious living area features a comfortable brown sofa positioned near a glass coffee table. Natural light pours in through large windows with blinds, illuminating a dining area with seating for four. A modern kitchen is visible in the background, equipped with sleek appliances.

Guest suite in Moonstone

RELAX @ our HOT TUB and SAUNA in the woods

4.88 out of 5 average rating, 279 reviews

Aerial view of a charming multi-unit building surrounded by lush greenery. The structure features a combination of yellow and white exteriors, with distinct architectural details. A paved parking area is visible in the foreground, providing ample space for vehicles.

Apartment in Oro

Spacious 1-br w jacuzzi at Horseshoe Valley

Guest suite in Orangeville

This inviting bedroom features a spacious bed adorned with soft linens and a textured throw. A large armoire stands alongside, complemented by decorative plants and soft lighting. Natural light is welcomed through an adjacent glass door leading to a private entrance.

4.93 out of 5 average rating, 801 reviews

Cozy HotTub & Fireplace - Headwaters Retreat

4.93 out of 5 average rating, 152 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!

4.85 out of 5 average rating, 97 reviews

A serene outdoor area features a spacious wood deck with a hot tub, patio furniture, and a large umbrella. The sauna, resembling a wooden barrel, is positioned nearby. A far view reveals the barn structure and seating area under a pergola, surrounded by lush greenery.

Cottage in Erin

Private oasis in Erin.Hot tub & Woodburning sauna.

4.96 out of 5 average rating, 155 reviews

The modern kitchen and living area feature sleek white cabinetry and stainless steel appliances. A light-toned island with seating is positioned near a comfortable sofa, which is complemented by decorative pillows. Soft lighting enhances the inviting atmosphere of this open-concept space.

Flat in Windfields

Family Friendly | HOT TUB | Near Toronto & UOIT

A spacious balcony features a cozy seating area with a large hanging chair and a fire table surrounded by stylish furnishings. A propane grill is positioned nearby, and warm lights create a soothing ambiance against a twilight backdrop over the water.

4.95 out of 5 average rating, 100 reviews

Luxury Beach Spa w/ Private Sauna!

4.91 out of 5 average rating, 285 reviews

Home in Keswick

Lakefront Retreat w/ Hot Tub, Game Room & Beach

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 230 reviews

The room contains two spacious beds with soft linens arranged neatly. A wall-mounted smart TV is positioned near a cozy electric fireplace. Natural light enters through two windows dressed with light curtains, and a small table with dining essentials is visible in the corner.

Flat in Gilford

Lakeside Simcoe Fisher's apartment

Home in Nestleton Station

4.99 out of 5 average rating, 148 reviews

Retreat 82

4.87 out of 5 average rating, 461 reviews

A cozy living and dining area features a wooden dining table set with plates and glassware. Two plush sofas surround a glass coffee table in front of a television, while bright yellow flowers add a pop of color to the space. Light-colored walls enhance the inviting atmosphere.

Flat in Berczy

spaciuos 2BD 3-6 ppl homestyle BSMT豪宅精装带窗地下一层130平

4.72 out of 5 average rating, 385 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

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, 258 reviews

Orchard cottage, experience the farm in the city

4.99 out of 5 average rating, 222 reviews

The interior of the cabin features warm wooden walls and a cozy woodstove. Two blue lounge chairs are positioned near a rustic table. Natural light floods through a large window, illuminating the space, while a striped rug adds comfort underfoot.

Tiny home in Schomberg

SNAKE CABIN(rustic, 'off-the-grid')

4.91 out of 5 average rating, 113 reviews

A modern living space features a comfortable couch positioned in front of a wall-mounted television. A dining area with sleek white chairs is visible, along with a cozy bed beyond a sliding door. Natural light is softly illuminated by recessed lighting.

Flat in Barrie

The Chieftain Suite

4.8 out of 5 average rating, 121 reviews

An outdoor pool area is featured, surrounded by lounge chairs and picnic tables. A large building with expansive glass windows serves as a backdrop, while bright blue umbrellas provide shade. The surrounding greenery enhances the tranquil ambiance of the resort.

Apartment in Oro

Hillside Haven: Serene Studio Retreat for 4

Family-friendly home rentals with a pool

A modern living area features a light-colored sofa adorned with decorative pillows, positioned next to a wooden coffee table. A striped area rug lies beneath, while a kitchen island with bar stools and stainless steel appliances is visible in the background.

4.97 out of 5 average rating, 101 reviews

Cozy Stays – Your Fall Getaway at Friday Harbour

4.95 out of 5 average rating, 294 reviews

A wooden dining area features a round table surrounded by four wooden chairs. The kitchen showcases wooden cabinets, a stove, a microwave, and a refrigerator. Natural light enters through a window above the sink, enhancing the warm wood tones of the room.

Cottage in Wasaga Beach

GATED RESORT COTTAGE

4.91 out of 5 average rating, 116 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

4.96 out of 5 average rating, 106 reviews

A spacious living area features a modern kitchen with stainless steel appliances and light cabinetry. A comfortable sofa is paired with a low coffee table, adorned with greenery. Natural light flows in through large windows, enhancing the inviting space.

Flat in Coldwater

Cozy getaway for two with hot tub!

4.9 out of 5 average rating, 240 reviews

A loft area features a wooden railing adorned with greenery, providing a cozy viewing spot. A circular wooden table is accompanied by two matching folding chairs, inviting relaxation. Warm lighting enhances the natural wood tones of the ceiling and walls, creating a welcoming ambiance.

Cottage in Alcona

Utopia villa and spa

4.96 out of 5 average rating, 136 reviews

A cozy sitting area is presented with a blue checkered sofa and a striped armchair, adorned with nautical-themed cushions. Light is provided by two lamps on either side, illuminating the artwork and rustic wooden beams above.

Guest house in Erin

The Captain's Cottage at Willow Pond

An open-concept kitchen features sleek white cabinetry and a black granite island with three modern bar stools. Natural light fills the space through large glass doors, which lead to a balcony. A minimalistic design with potted plants enhances the welcoming atmosphere.

4.87 out of 5 average rating, 169 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

The living room features a comfortable sofa adorned with decorative pillows. A Smart TV is positioned on the wall opposite a glass dining table set for four. Natural light floods the space through large glass doors, offering views of the private patio.