Family-friendly vacation rentals in Whitchurch-Stouffville

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Top-rated family-friendly rentals in Whitchurch-Stouffville

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Guest favorite

A charming entrance is featured with a stone pathway leading to a wooden staircase that ascends to the porch. Lush greenery and hanging planters decorate the entryway, while a white picket fence provides a welcoming border.

Guest suite in Leslieville

4.92 out of 5 average rating, 504 reviews

Newly renovated-1 bdrm suite in cute Leslieville

Hotel style lower level unit with separate entrance and parking in the heart of Leslieville. NY times travel calls Leslieville Toronto's hippest place to dine, drink, shop and live. Short transit to the Beaches and both Distillery & Financial dist. Close to a bunch of cool music venues We have a sweet golden retriever named Coco. She loves people and attention so if you happen to run into her in the yard while coming or going from the unit don’t be afraid but she will definitely want to say hi

Guest favorite

Condo in Innisfil

4.84 out of 5 average rating, 180 reviews

Marina view at Friday Harbour 2bd/2bth Pool option

This Black Cherry model condo is the most sought after layout at Friday harbour, featuring a spacious-well-designed kitchen, living room and balcony area with two bedrooms and two bathrooms ideal for families, couples, or solo travellers. Enjoy comfortable sleeping with a king bed in the master bedroom also featuring an ensuite bath and walking closet, and a Queen bed in the second bedroom. Enjoy a view of the beautiful landscaped courtyard out to the marina, while lounging or eating outside.

Superhost

The kitchen is equipped with modern appliances, including a stove, microwave, and fridge. White cabinetry complements the sleek gray countertops, while a window provides natural light. A minimalist design is achieved with a stylish pendant light hanging above the sink area.

Home in Barrie

4.81 out of 5 average rating, 255 reviews

Entire House w/ Games Room- by Beaches & Downtown

Entire, completely private, cozy, older 3 bedroom house: • Full kitchen w/ coffee maker, microwave • 3 beds, 1 sofabed, 1 foldable cot • 1 full bathroom & 1.5 bathroom • Bed linen/towels • Fast wifi • TV w/ netflix (living room & 1 bedroom) • Games room w/ pool table, darts, table soccer • Long driveway • Fenced backyard w/ patio set & kids swing set • 2-5 min to restaurants/shops • 5 min to downtown Barrie • 5 min to Lake Simcoe • 15 min to Innisfil • 15-20 mins to Horsehoe & Burls Creek

Guest favorite

A bright living area features large windows allowing natural light to fill the space. A cozy sofa is accompanied by a vibrant armchair. Colorful artwork adorns the walls, and a glass coffee table holds fresh flowers. A stylish fireplace adds warmth to the room.

Home in Toronto

4.94 out of 5 average rating, 155 reviews

Great House on Palmerston Blvd in downtown Toronto

Welcome to our elegant, renovated and modernized home in one of Toronto’s favourite, safe, Downtown neighbourhoods. The house is clean and spacious and features a gourmet kitchen, family room, separate living and dining rooms and a powder room. Upstairs there are five bedrooms, each with comfy beds plus two full bathrooms. Your choice of front porch or garden with patio outside. Minutes on foot from a heavenly choice of restaurants, cafes, bars & shops with easy access to the entire City.

Guest favorite

A modern living area features a sectional sofa and a coffee table on a colorful area rug. A fireplace adds warmth, positioned below a wall-mounted television. Accent chairs in yellow and green provide additional seating, while natural light spills in from a small window.

Guest suite in Toronto

4.92 out of 5 average rating, 107 reviews

Bright & Cheery Full Basement Suite walk to Subway

Our basement with private keypad entry in Toronto's tree-lined West End is ideal for tourists or folks coming to the city to work. It was completely renovated in early 2025 with a 1950s vintage travel vibe you'll love. Brand new bathroom, full separate bedroom with queen size bed (ENDY mattress), TV, desk, plus living area with fireplace & sofa bed. There is also a kitchenette/laundry. 3 min walk to Jane subway. Ceiling 6'5" with 1 lower beam. We live upstairs--the unit is noise insulated.

Guest favorite

A stylish living room features a fabric sofa and two accent chairs with a modern design. A coffee table occupies the center, complemented by a decorative bowl. A flat-screen TV is mounted above a fireplace, while natural light filters through sheer curtains.

Home in Maple

4.87 out of 5 average rating, 103 reviews

Lavish. Spotless. One's Own, 4 BR 4 BA Home!

Welcome to Maple Downtown! Live Large in a Luxury Brand New Concept Home surrounded by mature 30 ft high trees. My place has 2 stories (main & second level), 4 bedrooms, 3.5 bathrooms. Sleeps 8 in Beds (Max 8 people, confirm with the host ). Basement Apartment is not included in this listing and not occupied during your stay. MUST BE 25 or OLDER in order to BOOK. Do not book my home if you are planning on parting or gathering. Please ,note a 4% City Tax will be added to each booking.

Guest favorite

A round dining table is elegantly set with fine china and glasses of red wine. The view from the balcony includes other buildings and landscaped gardens, with the harbour visible in the background under a cloudy sky.

Condo in Innisfil

4.93 out of 5 average rating, 206 reviews

Designer Condo with beautiful harbour view.

Unique top floor. Rare views where every room overlooks the harbour. Professionally designed with new stylish furnishings. Ideal for those who like a little sophistication while spending time at the lake. Enjoy going out to eat every night or make a meal and curl up and relax in the beautiful living room, or a combination of both! Friday Harbour is a resort with beautiful walking trails, cafes, and restaurants, and a perfect get-away that celebrates the seasons with exiting activities.

Guest favorite

Bungalow in Innisfil

4.82 out of 5 average rating, 279 reviews

Lake Simcoe-3bdr,hot tub,sauna,swim,play,hike

NEW!!: seasonal or monthly rental available, contact me directly to get the exact pricing, thank you Our cottage is about a 800 m from the beach at family friendly Innisfil Beach Park! The kitchen is modern and bright with lots of room for lounging inside the cottage or entertaining outside in the large yard with a fire pit. Our cottage is ideal for couples and families. It is beautifully furnished. There is a BBQ, patio furniture & firepit, smart TV with Roku and Chromecast.

Guest favorite

An open-concept living area showcases a comfortable sofa and modern furnishings on a patterned area rug. Natural light streams through large windows, illuminating the space. A wooden floating staircase leads to the upper floor, while a stylish dining space and kitchen are visible in the background.

Home in York

4.89 out of 5 average rating, 190 reviews

Family Home Near St Clair W and Public Transport

Steps away from vibrant St Clair West with great dining, access to public transport and shopping. A real family home with space and amenities for everyone. Free parking for 2 cars. Open-concept living & dining, well-equipped kitchen. Sunny back deck. 3 comfortable bedrooms. Spa bathroom with heated floor. Perfect for families who are in town for reunions, weddings, birthday parties and visiting. Quiet hours after 10pm - not suitable for groups in town ‘to party’.

Guest favorite

The living room features soft blue couches arranged around a glass coffee table. A colorful area rug lies beneath, complementing the hardwood flooring. Natural light filters in through a large window, framed by sheer curtains, while a decorative fireplace adds a touch of warmth.

Bungalow in Erindale

4.87 out of 5 average rating, 232 reviews

3 Bdr Bungalow in Mississauga 20 min to Toronto

My place is close to shopping, public transport, parks, the airport, the city centre, and all amenities. You’ll love my place because of lovely detached bungalow house on a very quiet street, 10 mins from YYZ airport, 15 mins to DT Toronto, 5 mins from Square One Mall, 5 mins from University of Toronto Missisauga, and Erindale GO Station. My place is good for couples, solo adventurers, business travelers, and families. It has a walk score of 93 out of 100.

Guest favorite

A vibrant three-season room features yellow walls and a mix of textures, including stone flooring. Natural light floods in through large glass doors leading to the backyard. Furnished with a wooden table and chairs, the space is decorated with artwork and rustic accents.

Apartment in The Beaches

4.91 out of 5 average rating, 290 reviews

Honey House in the Beach

A clean, private two bedroom apartment in the fully finished basement of our funky and well kept bungalow. A great backyard with a hot tub, several decks and a 3-season garden room to share- all great places for a morning coffee or late night drink. The private washroom has just been totally renovated - new everything! Two bedrooms, each with one double bed. Sleeps four. *a heads UP for tall guests, this is a basement apartment 7foot ceilings

Guest favorite

A wooden dock extends into the calm water, leading to a cozy bungalow surrounded by trees. A grassy area features a picnic table, while the backdrop showcases a peaceful lake scene under a partly cloudy sky.

Cottage in Innisfil

4.83 out of 5 average rating, 218 reviews

Private lakefront cozy 3B1B 1hr from the city

Escape the city and unwind at our charming three-bedroom bungalow on Lake Simcoe, just one hour north of Toronto. With 129 feet of private lakefront, you’ll wake up to breathtaking sunrises and stunning water views, making it the perfect all-season getaway. 🌅 Unmatched Lakefront Views 🏖️ Private & Peaceful 🏊 Shallow, Swimmable Waters 🏞️ Spacious Outdoor Area 🎣 Cozy Year-Round Escape 🚗 Easy Access – Just a one-hour drive from Toronto