Family-friendly vacation rentals in Woodbridge, Vaughan

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

Country Cabin Escape | King Bed | Pet Friendly

Tucked away on our peaceful family farm, this private retreat offers tranquility and comfort—while not secluded in the woods, it provides a true countryside experience. ✨ Full kitchen 🔥 Wood fire pit 🔥Propane BBQ 📶 WiFi + 40” Smart TV 🚿 Cozy 3-piece bathroom 🧺 Laundry access 🌲 Scenic walking trails Located near our farmhouse, Country Suite, and Event Barn, the cabin remains fully private with blinds for added comfort. We look forward to welcoming you for a restful and memorable stay!

Spacious private apartment includes coffee/tea bar

Cozy-Contemporary Spacious Private Apt. in the Historical Downtown Core of Richmond Hill. 15 MINUTES FROM YYZ. Fully functional complete kitchen, NEWLY RENOVATED bathroom, heated floor, spacious shower, private entrance, parking COVID-Super-CLEAN Very quite, beautiful Mature trees and gardens. The Old Mill Pond area is known for it's canopy of trees, ponds and walking trails. Close to Yonge Street, GO transit, and 15 MINUTES FROM AIRPORT Walking distance to Major Mackenzie Health Hospital.

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

Luxury 5 beds, 6 Baths custom home

Multi-million dollar custom home in Richvale Ontario. Over 5000sqf 5 bedrooms, 6 washrooms, bar, entertainment room, custom kitchen, 1 in-garage & 3 outdoor parking. Private backyard with deck from the main floor & a walk-out Juliette from primary bedroom. 3 smart TVs & internet included 2 sofa beds in addition to 5 Beds Pool/Snooker Table No parties/loud music allowed Closet in the basement is not accessible for guests Please bring your own personal items e.g. shampoo, body wash etc.

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.

Clean & Beautiful Spacious Bungalow Near Airport

Clean, Beautiful and modern 3-Bedroom spacious semi-detached Bungalow. Bright sunny rooms with Hardwood floors and new full-size oak kitchen. Our place is good for families, couples, solo adventurers, and business travelers. We are close to Pearson Airport, Humber College, The International Center, Woodbine Shopping Center and OLG Slots at Woodbine Racetrack. Walking Distance to Walmart, Westwood Mall, Malton Rec Center and Restaurants, Wet 'n' Wild Toronto (Wild Water Kingdom) Water Park

Spacious,Cozy,Private 2+1BR/1.5BA Seprate Entrance

- separate private entrance / self check-in - ground floor rooms & partial basement with 2 queen beds and 1 sofa bed (living room as 3rd BR with curtains ENCLOSED/OPENED for privacy) - 55"TV & high-speed WiFi - Full size kitchen - 2 parking - 5 mins walking to Yonge st. next to VIVA bus stop (1 bus to Subway Yonge/Finch station & Go Bus to all Toronto & Downtown) - walk to Food Basics, Shoppers Drug Mart, clinic and different restaurants -3 mins drive to 407, shopping malls

Hockley valley, up country guest cottage

please read the entire post our beautiful cottage is located on 27 acres of land. Which is very secluded and quiet. Open concept cottage , with a loft bedroom with a double bed, a double sofa bed and a single folding bed. Wood burning fire place and a Small area with a hot plate , microwave, toaster oven, coffee maker , small fridge , BBQ on the porch. Swimming pond Vegetable garden and honey bees. Beautiful wooded trail No smoking Kids are welcome