Family-friendly vacation rentals in Oakville

Stunning, modern walkout with City and Lake Views

Ground floor level of large family vacation home! This modern bungalow is nestled on the bruce trail escarpment with wall to wall, floor to ceiling windows, offering a stunning view of the city & Lake Ontario. Enjoy open concept living & dining room, with a eat-in-kitchen & breakfast bar. 3 large bedrooms, 2 full bathrooms available, can sleep 10 comfortably. Enjoy your own private patio & backyard. Great for large families, wedding parties or group travel. Bring 10 guests & it’s only $50 each

Charming Century Home Close to Vibrant Shops

A great for-families home. Stay close to city centre yet unwind in our quiet hood. The inviting space is steps from landmark city parks and the vibrant Junction- one of the most eclectic districts in North America. We just call it home. Hang-out in the airy living room, this spacious gem has comfy seating for all, convenient amenities and period details. Cook meals in the renovated chef kitchen and enjoy dining - both indoors and out. We provide yummies for self-serve breakfast, mostly organic.

Jordan Wine Country Escape

Welcome to our warm & inviting home that is private & nestled in the middle of wine country. We offer a comfortable apartment - attached to our home - where you can come & go from your private entrance. Our kitchen is fully stocked with all necessary appliances, dishes and little extras for those looking for a longer term stay. You also have your own washer & dryer. You can view a winery across the field from your front door. You will enjoy the country setting & feel like you have escaped.

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.

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.

Nautica Beach House on Lake Ontario

License 23 110691 STR. Enjoy extraordinary sunsets and views of Lake Ontario and the Toronto Skyline while sitting in comfortable Muskoka chairs around a fire pit, enjoying a cup of coffee or a glass of wine. My home offers high-speed internet, multiple Smart HD TVs, indoor fireplace, 2 outdoor fire pits, and a large backyard with stairs leading to a Private Beach. Just a short walk to Lakeside Beach, downtown Port Dalhousie, and a short drive to Niagara wineries!

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’.

Twenty Valley Country Home

We invite you to enjoy a relaxing getaway in the Niagara Benchlands. This country property borders Rockway Golf Course & Winery and the Rockway Conservation area. This is the ideal accommodation for groups, golf weekends, and family vacations. This property offers country views, five bedrooms with ensuite washrooms, and ample outdoor space. @jordanvacationhomes The property is best suited to adult groups. Booking person must be 25+. License Number 25-0016

Amazing Lake-Front Retreat!

HIGHLIGHTS: - Priceless lake views that changes every day - Amazing wineries, Niagara attractions nearby - Hot tub - Lake access - Kayaks to explore the lake - Deck with BBQ - Putting green - Luxury boat rental to cruise the lake - Smart TVs (Netflix included) - Ping pong, air hockey - Clean linens, towels + surfaces disinfected to ensure guests have a clean and comfortable stay ** Please review the "Other details to note" section prior to booking **