Family-friendly vacation rentals in Milton

Five Star Hayloft Suite

This open space home is in the top level of a century-old bank barn. Witness the beautiful architecture while enjoying modern amenities like an open-concept kitchen, projector & movie lounge, and more! Enjoy 180 degree views from the bay window in the living room during your stay. Five Star Ranch offers a year-round getaway in a beautiful country setting. Situated on a working farm, and surrounded by gardens, animals and beautiful forest, it is a perfect destination for seclusion and peace.

Stylish Modern Luxury Stay

Welcome to your stylish modern luxury retreat! This beautifully designed suite offers a private entrance and free parking. Step inside to a sleek, open-concept space featuring: ✅ Kitchenette + Complimentary coffee & tea ✅ High-speed WiFi, Workspace & Smart TV for entertainment ✅ Cozy living room with a plush sofa bed ✅ Modern bathroom with a refreshing shower Book now for a relaxing, high-end getaway with easy access to local attractions and a short drive away from some incredible views!

Luxury Guest Suite

Welcome to our cozy basement apartment! This modern Airbnb is located in a peaceful residential neighborhood 40 min drive from Toronto downtown and an hour from Niagara Falls. The well-lit space features a comfortable queen-sized bed, ample storage in the spacious closet, and a beautifully designed interior with natural light flooding through large windows. Note: We have 2 single folding matresses available to place on the floor in the living room. Extra linen and pillows are provided.

Luxury tiny home on peaceful country estate

Escape to Heirloom Tiny Home - where macro luxury meets a micro footprint. Nestled on 23 peaceful acres, surrounded by aspen and pine forests, just 10 minutes from the picturesque town of Elora. Wake up to serene pond views as horses and sheep graze in your view. Organic linens, artisanal soaps, and a spa-like bathroom soothe the senses. Cozy up by the indoor fire and gaze at the stars. Enjoy fine dining at the Elora Mill and Spa, enjoy popular shops or hike the Elora Gorge nearby.

Modern Basement Apt. w/ King Bed

Welcome to our luxurious and contemporary basement apartment, a true urban retreat that will exceed your expectations. Nestled in a vibrant neighborhood, this stunning two-bedroom, two-bathroom haven is the perfect choice for discerning travelers seeking both style and comfort. With a plethora of top-notch amenities, including high-speed internet, on-site parking, and convenient laundry facilities, your stay with us promises to be truly exceptional.

Spacious, Pet Friendly Basement Apartment

Quiet, pet-friendly private basement suite designed for comfort and easy stays. Features a queen bed, sofa bed, fully equipped kitchen, dining area, in-suite laundry, free Wi-Fi, and complimentary coffee & tea. Guests enjoy a shared backyard with a seasonal pool and barbecue in summer. Loved for its privacy and comfort while being steps from a park, grocery store, pharmacy, bank, and nearby restaurants—perfect for short or extended stays.

Private 2BR Suite | Near Toronto | Full Kitchen

Private 2BR basement suite with separate entrance - no shared spaces. Fully equipped kitchen, in-unit washer/dryer, electric fireplace, smart TV, and lightning-fast Wi-Fi. Keypad self check-in means flexible arrival at any hour. Perfect for families, work trips, or groups up to 6. 30 min to Toronto Pearson Airport (YYZ), 40 min to downtown Toronto, 90 min to Niagara Falls. GO Transit nearby. Free driveway parking included.

Backyard Oasis Guesthouse.

POOL IS OPEN Welcome to our cozy walk-out basement apartment with no kitchen. It is a completely private unit with separate entrance. Perfect for making some memories at this unique and family-friendly place. Backing on to the Sixteen-mile creek, this backyard oasis has a sun-drenched inground pool surrounded by mature perennial gardens, a new manufactured stone patio, with upper and lower shaded lounge areas.

The Sleek Shelter - Cozy , Comfort, Convenience

Budget-friendly comfort -with all the essentials you need for a hassle-free visit 8 min to Glen Edan Ski Resort 10 min to Apple & Strawberry Farms 20 Min to Pearson Airport , 45 min to Niagara Falls, 45 min to Toronto downtown private backyard with stunning forest views— It’s private basement with - Separate entrance (Private Garage Entry) . - Separate Kitchen - Separate Washroom

Private 2BR Suite -Parking | Laundry | Outlet mall

Enjoy a peaceful stay in our private 2-bedroom legal basement suite located in a quiet Milton neighborhood. Featuring an open-concept layout with 8.5-ft ceilings and comfortable bedrooms, it’s ideal for couples, families, or longer stays. Minutes from Toronto Premium Outlets, Velodrome, scenic trails, and easy access to Oakville, Burlington, Mississauga, and Pearson Airport.

Horse Ranch with Hot tub

Your very own house with lots of open space outdoors. Equipped with wifi and many home comforts. Enjoy taking a dip in the Hot tub, feeding and petting horses, walking forest trails, BBQ, have a picnic for lunch. Options are limitless to spend your time in the country and take a break from the city life. Relax with whole family or friends at this peaceful place to stay!

Luxury Glamping on Elora Sunflower Farm -Sunflower

Luxury Glamping near Elora on a private 17-acre flower farm. Tucked within a forest, each tent offers a private hot tub for a refined, nature-forward stay, with Fox and Firefly also featuring private decks and fire pits. Visit the alpacas or walk to nearby trails and into town. As an active farm and event venue, weddings may take place in the barn during your stay.