
Family-friendly vacation rentals in Orangeville
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Top-rated family-friendly rentals in Orangeville
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Orangeville family-friendly rentals
Family-friendly home rentals with a hot tub

A Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi
Thank you for the wonderful stay! Our group loved our stay! Would highly recommend.

Beautiful Condo + CN Tower View + Free Parking
A few days in Toronto watching some baseball. Perfect location, 5 minute walk, view of the CN Tower from the balcony. Very spacious for 4 adults and two grown teenagers. Everything we required in the accommodation. Very easy check in and parking. Excellent, prompt communication from Katherine. Will definitely stay here again.

Downtown Markham Unionville
We had a great stay at Thomas' place. He met us at check in, showed us the building, parking and any details we needed to know. He was very responsive, provided early check in, and coordinated parking spots for both our vehicles. The place was very clean and quiet. We would definitely stay again!

1 Bedroom Suite - DT Core (Office/Bidet/Balcony)
Wow and thank you. To find such a perfect location was so fortunate. Cal sent a warm and welcoming message that just set the experience off to a great start. The condo was clean and modern and just felt so comfortable. There is something energizing about being right in the centre of thing’s, especially when you have such a wonderful space to come “home” to. Thanks to Cal for providing such a terrific space.

Lake Simcoe-3bdr,hot tub,sauna,swim,play,hike
Nice home in a quiet and safe feeling neighbourhood. Easy to find and access. Big back yard for kids and dog (although not fully fenced, which was fine as we brought our own leash). We arrived from out of province (via flying) and were surprised to find the beds already made with the necessary linens (we had packed our own via suitcase as per the ad details). But we appreciated the kind gesture had we somehow failed to bring our own! The kitchen is updated (so different from pictures) but still has all the appliances and cooking items a family would need for their stay. Lots of stores (grocery, banks, restaurants, Canadian Tire etc) are within a 10 min drive or less, making “going into town” to grab stuff a breeze. Plus having access to a hot tub, sauna and BBQ are a very nice treat :) We had a very comfortable stay and appreciated Tamila’s prompt responses for any questions we had. Would happily stay again!

Luxury heart of downtown by CN Tower/ MTCC/Union
Lovely place , felt right at home . Crystal was very helpful and responsive, given it was a very last minute booking. The street was very quiet and so was the building itself . Very cozy getaway in the heart of downtown Toronto for an incredibly good price . Thank you so much for making our short stay nothing short of AMAZING !

Heart of Kimberley - with views and a hot tub
We had an amazing experience. It’s a beautiful home with modern amenities and a beautiful outdoor area. We arrived in a cozy town with nearby restaurants and general store. It was a very clean and well prepped home. Our host was amazing. She was accommodating and very kind, always responsive and very welcoming. We highly recommend this stay. 10/10 experience.

Cosy Updated Lakefront Cottage
Robert’s cabin was perfect! We loved it so much that we would consider making another trip from where we live in Seattle just to stay here again. It was so clean and had everything we could want. I just love the vision they had when decorating their space. It was so beautiful. The hot tub was very spacious, we used the gas grill and it worked perfectly, wood was available for a fire, we used their cute seadoo pedal boat, which was so fun! Plenty of kayaks were available. The lake was a dream. We didn’t get to fish but there must be a lot of fish in there because they were constantly jumping out of the water. There were comfy seats all over the yard and a lovely gazebo. The inside was so cozy. Mattress was perfect. I could go on and on about all the things we loved but I’ll just say 10/10 recommend :)
Family- and pet-friendly home rentals

Lively 1+1 Lakeview Condo near CN Tower + Free Prk
Mehrdads condo was perfect for us. The view from the balcony, the proximity for bars and restaurants the CN tower and aquarium. Ten minute walk to union street train station. The condo was comfortable and well furnished and we felt very settled as soon as we moved in. Communication and entry on arrival was hassle free. Would totally recommend !

Cozy one bedroom apartment in Roncesvales village
The location of this apartment is fabulous. Easy to get from the airport and to get into the centre of Toronto. There is a big supermarket and liquor store a few minutes walk away and many restaurants, cafes and bars. High park is a short walk and the surrounding roads are very pretty. The bed in the apartment is comfortable, the shower is great. It’s quiet at night and easy to sleep.

Studio Apt in Milton Dorset Park
Steve and Melissa's place was perfect. They were fantastic hosts. The place had everything you needed. Would definitely stay again and recommend it.

Charming Century Home Close to Vibrant Shops
Beyond the house itself, the hosts were truly outstanding. They were not only extremely courteous but also incredibly responsive to any questions we had, making us feel welcomed and well-cared for throughout our entire stay. Their genuine hospitality added significantly to the positive experience. If you're looking for a unique and memorable stay in Toronto, especially if you appreciate the charm of a well-preserved historic home combined with the warmth of exceptional hosts, look no further. We highly recommend this house.

Designer Condo with beautiful harbour view.
Condo was beautiful, relaxing and everything was walkable. Will definitely be back!

Luxury 5 beds, 6 Baths custom home
Perfect spot for a group trip. Quiet neighborhood, close to the TTC for easy access to downtown. Jay was awesome at handling our request to drop off our luggage prior to our scheduled check-in time. Would definitely stay again!

All-Season Cottage on the Lake
Great place in a beautiful location! Perfect for our two families to get together and enjoy the outdoors in winter. The kitchen is well-supplied and it’s great to have towels and sheets provided. Carrie is friendly, flexible and well organized. Thanks so much!

Midtown Luxury Yonge/Lawrence Close to Downtown
I stayed here with my family for two nights while visiting the city! The space was super nice and welcoming. Spotless, updated, and comfortable. About a 10min walk to transit but straight forward and the neighbourhood felt very safe.
Family-friendly home rentals with a pool

New condo w/ gorgeous lake views
Really amazing view and building in a great location with easy access to GO trains and TTC. Building facilities are great! Check out is 10am

Modern Condo in the heart Downtown Toronto!
Myself and 2 friends enjoyed our 3 night stay to the fullest! Location was amazing! Jonathan was extremely responsive. Bed was very comfortable. Pull out bed not so comfy but was to be expected. Lots of feminine products under the sink for guests to use in including salon style hairspray. Roof top pool was amazing and not too busy! Would highly recommend Jonathan's place!

Casa Di Mama | Beautiful 2BR Downtown-Free Parking
We had a great weekend in Toronto. The location is perfect, 10 min walk from the Rodger center. The condo is great, easy check in!

Milton Home- a Family Oasis
This place was absolutely amazing. It had everything you could possibly need and want. We enjoyed everything- the qames, pool table and darts. We wish we hadn't planned so much so we could make better use of everything. Thomas was very responsive and went out of his way to help when there was something we couldn't figure out. We loved being there and will definitely look to return if we return to Toronto

Chic, High-Rise Apartment with CN Tower Views
We were in town to attend a couple Jays games and see DT Toronto. This location was great for both. Also easy access to Union station. Condo was just right for us.

King West Victorian Studio Gem
It was great to stay at Kathleen's. The place is very spacious and perfect for a one person or a couple. The location is very close to a lot of nice restaurants, coffee shops, bars, and a lot more. I like the neighborhood a lot. In the summer, you can also enjoy the park right across the street. The place was very clean, and Kathleen was a great communicator - on top of everything. It really felt like home. I stayed there for one month as I was in between places and honestly I wish I could have stayed more.

Marina view at Friday Harbour 2bd/2bth Pool option
Immaculately clean, spacious, and Beautiful condo. It had everything we need and a few steps to the marina. Easy instructions to get inside and parked. I highly recommend!

Spacious Bungalow Guest House
Our family had an excellent stay here for 2 days. Very nice grounds and easy to get around in. Bathroom is small but nice. Used the pool and celebrated a birthday with plenty of dishes and utensils a available. It's right on the highway which is convenient but busy.
Quick stats about vacation rentals that are family-friendly in Orangeville
Total rentals
20 properties
Nightly prices starting at
G$10,460 GYD before taxes and fees
Total number of reviews
1.4K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Budweiser Stage
- Blue Mountain Village
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- TPC Toronto at Osprey Valley
- Toronto Zoo
- Exhibition Place
- The Danforth Music Hall
- Harbourfront Centre
- CF Toronto Eaton Centre
- Massey Hall
- BMO Field
- Whistle Bear Golf Club
- Trinity Bellwoods Park
- Casa Loma
- Royal Woodbine Golf Club
- Dufferin Grove Park
- Royal Ontario Museum
- Royal Botanical Gardens