
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
Get the amount of space that is right for you
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.

HotTub & Cozy Getaway - Headwaters Retreat
Beautiful place, very close to town. All needs taken care of, didn't feel like anything was missing. I wish I could've stayed for longer

Beautiful Condo + CN Tower View + Free Parking
the check in instructions were extremely thorough and 100% accurate. checked into the condo building with no problems what so ever. 4 of us had plenty of room to sleep. amazing location near the rogers centre, can see it from the patio. all the bedding and laundry was clean and ready for use. fully functional kitchen. the entire place was pristine. Great location for any concerts or other events. Will definitely be staying here again!

1 Bedroom Suite - Downtown Core (near MTCC/Rogers)
Always a great host and a 2 minute walk to the Roger's Stadium......can't go wrong!

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 !

Casa Di Mama | Beautiful 2BR Downtown-Free Parking
If I ever have another event at the Rogers Centre or anything nearby I will absolutely be checking to see if this space is available. As someone who never has driven in Toronto Julian's easy to follow instructions made it a breeze, & the parking in the secure parking garage made us feel all the better. Julian was so understanding for our arrival & helped us every step of the way. The fact I was able to walk to both of my concerts & be in my seat within half an hour of leaving this apartment was outstanding. Thank you so much Julian, you have a repeat customer for sure!

Heart of Kimberley - with views and a hot tub
Great gals weekend. We really enjoyed the General Store and exploring the area. The house linens were great, beds comfy and the seating areas too :) Weather wasn't conducive to using the outdoor spaces and as older folks we didn't think we'd manage the step stool to get into the hot tub. If there's a next time, we'll try the bustling "Justin's Oven" !!

ReLive Hilltop Chalet w/brand-new hottub, sunrises
We had a great stay in this cabin on a GORGEOUS wooded property. Awesome to watch the snow fall against the old pines. I took my dog on the snowshoe trails. Very cozy and it was great to get out of the city.
Family- and pet-friendly home rentals

Cozy one bedroom apartment in Roncesvales village
Looked just like the pictures, the location was amazing! So close to the GO, UP express and subway line, Roncy is right there, and it's about 50meters from Bandit Brewery! Seher was responsive and accommodated a different check in time due to our flight being a bit later, met us and gave us the tour of the place and explained entry! Would stay again

Beautiful suite in Downtown Toronto
My 7 year old daughter and I flew in to Toronto for Taylor Swift's ERAS concert. I can not say enough about the location. The Rogers Center is right across the street- we could watch the line up at our gate and then head over when there was no line. Amazing view of Rogers Center and CN tour. We walked everywhere the entire time- CN Tower, Ripley Aquarium, Convention Center for the Tayl-gate party and could easily rest at the condo in between activities. The condo was super clean. The bed was SO COMFY! Fully stocked kitchen. My mom came to visit us for a night from Windsor and Oron was extremely responsive to my request for parking. He got us set up right away. I would 100% stay here again for an event!

Studio Apt in Milton Dorset Park
Had an amazing stay at David’s place. Super responsive hosts and the place was super clean!

Entire House w/ Games Room- by Beaches & Downtown
Great place, will stay again

Heritage Home (4+ Bedrooms) near Downtown Guelph
My crew and myself stayed the week in comfort at Mike’s. Lots of room for everyone, beds were clean and comfortable. Close to all amenities and easy to get to.

Luxury 5 beds, 6 Baths custom home
Loved the place. We were a party of 10 here to celebrate a 100th bday. It met everyones needs/expectations.

SNAKE CABIN(rustic, 'off-the-grid')
Exactly as advertised - Beautiful property, cozy and comfortable off-grid cabin and super friendly hosts. Would absolutely come back and recommend to a friend!

Midtown Luxury Yonge/Lawrence Close to Downtown
My hosts Lucy and Don were completely accommodating, communicative, and responsive. Coming and going was a breeze. A completely outfitted kitchen with all that you'd need. The space offers total privacy. A quiet, but lively-enough neighborhood, steps away from Yonge St. It checked off all the boxes and I'm very satisfied with the experience and my stay.
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

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!

The Trails Retreat (Private Cabin)
This little place is one of a kind!! Would return in a heart beat. Friendly and responsive host, beautiful, peaceful setting, Hiking and archery on property. The house itself was clean, cozy, and private . We enjoyed our stay so much!! Will definitely come again!

*Cozy&Chic LL 2Bed 2Bath-Kitchenette l *Near LAKE*
A truly intimate and comfortable internet spot perfect for a vacation

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 had an excellent stay at Virginia’s place! Four of us came to Toronto for a concert at the Rodger’s Centre which was just across the street. The unit was quite a bit bigger than I expected! There was plenty of room for all four of us, we never felt crowded. We were able to walk to a huge variety of restaurants and activities. Virginia was beyond kind and welcoming. Super quick to respond and easy to communicate with! I would highly recommend staying with Virginia to anyone coming to Toronto!

Sunny Pines Farm Studio Tennis Court/Bruce Trail
What a gorgeous place to get away from the city for a few days. The comfortable studio has everything you'd need during your stay. The fields are great for walking (especially if you have a dog), and there are all kinds of magnificent hiking trails nearby. My arrival coincided with a massive ice storm and Vince and Miranda were in touch every step of the way, keeping me updated on conditions and options. They were a pleasure to deal with. I look forward to returning next time I need a taste of the country.

2 Bedroom Condo Near Square One with Massage Chair
Very nice stay at Bose and Esther's. Thanks again!
Quick stats about vacation rentals that are family-friendly in Orangeville
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ184 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
- Blue Mountain Village
- Budweiser Stage
- Distillery District
- Port Credit
- Horseshoe Resort
- The Danforth Music Hall
- Metro Toronto Convention Centre
- Exhibition Place
- Toronto Zoo
- CF Toronto Eaton Centre
- TPC Toronto at Osprey Valley
- Massey Hall
- Royal Woodbine Golf Club
- Harbourfront Centre
- Whistle Bear Golf Club
- Snow Valley Ski Resort
- Yonge-Dundas Square
- Trinity Bellwoods Park
- Osler Bluff Ski Club
- Casa Loma