
Kid-friendly holiday rentals in Caledon
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Caledon
Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Caledon family-friendly rentals
Kid-friendly house rentals

Stylish 3 Bedroom Getaway in Orangeville
I felt very comfortable in Sonia’s home. She gave me great advice on things to do in the area and was quick to respond whenever we had questions. The beds were super comfortable, and everything I needed for my stay was provided. All the info on the listing was accurate, and the photos matched exactly what we saw in person. I would absolutely come back. Thank you, Sonia!

Studio Apartment
great

Live Lavishly: Modern Studio, 5G, Parking
We booked this place for three months as our home was being renovated, it felt just like home!! It was clean, bright and had everything we needed. Shinthu was always responsive when we had any questions or concerns. I would definitely recommend their home for long term or short term stay.

Small Town Escape
Stefanie was very helpful during my stay and made everything very comfortable. her space is beautiful and very welcoming. I will be back and hopefully can book again as it was close to everything I needed and within walking distance which was a bonus.

Stunning Luxury Estate - Your Memorable Retreat
We had a great experience renting this home. We stayed for 2 months. A lot of space for entertaining/ bonding with family. Really enjoyed having 2 separate kitchens. Very spacious house and huge backyard. Everything was perfect.

Central OVille,3 bed Victorian, walk to Lake, pets
We loved staying at George’s place. Easy to find and clean. Host was great. We will be back!

Caledon Place - Summer Booking Up Fast !
The house is lovely and worked perfectly well for our multi generation family stay. Naveed was very easy to work with and was flexible and accommodated our needs. Highly recommend if you’re in the area.

Halton Hills Hideaway_Private Suite
Second time I'm staying here and as the first time, I had a good stay. It's quiet and cozy place. I highly recommend it if you want to stay away from the noisy city.
Family-friendly apartment rentals

Beautiful Riverside Country Apartment
We had a lovely stay at Wendy’s place! Beautiful location right next to a river with a gorgeous back yard. It was a short drive to excellent hiking on the Bruce trail. The apartment had all the amenities we needed (including lots of coffee!), was very clean and super cozy. Wendy was very responsive and helpful. I’d highly recommend if you’re looking for a peaceful and pretty spot for a quiet getaway!

Vintage Dreams | Mid-Century Design in artsy area
We had a wonderful time! Would highly recommend!

Basement for Rent Bolton South Hill
Place was nice! Private entrance and exactly as Frank and Anta described!!

Private Basement Apartment , Private entrance
Very nice and clean. Shower water presser was great. Had little things like coffee and sugar Overall wonderful, would recommend The floors were a bit cold so bring slippers or socks, bath towels were a little small, and double bed was a bit squeaky

Brand New Basement Apartment in Brampton
Francis's place was one of the best air B&B's that we have stayed it. it is located in a beautiful neighborhood that is easy to get to. The space was immaculate, and felt right at home. The beds are comfy, and the space had everything we needed. Francis was easy to communicate with. Would 100% stay here again

Comfort, Style and Privacy.
Such a beautiful and clean place. Very quiet and private. My husband and I loved everything about it. Can’t wait to come back!!

R3 Suites in the Heart of Alton. RearUnit.
I highly recommend this establishment. It is well-equipped to meet various needs. For instance, when I requested an iron, it was promptly delivered to my location. The facility is clean and provides ample supplies for cooking. Additionally, all items were neatly folded, and there is a significant amount of space available.

Separate Basement Apartment
Our stay was very good, very clean and easy drive to the place, parking was also available.
Family-friendly apartment rentals

Spacious 1-br w jacuzzi at Horseshoe Valley
Great place to stay for a week….all the amenities, very quiet and quick access to The 400. Recommended highly

Modern & Luxury 1+Den Condo w/Parking
I would recommend anyone to take this place in case you looking for a very fine place to stay which is very clean / new! Manny has been very clear on all topics so big thumbs up for him! Manpreet from the Netherlands

Super Luxury Condominium in Brampton
Amazing stay, they had everything you could possibly need. Really clean and the host is really responsive and is open to help. Just fyi the address displayed on air bnb is wrong, it is in the same area though.

Beautiful Penthouse with Breathtaking View
Wafa was an incredible host and was always responsive and attentive to any questions we had. The place was just as described, clean, and had a wonderful view. Would definitely book again!

Cozy Condo-Apartment/Suite in Brampton
We must say that David's place was a steal. Yes, it is a studio but the way it's decorated and every detail is so thoughtfully crafted such as the sizing of the couch, to the little extra things that people may forget for toiletries. We were so happy that we picked this spot for overnight stay before some hospital appointments. The bed is so comfortable. It's not a huge space which makes it easier to keep in order with closets big enough that they will hold all your things - just remember to bring extra clothes hangers. The enclosed balcony is a nice touch as well, and it's clear David's cleaner do pay attention to the little details. We hope to be back one day and that we will be welcomed! It's a quiet building with respectful people and is fairly quiet until the GO starts running which is to be expected.

1-New Build Independent 2 Bed 2 floors Townhouse
Loved it would definitely book again!

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍
Great place , easy to find and there are many great things to do in the area , and the view front the condo was just beautiful..

Entire Condo - 20min from Toronto Airport
Yassine and Amela are exceptional hosts. They were very responsive and provided all the check-in information I needed to enter the condo especially since I arrived late at night. The condo is beautifully furnished and very clean. The kitchen has all the amenities needed and is well stocked with tea, coffee, and hot chocolate. It is located in a quiet neighborhood, close to grocery stores, a shopping mall, and great restaurants. It is conveniently located to major highways leading to the airport, Toronto, and Niagara Falls. I had a great stay and look forward to returning. Thank you Yassine and Amela for being such warm and welcoming hosts!
Quick stats about holiday rentals that are kid-friendly in Caledon
Total rentals
200 properties
Total number of reviews
5.7K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
150 properties have a dedicated workspace
Destinations to explore
- Niagara Falls Holiday rentals
- Grand River Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Brampton Holiday rentals
- London Holiday rentals
- Buffalo Holiday rentals
- Niagara-on-the-Lake Holiday rentals
- Pocono Mountains Holiday rentals
- Mississauga Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Rentals with a washing machine and dryer Caledon
- Smoking-friendly rentals Caledon
- Rentals with a firepit Caledon
- Fitness-friendly rentals Caledon
- Bungalow rentals Caledon
- Bed and breakfasts Caledon
- Guest house rentals Caledon
- Family-friendly rentals Caledon
- House rentals Caledon
- Rentals with a patio Caledon
- Rentals with a hot tub Caledon
- Waterfront rentals Caledon
- Private suite rentals Caledon
- Rentals with a fireplace Caledon
- Rentals with lake access Caledon
- Townhouse rentals Caledon
- Apartment rentals Caledon
- Rentals with breakfast Caledon
- Rentals with an EV charger Caledon
- Flat rentals Caledon
- Rentals with pools Caledon
- Rentals with outdoor seating Caledon
- Pet-friendly rentals Caledon
- Family-friendly rentals Regional Municipality of Peel
- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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