
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.
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Popular amenities for Caledon family-friendly rentals
Kid-friendly house rentals

Elegant & Spacious 1 Bd1Bth Private Apmt by Forest
This was my first stay at an Airbnb. I really enjoyed how easy and simple the overall experience was. Everything from the pictures and description was accurate. Everything worked properly and the layout felt very spacious. I really liked how the big windows let in fresh air and a lot of sunlight. The Host was very welcoming and responded quickly to any question I had. Thank you for the pleasant stay here, Mo. I would highly recommend.

Private Basement Apt, Separate Entry, Free Parking
Thanks for pleasant stay

Stylish 3 Bedroom Getaway in Orangeville
I stayed here for one night and truly enjoyed every moment in this townhouse. The space is modern feels bright, spacious, and welcoming. All the rooms had a cheerful, cozy vibe. The bathrooms were large, spotless, and offered an excellent hot shower which was perfect after a long day. The entire home was thoughtfully set up for comfort. The kitchen was one of my favorite parts, it came fully stocked with an ice and water dispenser, a dishwasher, microwave, coffee maker, kettle, tea bags, coffee, and stylish dishware. The location is convenient and close to the grocery stores, restaurants, and scenic walking spots in town. Sonia, the host, was incredibly responsive and made sure every question was answered promptly. I will definitely return with my family this summer to explore more of what Orangeville has to offer, including the local art scene and trails. Overall, it was a 5-star experience. I’d highly recommend this peaceful getaway to anyone looking for comfort and quality!

Charming and Peaceful Retreat with Hot Tub
My family (5 adults, 1 child, 1 infant) came to town for a wedding and were So Lucky to have stayed in this Beautiful home for 5 days last month. The house is spotless, modern, well maintained, and so spacious with plenty of very comfortable, well appointed rooms (4 upstairs, 2 basement) and bathrooms (2 upstairs, 1 basement, 1/2 main floor). The cozy living room is equipped with ample seating and board games. The dining room is large with a great table easily accommodating 10 people. The kitchen is huge and we found all we needed there. There is also a laundry room and mud room leading to the Fabulous hot tub in its own "house" on the outside deck. This Beautiful house is situated on a Gorgeous piece of property with Incredible views all around. The co-host, Brendan, was easy to communicate with and gave us clear instructions. This was the Perfect place for our day-trip into Toronto, "hiking day" in the Island Lake Conservation area, and relax-at-home day, before the wedding.

Opulent 4BR Home with Modern Charm
This house is just awesome! Really enjoyed our stay. Thank you for allowing us to use your space! It nice clean and just simply awesome. Thanks again everyone!!

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's place is always our "go-to" and we are not disappointed. She's an excellent, helpful and ji d host and we consider her place our best investment in a good trip. We know we are home♥️

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.
Family-friendly apartment rentals

Beautiful Riverside Country Apartment
I enjoyed a peaceful 2 weeks at this beautiful Airbnb! The setting is surreal surrounded by nature and a river! I had everything I needed and I enjoyed a few nights with a cozy fire in the wood stove. The bed and couches were very comfortable. The No Frills in Shelburne was a great grocery store nearby. Wendy was always very responsive and helpful. As clearly noted in the description, there is no cell service but not a big deal as there is wifi. I hope to be back again one day! A true gem!

The Johnnie Walker Suite.
Nice place for easy access to old Georgetown area. Perfect spot for a single or a couple to stay.

Basement for Rent Bolton South Hill
Exactly as pictured and described. Very convenient location and responsive hosts

Private Basement Apartment , Private entrance
Absolutely loved our stay! The place was spotless, and exactly as described. The host was friendly and responsive—would definitely book again!

1 Bedroom apartment Brampton
It was a pleasure to meet Marie. She vas very kind and welcoming. The place is really neat would highly recommend it

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

Rural Retreat, near to Elora
Geraldine is an exceptional host and has provides so many additional comforts. The location is gorgeous and a hot tub at the end of the day can't be beat!

Large Walk-out private apartment w/ parking
I had a great experience staying here. Gaby provides clear instructions before arrival for an easy and private check-in. I didn’t need to use many of the amenities during my stay, but it has everything you may need and there is plenty of space. Highly recommend if you need lodging in the northern Toronto suburbs!
Family-friendly apartment rentals

Lovely 2-bedroom at Friday Harbour
Lovely stay as described! Would recommend

Cozy StoneMill Retreat - Summer Getaway!
I went on a short road trip with my girlfriends and was very impressed with Susan’s home! It was a cold, rainy day and her fireplace made the living room warm and cozy. The place was immaculate and had lots of special touches like coffee pods and chocolates. The beds were comfortable and having two full bathrooms was greatly appreciated. Fergus is a lovely little town with lots of restaurants and charming stores within easy walking distance. We would definitely return.

Modern & Luxury 1+Den Condo w/Parking
ver nice space. and very easy self check in

Super Luxury Condominium in Brampton
It was quiet and peaceful building. Enjoyed the time stayed here

Beautiful Penthouse with Breathtaking View
Great place and the host was always quick to answer and very helpful!

Cozy Condo-Apartment/Suite in Brampton
I’ve stayed at David’s place a couple of times now and it always well kept and cozy. He has a really good response time as well. If you are looking for a cozy little studio for your partner and yourself or even just yourself I highly recommend

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

🔥Charming 1 BR Condo🔥 Steps To Square One!👌
Omar was easy to communicate with and the space was beautiful and clean. So close to square one and there's a ton of food places around the area. Highly recommend!
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
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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
- Toronto Zoo
- TPC Toronto at Osprey Valley
- Exhibition Place
- The Danforth Music Hall
- CF Toronto Eaton Centre
- Harbourfront Centre
- Massey Hall
- BMO Field
- Whistle Bear Golf Club
- Trinity Bellwoods Park
- Royal Woodbine Golf Club
- Casa Loma
- Dufferin Grove Park
- Royal Botanical Gardens
- Royal Ontario Museum