
Kid-friendly holiday rentals in Caledon
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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

Welcoming Basement Studio *Pine Nest Lodge*
Ivana's place was perfect! Very cozy and had all the essentials, with some lovely thoughtful touches thrown in. Communication and check-in was a breeze, you can tell Ivana cares about her guests and making it a good experience. She was kind and let me take the lead on whether I preferred contact or no contact during my stay. I'd definitely recommend staying at the pine nest :)

20 min from Blue Mountain -Relax & Enjoy Winter
Such a great place to stay after skiing at Blue Mountain! Definitely recommend.

Stunning 3 Bed Richmond Hill Home with Games Room
Amin and his team have a great setup, nice and clean home with everything you would need. They are professional and will respect your privacy. Although I didn’t use it, the deck and yard are nice to have and easily accessible. Parking is easy, check in and check out went smooth, I would stay here again.

Modern Home with Pool & Jacuzzi [no cleaning fee]
We had a wonderful stay at Angie's house. The place is amazing—clean, bright, and welcoming. The host is incredibly sociable, friendly, positive, helpful, and proactive. Overall, we had a fantastic time, and I just want to say thank you!

New Family Friendly Detached Home in Courtice
Very clean and spacious; no complaints!

Highland House
Jason’s Highland House was the perfect home for a family weekend! It was very comfortable with lots of space and special little touches like coffee and condiments. The home is brand new with high end finishes. Jason was extremely responsive and did everything to make the family stay pleasurable.

Home Away from Home
Clean house with all necessities included. very responsive host- overall great!

Family Friendly Home in Courtice
Overall a very good place. It was located near our destinations during a weekend east of Toronto.
Family-friendly apartment rentals

Niagara Comfort Suites 1BR Apartment 550sqft
Definitely a lovely place! Tried to extend my stay lol I loved it and will be back. He’s a great host and amazing home!

Location, location, location
Wonderful hosts and excellent location. I highly recommend this apartment to anyone who wants to visit Niagara Falls you will not be disappointed. We also ate at a great place for breakfast Basell’s Restaurant that was really close to the apartment.

Spacious apartment steps from University of Guelph
My stay at Svetlana and Vitaliy's cozy home was great! They were friendly, very quick to respond to my messages, and even shared their delicious baking with me. If I'm ever in Guelph again, I will definitely stay here again. Thank you, both, for a great stay!

Spacious 1 bedroom apartment downtown, own entry
Mary was a wonderful host and it was the nicest air bnb I’ve stayed in to date! We brought our 6 month old along, and Mary had lots of baby stuff for us to use. We forgot some stuff at her place and she was kind enough to mail it to us. Amazing host!

Jordan Wine Country Escape
Suzanne's place was peaceful and cozy, and the perfect location to enjoy the Niagara region. We appreciated how flexible she was with check in and how thoughtful she was with all the little treats. Would definitely stay here again!

Charming Apt w/ Private Deck in a 1890s Victorian
This space was very cozy with beautiful light and a great location. The host is friendly, communicative, and accommodating. We would stay here again!

Waterdown Hideaway. Separate 2 bedroom 1 bath Apt.
Hetty was an excellent host. They had specific directions with checkin and check out very easy and not overly complicated. We needed a place on short notice and Hetty confirmed the reservation almost immediately. Overall excellent experience.

Large Walk-out private apartment w/ parking
A great place at a very reasonable price
Family-friendly apartment rentals

Lovely 3 Bedroom Condo with Stunning View and Pool
We have a wonderful time at Sabine's place, which was an ideal space in every way. It was beautiful, well laid out, and had everything we needed. Sabine was very responsive and accommodating. We would gladly go back when we are next at Blue Mountain.

2BR Getaway at Friday Harbour All Season Resort
Brilliant location for the harbour everything in walkable distance, clean and well stocked kitchen . Responsive host would recommend.

Large, luxury, upper floor condo, steps to Village
Excellent place by a fantastic host. The place was clean, well located and has everything you would need such as kitchen utensils, games + TV, and plenty of clean quality towels. Ulana and Amir were also very friendly and responsive. We enjoyed our stay a lot.

Stylish & Spacious 2 Bdrm/2 bths/2 balc Condo Loft
Rosa’s was exactly as advertised. It was lovely and quiet and perfect for our trip to collingwood with our dog. We would definitely stay again!

Stylish getaway condo, resort living
very clean place, has everything you need for a great getaway. Ron is an amazing, always available host!

Friday Harbor Upscale 1Bed+Sofabed+Pool Option
Kevin was a responsive and friendly host, and his place is clean and comfortable and very close to Friday Harbour. We loved the balcony for breakfast and coffee, and the condo itself was full of friendly folks. We can't wait to go back sometime!

Beautiful Condo, 2 Bedrooms and a Den in a Resort!
Shahed's place at Friday Harbour is beautiful and well appointed. He gave very clear instructions for entry and parking, including photos. The condo was clean and had all the amenities needed, even extra charging cables for devices! The space was comfortable and uncluttered. Shahed was great at communicating and always responded quickly to any questions. Friday Harbour has activities and restaurants available on weekends in the winter and is a fun engaging place by the harbour in the spring, summer and early fall. We were there in the early part of the week in February so the harbourfront was quiet but still nice for a stroll. We spent time in both Barrie (20 minutes away) and Orillia (about 50 minutes away).

2 Bedroom, 2 Level Condo on Blue Mountain!
It was the best location in the village, and it was quiet and the sound of the stream was friendly. If you are skiing during the ski season, it would be very convenient because the bottom of the slope and the entrance to the building are in contact. The interior was clean and well-organized. Thanks, Richard.
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
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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