Kid-friendly holiday rentals in Caledon

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Caledon family-friendly rentals

Kid-friendly house rentals

Top guest favourite
Home in Brampton
5 out of 5 average rating, 13 reviews

Elegant & Spacious 1 Bd1Bth Private Apmt by Forest

BladimirRating, 5 stars4 days ago
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.
Guest favourite
Home in Brampton
4.9 out of 5 average rating, 186 reviews

Private Basement Apt, Separate Entry, Free Parking

PrithuRating, 5 stars2 weeks ago
Thanks for pleasant stay
Guest favourite
Home in Orangeville
4.89 out of 5 average rating, 83 reviews

Stylish 3 Bedroom Getaway in Orangeville

SharonRating, 5 stars2 weeks ago
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!
Superhost
Home in Caledon Village
4.89 out of 5 average rating, 18 reviews

Charming and Peaceful Retreat with Hot Tub

AimeeRating, 5 stars2 weeks ago
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.
Top guest favourite
Home in Caledon
5 out of 5 average rating, 7 reviews

Opulent 4BR Home with Modern Charm

KwameRating, 5 stars1 month ago
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!!
Superhost
Home in Caledon
4.86 out of 5 average rating, 21 reviews

Live Lavishly: Modern Studio, 5G, Parking

AmandeepRating, 5 stars1 week ago
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.
Top guest favourite
Home in Halton Hills
4.96 out of 5 average rating, 91 reviews

Small Town Escape

KathyRating, 5 stars4 weeks ago
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♥️
Superhost
Home in Caledon Village
4.65 out of 5 average rating, 26 reviews

Stunning Luxury Estate - Your Memorable Retreat

KiranjitRating, 5 stars8 months ago
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

Top guest favourite
Flat in Horning's Mills
4.95 out of 5 average rating, 288 reviews

Beautiful Riverside Country Apartment

MelissaRating, 5 stars1 month ago
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!
Guest favourite
Flat in Halton Hills
4.91 out of 5 average rating, 159 reviews

The Johnnie Walker Suite.

AdamRating, 5 stars2 weeks ago
Nice place for easy access to old Georgetown area. Perfect spot for a single or a couple to stay.
Guest favourite
Flat in Caledon
4.82 out of 5 average rating, 202 reviews

Basement for Rent Bolton South Hill

ShannonRating, 5 stars1 month ago
Exactly as pictured and described. Very convenient location and responsive hosts
Superhost
Flat in Brampton
4.82 out of 5 average rating, 223 reviews

Private Basement Apartment , Private entrance

TanviRating, 5 stars6 days ago
Absolutely loved our stay! The place was spotless, and exactly as described. The host was friendly and responsive—would definitely book again!
Guest favourite
Flat in Brampton
4.93 out of 5 average rating, 134 reviews

1 Bedroom apartment Brampton

Yann JordanRating, 5 stars2 weeks ago
It was a pleasure to meet Marie. She vas very kind and welcoming. The place is really neat would highly recommend it
Guest favourite
Flat in Brampton
4.96 out of 5 average rating, 106 reviews

Brand New Basement Apartment in Brampton

MicheleRating, 5 stars1 day ago
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
Top guest favourite
Flat in Ariss
4.96 out of 5 average rating, 162 reviews

Rural Retreat, near to Elora

TannisRating, 5 stars1 week ago
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!
Guest favourite
Flat in Oak Ridges
4.88 out of 5 average rating, 123 reviews

Large Walk-out private apartment w/ parking

ErikRating, 5 stars1 week ago
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

Superhost
Apartment in Innisfil
4.83 out of 5 average rating, 480 reviews

Lovely 2-bedroom at Friday Harbour

AlyssaRating, 5 stars1 week ago
Lovely stay as described! Would recommend
Guest favourite
Apartment in Fergus
4.94 out of 5 average rating, 305 reviews

Cozy StoneMill Retreat - Summer Getaway!

DorothyRating, 5 stars1 week ago
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.
Superhost
Apartment in Brampton
4.85 out of 5 average rating, 48 reviews

Modern & Luxury 1+Den Condo w/Parking

JorgeRating, 5 stars1 month ago
ver nice space. and very easy self check in
Guest favourite
Apartment in Brampton
4.95 out of 5 average rating, 22 reviews

Super Luxury Condominium in Brampton

UmerahRating, 5 stars1 day ago
It was quiet and peaceful building. Enjoyed the time stayed here
Guest favourite
Apartment in Mississauga
4.88 out of 5 average rating, 173 reviews

Beautiful Penthouse with Breathtaking View

SargonRating, 5 stars6 days ago
Great place and the host was always quick to answer and very helpful!
Guest favourite
Apartment in Brampton
4.89 out of 5 average rating, 183 reviews

Cozy Condo-Apartment/Suite in Brampton

DanielleRating, 5 stars1 month ago
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
Superhost
Apartment in Brampton
4.9 out of 5 average rating, 39 reviews

1-New Build Independent 2 Bed 2 floors Townhouse

AshantiRating, 5 stars1 month ago
Loved it would definitely book again!
Superhost
Apartment in Mississauga
4.87 out of 5 average rating, 216 reviews

🔥Charming 1 BR Condo🔥 Steps To Square One!👌

BlavenRating, 5 stars2 weeks ago
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

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