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

Guest favourite
Home in Toronto
4.96 out of 5 average rating, 49 reviews

Welcoming Basement Studio *Pine Nest Lodge*

SamanthaRating, 5 stars3 weeks ago
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 :)
Guest favourite
Home in Wasaga Beach
4.89 out of 5 average rating, 109 reviews

20 min from Blue Mountain -Relax & Enjoy Winter

TawnyaRating, 5 stars1 month ago
Such a great place to stay after skiing at Blue Mountain! Definitely recommend.
Guest favourite
Home in Richmond Hill
5 out of 5 average rating, 26 reviews

Stunning 3 Bed Richmond Hill Home with Games Room

JesseRating, 5 stars1 week ago
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.
Superhost
Home in North York
5 out of 5 average rating, 3 reviews

Modern Home with Pool & Jacuzzi [no cleaning fee]

Yalealem Rating, 5 stars5 months ago
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!
Superhost
Home in Courtice
4.91 out of 5 average rating, 11 reviews

New Family Friendly Detached Home in Courtice

KlydeRating, 5 stars4 months ago
Very clean and spacious; no complaints!
Top guest favourite
Home in Innisfil
5 out of 5 average rating, 30 reviews

Highland House

Anne MarieRating, 5 stars1 week ago
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.
Superhost
Home in Niagara Falls
4.84 out of 5 average rating, 154 reviews

Home Away from Home

AyaRating, 5 stars7 months ago
Clean house with all necessities included. very responsive host- overall great!
Superhost
Home in Courtice
5 out of 5 average rating, 4 reviews

Family Friendly Home in Courtice

AnthonyRating, 5 stars1 week ago
Overall a very good place. It was located near our destinations during a weekend east of Toronto.

Family-friendly apartment rentals

Guest favourite
Flat in Niagara Falls
4.94 out of 5 average rating, 163 reviews

Niagara Comfort Suites 1BR Apartment 550sqft

VictoriaRating, 5 stars2 days ago
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!
Top guest favourite
Flat in Niagara Falls
4.96 out of 5 average rating, 199 reviews

Location, location, location

WendyRating, 5 stars6 months ago
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.
Guest favourite
Flat in Guelph
4.91 out of 5 average rating, 161 reviews

Spacious apartment steps from University of Guelph

KeishaRating, 5 stars1 week ago
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!
Top guest favourite
Flat in Guelph
4.98 out of 5 average rating, 119 reviews

Spacious 1 bedroom apartment downtown, own entry

AbbyRating, 5 stars2 weeks ago
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!
Top guest favourite
Flat in Lincoln
4.98 out of 5 average rating, 408 reviews

Jordan Wine Country Escape

AngeloRating, 5 stars1 week ago
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!
Guest favourite
Flat in Parkdale
4.95 out of 5 average rating, 131 reviews

Charming Apt w/ Private Deck in a 1890s Victorian

JoanRating, 5 stars2 weeks ago
This space was very cozy with beautiful light and a great location. The host is friendly, communicative, and accommodating. We would stay here again!
Guest favourite
Flat in Waterdown
4.9 out of 5 average rating, 137 reviews

Waterdown Hideaway. Separate 2 bedroom 1 bath Apt.

SimonRating, 5 stars1 month ago
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.
Guest favourite
Flat in Oak Ridges
4.9 out of 5 average rating, 111 reviews

Large Walk-out private apartment w/ parking

JanesseRating, 5 stars1 day ago
A great place at a very reasonable price

Family-friendly apartment rentals

Guest favourite
Apartment in The Blue Mountains
4.98 out of 5 average rating, 151 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

SusanRating, 5 stars1 month ago
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.
Superhost
Apartment in Innisfil
4.87 out of 5 average rating, 222 reviews

2BR Getaway at Friday Harbour All Season Resort

JohnRating, 5 stars3 weeks ago
Brilliant location for the harbour everything in walkable distance, clean and well stocked kitchen . Responsive host would recommend.
Guest favourite
Apartment in The Blue Mountains
4.85 out of 5 average rating, 141 reviews

Large, luxury, upper floor condo, steps to Village

MatthewRating, 5 stars4 months ago
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.
Superhost
Apartment in The Blue Mountains
4.86 out of 5 average rating, 245 reviews

Stylish & Spacious 2 Bdrm/2 bths/2 balc Condo Loft

JillRating, 5 stars1 week ago
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!
Top guest favourite
Apartment in Innisfil
4.97 out of 5 average rating, 164 reviews

Stylish getaway condo, resort living

DanielleRating, 5 stars2 months ago
very clean place, has everything you need for a great getaway. Ron is an amazing, always available host!
Guest favourite
Apartment in Innisfil
4.89 out of 5 average rating, 139 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

DaveRating, 5 stars7 months ago
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!
Superhost
Apartment in Innisfil
4.91 out of 5 average rating, 139 reviews

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

LoriRating, 5 stars2 months ago
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).
Guest favourite
Apartment in Blue Mountains
4.92 out of 5 average rating, 340 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

JamesRating, 5 stars1 week ago
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

Destinations to explore