Family-friendly vacation rentals in Caledon

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Caledon

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Leslieville

4.92 out of 5 average rating, 489 reviews

Newly renovated-1 bdrm suite in cute Leslieville

Hotel style lower level unit with separate entrance and parking in the heart of Leslieville. NY times travel calls Leslieville Toronto's hippest place to dine, drink, shop and live. Short transit to the Beaches and both Distillery & Financial dist. Close to a bunch of cool music venues We have a sweet golden retriever named Coco. She loves people and attention so if you happen to run into her in the yard while coming or going from the unit don’t be afraid but she will definitely want to say hi

Superhost

Condo in Mississauga

4.85 out of 5 average rating, 199 reviews

Mississauga - Clean & bright. Close to airport

Clean and modern apartment with two washrooms and two bedrooms with laundry facilities. Full kitchen, television, internet, colour copier/scanner/printer for your use. 15 minutes from Pearson Airport (YYZ) Next to city bus stops and close to major highways for airport, Niagara Falls, and downtown Toronto. One parking spot is included for free. If you need to plug in your electric vehicle with a level one charger, the cost is $10 CAD/day. 2nd parking spot is also available for for $20 CAD/day.

Guest favorite

Home in Toronto

4.9 out of 5 average rating, 129 reviews

Charming Century Home Close to Vibrant Shops

A great for-families home. Stay close to city centre yet unwind in our quiet hood. The inviting space is steps from landmark city parks and the vibrant Junction- one of the most eclectic districts in North America. We just call it home. Hang-out in the airy living room, this spacious gem has comfy seating for all, convenient amenities and period details. Cook meals in the renovated chef kitchen and enjoy dining - both indoors and out. We provide yummies for self-serve breakfast, mostly organic.

Guest favorite

Guesthouse in Mansfield

4.99 out of 5 average rating, 103 reviews

Brookside Cottage - Charming Rural Getaway Mulmur

Our cozy guest house, situated in the Headwaters region, has it all! Close to hiking,golfing,biking,skiing. XCski/snowshoe from your door! Big skies for astronomers and astrophotography! We offer 32 acres of forest and fields for walking and taking in the magnificent views. The area boasts fine restaurants, boutiques, markets and artisans. Minutes to Mono Cliffs, Boyne, Mansfield Ski Club and easy driving to Blue Mountain and Wasaga Beach. Ideal for couples, solo adventurers or a small family.

Guest favorite

Rental unit in Horning's Mills

4.96 out of 5 average rating, 272 reviews

Beautiful Riverside Country Apartment

Bright, warm and newly renovated, this 900sqft apartment, a private floor of a charming country home with separate entrance and garden patio, awaits you in Melancthon. SmartHDTV, Wifi, tranquil surroundings, and next to the Bruce Trail. Close to Shelburne, Mansfield, Creemore, and many excellent restaurants (like The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, and Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

Guest favorite

Guest suite in The Beaches

4.95 out of 5 average rating, 102 reviews

Basement Apartment in Beaches near Lake Ontario

Free driveway parking. Self contained basement apartment with own keypad entry. Queen bed, small work table, full kitchen, bathroom. TV with full 178 channels including sports, WiFi. Own private entrance. Local area has shops, pubs, restaurants, Sunday market (in summer), easy walking to sandy Blue Flag beach. 501 Queen streetcar to from downtown. Closest Airbnb to Live Nation's HISTORY music venue. Electric vehicle Level 1 charging. Gift card for Simple Coffee (friendly local coffee shop).

Guest favorite

Guest suite in Toronto

4.92 out of 5 average rating, 106 reviews

West End basement suite temp closed for renovation

My private basement suite in Toronto's tree-lined West End is perfect for solo or coupled travellers who plan to spend most time out sight-seeing or at work. It has been refreshed for re-opening in March 2024 with new carpet and a high-end luxury queen size sleeper sofa. There is a kitchenette to make coffee/toast with a small fridge for snacks. 3 min from subway. Ceiling 5'11. My twin daughters (12yrs) & I live upstairs. We do our best to be quiet as we get ready for school/work on weekdays.

Guest favorite

Rental unit in Elora

4.91 out of 5 average rating, 182 reviews

Millers Mistress - Millview, 1 bedroom +, apt

Visit downtown Elora, in one of the oldest houses in town, private apartment. Perfect for weddings at the Mill, as we are next door to Mill's event venue; The Granary. Just a 2 min walk to Elora's boutiques, shops & restaurants ... leave the car, so no parking hassles View the beautiful Grand & Irvine river gorge, just a block up the street & left, via side entrance of Victoria Park. Let us provide you with a great home base, to enjoy all the events and activities in Elora & Fergus

Guest favorite

Bungalow in Innisfil

4.82 out of 5 average rating, 278 reviews

Lake Simcoe-3bdr,hot tub,sauna,swim,play,hike

NEW!!: seasonal or monthly rental available, contact me directly to get the exact pricing, thank you Our cottage is about a 800 m from the beach at family friendly Innisfil Beach Park! The kitchen is modern and bright with lots of room for lounging inside the cottage or entertaining outside in the large yard with a fire pit. Our cottage is ideal for couples and families. It is beautifully furnished. There is a BBQ, patio furniture & firepit, smart TV with Roku and Chromecast.

Guest favorite

Cottage in Flesherton

4.94 out of 5 average rating, 136 reviews

All-Season Cottage on the Lake

An entire cottage all to yourself right on the water of Lake Eugenia in the Grey Highlands. This fully furnished 3-bedroom cottage is equipped with a brand-new kitchen, appliances, wood burning stove, furnace and water heater. You'll also have FREE access to unlimited WiFi, so you can work or stay in touch, when needed. Our cottage is suitable for a great get-away with any group, family or friends who are looking for a peaceful and enjoyable holiday from their busy lives.

Superhost

Home in Hamilton

4.83 out of 5 average rating, 198 reviews

~HGTV RENO- King Bed Spacious Studio Suite~

As seen on HGTV's Buyers Bootcamp with Scott McGillivray! Happy to provide a self contained comfortable basement unit in desirable location. One bedroom private lower unit with new kitchen, bathroom, dining area, living space and laundry. Close to all amenities, downtown and public transit on a quiet street! Set scouting available! New to Airbnb? We can help! Receive $47 off your first stay when you register: https://www.airbnb.ca/c/vanessar223?currency=USD

Guest favorite

Farm stay in Fergus

4.95 out of 5 average rating, 247 reviews

Waterpark Acres

Waterpark Acres offers a unique country experience to relax with spectacular views from the balcony. You have complete privacy in this separate building. No other rooms are rented out while you are here. See farm animals ( horses, llama's, dogs, sheep, pheasants and other birds. Also some out of the ordinary animals including kangaroos, lemurs, kinkajou's, parrots etc. ) Please note : WEDDING EVENTS are not hosted on this property