Family-friendly holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Caledon family-friendly rentals
Family-friendly home rentals with a hot tub
Farm stay in Fergus
4.95 out of 5 average rating, 216 reviewsWaterpark Acres
4–11 Sep
Guest house in Saint Catharines
4.98 out of 5 average rating, 377 reviewsPrivate Estate Coachhouse + Hot Tub near NOTL!
4–11 Jan
Cottage in Lincoln
4.95 out of 5 average rating, 207 reviewsFox'sDen/Cozy/Romantic/Cottage/WineCountryNiagara
28 Nov – 5 Dec
Bungalow in Innisfil
4.82 out of 5 average rating, 272 reviewsLake Simcoe-3bdr,hot tub,sauna,swim,play,hike
22–29 Jan
Flat in Niagara Falls
4.87 out of 5 average rating, 431 reviewsNiagara Hilltop
11–18 Jun
Cottage in Kimberley
4.87 out of 5 average rating, 307 reviewsA Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi
1–8 Aug
Home in Kimberley
4.88 out of 5 average rating, 176 reviewsHeart of Kimberley - with views and a hot tub
13–20 May
Flat in Toronto
4.91 out of 5 average rating, 258 reviewsHoney House in the Beach
26 Dec – 2 Jan
Family- and pet-friendly home rentals
Barn in Eugenia
4.98 out of 5 average rating, 165 reviewsBlue Barn Bed n Bale / Blue Mountain
26 Dec – 2 Jan
Loft in Hamilton
4.91 out of 5 average rating, 429 reviewsA Cozy Loft in the Heart of Hamilton
24–31 Dec
Guest suite in King City
4.98 out of 5 average rating, 177 reviewsSpacious guest apartment on beautiful greenspace
28 Feb – 7 Mar
Flat in Milton
4.71 out of 5 average rating, 143 reviewsStudio Apt in Milton Dorset Park
26 Apr – 3 May
Bungalow in Elora
4.98 out of 5 average rating, 228 reviewsStudio Downtown Elora
11–18 Oct
Guest suite in Hamilton
4.92 out of 5 average rating, 191 reviewsCentrally located - beautiful one bedroom apt.
13–20 Aug
Home in Barrie
4.81 out of 5 average rating, 208 reviewsEntire Private House+Games Room-by Downtown/Skiing
21–28 Feb
Apartment in Innisfil
4.95 out of 5 average rating, 183 reviewsDesigner Condo with beautiful harbour view.
11–18 Sep
Family-friendly home rentals with a pool
Home in Cambridge
4.91 out of 5 average rating, 240 reviewsSpacious Bungalow Guest House
16–23 Dec
Apartment in Innisfil
4.84 out of 5 average rating, 171 reviewsMarina view at Friday Harbor 2bdm/2bth Pool option
9–16 Sep
Guest suite in Grimsby
4.96 out of 5 average rating, 224 reviewsBright, spacious 2 bedroom apartment
4–11 Oct
Guest suite in Mississauga
4.92 out of 5 average rating, 132 reviewsFull apt on Upper floor near HWY - S Mississauga
25 Aug – 1 Sep
Home in Toronto
4.91 out of 5 average rating, 264 reviewsKing West Victorian Studio Gem
9–16 Dec
Guest suite in Oakville
4.85 out of 5 average rating, 176 reviewsLL*1 BR Suite*Wi-fi*Parking*Near Lake
12–19 Aug
Home in Niagara-on-the-Lake
4.77 out of 5 average rating, 211 reviewsWhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool
20–27 Dec
Flat in Toronto
4.79 out of 5 average rating, 141 reviewsStunning Condo @ the Heart of Toronto (w/ Parking)
7–14 May
Quick stats about holiday rentals that are family-friendly in Caledon
Total rentals
570 properties
Rentals with dedicated workspaces
340 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
160 properties allow pets
Total number of reviews
9.8T reviews
Nightly prices starting at
₹834 before taxes and fees
Destinations to explore
- Niagara Falls Holiday rentals
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- Family-friendly rentals Regional Municipality of Peel
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