Family-friendly holiday rentals in Oakville
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Oakville
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 Oakville family-friendly rentals
Family-friendly home rentals with a hot tub
Cottage in Lincoln
4.95 out of 5 average rating, 207 reviewsFox'sDen/Cozy/Romantic/Cottage/WineCountryNiagara
14–21 Apr
Home in Lincoln
4.92 out of 5 average rating, 258 reviewsAmazing LakeHouse with Great Amenities
12–19 Jan
Apartment in Toronto
4.81 out of 5 average rating, 302 reviewsSpacious Downtown (midtown) 2bed 2 bath free parki
6–13 May
Flat in Toronto
4.91 out of 5 average rating, 257 reviewsHoney House in the Beach
2–9 Jan
Apartment in Toronto
4.84 out of 5 average rating, 121 reviewsModern 1 Bdrm Suite Downtown District - Lake View
11–18 May
Apartment in Toronto
4.93 out of 5 average rating, 189 reviewsCollege Park :2Bd+2bth + Free parking
3–10 Nov
Apartment in Toronto
4.89 out of 5 average rating, 273 reviewsCENTRAL DOWNTOWN LUXURY APT STEPS TO CN TOWER/LAKE
29 Sept – 6 Oct
Apartment in Toronto
4.97 out of 5 average rating, 291 reviewsBeautiful Condo + CN Tower View + Free Parking
22–29 Oct
Family- and pet-friendly home rentals
Flat in Milton
4.71 out of 5 average rating, 143 reviewsStudio Apt in Milton Dorset Park
29 Dec – 5 Jan
Guest suite in Hamilton
4.92 out of 5 average rating, 191 reviewsCentrally located - beautiful one bedroom apt.
16–23 Aug
Home in Toronto
4.93 out of 5 average rating, 178 reviewsClassic 1 Bedroom Suite
16–23 Dec
Apartment in Toronto
4.96 out of 5 average rating, 247 reviewsLively 1+1 Lakeview Condo near CN Tower + Free Prk
24–31 Dec
Apartment in Toronto
4.93 out of 5 average rating, 218 reviewsVibrant downtown place
30 Sept – 7 Oct
Apartment in Toronto
4.92 out of 5 average rating, 141 reviewsBeautiful suite in Downtown Toronto
8–13 Aug
Boat in St. Catharines
4.89 out of 5 average rating, 114 reviewsBob's Yer Uncle
8–15 Oct
Home in Richmond Hill
4.87 out of 5 average rating, 127 reviewsLuxury 5 beds, 6 Baths custom home
27 Jan – 3 Feb
Family-friendly home rentals with a pool
Home in Toronto
4.91 out of 5 average rating, 264 reviewsKing West Victorian Studio Gem
16–23 Jul
Apartment in Toronto
4.86 out of 5 average rating, 178 reviewsBest View in Downtown 5 Star Luxury 1+1 w/office
14–19 May
Apartment in Toronto
4.97 out of 5 average rating, 217 reviewsChic, High-Rise Apartment with CN Tower Views
8–15 May
Flat in Toronto
4.79 out of 5 average rating, 141 reviewsStunning Condo @ the Heart of Toronto (w/ Parking)
7–14 May
Townhouse in Toronto
4.74 out of 5 average rating, 152 reviewsKing West Triplex Main FLR PVT APT 1 BDRM Parking
17–24 Oct
Bungalow in Milton
4.89 out of 5 average rating, 27 reviewsMilton Home- a Family Oasis
27 Mar – 3 Apr
Apartment in Richmond Hill
4.76 out of 5 average rating, 41 reviewsStunning Appt. in Richmond Hill- Parking included!
18–25 Jun
Home in Grimsby
4.95 out of 5 average rating, 22 reviewsNiagara Wine Country Retreat - Sauna/spa/salt pool
29 Jan – 5 Feb
Quick stats about holiday rentals that are family-friendly in Oakville
Total rentals
410 properties
Rentals with dedicated workspaces
280 properties have a dedicated workspace
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
100 properties allow pets
Total number of reviews
5.5K reviews
Nightly prices starting at
£8 before taxes and fees
Destinations to explore
- Niagara Falls Holiday rentals
- Brampton Holiday rentals
- Niagara-on-the-Lake Holiday rentals
- Niagara Falls Holiday rentals
- Kitchener Holiday rentals
- Waterloo Holiday rentals
- Buffalo Holiday rentals
- Barrie Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Deep Creek Lake Holiday rentals
- London Holiday rentals
- Mississauga Holiday rentals
- Family-friendly rentals Toronto
- Family-friendly rentals Canada
- Family-friendly rentals Ontario
- Family-friendly rentals Downtown Toronto
- Family-friendly rentals Mississauga
- Rentals with lake access Oakville
- Townhouse rentals Oakville
- Flat rentals Oakville
- Apartment rentals Oakville
- Rentals with a firepit Oakville
- Rentals with a fireplace Oakville
- Rentals with a hot tub Oakville
- Rentals with beach access Oakville
- Rentals with an EV charger Oakville
- Rentals with a patio Oakville
- Rentals with a washing machine and dryer Oakville
- Monthly Rentals Oakville
- Fitness-friendly rentals Oakville
- Rentals with pools Oakville
- Private suite rentals Oakville
- Waterfront rentals Oakville
- House rentals Oakville
- Rentals with breakfast Oakville
- Rentals with outdoor seating Oakville
- Family-friendly rentals Oakville
- Pet-friendly rentals Oakville
- Family-friendly rentals Regional Municipality of Halton
- Yurt Rentals United States
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