
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

Oasis By The Water, Breathtaking Sunsets and Views

Inn The Orchard, Modern Cottage, private Hot Tub

Timber Haven

Waterfront Hillside Villa

Spacious Suite w/ HOT TUB & high-speed wifi

Heated Pool-tub Open 365 Days

Hager House: Charming retreat downtown Burlington

The Barn-Fieldstone Suite
Family- and pet-friendly home rentals

Horse Ranch with Hot tub

Beautiful Renovated Beach Cottage Home

The Best of Downtown Burlington - Safe & Clean

Private Room. Milton New Modern Basement Room

Lake Front Heaven - Gateway to Niagara/Vineyards

Cozy basement apartment in the heart of Oakville

Cottage On Lake Ontario Niagara

Spacious 2 bedroom walkout basement suite
Family-friendly home rentals with a pool

Stunning Waterfront Estate with private beach

Hollis Haven

HotTub & Pool Getaway - Headwaters Retreat

The Homelands Suite, 2 Bedroom with Pool.

The Penty: Luxurious Penthouse with Pool, Hot Tub

Tiny House with Nature Views and Swimming Pond

Luxury Stay w/phenomenal view!

The Captain's Cottage at Willow Pond
Quick stats about holiday rentals that are family-friendly in Oakville
Total rentals
470 properties
Nightly prices starting at
$15 AUD before taxes and fees
Total number of reviews
7.6K reviews
Pet-friendly rentals
150 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
330 properties have a dedicated workspace
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Mount Pocono Holiday rentals
- Niagara Falls Holiday rentals
- Grand River Holiday rentals
- St. Catharines Holiday rentals
- Pittsburgh Holiday rentals
- Northeast Ohio Holiday rentals
- Erie Canal Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- House rentals Oakville
- Rentals with outdoor seating Oakville
- Rentals with an EV charger Oakville
- Rentals with a fireplace Oakville
- Rentals with a patio Oakville
- Rentals with a hot tub Oakville
- Fitness-friendly rentals Oakville
- Townhouse rentals Oakville
- Private suite rentals Oakville
- Condo rentals Oakville
- Rentals with beach access Oakville
- Rentals with breakfast Oakville
- Rentals with a fire pit Oakville
- Pet-friendly rentals Oakville
- Rentals with a washing machine and dryer Oakville
- Waterfront rentals Oakville
- Rentals with lake access Oakville
- Apartment rentals Oakville
- Cottage rentals Oakville
- Rentals with pools Oakville
- Family-friendly rentals Regional Municipality of Halton
- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Budweiser Stage
- Distillery District
- Sherkston Shores Beach Resort & Campground
- Port Credit
- Metro Toronto Convention Centre
- Clifton Hill
- Financial District
- Exhibition Place
- The Danforth Music Hall
- Toronto Zoo
- Harbourfront Centre
- CF Toronto Eaton Centre
- Trinity Bellwoods Park
- Massey Hall
- BMO Field
- Niagara Falls State Park
- Whistle Bear Golf Club
- Casa Loma
- Legends on the Niagara Golf Course
- Dufferin Grove Park