
Family-friendly vacation 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.
Vacation 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

Hollis Haven

Beautiful Penthouse with Breathtaking View

Country Getaway in Puslinch

Luxury Stay w/phenomenal view!

The Barn-Fieldstone Suite

🔥Charming 1 BR Condo🔥 Steps To Square One!👌

Luxury Villa! Swim Spa! 6 Bedroom 3 Family Rooms
Family- and pet-friendly home rentals

THE NEST - Cuddle Up In This Quaint Retreat

Little Blue Barn on the Bench

Centrally located - beautiful one bedroom apt.

Pool is Open! Quiet 2-bdrm apt with cont. bfast

Somerset Cottage at West Avenue Cider House

Harbour front CHA CHA CHA - Lake view house

Adorable 1-Bedroom Basement Apartment in Hamilton

Cozy basement apartment in the heart of Oakville
Family-friendly home rentals with a pool

The Homelands Suite, 2 Bedroom with Pool.

The Penty: Luxurious Penthouse with Pool, Hot Tub

Bright and Airy Guest Suite with Pool

Stylish Basement Hideaway*1 BR Suite*Near Lake

The Captain's Cottage at Willow Pond

Hidden gem in Humber bay shores Toronto w/ parking

Sleeps 12 ADULT private hot tub pool Walk to Lake

The Fox's Retreat - A Cozy Cabin for Two
Quick stats about vacation rentals that are family-friendly in Oakville
Total rentals
470 properties
Nightly prices starting at
G$2,092 GYD 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 Vacation rentals
- Greater Toronto Area Vacation rentals
- Mississauga Vacation rentals
- Mount Pocono Vacation rentals
- Niagara Falls Vacation rentals
- Pittsburgh Vacation rentals
- Grand River Vacation rentals
- St. Catharines Vacation rentals
- Northeast Ohio Vacation rentals
- Detroit Vacation rentals
- Columbus Vacation rentals
- Erie Canal Vacation rentals
- Rentals with outdoor seating Oakville
- Apartment rentals Oakville
- Cottage rentals Oakville
- Waterfront rentals Oakville
- Rentals with a hot tub Oakville
- Pet-friendly rentals Oakville
- Rentals with a fire pit Oakville
- Rentals with a washer and dryer Oakville
- Fitness-friendly rentals Oakville
- Townhouse rentals Oakville
- Condo rentals Oakville
- Rentals with pools Oakville
- House rentals Oakville
- Rentals with an EV charger Oakville
- Rentals with a fireplace Oakville
- Rentals with breakfast Oakville
- Rentals with lake access Oakville
- Rentals with beach access Oakville
- Rentals with a patio Oakville
- Private suite rentals Oakville
- Family-friendly rentals Regional Municipality of Halton
- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Budweiser Stage
- Exhibition Place
- Distillery District
- Sherkston Shores Beach Resort & Campground
- Port Credit
- Metro Toronto Convention Centre
- Clifton Hill
- The Danforth Music Hall
- Toronto Zoo
- Harbourfront Centre
- Financial District
- CF Toronto Eaton Centre
- BMO Field
- Trinity Bellwoods Park
- Niagara Falls State Park
- Massey Hall
- Casa Loma
- Whistle Bear Golf Club
- Dufferin Grove Park
- Legends on the Niagara Golf Course