
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

hidden gem hot tub and igloo st-catharines

Oasis By The Water, Breathtaking Sunsets and Views

Modern Waterfront Villa | Hot tub, Kayak

Inn The Orchard, Modern Cottage, private Hot Tub

Timber Haven

Waterfront Hillside Villa

Heated Pool-tub Open 365 Days

Hager House: Charming retreat downtown Burlington
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

Farmview Sunset Cabin

Lake Front Heaven - Gateway to Niagara/Vineyards

Cozy basement apartment in the heart of Oakville

The Coastal Cottage
Family-friendly home rentals with a pool

HotTub & Pool Getaway - Headwaters Retreat

The Homelands Suite, 2 Bedroom with Pool.

Tiny House with Nature Views and Swimming Pond

Luxury Stay w/phenomenal view!

Hidden gem in Humber bay shores Toronto w/ parking

The Captain's Cottage at Willow Pond

The Nautical Nook | Luxury Beach House

The Fox's Retreat - A Cozy Cabin for Two
Quick stats about holiday rentals that are family-friendly in Oakville
Total rentals
470 properties
Nightly prices starting at
$13 SGD 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
- Rentals with a fireplace Oakville
- Private suite rentals Oakville
- Rentals with a patio Oakville
- Rentals with pools Oakville
- Rentals with a washing machine and dryer Oakville
- Apartment rentals Oakville
- Rentals with beach access Oakville
- Rentals with a firepit Oakville
- Rentals with breakfast Oakville
- Fitness-friendly rentals Oakville
- Townhouse rentals Oakville
- Rentals with an EV charger Oakville
- Rentals with outdoor seating Oakville
- Rentals with lake access Oakville
- Flat rentals Oakville
- Cottage rentals Oakville
- Waterfront rentals Oakville
- Rentals with a hot tub Oakville
- House rentals Oakville
- Pet-friendly rentals Oakville
- Family-friendly rentals Regional Municipality of Halton
- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- 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














