
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.

LUXURY CONDO, GREAT DECOR, WHEELCHAIR FRIENDLY!!!
NEW GORGEOUS LUXURY CONDO WHEELCHAIR ACCESIBLE. *** NEW BED in 2nd!*** PRIME BEDROOM has a queen size memory foam mattress & a desk. SECOND BEDROOM has a brand new bed with double mattress medium/firm and a working desk, now accessible to guests. 2 FULL BATHROOMS: The en-suite has has a step up shower and a Bidet. SECOND: Has a tub & shower, very spacious. *OPEN CONCEPT LIV. AREA. *OPEN BALCONY. TASTEFULLY FURNISHED, SOFT AND CLEAN COLORS HARDWOOD FLOORS THROUGHOUT EXTRA WIDE HALLS AND DOORS

Beautiful family Home near Downtown
A beautiful naturally bright, well-decorated, contemporary & open-concept home conveniently located in a peaceful & posh Oakville area. *Close to major highways QEW/403 & *Oakville GO Station. *A bus stop is right across its driveway. *The Beautiful view of Lake-Ontario, Shorewood-Promenade-Park, approx.1km; *Famous Kerr-Village, approx.1km & *Historic Downtown-Oakville, approx.2km are just at a walking distance. With multiple landmarks, upscale retail, exceptional dining, bars, cafes & etc.

Winter Escape Tropical Dome! Animal Lovers Dream
Jungle Dome Farm Stay in Burlington! Be completely immersed in farm life and all that it entails while staying in our 500 square foot geodesic dome “glamping” greenhouse dwelling! Complete with a fish and turtle pond and filled to the brim with tropical plants! Designed as a tropical vacation getaway when you can’t get away to the tropics! Situated on a 5 acre animal farm where guests can experience farm life with goats, horses, highland cows, sheep, pigs and poultry. An Animal Lovers Dream!

Condo Style Basement in Oakville (Walk Up)
Looking for a cozy and comfortable place to stay during your next vacation or business trip? This spacious and stylish Airbnb accommodates up to 6 guests! Our beautiful space features everything you need to feel right at home! This condo style basement apartment is located in Oakville, one of Ontario’s most desirable neighbourhoods. 2 bedrooms with walk in closets 2 full bathrooms Sofa-come bed Contemporary chef kitchen (including utensils ) TV with Disney Plus and Netflix Dryer and washers

Sun-kissed 3BR family home in a quiet neighborhood
♡ The fastest internet w/ 1Gb download speed ♡ Fully Equipped Kitchen ♡ minutes drive to Sheridan college, Walmart, Oakville Place, lakeshore ♡ 7 min. drive to Trafalgar GO Station, 20 min. to Toronto premium outlets 25 min. to Pearson airport 30 min. to Toronto downtown ♡ Walking distance to convenient store, trails, food, bus stop, library. ♡ Free Parking ( 2 Spots) ♡ Automated Check in & Check Out ♡ Flexible Check in Check out - Message for Details ♡ A/C ♡ Laundry ❤ Book today!

Bright, Spacious, Quiet 2 bedroom - Licensed
Quiet family neighborhood great for professionals, couples or family. Spacious and cozy home away from home. You control heat and cooling fan. Sound dampening so natural noises are minimized, not eliminated. 1 queen and 1 double bed. Two desks for computer work. Extra seating. Fast WiFi! Full kitchen. Bathroom with shower and bathtub. Close to highways, hospital, recreation centers, playgrounds, shopping, schools and college. All registered guests may be asked to provide ID upon request.

3Bd 2.5Bth House w/ Pool Table, Swing, Outdoor BBQ
Bring your friends and family to this family-friendly, centrally-located neighbourhood with lots of room for fun and find a home away from home during the travelling. Enjoy your stay in this licensed short-term accommodation for a modern, luxurious, and spacious three-bedroom and two-bathroom detached home with a huge backyard: watching a movie and cozying up by the fire, enjoying the company of friends and family seated around the dining table, or simply in between moving or renovations.

Modern Executive Townhome w/ Rooftop Hot Tub Oasis
Stylish contemporary townhome in Oakville! The perfect retreat for couples, families, and friends alike. Experience the rooftop terrace, complete with a Private Jacuzzi Hot Tub that provides the ultimate relaxation experience! It's the perfect spot to unwind after a long day of sightseeing or to enjoy an evening under the stars. You'll love the stunning and spacious living areas, fully equipped kitchen, and two comfortable bedrooms. Close to Three Major Highways in a Central Location!

Large Luxury Villa with Swim Spa! Near downtown!
Forget your worries in this spacious, serene and unique house! Large backyard with a Swim Spa to enjoy! Backyard filled with fire places! 6 Bedroom, 7 beds, 4 full baths, 4 offices, 3 family rooms, 9 TV, equipped kitchen, patio, board games, BBQ grill, fire place, Tesla charger. Quiet yet central from downtown Oakville, highways, groceries, shopping, bars, restaurants, cafe's and much more! Always professionally cleaned. For elderly guests a bedroom and full bath is on ground floor.

Cozy Basement Apartment in Oakville
Welcome to Your Cozy Oakville Basement Apartment! Newly built, this 2 bedroom apartment holds a open-concept living room that flows into the fully-equipped kitchen, offering a cozy space to relax along with backyard area. Guests have private access through a separate entrance and independent working area. Pond facing, located in a quite neighborhood in close proximity to restaurants and grocery stores. 10-15 mins from Oakville GO Station. 25-30 mins from YYZ Airport .

Cottage On Lake Ontario Niagara
OPEN TIMESLOTS APRIL 13-16 APRIL 23-25 (2 nights/3 days) Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include: beautiful lake views & orchards.

Waterfront Hillside Villa
Welcome to your stunning Hillside Villa situated on 150' of waterfront. Enjoy the peaceful surroundings and quiet Bay views from your 3 private outdoor decks & hot tub. Entertaining is easy in this gourmet kitchen, which is open to 1 of 2 fireplaces, family room & dining room with floor to ceiling views of the Bay. Breathe taking views of the Bay from your private dock. Hidden gems: gym, 2nd kitchen, foosball table, EV charging and private trail.
Popular amenities for Oakville family-friendly rentals
Family-friendly home rentals with a hot tub

hidden gem retreat-HotTub, Igloo & movie room

Contemporary Vineyard Barn on the Water + Hot tub

Timber Haven

Wake Up To Lake Views!

Luxury 4BR Oasis: Year Round Heated Pool & Hot Tub

Country Getaway in Puslinch

Lakefront Farm | Hot Tub | Fire Pit | Beach Access

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1
Family- and pet-friendly home rentals

Little Blue Barn on the Bench

Spacious 3-Bedroom Apartment|Perfect for Families

Langford House

Luxury & Modern 2 Bedroom w/Parking

California Chic +Breathe +Unwind +Restore

Somerset Cottage at West Avenue Cider House

Lovely Private Basement

Farmview Sunset Cabin
Family-friendly home rentals with a pool

Alpaca farm stay and bunkie getaway.

Headwaters Hot Tub & Fireplace-Cozy Spring Retreat

Ravine Paradise ! heated pool and hot tub!

Luxury Stay w/phenomenal view!

The Captain's Cottage at Willow Pond

Modern 1 Bed Condo Mississauga

The Fox's Retreat - A Cozy Cabin for Two

Modern Custom Built Walkout to Marble Pool Game RM
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $182 AUD | $173 AUD | $178 AUD | $188 AUD | $200 AUD | $213 AUD | $231 AUD | $240 AUD | $207 AUD | $191 AUD | $184 AUD | $198 AUD |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
Quick stats about holiday rentals that are family-friendly in Oakville

Total holiday rentals
Explore 450 holiday rentals in Oakville

Nightly prices starting at
Oakville holiday rentals start at $29 AUD per night before taxes and fees

Verified guest reviews
Over 8,950 verified reviews to help you choose

Pet-friendly accommodation
Find 160 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
310 properties have a dedicated workspace

Wi-Fi availability
440 of Oakville holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Oakville rentals

4.8 Average rating
Oakville stays are highly rated by guests—averaging 4.8 out of 5!
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- Rentals with a patio Oakville
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- Cottage rentals Oakville
- House rentals Oakville
- Waterfront rentals Oakville
- Rentals with outdoor seating Oakville
- Rentals with a fire pit Oakville
- Rentals with a hot tub Oakville
- Rentals with a fireplace Oakville
- Rentals with lake access Oakville
- Private suite rentals Oakville
- Rentals with pools Oakville
- Rentals with a washing machine and dryer Oakville
- Condo rentals Oakville
- Pet-friendly rentals Oakville
- Rentals with breakfast Oakville
- Rentals with an EV charger Oakville
- Family-friendly rentals Halton
- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Enercare Centre
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Distillery District
- Harbourfront Centre
- Nike Square One Shopping Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Niagara Falls State Park
- Financial District
- Massey Hall
- Wilfrid Laurier University
- Casa Loma
- Downsview Park
- Dufferin Grove Park
- Casino Niagara




