
Family-friendly vacation rentals in Oakville
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Oakville

Total vacation rentals
Explore 410 vacation rentals in Oakville

Nightly prices starting at
Oakville vacation rentals start at G$4,164 GYD per night before taxes and fees

Verified guest reviews
Over 9,020 verified reviews to help you choose

Pet-friendly vacation rentals
Find 150 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
290 properties have a dedicated workspace

Wi-Fi availability
400 of Oakville vacation 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!
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

New Studio Unit with Full kitchen in Oakville
This is a 500 square feet Studio unit at the ground level of town house with full kitchen, Full Washroom big screen smart TV, internet and one parking. Nothing is shared, separate entrance to the unitKitchen has utensils, kettle and toaster. All the major stores are under 3 kms. The house situated in the border of Oakville and Mississauga. Just 30 minutes to Toronto and 60 minutes to Niagara. Very clean and brand new place for your stay.Enjoy your stay at this place in a relaxing private space.

Jungle Dome on a Farm! 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!

Spacious Basement in Oakville
This spacious suite offers comfort and convenience. Nearby, you'll find Oakville Place Mall, bowling alleys, cinemas, trails, and parks. A train station and local bus services are close for travel. Grocery and convenience stores, plus a variety of restaurants are nearby. Inside, you can enjoy a fully equipped kitchen with stainless steel appliances and a sleek modern bathroom. The cozy living area is perfect for relaxation. Whether you stay for business or leisure, you will enjoy your stay!

Cottage On Lake Ontario Niagara
OPEN TIMESLOTS AUGUST 10-23 AUGUST 25-29 (4 nights/5 days) AUGUST 30-SEPTEMBER 17 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 orchards and the Lake.

“CasaDeLeon”- Modern and cozy Lakeview guesthouse
Forget your worries in this quiet,, spacious & serene space. King+queen air/4 twin , lrg patio doors overlooking lush greenery in private backyard oasis. Enjoy in/outdoor living & access to private basketball court, trampoline. Landscaped backyard w deck, bbq, tons of board games, 4K projector (stream from G00gle chromecast) for large screen media / movies, and wine fridge, espresso bar, fridge w ice maker, full bathroom, heated flooring. IMPORTANT: You MUST read “Other Details To Note”

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!

Luxurious 4 Bedroom home.
Situated in Oakville, Ontario and backing onto natural green space, the interior of this contemporary home is lavished in natural light and enhanced with panoramic views of sunsets. Located between Toronto and Niagara Falls, this home also offers the combination of convenient access to urban amenities and an array of outdoor attractions for sightseeing, exploration and adventure. A perfect retreat for groups and families seeking comfort, relaxation and roomy collaborative spaces.

Summertime! Steam shower+breakfast+rooftop hottub
Nestled in a picturesque escarpment community overlooking the historic town of Dundas, The Hayloft is a charming getaway for anyone looking for an escape and a breath of fresh air. Relax in the steam shower inside or the hot tub on the fully private rooftop deck overlooking gardens. Take a nap on the lounge chairs. Visit with the chickens, make friends with the fish or the frogs. Unwind at night with a movie in bed, with breakfast (surcharge) in the morning.

Cozy Modern Studio in Oakville | Free Parking
Welcome to your perfect retreat - an oasis for 1-2 guests seeking ultimate comfort. Enjoy seamless connectivity with WiFi, Netflix, and a luxurious Queen bed. Experience the essence of home in our inviting, modern basement studio. With a full kitchenette, in-unit laundry, and lots of storage. This modern unit is ideally situated in a serene, safe neighborhood in Oakville, steps from public transit, close to various amenities like restaurants, malls and trails
Popular amenities for Oakville family-friendly rentals
Family-friendly home rentals with a hot tub

Backyard Oasis | Hot Tub & Playground | Near DT

Captivating Waterfront Oasis - HOT TUB & 2King Bed

Wake Up To Lake Views!

Country within the City

Country Getaway in Puslinch

Luxury Stay w/phenomenal view!

The Captain's Cottage at Willow Pond

🔥Charming 1 BR Condo🔥 Steps To Square One!👌
Family- and pet-friendly home rentals

Horse Ranch with Hot tub

Toronto Island Wonderland View

" The Heart of the Village" Main Street, Jordan

Fully-Furnished Boutique 1 Bedroom Suites

Family Home | Uptown Oakville | 40 Mins to Toronto

3Bd 2.5Bth House w/ Pool Table, Swing, Outdoor BBQ

Farmview Sunset Cabin

Spacious 2 BR apartment | Glen Eden Ski
Family-friendly home rentals with a pool

20th Floor Condo w/ Celebration Square Views

Modern Luxury House w/EV Charger & Heated Pool

Luxurious 2 bdr suite near SQ1, UTM, parking/pool

Bright & Spacious 3Br/2Bth Suite Private Entrance

The Snug Oasis - Woodstock (Near Airport)

Bright and Airy Guest Suite with Pool

Condo in Heart of Mississauga

The Fox's Retreat - A Cozy Cabin for Two
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$26,024 GYD | G$27,065 GYD | G$27,898 GYD | G$27,065 GYD | G$28,731 GYD | G$30,604 GYD | G$33,311 GYD | G$34,560 GYD | G$29,771 GYD | G$27,481 GYD | G$26,440 GYD | G$28,522 GYD |
| 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 |
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- Rentals with a hot tub Oakville
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- Rentals with a patio Oakville
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- Rentals with lake access Oakville
- Rentals with pools Oakville
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- Rentals with an EV charger Oakville
- Rentals with breakfast Oakville
- Pet-friendly rentals Oakville
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- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- CN Tower
- Rogers Centre
- Scotiabank Arena
- University of Toronto
- Union Station
- Downsview Park
- Metro Toronto Convention Centre
- Niagara Falls State Park
- Toronto Eaton Centre
- Scarborough Town Center
- Toronto Zoo
- Niagara Falls
- Nike Square One Shopping Centre
- Exhibition Place
- Trinity Bellwoods Park
- Casa Loma
- Elora Gorge
- Massey Hall
- Sheppard–Yonge Station
- York University
- Enercare Centre
- Coca Cola Coliseum
- The International Centre
- Fallsview Indoor Waterpark





