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.

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Top guest favourite
The exterior of a two-level apartment is shown, featuring a wooden deck accessible by stairs. A light brick facade complements large windows, while potted flowers add color to the entrance. Surrounding greenery enhances the inviting atmosphere of the building.
Flat in Mississauga
4.98 out of 5 average rating, 105 reviews

Cozy apartment with Free Parking !

Centrally located prime location near buss, highway, parks, shopping, groceries, restaurants and movie theater. Minutes from major highway QEW, 35 min drive to Toronto and Airport. It is spacious, 2 level split apartment. Washroom and bedroom on the upper level. TV & Kitchen on the lower level. Kitchen is equipped with fridge, pots, microwave, toaster, air fryer, utensils, coffee maker. Smart TV, Netflix, Wifi, Parking, Private lawndry are all included. Not permitted: pets, smoking, parties.

Top guest favourite
A contemporary kitchen is highlighted by sleek cabinetry and a spacious island with bar seating. Stainless steel appliances, including a refrigerator and oven, are visible. Soft lighting enhances the modern design, and a mirror reflects the lush greenery in the corner, adding depth to the space.
Flat in Oakville
4.96 out of 5 average rating, 116 reviews

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

Guest favourite
Home in Oakville
4.93 out of 5 average rating, 109 reviews

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!

Top guest favourite
A cozy living area features a light grey sofa and a plush dark blue chair, arranged around a small white TV stand facing a flat screen television. A decorative rug covers the floor, and a dining table with two chairs is positioned nearby, complemented by a vase of flowers.
Flat in Oakville
4.99 out of 5 average rating, 139 reviews

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.

Top guest favourite
A charming two-story detached home is framed by well-maintained greenery and colorful flowerbeds. A paved driveway leads up to the garage, with light brick finishes on the exterior contrasting against the blue sky. The inviting entrance is accentuated by potted plants.
Home in Oakville
4.89 out of 5 average rating, 175 reviews

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.

Top guest favourite
A modern living room is presented with a grey sectional sofa and a plush armchair. Above, a wall clock adorns the light-colored wall, while large windows with soft sheer curtains allow natural light to enter. A small plant sits on a nearby table.
Home in Milton
4.98 out of 5 average rating, 165 reviews

Spacious and Comfy 2 BR Suite

Discover tranquility in our 2-bedroom legal basement apartment, nestled in Milton’s quiet and peaceful neighborhood. Enjoy an open-concept living room with 8.5 ft ceiling, and 2 roomy bedrooms; perfect for couples or families to relax in this comfortable, private, retreat. Easy access to Oakville, Burlington, Mississauga, and Toronto Pearson Airport, and minutes away from Toronto Premium Outlets, Mattamy Cycling Centre, and scenic trails, makes this location ideal for both work and play.

Top guest favourite
A private hot tub is situated on a rooftop terrace, surrounded by privacy screens. Soft lighting is positioned around the area, creating an inviting ambiance. Steam rises gently from the hot tub's surface, hinting at a warm and relaxing experience.
Home in Oakville
4.98 out of 5 average rating, 120 reviews

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!

Top guest favourite
An open-plan living area is visible, featuring a modern kitchen equipped with stainless steel appliances, including an oven and refrigerator. A cozy grey sofa is positioned in front of a wooden coffee table. A circular dining table is set against a bright window, enhancing the space.
Flat in Milton
4.94 out of 5 average rating, 156 reviews

Luxury Guest Suite

Welcome to our cozy basement apartment! This modern Airbnb is located in a peaceful residential neighborhood 40 min drive from Toronto downtown and an hour from Niagara Falls. The well-lit space features a comfortable queen-sized bed, ample storage in the spacious closet, and a beautifully designed interior with natural light flooding through large windows. Note: We have 2 single folding matresses available to place on the floor in the living room. Extra linen and pillows are provided.

Guest favourite
A modern two-story house is set against a green backdrop, featuring large windows that allow natural light to flood the interiors. The driveway leads to an attached garage, while a neatly maintained lawn surrounds the property, enhancing its curb appeal.
Home in West Oakville
4.9 out of 5 average rating, 115 reviews

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.

Top guest favourite
A bright and modern space features a cozy red sofa, complemented by a round coffee table resting on a textured rug. A spacious bed is seen in the background, with natural light filtering through a window, illuminating the soft bedding.
Flat in Mississauga
4.88 out of 5 average rating, 267 reviews

One bedroom Apt. ( 2 storeys unit ) in Mississauga

You will love this one bedroom self-contained 2 storeys unit with separated entrance near Square One mall in downtown Mississauga and 15 minutes to Pearson Airport, easy access to highway 401 and highway 403 and close to all amenities. Modern design bright & spacious with beautiful and private view. Enjoy with free high speed Wi-Fi & 43" tv Netflix available, one parking spot side by side , all included. Quiet neighborhood. - Sorry No party, No smoking, Filming nor Event Stay.

Superhost
A modern studio space is captured featuring a cozy bed adorned with white linen and decorative pillows. A sleek stainless steel refrigerator is positioned nearby, alongside a small wooden table with a potted plant. Natural light filters through a window, enhancing the inviting atmosphere.
Flat in Oakville
4.79 out of 5 average rating, 139 reviews

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

Top guest favourite
Dome in Aldershot Central
4.96 out of 5 average rating, 161 reviews

Winter Escape Tropical Dome! Animal Lovers Dream

Jungle Dome on a farm in Burlington! Enjoy a tropical stay 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 to be a tropical vacation getaway when you can’t get away to the tropics! Situated on a 5 acre animal farm where guests can feed and interact with goats, horses, highland cows, sheep, pigs and poultry. An Animal Lovers Dream!

Popular amenities for Oakville family-friendly rentals

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Quick stats about holiday rentals that are family-friendly in Oakville

  • Total holiday rentals

    Explore 430 holiday rentals in Oakville

  • Nightly prices starting at

    Oakville holiday rentals start at £8 per night before taxes and fees

  • Verified guest reviews

    Over 8,320 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 150 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    300 properties have a dedicated workspace

  • Wifi availability

    430 of Oakville holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oakville rentals

  • 4.7 Average rating

    Oakville stays receive an average rating of 4.7 out of 5 from guests

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