Family-friendly vacation rentals in Oakville

The exterior of the home is shown, featuring a well-maintained lawn with a pathway leading to the entrance. Two decorative trees frame the house, which has a welcoming porch with large windows allowing for natural light. A calm atmosphere is present in the surrounding area.

4.8 out of 5 average rating, 130 reviews

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.

FamilyKitchenDecor

4.8 out of 5 average rating, 167 reviews

A comfortable living area is presented with a dark coffee table and two blue couches adorned with patterned throw pillows. Light blue curtains frame the windows, and a large flat-screen TV is positioned on a black TV stand against the wall.

Guest suite in Oakville

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.

KitchenIndoor spacesDecor

4.93 out of 5 average rating, 138 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!

FamilyKitchenHospitality

4.96 out of 5 average rating, 286 reviews

Dome in Burlington

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!

FamilyIndoor spacesGrill

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.

4.95 out of 5 average rating, 150 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

KitchenFamilyParks

A spacious living area features a light-colored sofa and armchairs surrounding a glass coffee table. A plush area rug anchors the space, and a dining table with white chairs is positioned nearby. Modern kitchen appliances are visible, along with natural light from recessed lighting.

4.95 out of 5 average rating, 127 reviews

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!

KitchenFamilyOutdoor spaces

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.

4.98 out of 5 average rating, 179 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.

Indoor spacesFamilyCheck-in

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.

4.89 out of 5 average rating, 198 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.

KitchenIndoor spacesCheck-in

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.

4.99 out of 5 average rating, 145 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!

FamilyIndoor spacesParking

4.84 out of 5 average rating, 110 reviews

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.

KitchenIndoor spacesGetting around

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.

4.88 out of 5 average rating, 148 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.

KitchenFamilyQuiet

A spacious room features a modern geometric accent wall in various shades of blue, yellow, and green. A neatly made bed with soft linens is centered in the area, flanked by two bedside tables and lamps. A workstation with a comfortable chair is visible in one corner.

4.85 out of 5 average rating, 120 reviews

Family Home | Uptown Oakville | 40 Mins to Toronto

If you're looking for a stylish and comfortable home-away-from-home experience, you've come to the right place! We're in the heart of uptown Oakville, close to tons of restaurants, grocery stores, coffee shops and salons. 10mins to Oakville Place, 6mins to Sheridan College and 5mins to the 5-Drive In - an outdoor drive-in theatre perfect for family outings or date night! Our home is fully equipped with everything you need for a comfortable stay. We think you'll love it here :)

Indoor spacesKitchenOutdoor spaces

Popular amenities for Oakville family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.87 out of 5 average rating, 175 reviews

A modern condominium building is showcased from a street view, highlighting two tall, sleek towers with an expansive glass façade. The ground level features a multi-story section with large windows and contemporary architectural elements, set against a clear blue sky.

Condo in Mississauga

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

FamilyKitchenAccuracy

Guesthouse in Mississauga

A serene backyard is highlighted by a clear swimming pool surrounded by natural stone coping. Comfortable seating arrangements with dark wicker chairs and a sleek table are positioned nearby, offering a relaxing spot. Lush greenery frames the area, providing a peaceful atmosphere.

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

FamilyIndoor spacesAmenities

4.89 out of 5 average rating, 118 reviews

4.85 out of 5 average rating, 277 reviews

A spacious living area features a modern light fixture and a comfortable sofa with decorative pillows. A coffee table rests on a patterned rug. Behind the seating area, an open kitchen is visible, showcasing dark cabinetry and contemporary bar stools.

Condo in Mississauga

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

FamilyKitchenCheckout

4.92 out of 5 average rating, 115 reviews

A light-filled living area features a plush, beige sofa and armchairs arranged around a coffee table. A mirrored wall decoration reflects light, while a decorative chandelier hangs above. The space leads to a staircase and an entrance door with a decorative mirror nearby.

Home in Waterdown

Ninos Place

Indoor spacesFamilyBackyard

4.99 out of 5 average rating, 191 reviews

Farm stay in Lincoln

Lakefront Peach Farm | Hot Tub | Sauna | Fire Pit

KitchenIndoor spacesBackyard

4.95 out of 5 average rating, 114 reviews

A hot tub is positioned on a deck overlooking a calm, expansive lake. The water reflects soft gray skies, creating a serene atmosphere. Rocky shoreline is visible in the foreground, enhancing the tranquil lakeside setting.

Home in Hamilton

Wake Up To Lake Views!

KitchenIndoor spacesSleep quality

4.82 out of 5 average rating, 114 reviews

A spacious living area features a sectional sofa adorned with various cushions, arranged around a glass coffee table. Large windows allow natural light to flood the room, offering views of lush greenery. A decorative wall art piece and a potted plant add to the inviting atmosphere.

Home in Hamilton

Optimal Waterside Retreat - HOT TUB 2 King Bed

FamilyIndoor spacesGetting around

4.92 out of 5 average rating, 201 reviews

A modern living area features a large window with expansive views of the cityscape and surrounding landscape. A flat-screen television is mounted on the wall opposite a comfortable sofa and a coffee table, creating a welcoming space for relaxation.

Apartment in Mississauga

Luxury Stay w/phenomenal view!

Indoor spacesKitchenWifi

Family- and pet-friendly home rentals

The kitchen area includes white cabinetry and a stainless steel stove. A dining table with dark wooden chairs is positioned in front of a wall-mounted TV. A patterned rug covers the tiled floor, while a doorway leads to another room.

4.82 out of 5 average rating, 134 reviews

Cozy basement apartment in the heart of Oakville

Indoor spacesKitchenNearby

4.96 out of 5 average rating, 338 reviews

The exterior of the guest house features a wrap-around composite deck with glass railing, overlooking the direct waterfront views of Lake Ontario. The structure is surrounded by lush greenery and is complemented by large windows allowing natural light into the living space.

Guesthouse in Lincoln

Cottage On Lake Ontario Niagara

KitchenFamilyWalkability

4.92 out of 5 average rating, 232 reviews

Two brown horses are depicted in a snow-covered outdoor setting, closely positioned with their noses touching. Flakes of snow gently fall around them, creating a serene winter scene, while a house and snow-covered trees are subtly blurred in the background.

Bungalow in Hamilton

Horse Ranch with Hot tub

FamilyKitchenAccuracy

4.99 out of 5 average rating, 103 reviews

A spacious living area features a gray sectional sofa paired with a low coffee table, situated atop a light-colored rug. Soft natural light is allowed in through large windows, highlighting the open layout that connects to the modern kitchen and staircase.

Loft in Hamilton

Luxury Locke Street Loft

KitchenIndoor spacesHospitality

4.9 out of 5 average rating, 193 reviews

A modern kitchen features sleek cabinetry and a large central island with seating for four. Pendant lights hang above the island, illuminating the space. Large sliding glass doors provide access to outdoor areas, enhancing natural light within the open layout.

Home in Hamilton

Luxurious 5BR Beach House with Firepit

Indoor spacesKitchenNearby

4.92 out of 5 average rating, 210 reviews

The image captures a serene view of the lakeside property, featuring a lush green lawn that slopes towards Lake Ontario. A sandy beach area and rocky shoreline are visible, framed by trees on both sides and calm turquoise water reflecting the clear sky.

Cottage in Hamilton

Lake Front Heaven - Gateway to Niagara/Vineyards

Indoor spacesKitchenWifi

4.74 out of 5 average rating, 123 reviews

A comfortable sleeping area is furnished with a queen bed, dressed in a patterned blue and white blanket. A cozy sofa is positioned nearby. Warm lighting is provided by a wall-mounted fixture, and a piece of artwork featuring a tree is displayed above the bed.

Home in Milton

Spacious, Pet Friendly Basement Apartment

FamilyIndoor spacesAccuracy

4.79 out of 5 average rating, 411 reviews

A modern living area is showcased with large windows, allowing natural light to fill the space. A colorful yellow sofa and blue chairs provide seating. An entertainment unit features a television against a vibrant mural of cacti. Wooden flooring adds warmth to the contemporary design.

Hotel room in Hamilton

Fully-Furnished Boutique 1 Bedroom Suites

FamilyIndoor spacesCleanliness

Family-friendly home rentals with a pool

Guest suite in Mississauga

Full apt on Upper floor near HWY - S Mississauga

Indoor spacesFamilyGrill

4.92 out of 5 average rating, 174 reviews

4.96 out of 5 average rating, 123 reviews

Home in Erin Mills

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

Indoor spacesKitchenParks

4.99 out of 5 average rating, 208 reviews

The exterior of a cabin is depicted, featuring wooden siding and a stone base. A small wreath decorates the entrance, which is flanked by a snow-covered landscape. Tall trees stand in the background, hinting at the surrounding nature.

Cabin in Hamilton

The Fox's Retreat - A Cozy Cabin for Two

KitchenIndoor spacesDecor

5.0 out of 5 average rating, 129 reviews

A backyard seating area is viewed, featuring a dark outdoor sectional couch with a black coffee table placed on a striped rug. Surrounding the heated saltwater pool are lounge chairs and lush greenery, creating a serene outdoor space.

Guesthouse in Brampton

Bright and Airy Guest Suite with Pool

Indoor spacesFamilyCheck-in

4.76 out of 5 average rating, 184 reviews

Home in Mississauga

Cottage-like Apartment

Indoor spacesKitchenQuiet

4.86 out of 5 average rating, 222 reviews

A vibrant cityscape is illuminated by colorful fireworks, with numerous skyscrapers displaying warm lighting. A large crowd is gathered below, surrounded by modern buildings and open spaces, creating an inviting atmosphere for festivities during the evening.

Condo in Mississauga

Beautiful Penthouse with Breathtaking View

KitchenFamilyHospitality

A private pool area features a shaped, crystal-clear pool surrounded by a well-kept lawn and vibrant greenery. Two lounge chairs are positioned nearby, and colorful pool floats are visible in the water, creating an inviting outdoor space.

4.76 out of 5 average rating, 145 reviews

Cozy Retreat in Oakville

FamilyKitchenPool