Family-friendly vacation rentals in Oakville

4.8 out of 5 average rating, 153 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.

Indoor spacesFamilyCleanliness

4.87 out of 5 average rating, 121 reviews

The living area presents a spacious layout, featuring a white sofa and a glass coffee table. A large television is mounted on the wall. Decorative glass vases in teal shades are placed nearby. Natural light filters through the open space, creating a welcoming ambiance.

Condo in Oakville

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

Indoor spacesFamilyLong stay

4.97 out of 5 average rating, 262 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!

FamilyKitchenGetting around

4.93 out of 5 average rating, 130 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!

KitchenFamilyCheckout

4.96 out of 5 average rating, 143 reviews

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.

Apartment in Oakville

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

KitchenFamilyAmenities

4.99 out of 5 average rating, 179 reviews

Farm stay in Lincoln

Lakefront Farm | Hot Tub | Fire Pit | Beach Access

Welcome to our stunning modern farmhouse loft, nestled on a 10-acre farm with breathtaking lake views. This farm stay retreat offers a perfect blend of rustic charm & organic luxury. Our home has an open-concept living space with vaulted ceilings & an abundance of natural light. It also has a hot tub, sauna, deck, patio furniture, gas BBQ, and a lakefront bonfire pit. The farm soil is currently regenerating & we are between crops. Book your escape now & experience the our lakefront farm.

FamilyKitchenSleep quality

4.95 out of 5 average rating, 115 reviews

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.

Apartment in Oakville

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!

Indoor spacesFamilyCondition

4.96 out of 5 average rating, 324 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

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.

FamilyKitchenAccess

5.0 out of 5 average rating, 36 reviews

Townhouse in Oakville

Opulent Chic Town Home in the Heart of Oakville

Welcome to your chic getaway in the heart of Oakville! This opulent townhome is perfect for families, business travelers and friends. Relax in the spacious living room, cook your favorites or unwind on the patio. Fast Food & Grocery stores a short walk away & easy access to highways 403, 401 & 407. -McDonalds, Subway, Tim Hortons, Popeyes: 5 mins walk -Superstore, Walmart, LCBO: 5 mins drive -GO Station: 12 mins drive -Toronto Premium Outlet: 15 mins drive Your perfect stay awaits!

Indoor spacesFamilyQuiet

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, 138 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!

Indoor spacesFamilyAmenities

4.83 out of 5 average rating, 106 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.

Indoor spacesKitchenComfort

4.78 out of 5 average rating, 169 reviews

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.

Apartment in Oakville

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

KitchenIndoor spacesCondition

Popular amenities for Oakville family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.89 out of 5 average rating, 112 reviews

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

FamilyIndoor spacesValue

4.9 out of 5 average rating, 538 reviews

An inviting outdoor space features a wooden pergola with string lights, surrounding a dining table and seating area. A private hot tub is positioned nearby, with lush greenery and vibrant flower arrangements enhancing the serene environment.

Cabin in Erin

Cabin stay and play! 10 mins to Canadian Open!

FamilyIndoor spacesPets

4.86 out of 5 average rating, 104 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

Blissful Waterfront Home - HOT TUB & 2King Bed

Indoor spacesFamilyHospitality

4.88 out of 5 average rating, 108 reviews

A spacious living room is highlighted by tall wooden ceilings and large windows that invite ample natural light. Two comfortable sofas face each other over a coffee table, with a patterned area rug underfoot. A small fireplace and colorful stained glass add character to the warm design.

Barn in Milton

Five Star Hayloft Suite

FamilyKitchenHot tub

4.98 out of 5 average rating, 636 reviews

A vibrant sunset is captured with layers of orange, red, and yellow hues across the sky. Silhouetted trees and foliage frame the image, creating a contrasting foreground against the colorful backdrop.

Guest suite in Hamilton

Country Getaway in Puslinch

Indoor spacesKitchenWalkability

4.93 out of 5 average rating, 101 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

KitchenFamilyCheck-in

4.94 out of 5 average rating, 109 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 spacesParking

4.86 out of 5 average rating, 269 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!👌

KitchenIndoor spacesAmenities

Family- and pet-friendly home rentals

4.74 out of 5 average rating, 113 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 spacesWalkability

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.

4.88 out of 5 average rating, 191 reviews

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

Indoor spacesKitchenEV charging

4.78 out of 5 average rating, 392 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

KitchenIndoor spacesLaundry

4.93 out of 5 average rating, 290 reviews

A single-story cottage features a wooden exterior with large windows and a black roof. A path of gravel leads to the entrance, which is framed by greenery and stones. Surrounding the building, the landscape showcases well-maintained grass and a young tree.

Farm stay in Hamilton

Somerset Cottage at West Avenue Cider House

FamilyKitchenLocation

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, 105 reviews

Family Home | Uptown Oakville | 40 Mins to Toronto

Indoor spacesFamilyBackyard

4.93 out of 5 average rating, 105 reviews

An open-concept living area features a sleek electric fireplace beneath a mounted Smart TV. Two round tables with colorful chairs provide seating, while natural light enters through windows adorned with elegant coverings. A modern coffee table sits in front, completing the cozy ambiance.

Home in Milton

Spacious 2 BR apartment | Glen Eden Ski

FamilyKitchenCheck-in

4.78 out of 5 average rating, 145 reviews

Apartment in Burlington

10 min walk to DT, stylish, free parking | IOB1

Indoor spacesFamilyLayout

4.92 out of 5 average rating, 226 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

Indoor spacesKitchenQuiet

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 118 reviews

Home in Erin Mills

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

KitchenIndoor spacesDecor

4.98 out of 5 average rating, 196 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

Indoor spacesFamilyQuiet

4.93 out of 5 average rating, 214 reviews

The indoor swimming pool area features a tiled pool surrounded by natural light from large skylights. Two colorful floats are positioned on the water surface, and glass doors provide a view of the outdoors, enhancing the open and airy feel of the space.

Villa in Toronto

Toronto Vacation | ➊ The One Toronto Villa

FamilyKitchenCheckout

4.81 out of 5 average rating, 123 reviews

The image features a diamond-shaped solar-heated swimming pool reflecting the soft colors of sunset. Comfortable blue lounge chairs are positioned nearby, overlooking a serene lake. The distant skyline can be faintly seen across the water, blending into the horizon.

Home in Hamilton

California Chic +Breathe +Unwind +Restore

Indoor spacesKitchenCleanliness

Guest suite in Mississauga

4.92 out of 5 average rating, 173 reviews

Full apt on Upper floor near HWY - S Mississauga

FamilyKitchenOutdoor spaces

4.89 out of 5 average rating, 130 reviews

A spacious bedroom features large windows, allowing natural light to fill the room. A comfortable bed is centered against a dark accent wall, complemented by minimal artwork. A round mirror hangs on the adjacent wall, and warm lighting is provided by a bedside lamp.

Apartment in Mississauga

Condo in Heart of Mississauga

KitchenIndoor spacesAmenities

5.0 out of 5 average rating, 117 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

KitchenFamilyDecor