Family-friendly holiday rentals in Oakville

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.

4.96 out of 5 average rating, 113 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

A hand-lettered card features the phrase 'Let's make this Fall unforgettable,' surrounded by an elegant floral design. The card is set against a vibrant background of autumn leaves in shades of red, orange, and yellow, highlighting the seasonal theme.

4.93 out of 5 average rating, 107 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!

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.

4.99 out of 5 average rating, 136 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.

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, 172 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.

4.94 out of 5 average rating, 152 reviews

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.

Apartment in Milton

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.

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.

4.79 out of 5 average rating, 136 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

4.82 out of 5 average rating, 273 reviews

A spacious living area features a dark leather sofa and a wooden coffee table at its center. A framed winter landscape hangs on the wall, while two lamps provide soft lighting. In the background, a dining counter with stools is visible, leading to the kitchen.

Townhouse in Burlington

The Best of Downtown Burlington - Safe & Clean

Experience the magic of downtown Burlington voted Canada's best city to live your stay allows you to walk no more then 10 minutes to Award Winning Restaurants, Spencer Smith Park, Joseph Brant Hospital, and so much more. Get cozy in a self contained townhouse unit that's quiet, clean, safe, with free parking and a dog friendly fully fenced in backyard. All guests wishing to book must provide a valid first and last name. I'm sorry cats are not permitted

4.96 out of 5 average rating, 1,071 reviews

The open concept loft features a spacious living area with large windows and sky lights that illuminate the room. A dining table is surrounded by four chairs, a cozy seating area includes a sofa and a coffee table. Exposed wooden beams accentuate the high ceiling.

Loft in Lorne Park

Waterfront Coach House Loft

This friendly, private open concept loft apartment is located on the top floor of a guest coach house located on a 2 acre waterfront estate. The loft apartment is a separate building from the main house. There is a maximum occupancy for the loft of 2 people, parties, get togethers and events are not permitted. Due to the tall spiral staircase, children are not permitted due to safety. Extra charges will apply if additional guests are present in the loft.

Dome in Aldershot Central

The interior of the geodesic dome is adorned with lush tropical plants, creating a vibrant atmosphere. A wooden dining table with two benches is positioned on a patterned area rug, surrounded by greenery. Light filters through the transparent panels, enhancing the natural ambiance.

4.96 out of 5 average rating, 154 reviews

Animal Lovers Dream Dome Stay in Burlington!

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!

A modern kitchen features sleek white cabinetry and a large island with seating for four. Stainless steel appliances are visible, including a refrigerator and microwave. Bright lighting fixtures hang above the island, and a small green plant adds a touch of freshness to the countertop.

4.96 out of 5 average rating, 112 reviews

Elegant 2BR townhouse condo in central Oakville

Enjoy your stay in this elegant, clean, and fully equipped two bedroom and two-bathroom condo townhouse. Centrally located in Oakville and within walking distance to shops, restaurants, and parks. Beautiful upscale building in a quiet and safe neighborhood with large terrace overlooking a mature tree lined street. Abundant walking trails nearby for you to explore and enjoy. Easy access to highway 407, 403, QEW and Trafalgar GO Station.

4.82 out of 5 average rating, 192 reviews

A backyard oasis features a sun-drenched inground pool surrounded by lush perennial gardens. A stone patio is equipped with shaded lounge areas and outdoor seating, creating an inviting space for relaxation. The two-story house overlooks the pool, complementing the tranquil environment.

Apartment in Milton

Backyard Oasis Guesthouse.

POOL IS CLOSED TILL MAY 2026 Welcome to our cozy walk-out basement apartment with no kitchen. It is a completely private unit with separate entrance. Perfect for making some memories at this unique and family-friendly place. Backing on to the Sixteen-mile creek, this backyard oasis has a sun-drenched inground pool surrounded by mature perennial gardens, a new manufactured stone patio, with upper and lower shaded lounge areas.

4.96 out of 5 average rating, 144 reviews

A spacious living area features hardwood flooring and a ceiling fan. An entertainment unit with a television is centered against a white wall, coupled with a decorative fireplace. A comfortable gray sofa is positioned to the left, with a small dining table adorned with sunflowers on the right.

Home in Hamilton

Harbour front CHA CHA CHA - Lake view house

Live by the water! Relax with your family at this peaceful 2Bd 1Bath Lakeview property in Hamilton West Harbour. Enjoy a cup of Nespresso on the house. Steps from the Bayfront park with beautiful lake views, Collective Arts Brewing to enjoy a cold local beer, trendy James St N for all the restaurants, West Harbour Go Train Station , and much more! It is located within an hour from Toronto and Niagara Falls. Book your stay now!

Popular amenities for Oakville family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.87 out of 5 average rating, 103 reviews

Home in Clarkson

4BR Summer Cottage | 25mins from Downtown Toronto

Villa in Aldershot Central

The hillside villa features multiple levels with large windows offering expansive views. Smooth wooden decks are visible, surrounded by greenery, while a staircase leads to the entry. Reflective glass accents enhance the modern design, blending harmoniously with the natural surroundings.

4.96 out of 5 average rating, 156 reviews

Waterfront Hillside Villa

4.98 out of 5 average rating, 589 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

4.94 out of 5 average rating, 145 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!

4.77 out of 5 average rating, 120 reviews

The exterior of a modern building is displayed, featuring large glass windows and a sleek design. The ground level includes a storefront with signage for Starbucks, alongside decorative plants and a tree. Balconies are visible on the upper floors, adding to the contemporary look.

Condo in Mississauga

Luxur condo in downtown Mississauga

4.84 out of 5 average rating, 289 reviews

A modern living area is shown with a light-colored sectional sofa featuring dark blue accent pillows. A sleek, black coffee table contrasts against the soft, patterned rug. Abstract artwork adorns the wall, complemented by an open layout that invites natural light.

Condo in Mississauga

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍

4.74 out of 5 average rating, 135 reviews

An aerial view showcases a secluded backyard featuring a blue swimming pool surrounded by green trees. Umbrellas and seating areas are visible adjacent to the pool, and a separate structure can be seen nearby, adding to the serene outdoor space.

Bungalow in Shoreacres

Sleeps 12 ADULT private hot tub pool Walk to Lake

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.

4.98 out of 5 average rating, 117 reviews

Modern Executive Townhome w/ Rooftop Hot Tub Oasis

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 180 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

4.94 out of 5 average rating, 197 reviews

A doorway opens to a private deck featuring two wooden chairs with white cushions and a small table between them. The view showcases lush greenery and rolling farmland, under a clear sky.

Guesthouse in Lincoln

Little Blue Barn on the Bench

4.91 out of 5 average rating, 225 reviews

A spacious bedroom features a large bed adorned with white linens and decorative pillows. A textured basket holds towels beside the bed. A patterned throw blanket is draped over a wooden bench at the foot of the bed. A dark blue accent wall adds depth to the serene space.

Home in Hamilton Beach

Beautiful Renovated Beach Cottage Home

4.95 out of 5 average rating, 270 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

4.88 out of 5 average rating, 206 reviews

A modern kitchen area is displayed, featuring white cabinetry and stainless steel appliances. A sleek, circular coffee table is positioned in front of a comfortable white sofa, with light hardwood flooring throughout. Natural light illuminates the space from a nearby window, enhancing the contemporary décor.

Home in Mississauga

Private 1-br Apartment: Your Secluded Getaway!

4.84 out of 5 average rating, 188 reviews

An outdoor dining area is set up with a large table surrounded by several chairs. A gazebo provides cover, and the tranquil backdrop features a view of Lake Ontario during sunset, with greenery and yard games visible in the distance.

Cottage in Stoney Creek

Lakeview Oasis: EV Charger, Fire Pit, Sunset View

4.95 out of 5 average rating, 106 reviews

A spacious living area is presented with a comfortable gray sectional couch and a round wooden coffee table. A large TV is mounted on a textured wall, while a piece of artwork depicting waves adds character to the room. A guitar rests nearby, complementing the inviting atmosphere.

Guest suite in Hamilton

Adorable 1-Bedroom Basement Apartment in Hamilton

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.

4.83 out of 5 average rating, 119 reviews

Cozy basement apartment in the heart of Oakville

Family-friendly home rentals with a pool

Guest suite in Orangeville

This inviting bedroom features a spacious bed adorned with soft linens and a textured throw. A large armoire stands alongside, complemented by decorative plants and soft lighting. Natural light is welcomed through an adjacent glass door leading to a private entrance.

4.92 out of 5 average rating, 799 reviews

Cozy Hot Tub & Fireplace - Headwaters Retreat

Guest suite in Mississauga

A well-lit bedroom features a spacious bed with crisp white linens. Two wooden nightstands with lamps are positioned on either side, complemented by a wooden storage chest at the foot of the bed. Soft carpet blankets the floor, creating a cozy atmosphere.

4.97 out of 5 average rating, 115 reviews

The Homelands Suite, 2 Bedroom with Pool.

5 out of 5 average rating, 123 reviews

A bright and airy living space features large corner windows that offer expansive views of the city. A modern sectional couch is paired with a light rug, while a flat-screen television is mounted on the wall. Lush green plants add a touch of nature to the inviting décor.

Condo in Yorkdale

The Penty: Luxurious Penthouse with Pool, Hot Tub

4.99 out of 5 average rating, 126 reviews

A modern living room features a gray oversized sectional sofa adorned with various decorative pillows. A circular wooden coffee table and a potted plant enhance the space. The wall is decorated with a large, abstract artwork, and light filters through sheer curtains, creating a serene atmosphere.

Apartment in Fort York

The Fort York Flat

4.96 out of 5 average rating, 134 reviews

A cozy sitting area is presented with a blue checkered sofa and a striped armchair, adorned with nautical-themed cushions. Light is provided by two lamps on either side, illuminating the artwork and rustic wooden beams above.

Guesthouse in Erin

The Captain's Cottage at Willow Pond

Condo in Humber Bay Shores

A modern living area is featured, showcasing a white sofa adorned with colorful pillows. A round coffee table is centered in front of a wall-mounted TV. Large sliding doors open to a balcony, framed by greenery and offering city views.

4.93 out of 5 average rating, 168 reviews

Hidden gem in Humber bay shores Toronto w/ parking

4.91 out of 5 average rating, 102 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