Family-friendly holiday rentals in Oakville

4.91 out of 5 average rating, 102 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.

Apartment 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

4.81 out of 5 average rating, 105 reviews

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.

Home in West Oakville

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.

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.

4.97 out of 5 average rating, 107 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.

4.96 out of 5 average rating, 117 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.

Flat 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

4.93 out of 5 average rating, 110 reviews

Home in Oakville

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!

4.98 out of 5 average rating, 143 reviews

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

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.

4.93 out of 5 average rating, 159 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.

Flat 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.

4.76 out of 5 average rating, 198 reviews

A spacious common area features a comfortable dark sectional sofa with a soft throw blanket draped over it. A sleek desk with a chair is positioned nearby, complemented by decorative wall art. The warm wooden flooring contributes to a cozy and inviting atmosphere.

Home in Clarkson

Private 2Bed Basement Apt |Self-Check with Kitchn

Modern, entirely private and super spacious 2 bed+ bath basement apartment (over 1200 sq ft). Less than a 2 minute drive to the QEW and a 5 minute drive to one of Mississauga's hottest entertainment plaza (Demetres cafe, Cineplex, Dave & Busters, Indoor skydiving, Scadabush, KB Sushi and more!) Hosts a kitchen (with fridge, microwave, coffee machine/kettle, toaster etc.) and common space with 42" TV, Netflix app and high speed Wifi. Separate entrance and free parking (1 car) included.

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.

4.88 out of 5 average rating, 268 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.

4.88 out of 5 average rating, 110 reviews

A clean and modern studio space features a queen-size bed with soft pink bedding and a white headboard. A light-colored sofa is positioned beside a small black table. Natural light enters through two high windows, enhancing the neutral-toned walls and wooden flooring.

Flat in Etobicoke

Brand new lower-level studio in Toronto

Welcome to our totally renovated -modern clean- Lower Level studio apartment with everything you need for your stay. Our place is a 10 mins drive from the Pearson airport, 10 min to the subway and 30 mins - off peak - into downtown. The place is a walking distance from a grocery plaza ( Metro, Shoppers Drug Mart, LCBO ). We are located in the quiet green area, two parks are close by. We will be happy to help and to answer any questions! Short and Long stays are welcome.

4.86 out of 5 average rating, 101 reviews

A brick exterior home is set against a bright blue sky, featuring a manicured front lawn with green grass and white flowers. Large windows allow natural light to illuminate the entrance, where a welcoming white door is positioned. A tree provides shade, enhancing the outdoor space.

Home in Georgetown

Halton Hills Hideaway_Private Suite

🌿 Halton Hills Hideaway – Cozy Basement Suite Near Downtown Georgetown ✨ What You’ll Love: 🚪 Private Basement Suite – Separate entrance & no shared areas 🛏️ Queen Bed – Comfy and perfect for solo travelers or couples 🌳 Garden Views – Enjoy calming green views from your lookout window 🧼 Clean & Cozy – Thoughtfully prepared for a peaceful stay 🏘️ Charming Neighborhood – Quiet, friendly, and safe 🔍 Check the amenities section for full details—we’d love to host you!

4.79 out of 5 average rating, 140 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.

Flat 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

Popular amenities for Oakville family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest house in Normanhurst

A single-story guest house is presented with a brown shingle roof. A star decorates the exterior wall, complemented by a well-maintained garden featuring various plants and flowers. A stone pathway leads up to the entrance, with outdoor seating visible on the patio.

4.96 out of 5 average rating, 121 reviews

Hollis Haven

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, 819 reviews

HotTub & Cozy Fireplace - Headwaters Retreat

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, 159 reviews

Waterfront Hillside Villa

4.87 out of 5 average rating, 201 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.

Apartment in Mississauga

Beautiful Penthouse with Breathtaking View

4.95 out of 5 average rating, 310 reviews

A galvanized metal bucket featuring the phrase 'Home Sweet Home' in a decorative style is placed on a black metal outdoor table. Lush green foliage serves as a natural backdrop, enhancing the serene outdoor setting.

Guest suite in Grimsby

Spacious Suite w/ HOT TUB & high-speed wifi

4.98 out of 5 average rating, 599 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

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.

4.94 out of 5 average rating, 155 reviews

Luxury Stay w/phenomenal view!

4.93 out of 5 average rating, 281 reviews

An open concept living area showcases a spacious seating arrangement with a neutral-colored sofa, paired with a wooden dining table. Exposed wooden beams and a rustic stone wall add character to the space, with natural light flowing through large windows.

Barn in Hamilton

The Barn-Fieldstone Suite

Family- and pet-friendly home rentals

Apartment in Harbourfront

A small balcony features a bistro table and two wooden chairs, overlooking a serene view of Lake Ontario. A potted plant sits in the center of the table, with the shimmering water and distant shore visible in the background.

4.97 out of 5 average rating, 314 reviews

Lively 1+1 Lakeview Condo near CN Tower + Free Prk

4.93 out of 5 average rating, 189 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, 204 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.

Guest house in Lincoln

Little Blue Barn on the Bench

4.83 out of 5 average rating, 286 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

4.89 out of 5 average rating, 177 reviews

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

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

4.89 out of 5 average rating, 213 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!

4.79 out of 5 average rating, 109 reviews

A serene living area is depicted, featuring a spacious bed, a smart TV, and a dining table set for two. Natural light enters through the door, which leads to an outdoor space. Soft carpeting and neutral-colored walls create a calm environment.

Home in Brampton

Your Own Suite-Moderncharm Hideaways Near TorAirp

4.95 out of 5 average rating, 108 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

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 103 reviews

Five alpacas are seen walking across a grassy area in front of a large, restored barn. The barn features a dark roof and wooden siding, with a door visible on the lower level. A clear blue sky and scattered clouds provide a bright backdrop.

Farm stay in Caledonia

Alpaca farm stay and bunkie getaway.

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, 116 reviews

The Homelands Suite, 2 Bedroom with Pool.

4.84 out of 5 average rating, 185 reviews

A scenic lake view is presented, featuring a wooden bench positioned on a grassy area beside the water. The sun reflects off the lake's surface, and a clear blue sky is adorned with a few fluffy clouds, creating a serene atmosphere.

Guest suite in Bronte

Stylish Basement Hideaway*1 BR Suite*Near Lake

4.85 out of 5 average rating, 104 reviews

A spacious living room is presented with a neutral-colored sectional sofa adorned with yellow accent pillows. A small glass side table complements the seating area, while a patterned area rug adds texture to the floor. Natural light enters through a window placed above the sofa.

Flat in Oakwood Village

Bright, spacious luxury basement apartment

Apartment 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.

4.92 out of 5 average rating, 179 reviews

Hidden gem in Humber bay shores Toronto w/ parking

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.

4.88 out of 5 average rating, 109 reviews

Condo in Heart of Mississauga

4.74 out of 5 average rating, 136 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