Vacation rentals in Oakville

4.93 out of 5 average rating, 196 reviews

An open studio layout displays a cozy sleeping area alongside a well-equipped kitchen. Light grey walls enhance the space, while two bedside lamps provide soft illumination. In-suite laundry is visible next to the kitchen, and a welcoming couch adds comfort to the environment.

Guesthouse in Oakville

Self Contained Luxury Studio Coach House

Your Perfect Home Away from Home! This immaculate, private studio with a separate entrance is designed for comfort and convenience. Nestled in a peaceful suburb yet centrally located near major highways, it offers walking access to restaurants, grocery stores, and a park. Thoughtfully furnished, it’s cozy in winter, cool in summer, and fully equipped for a hassle-free stay. Guests love the warm ambiance, calling it a truly special experience. Come see why our coach house is the perfect getaway!

4.91 out of 5 average rating, 33 reviews

Home in Oakville

Private Home : Kitchen-Bath-Laundry-Gym-Parking

Private basement suite with separate entrance — no shared areas Full kitchen Private full bathroom with shower and essentials Private gym exclusively for guest use Keyless entry with secure passcode for easy self check-in/out Free parking on-site High-speed Wi-Fi Walking distance to Walmart, Tim Hortons, Superstore, bus stops Close to Sheridan College and White Oaks Secondary School Host speaks English, Mandarin, and Cantonese Ideal for students, business travelers, and leisure guests

5 out of 5 average rating, 48 reviews

A rooftop terrace is displayed, featuring a modern heater and comfortable outdoor seating arrangements. Soft string lights create a gentle glow against the evening sky, illuminating the inviting space designed for relaxation and social gatherings.

Home in Oakville

Modern 4-Bed Townhome with Cinema & Roof Terrace

Stylish contemporary brand new townhome in Oakville! The perfect retreat for families, and friends alike. You'll love the stunning home theatre with a 115" screen and Kef 5.1 sound system. Spacious areas, fully equipped kitchen, and 4 comfortable bedrooms. Relaxing Massage Chair for your use! Experience the rooftop terrace! It's the perfect spot to unwind after a long day of sightseeing or to enjoy an evening under the stars. Close to Three Major Highways 403/407/QEW in a Central Location!

4.94 out of 5 average rating, 64 reviews

An inviting entryway features a sleek bench and a round mirror, with light filtering through the blinds. A small table is adorned with decorative plants and a framed sign, enhancing the welcoming atmosphere of this modern townhome.

Townhouse in Oakville

Luxury Urban Town home

Discover urban sophistication at our modern townhome, ideally located for both comfort and convenience. Thoughtfully designed with stylish decor and all the amenities you need, you'll find grocery stores just a short walk away and easy access to highways 401 and 403 for effortless travel. - Superstore, Walmart, LCBO: 10-minute walk - Oakville Trafalgar Memorial Hospital: 10-minute drive - Oakville GO Station: 12-minute drive - Toronto Premium Outlets: 14-minute drive Book your stay today!

4.87 out of 5 average rating, 103 reviews

Home in West Oakville

Luxury Villa! Swim Spa! 6 Bedroom 3 Family Rooms

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.

4.96 out of 5 average rating, 1,025 reviews

A cozy nook features a curved window with multiple panes, allowing natural light to fill the space. Two benches covered in warm fabric are adorned with decorative pillows. The exposed brick walls enhance the inviting atmosphere of the seating area.

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.

Villa in Aldershot Central

The modern hillside villa is showcased with extensive glass balconies and a layered wooden facade. A private hot tub is positioned on the deck, offering relaxing views of the surrounding waterfront. Landscape elements include natural greenery and a wooden walkway leading to the lake.

4.95 out of 5 average rating, 131 reviews

Waterfront Hillside Villa

Welcome to your stunning Hillside Villa situated on 150' of waterfront. Enjoy the peaceful surroundings and quiet Bay views from your 3 private outdoor decks & hot tub. Entertaining is easy in this gourmet kitchen, which is open to 1 of 2 fireplaces, family room & dining room with floor to ceiling views of the Bay. Breathe taking views of the Bay from your private dock. Hidden gems: gym, 2nd kitchen, foosball table, EV charging and private trail.

Cabin in Aldershot Central

4.97 out of 5 average rating, 264 reviews

Animal Lovers Dream! Barn Loft in Burlington

Experience life on a tiny farm just outside the city! Stay in our charming and comfortable barn loft and wake up to the sounds of chickens, ducks, geese, pigs, goats and horses and our adorable Highland cows. Spend time watching or interacting with all the very friendly animals that surround the barn. You will meet all the animals as they all come up readily to anyone who visits the farm. Guests are welcome to participate in the morning feeding.

4.98 out of 5 average rating, 210 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 JUNE 11 (1 night/2 days) JUNE 28-JULY 25 AUGUST 1-31 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. We are located along the south shore of Lake Ontario amongst the fruit belt of the Niagara. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging on-site.

4.88 out of 5 average rating, 32 reviews

The modern townhouse exterior features a combination of sleek gray, white, and orange accents. Large windows allow natural light to filter in, while landscaped greenery enhances the inviting atmosphere of the neighborhood.

Townhouse in Oakville

Luxury Corner Home near Restaurants, Parks & Shops

Welcome to our stylish Oakville townhouse — perfect for families or business travelers! Near Dundas & Trafalgar, walk to parks, Walmart, cafés, and more. Enjoy cozy bedrooms, fast Wi-Fi, full kitchen, and a relaxing living space. Whether you're here for work or a getaway, you’re just 10–15 mins from the Oakville waterfront and Ridgeway Plaza — the largest halal food hub in town. Comfort, convenience, and location all in one!

5 out of 5 average rating, 51 reviews

A white picket fence encloses a well-kept garden, with vibrant autumn foliage highlighting the entrance. A blue sign with the number '140' is mounted on the fence, leading to a charming house visible in the background.

Guesthouse in Oakville

140 - Olde Oakville Downtown Heritage District

“140" is an adorable, lovingly-renovated, private apartment on the second floor of the coach house of a prominent heritage-plaqued home in the heart of picturesque Olde Oakville. Located just up the hill from Oakville Harbour, two short blocks from both Lakeside Park on Lake Ontario and the downtown high street, Lakeshore Road with its many restaurants and unique shops makes "140" the perfect place for a couple's getaway!

4.96 out of 5 average rating, 224 reviews

A modern kitchen area is visible, featuring stainless steel appliances, including a large refrigerator. Light-colored cabinetry and counter space accentuate the room. The flooring is a light wood design, and soft lighting from ceiling fixtures creates a bright atmosphere. A bathroom doorway is seen in the background.

Guest suite in Milton

Beautiful Basement& Ent via Garage

Spacious one bedroom (about 820 SQ Feet ) Clean, non smoking unit with two 65 inches TVs, The space is private and only for the guests who booked it. Onsite Parking is available, if needed This is a family-friendly property and 5 minutes to 401, Toronto Premium Outlet and Milton Go. A Park is just infront. Grocery store RABA 24*7 and Access is via Garage using keypad.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Oakville vacation rentals

Laptop-friendly workspace

Apartment rentals in Oakville

Apartment in Downtown St. Catharines

A modern living area features an oversized dark couch arranged invitingly with a soft throw. A large window with shades allows natural light to fill the space. A round, woven rug enhances the cozy atmosphere, and stylish decor accents are placed thoughtfully around the room.

4.93 out of 5 average rating, 441 reviews

hidden gem hot tub and igloo st-catharines

MahyarRating, 5 stars1 week ago

⭐️⭐️⭐️⭐️⭐️ My family and I had a fantastic two-night stay at this lovely home! The house was exactly as shown in the pictures—very clean, comfortable, and had everything we needed. The location was perfect, just a short drive from Niagara Falls, which made our trip even more enjoyable. The neighborhood was peaceful and safe, and we had easy access to local shops and restaurants. The host was incredibly kind and responsive, and the check-in/check-out process was smooth and easy. We truly felt at home and would definitely love to stay here again. Highly recommended for anyone visiting the Niagara Falls area!

4.9 out of 5 average rating, 149 reviews

The living area features a double sofa bed adorned with multicolored cushions, complemented by a small round table and four white chairs. A large mirror reflects the space, while a cozy armchair and decorative round rug add warmth. A television is mounted on the wall.

Apartment in Burlington

S Burlington on Chamberlain Rd Close to Go Stn

DonnaRating, 5 stars3 weeks ago

Great stay in a comfortable, tastefully decorated and well equipped apartment. Considerate, friendly and very responsive host. Great location with close proximity to the lake and backyard park. Great stay!

4.82 out of 5 average rating, 119 reviews

A serene outdoor space is presented with four lounge chairs and a small table on a wooden deck overlooking the water. The bright blue sky reflects in the calm lake, while lush green grass frames the area.

Apartment in Long Branch

Waterfront Cozy Escape

BillyRating, 5 stars5 months ago

Very comfortable and close to a great Italian restaurant!

4.98 out of 5 average rating, 375 reviews

A bright living area features a mid-century style orange sofa positioned against a white wall. Two blue velvet chairs face the sofa, with a natural wood floor adding warmth. Large windows allow sunlight to stream in, and a vintage record player sits beside a decorative fireplace.

Apartment in Hamilton

Vintage Dreams | Mid-Century Design in artsy area

BrontëRating, 5 stars1 week ago

We had a wonderful time! Would highly recommend!

4.96 out of 5 average rating, 104 reviews

A welcoming entryway features a stylish blue sofa adorned with decorative pillows, complemented by a round mirror above. Natural light floods in from sliding glass doors that lead to an outdoor space. A neutral area rug adds warmth, while a potted plant brings a touch of greenery.

Apartment in Mississauga

Bright Luxurious Peaceful Home - Mississauga

AshleyRating, 5 stars1 week ago

Needed somewhere to stay outside of Toronto & Harsh’s place was a wonderful choice! He was very communicative & everything was very clean. Located in a quiet neighborhood & I would highly recommend!

Apartment in Churchill Meadows

An open concept living area showcases a comfortable sectional sofa and a glass dining table. A spacious bed is visible in the background, complemented by soft lighting. A workspace with two chairs and a TV is positioned nearby, creating a functional and inviting environment.

4.97 out of 5 average rating, 157 reviews

Comfort, Style and Privacy.

DannyRating, 5 stars1 week ago

Check-in was very easy. Dolcie was very helpful and quick to respond when emailed. The space was very nice. The bed was very comfortable, and the kitchen had everything we needed. We had a little trouble figuring out the TV, but Dolcie came down immediately and helped us figure it out. The neighborhood was very quiet, and there was a beautiful walking path around a lake very close by. Travelling to downtown Toronto was only about a 30 minute trip. Within 2 blocks of the house was a small strip mall with a grocer, pizza place, and a wonderful Polish deli that sold delicious sausages, cheeses, breads, and homemade hot dishes and desserts for takeout. We really enjoyed our stay and would definitely come back on our next visit.

4.83 out of 5 average rating, 126 reviews

The kitchen features modern appliances, including a microwave and a fridge, complemented by white cabinetry. A round dining table with chairs is positioned near a large window, adorned with potted plants. A circular mirror adds elegance to the space, which is illuminated by abundant natural light.

Apartment in Mississauga

Separate Basement Apartment

TorenoRating, 5 stars2 weeks ago

This host’s place is extremely clean and spacious. The price is perfect and I’d love to stay again!

4.82 out of 5 average rating, 153 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.

TChallaRating, 5 stars1 week ago

super beautiful place our stay was amazing had everything you need

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Other great vacation rentals in Oakville

4.97 out of 5 average rating, 75 reviews

The living area features a comfortable seating arrangement with a dark leather couch and a light-colored chair, positioned around a coffee table. A smart TV is present for entertainment. The dining space displays a table set with dishes and utensils, adjacent to the kitchen with modern cabinetry.

Apartment in Mississauga

Cozy apartment with Free Parking !

IljaRating, 5 stars1 week ago

A cozy place for one or the couple. Really lovely location and rather quiet, while still being able to easily navigate around. Daniela has been amazing, and easy to talk to. Has been really helpful throughout the stay. Would definitely recommend and if i'm visiting Canada again I would definitely stay here if its available

4.91 out of 5 average rating, 11 reviews

Modern & Cozy Walkout Basement with Scenic Views

ZiaoRating, 5 stars1 month ago

Everything is perfect! I would recommend travelers to stay here, it’s very quiet and peaceful! If you went to Toronto, then this is a nice play to stay!

An open living area and kitchen are depicted, featuring modern appliances and a dark countertop. A comfortable seating arrangement with a low table is present, complemented by plants. Natural light flows in through a sliding door, offering a view of the outdoor scenery.

4.77 out of 5 average rating, 39 reviews

Spacious Urban Oasis:Stylish 2 Bed, 2 Bath Getaway

JusticeRating, 5 stars1 week ago

I had a great experience staying at this apartment! The space was clean, stylish, and exactly as described in the listing. It had everything I needed for a comfortable stay — from a well-equipped kitchen to cozy bedding. The location was also super convenient, close to [restaurants, public transport, attractions, etc.]. Communication with the host was easy and quick, and check-in/check-out was seamless. I would absolutely stay here again and highly recommend it to anyone visiting the area!

5 out of 5 average rating, 8 reviews

A warm living area features a tan leather sofa accented by light-colored cushions. A wooden coffee table sits in front, adorned with potted plants. The space is brightened by recessed lighting and offers a view of a modern kitchen in the background.

Apartment in Burlington

2Beds/1Bath Apt: Mins toTrain,Trails, DT & Golfing

SteveRating, 5 stars2 weeks ago

Great little place Brandon + Carolina were wonderful hosts Would recommend to anyone I'LL BE BACK

4.9 out of 5 average rating, 31 reviews

A well-lit living area features a modern sofa positioned near a wall-mounted television. A light wood table with a comfortable chair is seen in the corner, against white walls adorned with framed artwork. A soft rug grounds the space, complementing the neutral furnishings.

Guest suite in Oakville

Debonair Home near Downtown Oakville

Scott WilliamRating, 5 stars2 weeks ago

Lovely clean property in an excellent location!

5 out of 5 average rating, 5 reviews

The outdoor patio features comfortable seating arrangements made of woven materials, including a sectional sofa and cushioned ottoman. A modern gas fire pit serves as the centerpiece, surrounded by stylish wooden decking and a brick wall background.

Home in Oakville

Oakville Oasis

AnnaRating, 5 stars2 months ago

there's not enough words to describe how beautiful and spacious this home is. quite area however stores just seconds away . Anna was an amazing host she went over and beyond for my family. upon check out I had left an item behind Anna was quick to message me and let me know she had taken the item and was willing to meet with me to return it . great stay can't wait to go back again and refer to friends and family . diffenitly worth every penny!

A modern kitchen area with a marble-topped island and white cabinetry is highlighted. Stainless steel appliances, including a refrigerator, complement the space. A small dining table with folding chairs can be seen, while soft lighting enhances the inviting atmosphere.

4.99 out of 5 average rating, 99 reviews

Bright and Spacious 2 bedroom. Quiet house.

MariteRating, 5 stars4 days ago

My parents and I absolutely loved Marina’s place. Her attention to detail and cleanliness really stood out for us. The place is very cozy and peaceful, and to top it all off, Marina is so warm, kind and always available to help. Highly recommend.

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.