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!

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, 100 reviews

Bright and Spacious 2 bedroom. Quiet house.

Quiet family neighborhood great for professionals, couples or small 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 must provide identification upon request

A rooftop terrace is featured with warm string lights illuminating a wooden deck. A dining table surrounded by woven chairs is positioned alongside a private hot tub. Comfortable seating is arranged on one side, creating a welcoming outdoor space.

4.98 out of 5 average rating, 106 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!

4.87 out of 5 average rating, 103 reviews

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.

4.95 out of 5 average rating, 41 reviews

Elegant Condo in Oakville, Ontario

Welcome to this newly furnished, 1-year-old, 1-bedroom condo in the vibrant uptown core. Close to grocery stores. The open-concept layout blends the kitchen, dining, and living areas under high 10-foot ceilings, creating a serene atmosphere. The living room includes a sofa bed, accommodating up to 3 guests. The well-equipped bathroom ensures a comfortable stay. Enjoy free underground parking and access to amenities like a pool and gym. Essentials are provided for two days only.

4.92 out of 5 average rating, 12 reviews

A bright, modern kitchen features sleek white cabinetry and stainless steel appliances. A spacious countertop provides ample preparation area, while pendant lighting adds a soft glow. The layout is open, connecting seamlessly with the surrounding spaces.

Bungalow in Oakville

Modern & Spacious 2B+2B Bungalow in Oakville

Nestled in a peaceful neighborhood, our tastefully decorated 2 bedroom, 2 bathroom bungalow offers comfort and convenience for business, leisure, or exploring Oakville and the GTA. Tastefully decorated with spacious bedrooms, plush living area with Smart TV and a massaging recliner, fully equipped kitchen, private outdoor space. Minutes from Oakville Hospital, QEW, and nature trails. Explore Toronto, Niagara, and more nearby. Book now for a seamless stay!

4.96 out of 5 average rating, 1,026 reviews

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 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.

4.95 out of 5 average rating, 132 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, 265 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.

4.88 out of 5 average rating, 34 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!

4.83 out of 5 average rating, 155 reviews

A well-maintained inground pool is surrounded by a stone patio, featuring two lounge chairs positioned nearby. Lush green trees offer a natural backdrop, while a shaded area and stairs provide access to an upper deck. A tranquil setting is enhanced by garden accents.

Apartment in Milton

Backyard Oasis Guesthouse.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

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A space thats all yours, with room for everyone

Popular amenities for Oakville vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Oakville

5 out of 5 average rating, 17 reviews

Townhouse in Oakville

TG’s Luxurious House

IfeomaRating, 5 stars2 weeks ago

Tamer place feels like home , peaceful environment, easy to access the sheridan college ,malls and groceries stores . Best place for family vacation . Lastly Tamer always check up on us

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.

4.78 out of 5 average rating, 41 reviews

Spacious Urban Oasis:Stylish 2 Bed, 2 Bath Getaway

KatrinaRating, 5 stars1 week ago

Enjoyed the place. Met expectations

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 stars3 weeks ago

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

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, 92 reviews

Condo Style Basement in Oakville (Walk Up)

DanielRating, 5 stars2 days ago

Good spot for any groups looking to stay in Oakville, 20 min drive to downtown area and many accessible golf courses in the area

4.91 out of 5 average rating, 32 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

NicolaRating, 5 stars3 days ago

Everything was perfect! Thank you!

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.

5 out of 5 average rating, 5 reviews

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!

4.89 out of 5 average rating, 61 reviews

The kitchen is equipped with dark cabinetry and a large island featuring seating for four. A stainless-steel refrigerator and stove are included, alongside a sink and modern appliances. Natural light enters through large windows, enhancing the atmosphere of the space.

Townhouse in Oakville

Sweet and Cozy 3 beds TownHouse

NgoziRating, 5 stars2 weeks ago

My cousin and I had a great stay at Caroline’s Airbnb. The place looked even better in person and everything was clean and ready for guests. The beds were very comfortable. Very quaint and quiet neighbourhood. Location was perfect for us as it was just a 5 minute drive from where the rest of my family was staying and there are also plenty of restaurants, shops, and grocery stores close by. Caroline was very responsive and I see why she earned superhost status. Would definitely stay here again.

A well-maintained exterior of a two-story house features a front driveway leading up to a garage. The entrance is adorned with a covered porch and surrounded by landscaped greenery. A wooden fence and tall trees are visible in the background against a clear blue sky.