Vacation rentals in Oakville

4.93 out of 5 average rating, 198 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, 102 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

5 out of 5 average rating, 10 reviews

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.

Home in Oakville

Entire suite in Oakville

One bedroom walk out basement with separate entrance from back yard door. The incredible park views make for a relaxing, enjoyable and unforgettable trip. Newly renovated suite with one bedroom、living room、 bathroom、 kitchen、 office area、 laundry room. Host provides disposable items such as slippers、 toothbrushes、toothpaste、 bath towels etc, bring great convenience to your travel. It located close to commercial block, within 10 minutes' walk to all major banks、Walmart、Restaurant、 Starbucks.

4.95 out of 5 average rating, 44 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.

4.96 out of 5 average rating, 1,029 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.

4.97 out of 5 average rating, 273 reviews

A close-up view captures the snout of a Highland cow, showcasing its distinctive facial features. The sun reflects softly off its nose, highlighting the texture of the skin and fur. The background reveals a lush green pasture, typical of farm surroundings.

Cabin in Aldershot

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.

4.97 out of 5 average rating, 100 reviews

A modern dining area is highlighted by a glass table surrounded by four upholstered chairs. A contemporary chandelier hangs above. In the background, a living space features a comfortable seating arrangement and a flat-screen TV. Natural light enters through large windows, enhancing the open layout.

Home in Oakville

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.

4.89 out of 5 average rating, 9 reviews

The kitchen area features a vintage-style mint green gas stove, a large farmhouse sink, and modern cabinetry. A small television and decorative plants are visible on the countertop. The space is well-lit with ceiling lights, creating a bright cooking environment.

Guest suite in Oakville

Modern Retro Oak guest suite

Forget your worries in this spacious and serene space in the heart of Oakville. We are centrally located within walking distance to Oakville Place mall, gym, Go transit and the highways. Come stay in our guest suite and enjoy our bright, private suite that has its own separate entrance. **We provide pool access which will be additional cost. Speak to us directly pls. *** for longer stays (over 28 days) you get a discount.

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, 156 reviews

A serene outdoor lounge area is featured, illuminated by soft string lights. Comfortable seating is arranged around a central table, providing a cozy spot to relax. The backdrop showcases a well-maintained pool and lush greenery, creating an inviting evening ambiance.

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.

4.96 out of 5 average rating, 229 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.

4.98 out of 5 average rating, 164 reviews

A sliding glass door opens to a private outdoor patio with a small table and two chairs. Lush green grass extends toward a scenic view of the lake, creating an inviting space to relax and enjoy the natural surroundings.

Home in Hamilton Beach

The Coastal Cottage

Escape to our modern bohemian beachfront cottage for a serene and stylish getaway. Whether you're seeking a romantic retreat or a peaceful solo adventure, our little slice of paradise is the perfect backdrop for creating lasting memories. Book your stay today and start counting down the days until you wake up to the sound of crashing waves and breathtaking sunrises. t4yh7

Vacation rentals for every style

Get the amount of space that is right for you

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Apartments

Convenient locations with everyday essentials

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Quaint homes, peaceful surroundings

Popular amenities for Oakville vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Oakville

4.97 out of 5 average rating, 79 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 !

IsiahRating, 5 stars3 days ago

it was a comfortable place and I enjoyed my stay. I appreciated the peace amd quiet it allowed me to recharge.

An open living area features light wood flooring and modern recessed lighting. A kitchen is visible in the background, showcasing sleek cabinetry and appliances. A colorful wall art piece depicting a serene landscape adds a touch of color. A bathroom is accessible through a door on the right.

4.79 out of 5 average rating, 57 reviews

Elegant Suite: Private Entrance & Full Amenities

R. JackRating, 5 stars2 weeks ago

Superb. Wish I had found this place before my son finished three years at Sheridan. Highly recommended

Superhost

A spacious living area is visibly arranged with a comfortable sofa facing a wall-mounted television. A light-colored cabinet is positioned in the foreground, complemented by a dining table and black chairs. Natural light enters through small windows, enhancing the neutral color scheme.

Guest suite in Clarkson

4.93 out of 5 average rating, 54 reviews

Adorable bachelor suite with all you need

KaoriRating, 5 stars3 weeks ago

I enjoyed the stay in this unit with my 2 kids for a month. The host was super kind, she provided us a baby chair and crib for my 6 months old baby. She always took care of us so we could stay the unit comfortably, she provided us an extra bed, blanket and pillow, too. I met some bugs in the unit sometimes actually, but taking it into account , our stay was really comfortable.

Superhost

A sleek living space features a comfortable gray sofa paired with a black leather couch. A round, colorful area rug adds visual interest to the floor. Nearby, a wall-mounted television is positioned opposite the seating area, with large glass doors allowing light into the room.

4.57 out of 5 average rating, 7 reviews

Luxurious Upper Oakville Condo

JohnRating, 5 stars1 month ago

He was very responsive, accommodating and kind!

A modern living area features a light-colored sofa, complemented by accent pillows. A glass coffee table sits on a textured rug, while a tall indoor plant adds natural greenery. Large windows provide ample light and a view, with a minimalist shelf visible in the background.

5 out of 5 average rating, 12 reviews

Oakville 2BR: Central, Comfy & Close to Everything

DavidRating, 5 stars2 months ago

Felipe’s Airbnb was easy to find, reasonably priced, and conveniently located near Sheridan College. The condo was more spacious than expected, with a large living area and open kitchen that made the space feel comfortable. Both beds were neatly made, and the bedding was very comfortable. We had a pleasant stay—thank you, Felipe!

4.88 out of 5 average rating, 34 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

ElezaRating, 5 stars4 days ago

Great location and space! Very clean and well equipped. Super comfortable beds as well.

4.89 out of 5 average rating, 28 reviews

A modern kitchen features sleek cabinetry in a dark hue and a clean white countertop. Stainless steel appliances, including a refrigerator and microwave, are visible along with a compact oven. Under-cabinet lighting illuminates the workspace, creating a functional cooking area.

Home in Oakville

Luxury walkout basement apartment in Oakville

OziegbeRating, 5 stars2 months ago

This is by far the best Airbnb I’ve ever stayed in. The hospitality was exceptional, and the reception was warm and welcoming. The apartment was immaculately clean, beautifully designed, and thoughtfully detailed, creating a truly comfortable atmosphere. Every corner reflected care and quality. It genuinely felt like a home away from home—I found myself wishing it were mine. I highly recommend this place to anyone seeking comfort, style, and a memorable stay