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

4.94 out of 5 average rating, 65 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!

A rooftop terrace features a private hot tub under soft ambient lighting and a spacious wooden deck. A rectangular dining table surrounded by four woven chairs offers a place to relax. Dark fence panels create privacy, complemented by gently glowing string lights overhead.

4.98 out of 5 average rating, 108 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!

Superhost

4.88 out of 5 average rating, 104 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.

4.87 out of 5 average rating, 45 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.

4.98 out of 5 average rating, 377 reviews

A clawfoot tub is positioned prominently in the bathroom, complemented by a pedestal sink and a mirror above it. Exposed brick accents provide a rustic backdrop, while a washer and dryer are neatly stacked beside the sink, adding modern convenience to the vintage space.

Apartment in Hamilton

Vintage Dreams | Mid-Century Design in artsy area

Love is in the details, so we know you’re going to fall madly in love with The Aberdeen. This mid-century gem is dripping with style, comfort and touches that'll make you feel like it was designed just for you. Whether you have plans to stay in and dance barefoot to the record player or cuddle up on the couch to write a bestseller, one thing is sure - the creative vintage vibes of the space, the private outdoor courtyard and the eclectic neighbourhood will leave you inspired.

4.96 out of 5 average rating, 1,028 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.

4.96 out of 5 average rating, 135 reviews

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.

Villa in Aldershot

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.

4.97 out of 5 average rating, 273 reviews

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.

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.

4.97 out of 5 average rating, 100 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.

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!

Vacation rentals for every style

Get the amount of space that is right for you

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Popular amenities for Oakville vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Oakville

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

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!

4.9 out of 5 average rating, 83 reviews

Condo in Oakville

LUXURY CONDO, GREAT DECOR, WHEELCHAIR FRIENDLY!!!

MaggieRating, 5 stars1 week ago

Great host and her space is amazing.

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 stars2 days ago

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

A modern kitchen countertop displays a sleek Nespresso machine accompanied by two white coffee cups. Above, glass-front cabinets reveal an arrangement of glassware. The backsplash features hexagonal tiles with a subtle pattern, and a small plant adds a touch of greenery.

5 out of 5 average rating, 33 reviews

Cozy & Beautiful, Entire Oakville House,

ErinRating, 5 stars1 month ago

We had a great stay. The house was well organized and prepared for our arrival. The host was very detailed and responsive once we made the initial contact and throughout the process. The communication was excellent and the house is very well taken care of in terms of cleanliness and the layout. We would definitely stay again in the future.

A modern dining area is showcased with a wooden table set for four, featuring textured gray chairs. A stylish light fixture hangs above, and a staircase leads to the upper level. Natural light floods in through large windows, complementing the warm tones of the hardwood floor.

4.99 out of 5 average rating, 78 reviews

Exclusive Luxury Townhouse - Prime Location

StephanieRating, 5 stars1 month ago

Super clean and beautiful stay. The host was super responsive and there was plenty of space for me, my bridesmaids, makeup team, and family the morning of my wedding day as we were getting ready.

A spacious living area features a contemporary all-leather reclining sofa and a light-colored accent chair. Natural light floods the room through large windows. A coffee table sits atop a plush area rug, while a decorative plant adds a touch of greenery in the corner.

4.94 out of 5 average rating, 32 reviews

Luxurious Prince Mansion

SharadRating, 5 stars1 month ago

Honestly, this house was well worth the cost. I would have preferred unattended checkin (mostly because we arrived so late and I felt bad for Aziz!) but he was punctual and didn't complain a whit about the hour. The shower was so fancy (3 showerheads, 4 knobs!) that it likely would have taken me another day to fully figure out all the permutations. The house overall was exquisite, from furnishing to location, we couldn't have asked for more. There were a host of restrictions about "partying" but honestly this was a family trip and not a concern for us. The family still enjoyed the hot tub until 1am while older members of the group went off to a perfectly peaceful sleep before 10pm. There was room enough for everyone to have their own way and plenty of spaces in which to come together.

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.