Vacation rentals in Oakville

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Top-rated vacation rentals in Oakville

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Guest favorite
A round glass dining table is set for four with white plates, silver cutlery, and drinking glasses. Modern white chairs surround the table. A well-equipped kitchen with stylish finishes is visible in the background, alongside a cozy living area filled with natural light.
Apartment in Oakville
4.84 out of 5 average rating, 37 reviews

Oakville Oasis - Free Parking and WiFi

Well Equipped Luxury Suite Centrally Located is Perfect For Couples or Small Groups. Quiet Neighborhood and Brand New Finishes Await You at This Urban Oasis! This Pristine Space Has an Open-Concept Kitchen/Living/Dining to Maximize Flow and Usage, and Stimulates the Creative Mind. Step Out onto the Massive Balcony to Enjoy the Outdoor Space, You Will Be Amazed at the Peace and Quiet! Wake Up and Get Cooking in a Fully Equipped Suite! -- 1 Parking and Free WiFi Included. Don't Wait, Book Today

Top guest favorite
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.
Apartment in Oakville
4.96 out of 5 average rating, 117 reviews

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

Guest favorite
A modern kitchen area features stainless steel appliances and dark wood cabinetry. An island with bar stools invites casual dining. Soft lighting is complemented by natural light streaming through a large window, with a view of greenery outside.
Condo in Oakville
4.92 out of 5 average rating, 25 reviews

1 BR Boutique Charm, Urban Calm!

Experience modern living in our boutique one-bedroom, private apartment in the heart of Oakville. This stylish 750-square-foot unit blends contemporary elegance with urban charm, offering a cozy retreat. Located in the vibrant Dundas/Trafalgar area, it includes underground parking, high-speed internet, and fully equipped kitchen and bathroom. Just steps from public transport, shops, and grocery stores, this ground-floor unit offers easy access from both inside the building and street level.

Guest favorite
A modern bedroom features a spacious bed with a grey quilt and coordinating pillows. A small nightstand is placed beside the bed. A white desk and ergonomic chair provide a work area, with natural light filtering through dual-layer window shades.
Home in Oakville
4.92 out of 5 average rating, 25 reviews

Spacious Private Suite | King Bed

Relax in a spacious, private suite in a newly built home. This modern retreat features a comfortable king bed, a walk-in closet, a private bathroom, and a office work area. A kitchenette is also available for your convenience of making light meals and drinks. Located in a great area, you'll be just minutes from shopping, dining, and grocery stores, making it easy to meet all your daily needs. Feel free to reach out with any questions about the suite or the neighbourhood—I’m happy to help!

Top guest favorite
The living area features a white, curved sofa and two black accent chairs, arranged on a patterned area rug. A modern coffee table sits in the center, while a television is mounted above a minimalist fireplace. Natural light enters through large windows adorned with blinds.
Townhouse in Oakville
4.94 out of 5 average rating, 84 reviews

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!

Top guest favorite
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.
Apartment in Oakville
4.98 out of 5 average rating, 143 reviews

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.

Top guest favorite
A private hot tub is situated on a rooftop terrace, surrounded by privacy screens. Soft lighting is positioned around the area, creating an inviting ambiance. Steam rises gently from the hot tub's surface, hinting at a warm and relaxing experience.
Home in Oakville
4.98 out of 5 average rating, 122 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!

Guest favorite
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.
Apartment in Milton
4.93 out of 5 average rating, 159 reviews

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.

Guest favorite
Apartment in Oakville
5 out of 5 average rating, 16 reviews

Feel at home

Welcome to our lovely 2-bedroom, 1-bath legal basement suite in Oakville, great for families or small groups looking for a comfortable and practical stay. It features tall ceilings and all essential amenities. Relax in the inviting living room with soft seating and a smart TV. Cook in the well-stocked kitchen with modern appliances and dine together in the cozy eating area. Rest well in the neatly arranged bedrooms. High-speed Wi-Fi and convenient driveway parking for 1 car included.

Guest favorite
A modern two-story house is set against a green backdrop, featuring large windows that allow natural light to flood the interiors. The driveway leads to an attached garage, while a neatly maintained lawn surrounds the property, enhancing its curb appeal.
Home in West Oakville
4.91 out of 5 average rating, 116 reviews

Large Luxury Villa with Swim Spa! Near downtown!

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.

Guest favorite
A living area features a mix of seating options, including a gray sofa and two green armchairs, arranged around a central coffee table. Natural light enters through two windows. A wall-mounted television is visible, alongside decorative elements like plants and wall accents.
Apartment in Oakville
4.95 out of 5 average rating, 22 reviews

Luxury & Modern 2 Bed w/Parking

Welcome to our Modern & Spacious 2 Bedroom Apartment in Oakville w/ Free Parking & High Speed Wi-Fi Open Concept, Large Windows, Modern Finishes, King Size Bed & Queen Sized Bed with Premium Linens. Modern Bathroom w/Shower. Kitchen is Fully Stocked. Smart TV & In-Suite Laundry. Can Accommodate Up To 4 People Minutes From Major Highways, GO Train & Shopping. Direct Train to Downtown Toronto in 40 Minutes Complimentary Welcome Pack Provided including Coffee, Snacks & Drinking Water

Top guest favorite
A modern living area features a large television mounted above a low wooden cabinet. A cozy armchair is draped with a patterned blanket, complementing a light rug. Decorative framed artwork adorns the wall, while curtains with a flowing design frame the window.
Condo in Oakville
5 out of 5 average rating, 24 reviews

Condo in Oakville

Peaceful and modern stay ideal for short-term rentals, vacations, or remote work. Located in a quiet, family-friendly neighborhood with high-speed Wi-Fi, smart TV, gym access, and secure on-site parking. Enjoy easy access to Canadian Tire, Walmart, grocery stores, and a variety of dining options just minutes away. Perfect for solo travelers, couples, or professionals seeking a comfortable and convenient home base. Experience a blend of relaxation and accessibility in one place.

Popular amenities for Oakville vacation rentals

When is the best time to visit Oakville?

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Frequently Asked Questions

  • What are the best places to stay in Oakville?

    Oakville has welcoming neighbourhoods such as Old Oakville, Bronte, and Kerr Village, each with a mix of historic charm and access to shops, waterfront areas, and parks. Many visitors enjoy stays that are close to the downtown core or along the lake for easy exploring.

  • What are the best things to do in Oakville with kids?

    Families in Oakville often explore local parks, playgrounds, and the waterfront trails. The Oakville Museum at Erchless Estate and indoor play centres are frequently suggested for educational fun and interactive experiences.

  • What are some of the best things to do in Oakville?

    Explore the trails and gardens at Lakeside Park, stroll vibrant Kerr Village, and visit the Oakville Museum at Erchless Estate for local history. Waterfront activities and the lively arts scene are often recommended by visitors.

  • How is the weather in Oakville?

    Oakville experiences cold winters around 20–33°F (-7–1°C) and warm summers near 65–81°F (18–27°C), with spring and autumn bringing mild temperatures. Rainfall is spread throughout the year; packing layers and a rain jacket is suggested.

  • When is the best time to visit Oakville?

    Late spring through early autumn is often recommended for mild weather and accessible outdoor activities. Summer brings warmer temperatures, frequent community events, and lively waterfront gatherings.

  • What are the best places to visit in Oakville?

    The Oakville Museum at Erchless Estate, Lakeside Park, and Bronte Harbour are frequently suggested for history, green spaces, and scenic lake views. Kerr Village is known for local shops and arts venues around the downtown area.

  • What are some hiking trails in Oakville?

    Oakville has several scenic walking and hiking trails, including the Bronte Creek Trail, Sixteen Mile Creek Trail, and paths through Lakeside Park. These trails wind through forests, meadows, and along the waterfront.

  • What are some family activities we can do in Oakville?

    Families often explore Oakville's parks, splash pads, and interactive exhibits at the local museum. Seasonal festivals, community markets, and family-friendly waterfront events are popular throughout the year.

  • What are some of the best day trip ideas from Oakville?

    Around Oakville, you can discover vibrant nearby cities, nature reserves, and regional art galleries for a full day of exploring. The Niagara region and Royal Botanical Gardens are often recommended for unique landscapes and cultural experiences.

  • Are there any pet friendly accommodations available in Oakville?

    Many Oakville stays welcome pets, especially in neighbourhoods near parks and waterfront trails like Bronte and Old Oakville. Check for listings with amenities suited for pets and easy access to outdoor spaces.

  • What are some local tips for visiting Oakville?

    Exploring Oakville’s waterfront trails early in the morning lets you enjoy quieter scenery. Support local businesses in Kerr Village, and many community events are held throughout the year—check local calendars for festive happenings.

  • What is Oakville known for?

    Oakville is known for its extensive waterfront, green parks, and its lively arts and cultural community. The downtown area blends historic architecture, local shops, and galleries with a relaxed, welcoming atmosphere.

  • What are the best hidden gems to explore in Oakville?

    Visitors often mention Gairloch Gardens for its art gallery and landscaped grounds, and hidden paths along Sixteen Mile Creek Trail. Smaller independent cafés and boutique shops in Kerr Village add to the distinct local character.

  • What are the best foods to try in Oakville?

    Oakville’s dining scene features locally sourced seafood, seasonal Canadian ingredients, and diverse global cuisines. Bakery treats, fresh lake fish, and handcrafted coffees are often enjoyed by visitors exploring downtown and Kerr Village.

  • What should I bring for a trip to Oakville?

    Pack layers for changing weather, including a rain jacket and comfortable walking shoes for exploring trails. A reusable water bottle and sunscreen are useful for outdoor activities, especially during spring and summer.

  • What is the nightlife in Oakville like?

    Oakville’s nightlife centers around local pubs, cozy wine bars, and live music venues in downtown and Kerr Village. Many visitors enjoy relaxed evenings with art spaces, cafes, and performances creating a welcoming community feel.

  • What are the most popular events or festivals in Oakville?

    Oakville has a variety of community festivals throughout the year, such as summer celebrations focused on food, arts, and live music. Cultural events often take place around Labor Day weekend, drawing visitors to explore local traditions and performances.

  • Are there family friendly vacation rentals in Oakville?

    Oakville has many family friendly rentals in neighbourhoods near parks, playgrounds, and the waterfront. Look for stays in Bronte, Old Oakville, or around Kerr Village for convenient access to family activities.

Quick stats about vacation rentals in Oakville

  • Total vacation rentals

    Explore 870 vacation rentals in Oakville

  • Nightly prices starting at

    Oakville vacation rentals start at € 8 per night before taxes and fees

  • Verified guest reviews

    Over 18,900 verified reviews to help you choose

  • Family-friendly vacation rentals

    430 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 200 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    560 properties have a dedicated workspace

  • Wi-Fi availability

    860 of Oakville vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Oakville rentals

  • 4.7 Average rating

    Oakville stays receive an average rating of 4.7 out of 5 from guests

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