Holiday rentals in Oakville

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Top-rated holiday rentals in Oakville

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Guest favourite
The spacious living area features a comfortable gray sectional sofa with decorative pillows, facing a modern coffee table. A sleek kitchen island with pendant lighting is visible in the background, complemented by modern appliances and cabinetry.
Apartment in Oakville
4.94 out of 5 average rating, 31 reviews

Beautifully Upgraded One Bedroom and Den + Balcony

Charming 1-bedroom plus den condo located in a central area with easy walking access to major attractions. This well-appointed upgraded unit features a spacious living area, a versatile den perfect for an office or guest room, and modern amenities. Enjoy the convenience of nearby shops, dining, and entertainment options right at your doorstep. Ideal for those seeking both comfort and a vibrant urban lifestyle. Includes a dedicated underground parking spot and balcony. Fully upgraded and modern!

Guest favourite
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.
Apartment 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.

Top guest favourite
Flat in Oakville
4.92 out of 5 average rating, 78 reviews

Spacious Basement in Oakville

This spacious suite offers comfort and convenience. Nearby, you'll find Oakville Place Mall, bowling alleys, cinemas, trails, and parks. A train station and local bus services are close for travel. Grocery and convenience stores, plus a variety of restaurants are nearby. Inside, you can enjoy a fully equipped kitchen with stainless steel appliances and a sleek modern bathroom. The cozy living area is perfect for relaxation. Whether you stay for business or leisure, you will enjoy your stay!

Guest favourite
The exterior of the spacious home features a combination of red brick and stone accents, complemented by white trim. Large windows provide ample natural light, while a prominent entrance with an arched doorway invites guests inside. A well-maintained lawn surrounds the house.
Home in Oakville
4.98 out of 5 average rating, 60 reviews

Comfortable Luxury Home in Oakville

This spacious, distinctive home offers more than your average house. Consecutively rated by airbnb and guests as "Guest favourite house" Located in one of Toronto's sought-after neighbourhood, elegant and thought through furnished. It has everything you might need, living room, family room, dining, breakfast table, high-end kitchen, fibre optic internet, an office and much more. Conveniently situated near highways, grocery stores, bars, and more. Can't wait to welcome you as our guests

Superhost
Apartment in Oakville
4.86 out of 5 average rating, 44 reviews

Charming spacious townhome in Prime Oakville

Welcome to our spacious and inviting retreat! Nestled in a prime location in Oakville, this entire house offers a perfect blend of comfort and convenience. Unwind in the ample living spaces, and relish the privacy of having the entire house to yourself. With nearby attractions and a tranquil atmosphere, our Airbnb is your ideal home away from home. Explore the city by day which is 30 min drive, and return to the spacious serenity of your temporary abode by night. Your perfect getaway awaits

Guest favourite
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, 24 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 favourite
The living area is furnished with a light-colored loveseat adorned with decorative pillows. A small round glass coffee table sits centrally on a neutral area rug. A compact microwave is positioned nearby, and a slender chair is placed in the corner, complemented by natural light from the window.
Flat in West Oakville
5 out of 5 average rating, 37 reviews

*Top 5% Airbnb* Private Studio near Lake + parking

*Long-term stays are possible* ** Private Bedroom // Private Living Room // Private Dining Room // Private Bathroom** Top 1% of listings with Airbnb! Cozy Alternative to a Hotel. Premium neighbourhood close to Lake Ontario Experienced Hosts legally licensed Airbnb w/ the Town of Oakville Safe, quiet, clean, comfortable, bright & cozy Studio, recently renovated with natural light all day Fast Internet, SmartTV w/ Netflix, Amazon Free on-street parking for *1* one vehicle up to 15 days

Top guest favourite
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, 83 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 favourite
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.
Flat in Oakville
4.99 out of 5 average rating, 141 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.

Guest favourite
Flat in Oakville
5 out of 5 average rating, 15 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 favourite
The open-concept space features a circular glass dining table set for six, with stylish white chairs. The cozy living area includes a gray sofa adorned with colorful cushions, a large window providing natural light, and a modern kitchen area equipped with updated appliances.
Apartment in Oakville
4.84 out of 5 average rating, 25 reviews

King Bed, Queen Bed, Free Parking, Gym, WiFi

Well Equipped Luxury Suite Centrally Located is Perfect For Couples or Families. 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 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

Guest favourite
A comfortable living area is featured, showcasing a spacious sofa and armchair on a patterned rug. Shelves with decorative items line one wall, and natural light enters through a nearby window. A coffee table is positioned centrally, enhancing the inviting ambiance.
Flat in Oakville
4.95 out of 5 average rating, 92 reviews

Cozy Basement Apartment in Oakville

Welcome to Your Cozy Oakville Basement Apartment! Newly built, this 2 bedroom apartment holds a open-concept living room that flows into the fully-equipped kitchen, offering a cozy space to relax along with backyard area. Guests have private access through a separate entrance and independent working area. Pond facing, located in a quite neighborhood in close proximity to restaurants and grocery stores. 10-15 mins from Oakville GO Station. 25-30 mins from YYZ Airport .

Popular amenities for Oakville holiday rentals

When is the best time to visit Oakville?

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Frequently Asked Questions

  • How is the weather in Oakville?

    Oakville experiences a humid continental climate. Summers are typically warm, with temperatures around 82°F (28°C). Winters can be cold, with temperatures often around 23°F (-5°C), and are perfect for winter activities like ice skating. Fall and spring are mild and invite outdoor exploration.

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

    Oakville is a treasure trove of activities. Explore the beautiful waterfront parks, wander through the Oakville Museum, or stroll through the Royal Botanical Gardens. Don't miss the opportunity to visit the Oakville Galleries for a taste of contemporary art.

  • What is the best time of year to visit Oakville?

    Summer, from June to August, attracts many visitors to Oakville with warm weather and outdoor activities. Popular local events include the Oakville Children's Festival in July and the Downtown Oakville Jazz Festival in August, which bring a festive atmosphere to the town.

  • What are the best places to stay in Oakville?

    You can find a range of accommodation options across Oakville. Downtown Oakville, with its historic charm, shops, and eateries is a popular choice. Bronte Village, known for its waterfront views and vibrant community, is another preferred area. Kerr Village is also appealing with its art galleries and a lively dining scene.

  • What are the best places to visit in Oakville?

    Some popular places in Oakville include the Oakville Lighthouse, Bronte Heritage Waterfront Park, and Gairloch Gardens. History enthusiasts often explore the Oakville Museum, while art lovers enjoy the Oakville Galleries.

  • What are some hiking trails in Oakville?

    For hiking enthusiasts, Oakville has scenic trails. The Waterfront Trail offers stunning lake views, while the Sixteen Mile Creek Trail provides diverse landscapes. The Lions Valley Park also has a network of trails through picturesque woodland.

  • What are some family activities to do in Oakville?

    Families in Oakville can enjoy a picnic at one of the many parks, explore the interactive exhibitions at the Oakville Museum, or take a walk along the Waterfront Trail. A visit to the Bronte Creek Provincial Park, with its outdoor pool and farm, is a popular option for families.

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

    Consider a day trip to the charming town of Niagara-on-the-Lake, just 65 miles (105 km) away. You could also venture to Toronto, just 25 miles (40 km) away, for an urban adventure. Another popular option is a visit to the Royal Botanical Gardens in nearby Burlington.

  • Are there pet-friendly vacation rentals in Oakville?

    Four-legged friends are welcome in Oakville. Choose from more than 200 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Oakville?

    Yes! Work meets play with ease at over 560 vacation rentals in Oakville featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Oakville vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Oakville, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly condo rentals in Oakville?

    Oakville has more than 20 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Oakville have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Oakville. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Oakville have air conditioning?

    Absolutely! We offer over 50 condo rentals with air conditioning in Oakville. Enjoy a tailored experience with all the comforts you desire.

  • Do private suite rentals in Oakville have wifi?

    Absolutely! We offer over 40 private suite rentals with wifi in Oakville. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Oakville have a gym?

    Absolutely! We offer over 50 apartment rentals with a gym in Oakville. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in townhouse rentals in Oakville?

    Experience the best of Oakville with our townhouse rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for Bungalow Rentals in Oakville?

    Enhance your stay in our Bungalow Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Oakville

  • Total holiday rentals

    Explore 870 holiday rentals in Oakville

  • Nightly prices starting at

    Oakville holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 18,900 verified reviews to help you choose

  • Family-friendly holiday rentals

    430 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 200 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    560 properties have a dedicated workspace

  • Wifi availability

    860 of Oakville holiday rentals include wifi 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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