Holiday rentals in Oakville

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Top-rated holiday rentals in Oakville

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Guest favourite
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.
Flat in Oakville
4.85 out of 5 average rating, 40 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 favourite
The exterior of a two-level apartment is shown, featuring a wooden deck accessible by stairs. A light brick facade complements large windows, while potted flowers add color to the entrance. Surrounding greenery enhances the inviting atmosphere of the building.
Flat in Mississauga
4.97 out of 5 average rating, 112 reviews

Cozy apartment with Free Parking !

Centrally located prime location near buss, highway, parks, shopping, groceries, restaurants and movie theater. Minutes from major highway QEW, 35 min drive to Toronto and Airport. It is spacious, 2 level split apartment. Washroom and bedroom on the upper level. TV & Kitchen on the lower level. Kitchen is equipped with fridge, pots, microwave, toaster, air fryer, utensils, coffee maker. Smart TV, Netflix, Wifi, Parking, Private lawndry are all included. Not permitted: pets, smoking, parties.

Top 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, 34 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!

Top guest favourite
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.
Flat in Oakville
4.96 out of 5 average rating, 122 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

Superhost
Apartment in Oakville
4.87 out of 5 average rating, 47 reviews

Modern 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
4.93 out of 5 average rating, 28 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
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
4.98 out of 5 average rating, 150 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.

Superhost
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
4.91 out of 5 average rating, 98 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 .

Guest favourite
The open-concept living area features a fully equipped kitchen with modern appliances and a dining nook. A sofa bed offers extra seating and sleeping space. Large windows provide ample natural light and views, while the private balcony is designed for outdoor relaxation.
Apartment in Oakville
5 out of 5 average rating, 18 reviews

Stylish Oakville Condo to call home

Welcome to your stylish home away from home in the heart of Oakville! This modern 1 bed, 1 bath condo at Dundas & Trafalgar offers comfort and convenience in a vibrant neighborhood. Enjoy a fully equipped kitchen, cozy living space, in-suite laundry, and a private balcony. Steps from shops, restaurants, parks, and transit, it’s perfect for solo travelers, couples, or business guests. Experience Oakville’s charm with easy access to Toronto and local attractions.

Top guest favourite
Flat in Oakville
5 out of 5 average rating, 17 reviews

Entire basement apartment with separate entrance

Welcome to our lovely private basement apartment in beautiful Oakville — just 45 minutes from downtown Toronto and 35 minutes from Pearson Airport. The home is conveniently located near Oakville Trafalgar Hospital and several shopping plazas. Enjoy a newly furnished one-bedroom basement apartment with a private entrance and self check-in for your convenience. The unit is clean, bright, and fully equipped for both short and extended stays.

Guest favourite
A modern kitchen features sleek white cabinetry and a large island with seating for four. Stainless steel appliances are visible, including a refrigerator and microwave. Bright lighting fixtures hang above the island, and a small green plant adds a touch of freshness to the countertop.
Home in Oakville
4.96 out of 5 average rating, 122 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.

Guest favourite
Apartment in Glen Abbey
4.9 out of 5 average rating, 118 reviews

Cozy Oakville Oasis | Modern & Peaceful Stay

Enjoy a peaceful stay in this stylish apartment near Saw Whet Golf Club and beautiful Bronte Creek Provincial Park. 3 min from the QEW, Bright, open-concept living space, full kitchen, private balcony, high-speed WiFi, and free parking. Just a short drive to Bronte Village with its waterfront trails, cafes, and shops. Ideal for couples, solo travelers, or business guests seeking comfort and convenience in Oakville.

Popular amenities for Oakville holiday 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 holiday rentals in Oakville

  • Total holiday rentals

    Explore 890 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 19,610 verified reviews to help you choose

  • Family-friendly holiday rentals

    450 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 210 rentals that welcome pets

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    570 properties have a dedicated workspace

  • Wifi availability

    880 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

Destinations to explore

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