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
4.84 out of 5 average rating, 38 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

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, 109 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.

Guest favourite
The image captures a compact bedroom featuring a spacious bed dressed in a patterned burgundy cover. A comfortable rocking chair sits beside the bed. In the background, light filters through a window covered with sheer curtains, and wooden cabinetry offers additional storage.
Home in North York
4.83 out of 5 average rating, 12 reviews

Private Bedroom, Bathroom, Kitchen -Basement Apt

Take a break and unwind at this peaceful oasis. This is a rare gem as the bedroom, bathroom and kitchen are all private, for an affordable price. It is very simple and some of our personal belongings are in the space but we keep the price low to make up for it. Most rentals in this area of Toronto have shared bathroom or kitchen or are very expensive. Within walking distance to Parkway Mall. 5 minute drive to the 401 or DVP which will take you to downtown Toronto in 25 minutes (if no traffic).

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, 26 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.

Superhost
Apartment in Oakville
4.87 out of 5 average rating, 46 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
4.92 out of 5 average rating, 26 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, 38 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
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, 144 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
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
4.93 out of 5 average rating, 96 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 .

Superhost
A modern studio space is captured featuring a cozy bed adorned with white linen and decorative pillows. A sleek stainless steel refrigerator is positioned nearby, alongside a small wooden table with a potted plant. Natural light filters through a window, enhancing the inviting atmosphere.
Flat in Oakville
4.8 out of 5 average rating, 142 reviews

Cozy Modern Studio in Oakville | Free Parking

Welcome to your perfect retreat - an oasis for 1-2 guests seeking ultimate comfort. Enjoy seamless connectivity with WiFi, Netflix, and a luxurious Queen bed. Experience the essence of home in our inviting, modern basement studio. With a full kitchenette, in-unit laundry, and lots of storage. This modern unit is ideally situated in a serene, safe neighborhood in Oakville, steps from public transit, close to various amenities like restaurants, malls and trails

Superhost
Flat in Oakville
5 out of 5 average rating, 3 reviews

Unbeatable Location-Upscale 1 Bedroom-Free Parking

A beautiful brand-new 1-bedroom, ideally located in Upper Joshua Creek, right between Oakville and Mississauga. Just 30 minutes to downtown Toronto. This modern condo has a large balcony with a beautiful unobstructed views. The building offers incredible amenities like a rooftop terrace, fitness studio and stylish lounge. A CAD150 refundable Key Security Deposit will be collected upon booking. Guests are required to show a photo ID card upon check-in.

Top guest favourite
Flat in Oakville
5 out of 5 average rating, 14 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.

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 € 9 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

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