Holiday rentals in Oakville

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Quick stats about holiday rentals in Oakville

  • Total holiday rentals

    Explore 860 holiday rentals in Oakville

  • Nightly prices starting at

    Oakville holiday rentals start at £7 per night before taxes and fees

  • Verified guest reviews

    Over 18,540 verified reviews to help you choose

  • Family-friendly holiday rentals

    400 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

    550 properties have a dedicated workspace

  • Wifi availability

    850 of Oakville holiday rentals include wifi access

  • Popular amenities for guests

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

  • 4.8 Average rating

    Oakville stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated holiday rentals in Oakville

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A comfortable living area is presented with a dark coffee table and two blue couches adorned with patterned throw pillows. Light blue curtains frame the windows, and a large flat-screen TV is positioned on a black TV stand against the wall.
Guest suite in Oakville
4.8 out of 5 average rating, 149 reviews

New Studio Unit with Full kitchen in Oakville

This is a 500 square feet Studio unit at the ground level of town house with full kitchen, Full Washroom big screen smart TV, internet and one parking. Nothing is shared, separate entrance to the unitKitchen has utensils, kettle and toaster. All the major stores are under 3 kms. The house situated in the border of Oakville and Mississauga. Just 30 minutes to Toronto and 60 minutes to Niagara. Very clean and brand new place for your stay.Enjoy your stay at this place in a relaxing private space.

Guest favourite
Dome in Burlington
4.96 out of 5 average rating, 257 reviews

Jungle Dome on a Farm! Animal Lovers Dream!

Jungle Dome Farm Stay in Burlington! Be completely immersed in farm life and all that it entails while staying in our 500 square foot geodesic dome “glamping” greenhouse dwelling! Complete with a fish and turtle pond and filled to the brim with tropical plants! Designed as a tropical vacation getaway when you can’t get away to the tropics! Situated on a 5 acre animal farm where guests can experience farm life with goats, horses, highland cows, sheep, pigs and poultry. An Animal Lovers Dream!

Top guest favourite
Home in Oakville
4.93 out of 5 average rating, 126 reviews

Sun-kissed 3BR family home in a quiet neighborhood

♡ The fastest internet w/ 1Gb download speed ♡ Fully Equipped Kitchen ♡ minutes drive to Sheridan college, Walmart, Oakville Place, lakeshore ♡ 7 min. drive to Trafalgar GO Station, 20 min. to Toronto premium outlets 25 min. to Pearson airport 30 min. to Toronto downtown ♡ Walking distance to convenient store, trails, food, bus stop, library. ♡ Free Parking ( 2 Spots) ♡ Automated Check in & Check Out ♡ Flexible Check in Check out - Message for Details ♡ A/C ♡ Laundry ❤ Book today!

Superhost
The exterior of a mid-century modern home is presented, featuring a brick facade with large front windows. Lush greenery surrounds the house, and a spacious lawn enhances the serene atmosphere. Mature trees are visible in the background, contributing to the natural setting.
Home in Oakville
4.75 out of 5 average rating, 8 reviews

Serene Mid-Century Home, Ravine & Lake Access

Escape to this serene Oakville retreat and leave your worries behind. This exceptional mid-century modern home on prestigious Lakeshore Road features a unique split-level design, soaring vaulted ceilings, and a warm cottage-like atmosphere. Nestled on a spacious ravine lot surrounded by nature, it’s ideal for families and groups seeking relaxation. Just 5 minute walk to the lake, with easy access to parks, trails, restaurants, shops, and local attractions. Peaceful, stylish, and unforgettable.

Top guest favourite
Townhouse in Oakville
5 out of 5 average rating, 30 reviews

Opulent Chic Town Home in the Heart of Oakville

Welcome to your chic getaway in the heart of Oakville! This opulent townhome is perfect for families, business travelers and friends. Relax in the spacious living room, cook your favorites or unwind on the patio. Fast Food & Grocery stores a short walk away & easy access to highways 403, 401 & 407. -McDonalds, Subway, Tim Hortons, Popeyes: 5 mins walk -Superstore, Walmart, LCBO: 5 mins drive -GO Station: 12 mins drive -Toronto Premium Outlet: 15 mins drive Your perfect stay awaits!

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, 166 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 favourite
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
4.99 out of 5 average rating, 136 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
A modern living area is showcased with large windows, allowing natural light to fill the space. A colorful yellow sofa and blue chairs provide seating. An entertainment unit features a television against a vibrant mural of cacti. Wooden flooring adds warmth to the contemporary design.
Hotel room in Hamilton
4.78 out of 5 average rating, 385 reviews

Fully-Furnished Boutique 1 Bedroom Suites

The Laundry Rooms is situated on one of our favourite streets in Hamilton. Featuring cozy pubs, local coffee shops, and a 10-minute walk from the downtown core, Augusta Street has a small-town vibe in the heart of the city. Live like a local with all the comforts and amenities of home in our contemporary suites designed for the professional traveller. Pets are welcome and we can't wait to meet your dog (a deep cleaning fee applies (except for assistance animals))... and you, of course.

Guest favourite
Flat in Oakville
4.82 out of 5 average rating, 68 reviews

Oakville 2BR: Central, Comfy & Close to Everything

Enjoy the convenience of a central Oakville location perfect for families. You’ll be close to everything, including the Waltmar Superstore, Shoppers, Oakville Place, and Toronto Premium Outlets. With easy access to three major highways, public transportation, and the train station, getting around is a breeze. Plus, the nearby hospital offers extra peace of mind. This modern 2-bedroom space is thoughtfully designed for comfort, making it the ideal home base for your Oakville visit.

Superhost
A stylish living area features a comfortable gray sectional sofa adorned with colorful cushions. A round coffee table sits at the center, and a television is positioned on a white console. Large sliding doors provide access to an enclosed balcony with views of the surrounding area.
Flat in Oakville
4.85 out of 5 average rating, 78 reviews

Spacious Urban Oasis:Stylish 2 Bed, 2 Bath Getaway

Welcome to our spacious and stylish property. This is a spacious (>900 sq ft) and modern 2-bedroom, 2-bathroom condo, perfectly nestled in the picturesque town of Oakville, Ontario. Ideal for families, couples, or small groups, this condo promises a comfortable and unforgettable stay. Don't miss the opportunity to experience the best of Oakville and Toronto from the comfort of this stylish condo. Book your stay and create lasting memories! We look forward to hosting you.

Top guest favourite
Guest suite in Hamilton
5 out of 5 average rating, 72 reviews

Summertime! Steam shower+breakfast+rooftop hottub

Nestled in a picturesque escarpment community overlooking the historic town of Dundas, The Hayloft is a charming getaway for anyone looking for an escape and a breath of fresh air. Relax in the steam shower inside or the hot tub on the fully private rooftop deck overlooking gardens. Take a nap on the lounge chairs. Visit with the chickens, make friends with the fish or the frogs. Unwind at night with a movie in bed, with breakfast (surcharge) in the morning.

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
4.78 out of 5 average rating, 157 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

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 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.

  • 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.

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