House holiday rentals in Oakville

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Top-rated house rentals in Oakville

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

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Top guest favourite
A bright kitchen is highlighted by clean white cabinetry and open shelving displaying dishware. A central island provides seating for four, with a fruit bowl and a potted orchid as decorative accents. Natural light enters through a window overlooking a landscaped area.
Home in Port Dalhousie
4.99 out of 5 average rating, 177 reviews

Christie St. Coach House

Located steps from Lake Ontario you will find peace and quiet at the Coach House. One of the best streets to view the sunset over Lake Ontario! A short 10min walk to Port Dalhousie business district and Lakeside Park Beach. Find all you need to eat and drink at several restaurants and cafés. Quick access to the QEW and 406 highways. Centrally located between the Wine Regions of Niagara-on-the-lake and The Bench. 15mins East or West will find you at most Niagara Wineries. Licence No: 23112230 STR

Guest favourite
Home in Oakville
4.93 out of 5 average rating, 115 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!

Top guest favourite
Home in Oakville
5 out of 5 average rating, 21 reviews

Luxurious Ravine 3 BR Town Home

Wake up to peaceful ravine views in this bright, modern home just 10 minutes from 3 major highways (403, QEW, 407), Lakeshore, and the GO train station with trains to Toronto all day. Enjoy a quiet, safe neighborhood near grocery stores, cafés, and restaurants. Features include a fully equipped kitchen with an induction range, 75" SmartTV, fast Wi-Fi, and a dedicated home office with dual 4K monitors and a Herman Miller chair. Making our home the perfect space for both work and relaxation.

Top guest favourite
A dining table is elegantly set with two decorative plates, glasses of varying sizes, and utensils arranged symmetrically. A soft glow is provided by a small candle flickering in a metallic holder, creating a subtle ambiance for mealtime.
Home in Vaughan
4.99 out of 5 average rating, 404 reviews

Quiet Vaughan Retreat near Wonderland & Hwy 400

Enjoy a stylish and peaceful stay at this centrally located one-bedroom lower-level unit, perfect for both leisure and business travelers. With your private entrance, parking, and all the essentials, it’s your ideal home away from home. Features include a full kitchen, bathroom, internet, smart TV, one Queen and one sofa bed, and a functional workspace. Steps from FreshCo, Walmart, restaurants, and services. Minutes to Vaughan Mills, Canada’s Wonderland, Cortellucci Hospital and transit.

Guest favourite
A charming two-story detached home is framed by well-maintained greenery and colorful flowerbeds. A paved driveway leads up to the garage, with light brick finishes on the exterior contrasting against the blue sky. The inviting entrance is accentuated by potted plants.
Home in Clearview
4.89 out of 5 average rating, 180 reviews

3Bd 2.5Bth House w/ Pool Table, Swing, Outdoor BBQ

Bring your friends and family to this family-friendly, centrally-located neighbourhood with lots of room for fun and find a home away from home during the travelling. Enjoy your stay in this licensed short-term accommodation for a modern, luxurious, and spacious three-bedroom and two-bathroom detached home with a huge backyard: watching a movie and cozying up by the fire, enjoying the company of friends and family seated around the dining table, or simply in between moving or renovations.

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
4.98 out of 5 average rating, 130 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 favourite
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
4.89 out of 5 average rating, 130 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.

Top guest favourite
A comfortable living area features a blue sectional sofa adorned with decorative pillows. A wooden coffee table sits in front, complemented by a potted orchid and a bottle of wine. A gallery wall with artwork adds personal touches alongside a bookshelf filled with curated decor.
Home in Niagara-on-the-Lake
4.98 out of 5 average rating, 140 reviews

Enchanted Creekside Cottage in NOTL

Welcome to Enchanted Creekside House! Our tranquil cottage is nestled alongside a creek, offering the perfect location for a peaceful family getaway. Enjoy the serene beauty of nature while still being just a short 9-minute drive from the heart of Niagara-on-the-Lake, where you can explore charming shops, restaurants, and a variety of wineries. Enchanted Creekside House is the perfect home base. Whether you're looking to unwind and recharge, or seeking adventure and exploration!

Guest favourite
An open-concept living area features a light-colored sofa and a chic coffee table, complemented by a neutral rug. A staircase leads to the upper floor, while a dining area is visible in the background near large windows allowing natural light.
Home in West Deane Park
4.91 out of 5 average rating, 123 reviews

Luxury Home - 5 min from airport, 15 to downtown

The stunning house in Etobicoke is only a few minutes from the Airport and City Centre. This spacious open concept, rare luxury modern home, is beautifully designed and decorated. It is a fully stocked home and will have everything you could ever wish for a short-term stay. Perfect for large families and groups! min age 25 yrs to book. Room 1 king bed Room 2 queen Room 3 twin and another twin roll out Room 4 queen no party policy or excessive noise. this is a quiet listing

Top guest favourite
Home in Port Dalhousie
4.96 out of 5 average rating, 313 reviews

Lux Lake Ont Beachfront - Fire Pit & Sunset Views

License 23 110691 STR. Enjoy extraordinary sunsets and views of Lake Ontario and the Toronto Skyline while sitting in comfortable Muskoka chairs around a fire pit, enjoying a cup of coffee or a glass of wine. My home offers high-speed internet, multiple Smart HD TVs, indoor fireplace, 2 outdoor fire pits, and a large backyard with stairs leading to a Private Beach. Just a short walk to Lakeside Beach, downtown Port Dalhousie, and a short drive to Niagara wineries!

Top guest favourite
A hot tub is positioned on a deck overlooking a calm, expansive lake. The water reflects soft gray skies, creating a serene atmosphere. Rocky shoreline is visible in the foreground, enhancing the tranquil lakeside setting.
Home in Hamilton
4.94 out of 5 average rating, 102 reviews

Wake Up To Lake Views!

Licence #26-000115. Book now! Bring your whole family to the lake! Need a relaxing weekend? Family Get togethers, Girl’s Trip! Guy’s weekend! Couple’s getaway! Go for a hike, a wine tour, cozy up with friends. Welcome to a beautiful, spacious Lake House. Located 20 min from the wineries in Niagara-on-the-lake, the waterfront trail 5 minutes away. Bring your bikes for a ride along the lake and a local lunch. This property has 180 degree lake views.

Top guest favourite
The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.
Home in The Beaches
4.99 out of 5 average rating, 177 reviews

Luxury 4BR Oasis: Year Round Heated Pool & Hot Tub

A Private Luxury Getaway in Toronto’s Most Coveted Neighbourhood Escape to an extraordinary 4-bedroom luxury home in Toronto’s iconic Beaches, where sophisticated design meets relaxed lakeside living. This top 1% rated Airbnb property offers an unforgettable weekend experience—perfect for families, couples, or a curated group of friends seeking both comfort and wow-factor. A year round private heated pool and hot tub are yours to enjoy !

Popular amenities for house rentals in Oakville

When is the best time to visit Oakville?

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Avg. price$115 SGD$126 SGD$118 SGD$116 SGD$145 SGD$160 SGD$160 SGD$167 SGD$146 SGD$144 SGD$130 SGD$155 SGD
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Quick stats about house rentals in Oakville

  • Total holiday rentals

    Explore 470 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 10,130 verified reviews to help you choose

  • Family-friendly holiday rentals

    250 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 110 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    300 properties have a dedicated workspace

  • Wifi availability

    460 of Oakville holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oakville rentals

  • 4.8 Average rating

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

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