House holiday rentals in Oakville

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!

Stunning Home on Lake Ontario

Welcome to this cozy lakeside getaway on the shores of Lake Ontario - a beautifully updated modern bungalow/cottage designed for comfort, relaxation with a bright open-concept living, dining, and kitchen. Enjoy breathtaking sunrise and stunning sunset views from the lakeside patio. Located near Fifty Point Conservation Area, an 80-hectare park with marina, as well as water park, Costco, and dinning options. Enjoy free unlimited high-speed internet and a Smart TV for a comfortable stay.

Luxurious & Modern Home in Oakville - Sleeps 12

In this equisite Oakville home, luxury meets comfort in every detail. The stunning home has been designer curated & is tailored to provide an unforgettable stay. ✨ Spacious 5BR with 5.5 bath 🛏️ Sleeps 10+ | 2 Kings, 2 Queens, 1 Double & 1 Sofa Bed ⚡ 1.5 Gbps Wi-Fi + Dedicated Office 📺 75" & 82" Smart TVs for ultimate downtime 🚗 Free 2-car parking; EV Charging available for your convenience 🛍️ 5 mins - 403/407/QEW, Walmart, Longo’s, Starbucks ✨Welcome families, groups & extended stay

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.

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!

Luxurious 4 Bedroom home.

Situated in Oakville, Ontario and backing onto natural green space, the interior of this contemporary home is lavished in natural light and enhanced with panoramic views of sunsets. Located between Toronto and Niagara Falls, this home also offers the combination of convenient access to urban amenities and an array of outdoor attractions for sightseeing, exploration and adventure. A perfect retreat for groups and families seeking comfort, relaxation and roomy collaborative spaces.

Maia's cozy Bronte cottage by the Lake

Take it easy at this unique and tranquil getaway. Cute and cozy, secluded 3 bedroom bungalow on quiet private street in the heart of Bronte Village. 6 minute walking distance to the lake and all amenities including restaurants, cafe's, parks, and incredible walking trails. Convenient highway access to the QEW, 407 and GO train station nearby. Enjoy the local golf courses, heritage parks with easy access to Toronto, Niagara Falls and Pearson Airport from this centralized location.

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

Family Home | Uptown Oakville | 40 Mins to Toronto

If you're looking for a stylish and comfortable home-away-from-home experience, you've come to the right place! We're in the heart of uptown Oakville, close to tons of restaurants, grocery stores, coffee shops and salons. 10mins to Oakville Place, 6mins to Sheridan College and 5mins to the 5-Drive In - an outdoor drive-in theatre perfect for family outings or date night! Our home is fully equipped with everything you need for a comfortable stay. We think you'll love it here :)

Spacious 2 BR apartment | Glen Eden Ski

Escape to our cozy 2-bedroom basement apartment, minutes from Milton’s downtown, 500m from No Frills, and just a 10-minute drive to Toronto Premium Outlets. Perfect for travelers, this inviting retreat is close to both nature and city attractions. Explore nearby Glen Eden Ski Resort and Rattlesnake Point Conservation Area, or enjoy easy access to Oakville, Burlington, Mississauga, and Toronto. Ideal for work or leisure, it offers the perfect mix of comfort and convenience.

Exclusive Luxury Townhouse - Prime Location

Welcome to the perfect getaway! Nestled in a family-friendly, centrally-located neighbourhood just 25 minutes from the entertainment & action of downtown Toronto and under an hour away from the vineyards & majestic falls in Niagara. Whether you're 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, this spacious and modern townhouse is sure to be a highlight!

Stylish 4BR Townhome•with Parking•NearGO•30 min DT

Refined 4-bedroom, 3.5-bath townhouse in upscale Oakville, just 30 minutes from downtown Toronto. Thoughtfully designed across multiple levels with bright open-concept living, a modern kitchen, spacious bedrooms, fast Wi-Fi, smart-home features, laundry, and garage parking. Located in a quiet family-friendly community near parks, trails, shopping, restaurants, highways, and GO Transit — ideal for families, groups, business, and extended stays.