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!

Value · Location · Nearby

California Chic +Breathe +Unwind +Restore

Enter through the grand foyer with a winding staircase, pass the kitchen, and step into the relaxing backyard featuring an in-ground, diamond-shaped, solar-heated swimming pool and a stunning lake. The view of the lake is beautiful! The area is quiet and scenic, with the soothing sounds of the lake lulling you to sleep. You are just 30 minutes away from Niagara Falls and 1 hour from Toronto. On a clear day, you can even see the Toronto skyline. It's the perfect place for a group or family of 9.

Family · Value · Nearby

Comfortable Luxury Home in Oakville

This spacious, distinctive home offers more than your average house. Consecutively rated by airbnb and guests as "Guest favourite house" Located in one of Toronto's sought-after neighbourhood, elegant and thought through furnished. It has everything you might need, living room, family room, dining, breakfast table, high-end kitchen, fibre optic internet, an office and much more. Conveniently situated near highways, grocery stores, bars, and more. Can't wait to welcome you as our guests

Location · Family · Hospitality

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.

Location · Family · Pool

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!

Value · Family · Check-in

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.

Location · Family · Bathroom

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 · Location · Nearby

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 :)

Location · Family · Bathroom

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.

Location · Family · Indoor spaces

Spacious, Pet Friendly Basement Apartment

Quiet, pet-friendly private basement suite designed for comfort and easy stays. Features a queen bed, sofa bed, fully equipped kitchen, dining area, in-suite laundry, free Wi-Fi, and complimentary coffee & tea. Guests enjoy a shared backyard with a seasonal pool and barbecue in summer. Loved for its privacy and comfort while being steps from a park, grocery store, pharmacy, bank, and nearby restaurants—perfect for short or extended stays.

Location · Value · Comfort

2,800 Sq Ft Oakville Executive Home | 4BR 4BA

Elegant 4 bed, 4 bath 2,800 sq ft home with parking for 4 cars, large laundry, beautiful deck, and a spacious gourmet kitchen with coffee stations. Main-floor office converts to a bedroom, perfect for guests with mobility needs. Minutes from Oakville’s scenic waterfront trails, Gairloch Gardens, Bronte Creek Park, Kerr Village cafés, fine dining, boutique shops, and the Oakville Centre for the Performing Arts.

Family · Value · Air conditioning

Luxurious 5BR Beach House with Firepit

Spatious and luxirious house by the beach has 5 bedrooms with a large comfy sectional, enough to sleep 10 guests total. Our kitchen is fully stocked with everything you need to make grand dinners. We have a beautiful long custom designed dining table for memorable family gatherings. Enjoy serene views of the lake on our large furnished deck, where there is a large BBQ, dining area, sofa, and fire table.

Location · Family · Biking