House holiday rentals in Oakville

Family-Ready 4BR | Close to Trails, Shops & More

Welcome to your home away from home in Oakville! This stylish 4-bedroom, 4-bathroom retreat is perfect for families, professionals, or long-term guests. Enjoy soaring ceilings, hardwood floors, and a fully equipped chef’s kitchen — ideal for cooking and entertaining. Located in a family-friendly neighborhood just minutes from highways (403/407), parks, shopping, and dining. Whether it’s a weekend getaway, family trip, or extended stay, this home offers comfort, convenience, and a warm welcome.

Private Walk Out Garden Apartment With Patio

Welcome to your spacious, private walk-out garden apartment! Relax comfortably with a king-size bed, plus a pull-out queen sofa bed accommodating two extra guests. Enjoy a full bathroom featuring a luxurious jacuzzi whirlpool. Amenities include a fully-equipped kitchen, spacious lounge with fireplace, central heating, and a large mirrored closet. Close to shopping & Ridgeway Food Plaza, transit, highways 401 & 403,UTM, Square One, and Oakville.Perfect for family getaways or peaceful retreats

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.

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 Prince Mansion

Enjoy royal-class living in South Oakville with exceptional amenities and furnishings! The almost 5,700 sq. ft living area has been beautifully furnished to maximize entertainment and comfort for up to 10 guests. The home features 5 bedrooms each with their own bathroom. Amenities include a 6-person hot tub usable year-round, a high-end BBQ, a home theatre with a 4K projector, 130-inch cinema scope screen and 5.1 surround sound audio, and a standard-size pool table. License Number: 23-124896

Stylish 1870s Home near Distillery District & Old Toronto

Visiting for fifa? Stop here...Steps from the Distillery District downtown, this Top rated listing is a beautifully restored 1870s row-house (townhouse) that blends historic charm with modern refinement. Thoughtfully designed throughout, it’s located downtown also close to St. Lawrence Market, and some of the city’s best cafés and restaurants. In the evening, unwind in the serene, charcoal-toned bedroom beneath the warm glow of a statement chandelier—your refined Toronto retreat awaits

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.

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!

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.

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