Holiday rentals in Oakville

Debonair Home near Downtown Oakville

Discover our delightful 2-bedroom basement apartment featuring a private entrance, ideally situated near downtown Oakville. Tucked away on a tranquil, tree-lined street, this inviting haven seamlessly combines comfort with convenience. Steps from the following (walking times): - Forster Park (splash pad, playground, basketball ball and tennis court) - 4 min - Kerr Street Village - 8 min - Food Basics - 15 min - Shopper's Drug Mark - 16 min - Downtown Oakville and Waterfront Trail - 20 min

Modern 4-Bed Townhome with Cinema & Roof Terrace

Stylish contemporary brand new townhome in Oakville! The perfect retreat for families, and friends alike. You'll love the stunning home theatre with a 115" screen and Kef 5.1 sound system. Spacious areas, fully equipped kitchen, and 4 comfortable bedrooms. Relaxing Massage Chair for your use! Experience the rooftop terrace! It's the perfect spot to unwind after a long day of sightseeing or to enjoy an evening under the stars. Close to Three Major Highways 403/407/QEW in a Central Location!

Modern Urban Retreat with Smart Tech & Pond Views

Experience urban luxury in this modern 1-bed + den, 1-bath, 700 sqft condo. With high-end finishes and contemporary furniture, this stylish retreat offers comfort, convenience and safety. This unit features smart technology for enhanced safety, upgraded interior, and a private balcony overlooking a serene pond. Enjoy proximity to parks, schools, groceries stores, resteraunts, cofee shops and much more. Easy access to public transit and free local parking. Enjoy a tranquil yet connected stay!

Luxury Villa! Swim Spa! 6 Bedroom 3 Family Rooms

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.

Cozy Basement Apartment in Oakville

Welcome to Your Cozy Oakville Basement Apartment! Newly built, this 2 bedroom apartment holds a open-concept living room that flows into the fully-equipped kitchen, offering a cozy space to relax along with backyard area. Guests have private access through a separate entrance and independent working area. Pond facing, located in a quite neighborhood in close proximity to restaurants and grocery stores. 10-15 mins from Oakville GO Station. 25-30 mins from YYZ Airport .

Waterfront Coach House Loft

This friendly, private open concept loft apartment is located on the top floor of a guest coach house located on a 2 acre waterfront estate. The loft apartment is a separate building from the main house. There is a maximum occupancy for the loft of 2 people, parties, get togethers and events are not permitted. Due to the tall spiral staircase, children are not permitted due to safety. Extra charges will apply if additional guests are present in the loft.

Luxury Corner Home near Restaurants, Parks & Shops

Welcome to our stylish Oakville townhouse — perfect for families or business travelers! Near Dundas & Trafalgar, walk to parks, Walmart, cafés, and more. Enjoy cozy bedrooms, fast Wi-Fi, full kitchen, and a relaxing living space. Whether you're here for work or a getaway, you’re just 10–15 mins from the Oakville waterfront and Ridgeway Plaza — the largest halal food hub in town. Comfort, convenience, and location all in one!

140 - Olde Oakville Downtown Heritage District

“140" is an adorable, lovingly-renovated, private apartment on the second floor of the coach house of a prominent heritage-plaqued home in the heart of picturesque Olde Oakville. Located just up the hill from Oakville Harbour, two short blocks from both Lakeside Park on Lake Ontario and the downtown high street, Lakeshore Road with its many restaurants and unique shops makes "140" the perfect place for a couple's getaway!

The Coastal Cottage

Escape to our modern bohemian beachfront cottage for a serene and stylish getaway. Whether you're seeking a romantic retreat or a peaceful solo adventure, our little slice of paradise is the perfect backdrop for creating lasting memories. Book your stay today and start counting down the days until you wake up to the sound of crashing waves and breathtaking sunrises. t4yh7