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.

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

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.

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.

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.

Studio 1BR Private Suite In Oakville

Discover Our Private Suite with Separate Entrances - perfect for business trip or couples seeking convenience What You’ll Love • Private Separate Entrance • Convenient Amenities • Free High Speed Wi‑Fi • Microwave, refrigerator & electric kettle • Bottled water, Coffee, tea, and snacks • Fresh towels & toiletries • Free parking • Weekly bedding replacement Location Highlights • Situated close to shops, restaurants, and entertainment • Easy access to local transportation

Cottage Style House with Hot Tub

Step into comfort at this sun-filled home where warmth and relaxation come naturally. Thoughtfully designed for families, perfect place to unwind, connect and make memories. What You’ll Love: ✨ Cozy living spaces and a relaxing hot tub ✨ Smart TVs for movie nights ✨ Work from home with two desks ✨ Private deck, patio, and backyard for fun and fresh air ✨ Reliable fast Wi-Fi and 4 car parking ✨ Just 7 minutes from downtown Oakville and lake ✨ Spotless & safe with enhanced cleaning

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.