Holiday rentals in Oakville

Self Contained Luxury Studio Coach House

Your Perfect Home Away from Home! This immaculate, private studio with a separate entrance is designed for comfort and convenience. Nestled in a peaceful suburb yet centrally located near major highways, it offers walking access to restaurants, grocery stores, and a park. Thoughtfully furnished, it’s cozy in winter, cool in summer, and fully equipped for a hassle-free stay. Guests love the warm ambiance, calling it a truly special experience. Come see why our coach house is the perfect getaway!

Beautifully Upgraded One Bedroom and Den + Balcony

Charming 1-bedroom plus den condo located in a central area with easy walking access to major attractions. This well-appointed upgraded unit features a spacious living area, a versatile den perfect for an office or guest room, and modern amenities. Enjoy the convenience of nearby shops, dining, and entertainment options right at your doorstep. Ideal for those seeking both comfort and a vibrant urban lifestyle. Includes a dedicated underground parking spot and balcony. Fully upgraded and modern!

Condo Style Basement in Oakville (Walk Up)

Looking for a cozy and comfortable place to stay during your next vacation or business trip? This spacious and stylish Airbnb accommodates up to 6 guests! Our beautiful space features everything you need to feel right at home! This condo style basement apartment is located in Oakville, one of Ontario’s most desirable neighbourhoods. 2 bedrooms with walk in closets 2 full bathrooms Sofa-come bed Contemporary chef kitchen (including utensils ) TV with Disney Plus and Netflix Dryer and washers

Luxury Urban Town home

Discover urban sophistication at our modern townhome, ideally located for both comfort and convenience. Thoughtfully designed with stylish decor and all the amenities you need, you'll find grocery stores just a short walk away and easy access to highways 401 and 403 for effortless travel. - Superstore, Walmart, LCBO: 10-minute walk - Oakville Trafalgar Memorial Hospital: 10-minute drive - Oakville GO Station: 12-minute drive - Toronto Premium Outlets: 14-minute drive Book your stay today!

Bright, Spacious, Quiet 2 bedroom - Licensed

Quiet family neighborhood great for professionals, couples or family. Spacious and cozy home away from home. You control heat and cooling fan. Sound dampening so natural noises are minimized, not eliminated. 1 queen and 1 double bed. Two desks for computer work. Extra seating. Fast WiFi! Full kitchen. Bathroom with shower and bathtub. Close to highways, hospital, recreation centers, playgrounds, shopping, schools and college. All registered guests may be asked to provide ID upon request.

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.

Private Boutique Style Smart Suite with Patio

A Charming private suite with a main-floor bedroom and a cozy basement living room featuring a TV and a mini kitchenette. Step out to your backyard oasis with a patio for morning coffee or evening wine. Perfect for a peaceful getaway in the modern city, this stylish retreat blends comfort, privacy, and convenience - just minutes from local cafes, shops, and Oakville's Downtown Area, as well as the GO station and a beautiful lakeshore. Steps away from a family-friendly park.

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.

Luxurious Upper Oakville Condo

This comfortable, fresh and newly furnished one bedroom executive suite is perfect for both long-term stays and short getaways. Located in Oakville, Ontario's largest town, this prime location offers the best of both worlds. Conveniently situated between Toronto and Niagara Falls, you'll enjoy the best of both worlds. Easy access to major city hubs and a variety of outdoor attractions, making it ideal for sightseeing, exploration and adventure.