Pet-friendly 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

Peaceful 2BR Condo EV Charger: FIFA World Cup

Experience refined urban living in this stylish 2-bedroom condo in Oakville. Located in a fully automated building with seamless app-based access, this 3rd-floor unit offers comfort and convenience. Step into a bright open-concept living space with floor-to-ceiling windows, a fully equipped kitchen, and two bedrooms; each with a queen bed and private ensuite. Enjoy access to premium building amenities, including a modern gym and EV charging station; perfect for both short and extended stays.

Downtown Gem - 2026 FIFA - 40 Mins to BMO Field

Welcome to our home in the heart of downtown Burlington! It's the perfect spot for a family looking for a home-away-from-home with a ton to see and do (and eat!) within walking distance. Cook your favourite meal in our fully-stocked kitchen or relax in our comfortable living room in front of the 65" Smart TV. This home also has a king bed and 2 queens. A 3-minute walk to Spencer Smith Park and the beautiful lakefront and steps to a ton of restaurants and shops. We think you'll love it here :)

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.

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS JUNE 29-JULY 3 JULY 8-18 JULY 21-31 AUGUST 5-7 (2 nights/3 days) Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include orchards and the Lake.

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.

Fully-Furnished Boutique 1 Bedroom Suites

The Laundry Rooms is situated on one of our favourite streets in Hamilton. Featuring cozy pubs, local coffee shops, and a 10-minute walk from the downtown core, Augusta Street has a small-town vibe in the heart of the city. Live like a local with all the comforts and amenities of home in our contemporary suites designed for the professional traveller. Pets are welcome and we can't wait to meet your dog (a deep cleaning fee applies (except for assistance animals))... and you, of course.

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.

Cabin stay and play! 10 mins to Canadian Open!

Take it easy at this unique and tranquil getaway. Located steps from Calerin Golf Course (350 m) and includes many amenities, such as: a BBQ, patio w/ dining area, private hot tub, acres of groomed trails, games galore, pool table, fire pit, comfy queen bed w/ separate heated bunkie with a second queen bed and more! Optional pull out available, please inquire within (fee may apply). 2 km or 5 mins, from the picturesque town of Erin. Lots of restaurants, shops, and plenty to do!

Contemporary Vineyard Barn on the Water + Hot tub

Relax in Niagara’s wine country and enjoy the tranquility of being in a nature's paradise on the water. A mix of modern architecture and old-world charm makes this stunning century old barn, perched over 16th Mile Creek, an inspired vacation destination and offsite work location. Set amongst vineyards and orchards on an estate minutes from wineries, restaurants and downtown St Catharines, just off the QEW, our industrial chic wine country retreat sleeps 2 adults and 1 child.

Guest Favorites Oakville Condo | Modern & Stylish

Welcome to your stylish home away from home in the heart of Oakville! This modern 1 bed, 1 bath condo at Dundas & Trafalgar offers comfort and convenience in a vibrant neighborhood. Enjoy a fully equipped kitchen, cozy living space, in-suite laundry, and a private balcony. Steps from shops, restaurants, parks, and transit, it’s perfect for solo travelers, couples, or business guests. Experience Oakville’s charm with easy access to Toronto and local attractions.

The Best of Downtown Burlington - Safe & Clean

Experience the magic of downtown Burlington voted Canada's best city to live your stay allows you to walk no more then 10 minutes to Award Winning Restaurants, Spencer Smith Park, Joseph Brant Hospital, and so much more. Get cozy in a self contained townhouse unit that's quiet, clean, safe, with free parking and a dog friendly fully fenced in backyard. All guests wishing to book must provide a valid first and last name. I'm sorry cats are not permitted