Pet-friendly holiday rentals in Oakville

Frenchman’s Pass - Cozy nook on the Hamilton brow

Welcome to your home away from home! This charming suite at the back of our home has a separate entrance and a convenient private deck. Nestled on the Hamilton Mountain in one of Hamilton's most upscale neighborhoods, we are steps from the scenic brow offering the perfect blend of tranquility and convenience. High-speed Wi-Fi, smart TV, private, on-site parking and essentials for a relaxing stay. Situated centrally, you're just minutes from hospitals, shopping, restaurants, and public transit.

Pets · Walkability · Sleep quality

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

YES Hot tub and heated pool are open! Forget your worries in this spacious & serene space. King+queen air/4 twin , lrg patio doors overlooking lush greenery in private backyard oasis. Enjoy in/outdoor living & access to private basketball court, trampoline. Landscaped backyard w deck, bbq, tons of board games, 4K projector (stream from G00gle chromecast) for large screen media / movies, and wine fridge, espresso bar, fridge w ice maker, full bathroom, heated flooring. **25+ ID & waiver req**

Outdoor spaces · Pets · View

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 :)

Walkability · Outdoor spaces · Access

Luxury Tiny Home at the Farm - Botanical Oasis

Get away from it all, and enjoy time away. Spend time in the country, with all the comforts of home (and then some!). Pet / feed the animals, enjoy a campfire, walk the trails through the fields and the forest. Take an adventure outing at one of our suggested venues, or pick one of you own. Try it before you buy it! This tiny home is at the same location where True North Tiny Homes builds their homes. If you're lucky, you can tour some other tiny homes under construction while you're here.

Walkability · Pets · Hiking

Sun-Filled Two-Storey Loft | 15 Minute FIFA Walk!

Welcome to our two-storey loft in the heart of entertainment! You have the place to yourself, and location strikes the perfect balance of quiet, yet close to the action. Most popular booking reasons: access to concert venues, conference centres, downtown core, waterfront and all professional sports. Work from home is ideal with a dedicated work space. The balcony gets lots of sun light; it's a cozy place to relax, have a drink and read a book. Make yourself at home and enjoy the area!

Walkability · Pets · Nearby

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.

Walkability · Outdoor spaces · Indoor spaces

The Rosé Garden Wiley Loft, downtown St. Davids

Nestled in heart of St. Davids at the start of the wine route. These unique loft suites which back onto the ravine were professionally curated by winner of Canada's Next Designer, Marcy Mussari. A 10 minute drive to downtown historic Niagara-on-the-Lake or to stunning Niagara Falls. Within walking distance to prestigious Ravine Winery, The Grist, Junction Coffee Bar, and The Old Fire Hall Restaurant. Situated minutes to wineries, golf courses, nature trails, restaurants, shops, and more!

Pets · Outdoor spaces · Comfort

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.

Walkability · Pets · Nearby

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.

Outdoor spaces · Pets · Access

Toronto Island Wonderland View

Toronto Islands are a 10 minute ferry ride away from downtown Toronto. Switch from the hustle and bustle of the city to the tranquillity of one of Toronto's most coveted parks. Unique to any other metropolitan city, Toronto Island has limited vehicle access. This car free area boasts 6 kilometres of nature walks, children and pet friendly access to beaches, Centre island amusement park, artist exhibitions, restaurants and even a nude beach. A perfect getway for the hybrid vacationer.

Pets · Outdoor spaces · Amenities

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!

Outdoor spaces · Pets · TV

Ace Mongolian Yurt

Unplug, unwind, and experience a unique stay in this handcrafted Mongolian yurt, blending traditional craftsmanship with a deep connection to nature. A Perfect Summer Escape: Embrace the beauty of the season. Open the traditional toono (skylight) to catch the gentle summer breeze and fall asleep under a clear, starry sky. Surrounded by vibrant, quiet fields, the round walls and soft lighting create a grounding space to breathe, disconnect, and enjoy the longer, warmer days.

Walkability · Pets · Bathroom