Pet-friendly holiday rentals in Oakville

“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**

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.

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!

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.

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.

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!

Stylish Modern 2 bedroom house across from Beach

Beautifully renovated one floor 2 bedroom modern House across from the beach. Open concept through out dinning room, living room and large gourmet chefs kitchen with seating along island. The bathroom is very large with double sinks and oversized shower. The Master Bedroom is a nice retreat after a long day at the beach or work. King Size bed, luxurious bedding/Smart TV and a work station. The second bedroom is very cozy with a Double bed. BBQ/laundry/keruig/parking and more!

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.

Elegant NOTL Retreat • Swiming Pool •Spacious Deck

Enjoy a private Niagara-on-the-Lake retreat, now offered as an entire home. This peaceful property features two King bedrooms with ensuite bathrooms, plus a Queen bedroom with its own dedicated full bathroom. Relax in bright living spaces, unwind in the cozy lower-level family room with a smart TV, or enjoy the spacious backyard with a pool, huge deck(over 1000 square feet), and pergola area. Perfect for families or small groups seeking comfort, privacy, and a quiet getaway.

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS JUNE 17 (1 night/2 days) JUNE 21-JULY 6 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

Waterfront Hillside Villa

Welcome to your stunning Hillside Villa situated on 150' of waterfront. Enjoy the peaceful surroundings and quiet Bay views from your 3 private outdoor decks & hot tub. Entertaining is easy in this gourmet kitchen, which is open to 1 of 2 fireplaces, family room & dining room with floor to ceiling views of the Bay. Breathe taking views of the Bay from your private dock. Hidden gems: gym, 2nd kitchen, foosball table, EV charging and private trail.