Pet-friendly holiday rentals in Windsor

OLDE WALKERVILLE, Windsor, Ontario

Do you need a nice quite, non-shared clean place to stay ? This cute one bedroom, living room /sleeper sofa, kitchen, full bath (washer/dryer 6 nights + ) Located on the second floor, above our family home, is ready for you to enjoy your stay. In Olde Walkerville, walking distance to restaurants, pubs, boutiques and, the river with walking and bike paths along with summer activities. Short drive to the Casino, Chrysler Theatre / St. Clair Arts, U.S.A Boarder, down town Train Station.

David's Dwelling: Spa-like bathrooms, Full Wetbar!

Stylish ranch. Sits on a quiet one way street just a few minutes from Detroit. High speed wi-fi and 55 inch smart TV. Spa-like bathrooms, deep soaking tub, mood lights, 2 person shower and Bluetooth speakers and towel warmer. His and Hers bathrobes. Full wetbar and stocked bar fridge. Stainless steel washer and dryer with all the supplies. 2 bedrooms, brand new Queen mattresses and linens. Towels and other linens also available. Pack and Play, large dog kennel on site. Iron firepit and chairs.

Stylish South Walkerville Home w Hot-Tub & Firepit

Welcome to this Stylish Home Away From Home! 1 King Bed & Ensuite on the 2nd Floor. 2 Bedrooms (2 Queens+1 Top Twin Bunk) & Full Bath on the Main Floor + 1 Queen Bed in the Basement. Bring Together 1 or 2 Families of up to 9 people for your next visit to Windsor ON. Located in the Very Desirable Neighbourhood of South Walkerville. Enjoy an evening Soak in the Hot-Tub & a Relaxing Experience by the Gas Fire-Pit in the Backyard. Please note the basement has a kitchenette not currently functional.

Walkerville Charm Home

This stunning 4 bedroom, 6 bed home is dressed to impress! We have spared no detail to ensure your comfort, including: *4 Casper queen beds; * 2 Casper full beds; * a Weber gas BBQ; * lightning fast WIFI connection; * a 50-inch smart Samsung TV in the living room; * a 55-inch smart Samsung TV on the upper floor; * a large formal dining room; * an open concept dining/living/sitting space which can comfortably seat 10 people; * a kids' korner for playtime; * and+++ *Note: Hot tub not available

Blue Breeze Cottage Ontario

Tranquil Farmhouse Retreat with a Pet-Friendly Twist Welcome to your picturesque escape in the heart of Amherstburg, Ontario! Nestled on a peaceful street and mins away from Downtwon river front area. Whether you're a nature enthusiast looking to discover the beauty of Canada's southernmost tip, Point Pelee National Park, a wine connoisseur, or simply seeking a tranquil getaway to indulge in golf and visit museums, our Amherstburg retreat offers the perfect blend of relaxation and adventure

Luxury 2BR home with high ceilings and BBQ w/patio

Labelle Lodge invites you to this bright home with 2 spacious bedrooms and a living area with high ceilings and tons of natural light. Nestled amongst majestic trees, the serene getaway is just 7 minutes away from the US border. Conveniently located near EC Row, you’re minutes away from the Riverside and the entertainment district. Enjoy high speed internet and two smart TVs with all your streaming apps. Indulge in the outdoor dining area and experience the tranquility of South Windsor.

Cozy & Spacious Family Home w/Fireplace & Sunroom!

*HEATED POOL IS OPEN APRIL 1 - OCT 31* Welcome to Windsor’s largest and coziest stay! This gorgeous home blends modern design with comfort, featuring an inviting sunroom with soaring ceilings and natural light, perfect for morning coffee or quiet evenings. The chic decor creates a stylish, yet homey feel :) Unwind in a private backyard oasis with a 15x30, 8’ deep, in-ground oval pool with a brand NEW heater and BBQ lounge! Our backyard designed for a unique and relaxing family experience!

2 bedroom Getaway/lake St.Clair/boatslip

Escape to tranquility at our fully-equipped and cozy home, nestled in a scenic location. Dive into adventure with complimentary kayaks and paddle boards, allowing you to explore the breathtaking natural landscape and even reach Lake St. Claire by kayak. Our kitchen is stocked with all the essentials for culinary delights. The marina and beach are just a 5-minute drive away, while the hockey arena is only 6 minutes away. Perfect for fishing enthusiasts, we even offer daily boat slip rentals.

Charming Old Walkerville 2-Bedroom Luxury Suite

Located in the heart of Old Walkerville. Steps from restaurants, bars, shops, parks and the waterfront. A bright and comfortable main level suite that's part of a large duplex home. Perfect for relaxing visitors or working professionals. There are two spacious bedrooms with queen beds, closet and drawer storage. The grand room and kitchen are fully equipped just like home. The deck and yard space are available for fresh air fun and entertainment. There are 2 parking spots on site.

Cozy Forest Retreat • Sauna • Hiking • Event Space

Escape to Kings Woods Lodge for a cozy winter getaway! Enjoy hiking in the woods, bird watching, crackling fires, heated blankets, rejuvenating sauna sessions, and nights filled with board games and shuffleboard. Surrounded by peaceful forest views, it’s the perfect spot to relax and reconnect. Hosting an event? Kings Woods Hall, our boutique on-site venue, is just steps away and can host up to 80 guests. Great for Christmas parties, bridal or baby showers or intimate weddings.

4 Bedroom Waterfront Oasis Getaway with Hot Tub

Headline: ♨️ The Ultimate Chill: Hot Tub, Lake Views & Cozy Vibes Embrace the beauty of winter at our waterfront home. Don't let the cold stop you—this is the best time of year to visit! Watch the dramatic winter waves or brave the crisp air for a dip in our bubbling hot tub. We’ve curated the perfect space for you to disconnect and recharge. Bring a good book, a bottle of local wine, and enjoy the absolute silence of winter by the water.

Family-Sized 3BR • 5 Beds • Near Downtown

Stay close to downtown Windsor in our 3-bedroom home, with an extra bedroom/living space in the finished basement. We've got 5 beds (2 queens, 3 twins, and a sofa bed in the basement), plus a TV in every bedroom. It's pet-friendly with a big backyard. Ideal for families – we've got a high chair and playpen. Kids can have their own space in the basement with a big TV. Enjoy a convenient and comfortable stay!