Family-friendly holiday rentals in Windsor

The Ambassador’s Stay • Bright 1BR Family Retreat

Luxurious 1BR Retreat Prime Location, Perfect for Your Getaway! Escape to this stunning one-bedroom haven in LaSalle, where comfort and convenience meet! Whether you're here for a romantic getaway, a solo retreat, or a business trip, this modern sanctuary has everything you need for a perfect stay. Whether you're here for business or leisure, this luxurious one-bedroom retreat is the perfect home base for your LaSalle getaway. Book now and experience all the comfort and convenience you deserve!

Perfect hideaway with a hot tub and a fireplace

Find your sanctuary at Little River Retreat. Bordering parks, with luxe vibes, a crackling fireplace, and a dreamy hot tub. Enjoy a walk or bike ride through beautiful parks and beaches, including the 10 km+ Ganatchio Trail and Sandpoint Beach (both 5 minutes away). In under 45 min, find yourself in wine country, or for nature lovers, Point Pelee National Park. WFCU Centre 3 min away. Caesars Windsor, tunnel & bridge to USA 10-15 min away. Detroit airport approx 45 min, new battery plant 9 min

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.

Modern guest suite downtown

Self contained 1 bedroom suite in the heart of downtown Windsor. This thoughtfully designed space combines both modern comfort and old world charm. Perfect for working professionals, couples or solo travelers. This unit features a separate entrance, stainless steel appliances, an oversized shower, spacious bedroom, a work space, large windows and laundry access. Relax and unwind in the backyard or enjoy the convenience of local shops, cafés, restaurants and vibrant nightlife just steps away.

Beautiful 2 bdrm Entire Level Sport Themed Suite

This private spacious 2 bedroom lower level sport themed/sport pool backyard getaway is nestled in the heart of South Windsor, ON Canada. This space is unique, clean and well maintained and is sure to exceed your expectations! This quiet and safe neighborhood is conveniently centered near everything -International bridge, major roads highways & expressway, shopping, restaurants & casino. Ideal for workers, couples, business traveller’s. Come enjoy the space but absolutely NO CRAZY PARTIES

Waterfront Cottage | Private Pool |Lakeshore

Waterfront Modern Executive Cottage with lots of natural light and stunning views. This cottage is a breath of fresh air and provides all of the comforts and conveniences that you need in a luxurious relaxing getaway . The cottage boasts a unique layout that sleeps 4 with a bright fully stocked kitchen and dinette, master bedroom, an eclectic second bedroom, barn doors, Smart TV and plenty of closet space, gas fireplace, swimming pool and giant waterfront backyard with lake access to swim.

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.

Modern Walkerville Gem | HotTub & Cozy Backyard

This beautifully renovated townhome combines upscale and comfort. Cook in the spacious kitchen with new stainless steel appliances and granite countertops, dine at the custom live-edge wood table, and enjoy your favorite shows on a 65" Roku TV with Sonos soundbar. Relax in the deep bathtub or retreat to the backyard oasis featuring a large deck, hot tub, natural gas BBQ, patio furniture, and beautiful lighting. At night, rest easy on two plush queen size beds and comfy queen pillows.

Luxurious 3BR, King Bed, Ensuite. Perfect Stay!

Welcome to our 2 year old, modern and bright 3-bedroom, 3-bathroom townhome in East Windsor! Our home features a spacious layout with a clean and contemporary design, making it the perfect spot for your next getaway. The king-sized bed in the master bedroom comes with an ensuite bathroom for added privacy and convenience. Great location, close to WFCU Centre. Perfect for family vacations, weekend getaways, or business trips. Experience the best of East Windsor from our cozy home!

Lakeshore Hidden Oasis (heated pool / jacuzzi)

Located in Lakeshore, minutes from Windsor / Detroit, a perfect oasis for the couple looking for a quiet escape. The suite's private jacuzzi tub makes it the ideal place in any season! The suite is fully equipped, including a complete kitchenette, Smart TV, etc. A private BBQ is at your door. During your stay you will have access, day and night, to our heated salt water pool. It is open from mid March to early November at 32°C (90°F). The hot tub is open year round.

Walkerville Loft - Exclusive Main floor unit

Welcome to our charming main floor private loft in the heart of a Walkerville, Windsor. This space combines modern comfort with some abstract charm. Perfect for couples or solo travelers, our cozy loft features fire place, high ceilings, and large windows. Enjoy the convenience of being centrally located, with iconic landmarks, local shops, and cafes just steps away. Enjoy the city's historic areas during the day and unwind in the unique loft at night.

Family-Sized 3BR • 5 Beds • Near Downtown

Stay close to downtown Windsor in our 3-bedroom home, with an extra 4th 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!