Family-friendly holiday rentals in Windsor

4.96 out of 5 average rating, 313 reviews

The exterior of the two-story property features light blue siding and a decorative gabled roof. A covered porch with a white railing and steps leads to the entrance. A wooden gate is visible to the side, providing access to the backyard.

Apartment in Walkerville

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.

4.84 out of 5 average rating, 293 reviews

A bright living area features a blue sectional sofa positioned beside a modern, round coffee table. Natural light enters through large windows, illuminating the space. A sleek fireplace and a mounted television are visible along the white brick wall, creating a cozy gathering spot.

Home in Walkerville

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

A private outdoor patio features a hot tub surrounded by wooden fencing and a pergola. Comfortable seating is provided by two chairs, with a BBQ grill situated nearby. Natural light filters in through the overhead structure, enhancing the relaxing atmosphere.

4.98 out of 5 average rating, 162 reviews

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

An outdoor dining area is set with a red table and chairs under a retractable awning. The grey exterior of the lodge is framed by a manicured lawn and wooden fencing, creating a secluded and private atmosphere. Natural light enhances the inviting space.

4.95 out of 5 average rating, 151 reviews

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.

4.94 out of 5 average rating, 210 reviews

A modern living area is featured, furnished with a soft gray sofa and a stylish coffee table. A wooden sideboard is placed against the wall, complemented by decorative items. Light walls enhance the spacious feel, while a chandelier adds subtle brightness to the room.

Home in Walkerville

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.

4.97 out of 5 average rating, 132 reviews

A spacious backyard is presented, showcasing a hot tub situated on a concrete pad. Green grass lines the space, complemented by wooden fencing and ambient lighting. A small tree is visible in the corner, and utility lines are present in the sky against a colorful sunset backdrop.

Home in Walkerville

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.

A modern kitchen features sleek white cabinetry and stainless steel appliances. A quartz island is complemented by a decorative tray with coffee essentials. A wall clock adds a touch of functionality, while a bowl of green apples offers a fresh accent.

4.99 out of 5 average rating, 134 reviews

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!

An inviting outdoor area showcases a glistening in-ground oval pool framed by a spacious deck. Comfortable lounge chairs are situated nearby, and the house features large windows that allow for ample natural light. A dining set is visible under the covered patio, ideal for outdoor meals.

4.81 out of 5 average rating, 229 reviews

Gorgeous Poolhouse! Spacious Family Home w/Sunroom

*HEATED POOL IS READY!* 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!

4.96 out of 5 average rating, 122 reviews

A cozy living area features a light-colored sectional sofa adorned with patterned pillows. A modern glass coffee table sits in the center, complemented by a decorative plant on the side. Exposed brick walls add texture, while a window with an arch design enhances natural light.

Townhouse in Walkerville

Cozy Downtown Walkerville Home

Welcome to your perfect home away from home in the heart of Windsor! This charming and cozy residence offers the perfect blend of comfort, style and convenience making it an ideal spot for both short and long stays. Whether you're in town for business, leisure, or a family visit, you'll find everything you need to feel right at home. Situated downtown Windsor just minutes from the VIA train station, Casino Windsor, Detroit tunnel and great popular restaurants

A spacious living area with modern furnishings is visible. A dark sectional sofa and a matching ottoman are arranged near a large window, with natural light illuminating the space. A mounted television is positioned on the wall opposite a dining table set with plates and glasses.

4.88 out of 5 average rating, 242 reviews

Downtown 2 Bed 1 Bath Unit w/ Free Parking

Welcome to our updated 2 bed 1 bath upper unit in downtown Windsor! With a fully equipped kitchen including stainless steel appliances & quartz countertops and a 65in TV with Netflix in the living room, this apartment has everything you need for a comfortable stay. Located near transit, shopping, and restaurants. This location is on a quiet block just minutes walk to the heart of downtown. Book now for a cozy and convenient home-away-from-home experience!

4.95 out of 5 average rating, 111 reviews

The loft showcases an open living space with warm wooden floors and a cozy sofa. A stylish chandelier hangs above the kitchen area, which features wooden cabinetry and colorful tile accents. A kitchen island is positioned near the seating area, providing an inviting space for dining or working.

Loft in Walkerville

OldeWalkerville Loft Gem on the River

This loft is available for longer stays/ monthly rental. Private sunny deck entrance. Parking on site. Bell’s fastest fibe internet. Perfect home/ artist, office space Beautifully restored 1902 Grande Queen Ann loft with all new amenities. Windows and skylights look over the Detroit River. Enjoy 800 sqft balloon framed open studio style space with private laundry. River walk trail outside your door. In the heart of popular Olde Walk

Guest suite in Walkerville

The sleeping area features a spacious, dark wood bed with a neutral plaid comforter. A flat-screen television is mounted on the wall, and a small nightstand is positioned beside the bed. A striped area rug lies on the floor, completing the room's look.

4.8 out of 5 average rating, 240 reviews

Spacious Wonder

Forget your worries in this spacious and serene space. Free street parking on both Erie and Gladstone. About 7 min from Downtown by car. Entrance is the right side door which is not shared along with everything else to make it completely private for our valued guests! Heaters are provided for guests and thermostat is always on Heat mode for the winter season especially so our guests can feel comfortable!

Popular amenities for Windsor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.75 out of 5 average rating, 138 reviews

An open-concept living area features a sectional sofa and a modern entertainment unit with a wall-mounted TV. Natural light fills the space, complemented by a decorative area rug. A breakfast bar with gray stools offers additional seating, enhancing the inviting atmosphere.

Home in Dearborn

Top-Rated 4BR Dearborn Oasis | Jacuzzi • Near DTW

4.87 out of 5 average rating, 110 reviews

A spacious bedroom is presented with large windows allowing ample natural light. A wooden bed with a blue-patterned blanket is complemented by two bedside lamps. A cozy armchair and a light wood crib are featured, alongside a geometric area rug on a hardwood floor.

Home in Detroit

Massive Detroit-Themed Stay | HT, Games, Fire Pit

4.88 out of 5 average rating, 220 reviews

Villa in LaSalle

4 Bedroom Waterfront Oasis Getaway with Hot Tub

Farm stay in Essex County

A covered outdoor seating area features a cozy arrangement of a sofa and decorative pillows, illuminated by string lights. The space is surrounded by lush greenery, with a landscaped patio and wooden railing adding to the inviting ambiance.

5 out of 5 average rating, 185 reviews

The Fir&Feather Tree Farm 1Bedroom Suite & Hot tub

4.94 out of 5 average rating, 196 reviews

Home in Detroit

Adults-Only Cozy Getaway with Hot Tub (No Parties)

4.92 out of 5 average rating, 119 reviews

The exterior of a two-story brick home features large windows framed by wooden shutters. A stone pathway leads to the entrance steps, which are flanked by neatly landscaped flower beds and ornamental plants in decorative pots. The entrance is inviting, with a warm color palette.

Home in LaSalle

The Ambassador Estate Inn

4.93 out of 5 average rating, 441 reviews

A serene outdoor space features a salt-water pool surrounded by lush greenery, lounge chairs, and shaded seating areas. Natural stone accents are present near the water's edge, with steps leading up to a covered patio area. Tree silhouettes frame the background, enhancing the tranquil setting.

Guest suite in Windsor

Lakeshore Hidden Oasis (heated pool / jacuzzi)

4.85 out of 5 average rating, 106 reviews

A spacious outdoor deck is visible, featuring a fire pit surrounded by seating. Lounge chairs and a dining table with chairs occupy the area, while a barbecue grill is positioned nearby, all set against a scenic view of the lake.

Home in Belle River

Breathtaking Waterfront Home

Family- and pet-friendly home rentals

4.87 out of 5 average rating, 164 reviews

The upstairs bedroom features two double beds, each dressed in white linens with soft, fur throws draped on top. Light fills the space through large sliding glass doors leading to a balcony, with nature-themed wall art accentuating the neutral decor.

Home in LaSalle

Quiet LaSalle Newly Renovated Entire Country Home

A striking Victorian manor showcases intricate brickwork and a prominent tower, framed by lush greenery. The entrance is highlighted by a charming porch with decorative trim and large windows. A well-maintained lawn extends towards a wrought iron fence, adding to the home's inviting curb appeal.

4.92 out of 5 average rating, 26 reviews

The Victorian on Victoria

4.96 out of 5 average rating, 24 reviews

Modern & Cozy Home Retreat

5 out of 5 average rating, 23 reviews

1 BR Modern Loft Windsor (WEST) by the Bridge

A light-filled living area features a neutral sofa and a modern armchair, paired with a round coffee table atop an area rug. Large windows provide views of the outdoor greenery, while a brick fireplace adds a touch of warmth to the space.

4.89 out of 5 average rating, 82 reviews

Cozy, Modern 2BR w/ Remote Workspace, Patio & Gym

5 out of 5 average rating, 11 reviews

Apartment in Walkerville

The Serene Walkerville Stay

5 out of 5 average rating, 15 reviews

The bedroom features two spacious beds adorned with neutral bedding, placed side by side. Windows with layered shades provide natural light and privacy. A small, dark chair is situated in the corner, complementing the light wood flooring and subtle artwork on the walls.

Home in Tecumseh

Relaxed Living in the Heart of Tecumseh

4.83 out of 5 average rating, 18 reviews

Apartment in Windsor

Cozy Waterfront Stay with Detroit Skyline Views

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 34 reviews

A heated sports pool, surrounded by a spacious patio area, is complemented by comfortable seating options including loungers and umbrellas. A contemporary pool house with large windows is visible in the background, featuring a clean design that enhances the outdoor space.

Home in Belle River

The Grand River Retreat. Pool/ hot tub avail Sep

4.84 out of 5 average rating, 100 reviews

A two-story cottage with a light grey exterior is showcased, featuring a welcoming front porch with white railings. A spacious yard surrounds the home, with a gravel driveway leading up to it. Lush green grass complements the serene environment.

Home in Amherstburg

Cottage Escape by the Water

4.59 out of 5 average rating, 34 reviews

The exterior of a single-story home is shown, featuring a spacious driveway lined with paving stones. Lush greenery, including a large evergreen tree and manicured shrubs, frames the entrance, which includes a blue door and large front windows under a lightly clouded sky.

Home in Tecumseh

Luxury at its finest (Windsor) Swimming Pool

4.94 out of 5 average rating, 173 reviews

A clear view of a seasonally available swimming pool bordered by a sun-soaked patio. Outdoor seating is arranged under a wooden covered area. The vibrant greenery and lake beyond provide a relaxing backdrop, enhancing the inviting ambiance of the outdoor space.

Cottage in Lakeshore

Waterfront Cottage | Private Pool |Lakeshore

A spacious living room features a large sectional couch and a coffee table, with a television displaying a beach scene. Bright natural light enters through the window, which is complemented by light curtains. The polished wooden floor adds warmth to the space.

4.98 out of 5 average rating, 46 reviews

Spacious Family Getaway w/ Pool -Sleeps 12 - 2 TVs

4.8 out of 5 average rating, 136 reviews

A spacious studio apartment features a comfortable bed with crisp white linens and a cozy gray blanket. Soft lighting from bedside lamps illuminates the room, which includes a wooden dresser and armchair. An entryway is visible in the background, along with a kitchenette area.

Apartment in Detroit

Midtown Gem – Walkable & Bright Hotel Style Unit

A modern retreat is highlighted by a sleek, heated pool reflecting the evening sky. Floor-to-ceiling windows provide glimpses of illuminated indoor spaces, while a rooftop terrace is accessible. A landscaped patio is bordered by a wooden fence, offering privacy.

4.76 out of 5 average rating, 37 reviews

Architectural Gem | Direct-Entry Pool