Family-friendly holiday rentals in Windsor

4.96 out of 5 average rating, 316 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.

4.8 out of 5 average rating, 138 reviews

A private guest suite features a spacious bed with a dark blue coverlet, a cozy sofa, and a TV mounted on the wall. Natural light enters through large sliding doors, complemented by dark blue curtains. A small round table stands nearby, adding to the inviting atmosphere.

Guest suite in Windsor

Private unit for professionals! Seperate access

Discover comfort in this private guest suite w/ self-check-in and a separate entrance, located in the tranquil Southwood Lakes neighborhood. Close to golf courses and Devonshire Mall, it’s perfect for relaxation or exploring nearby amenities. Enjoy a swivel mount TV with Netflix from the cozy sofa or bed. Step into the spacious backyard with a stunning gazebo and elegant seating. Luxury bathroom w/ supplies. Coffee bar! Have child with autism - sometimes agitated / possible noise during day

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, 164 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, 156 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.

4.92 out of 5 average rating, 182 reviews

A serene backyard features a circular arrangement of four light-colored Adirondack chairs surrounding a fire pit. Lush green grass extends toward a calm river, with kayaks and paddle boards visible in the distance, framed by trees and bushes, creating a tranquil outdoor space.

Home in Belle River

2 bedroom Getaway/Lake St. Claire, Canada/kayak

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.

4.93 out of 5 average rating, 158 reviews

A comfortable living room area is shown, featuring a gray sectional sofa and a blue armchair. A round wooden coffee table sits on a decorative rug, while a flat-screen TV is mounted on the wall. Soft lighting enhances the inviting atmosphere.

Townhouse in Belle River

little cozy house 2 bedroom

Cozy 2-Bedrooms dwelling unit with Spacious Living Area – Perfect for Relaxing Welcome to our charming two-bedrooms dwelling unit , thoughtfully designed to offer you a warm and inviting stay. Ideal for couples, small families, or business travelers, our home provides a comfortable retreat with all the amenities you need. Our home is fully equipped with all the essentials our guests may need. We use white towels, bedding, and pillows to reflect our high standards of cleanliness and care.

4.94 out of 5 average rating, 212 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, 136 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, 137 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!

4.98 out of 5 average rating, 229 reviews

The entrance features a pair of glass-paneled doors surrounded by natural stone walls, illuminated by warm lighting. A wooden staircase is visible beyond the doors, leading to the upper level, with a welcome mat positioned in front.

Guest suite in Windsor

Glenn & Deb’s Place

1100 sq. ft guest suite attached to main residence but completely separate space on quiet residential street. Upper level with two bedrooms, washer/dryer and 1 bathroom with custom shower. Lower level has full kitchen, living room with gas fireplace, 42'' television and high speed internet. Independent heating and cooling. Owners are on site for quick response to all your needs. Close to WFCU, Caesars Windsor and all major arteries. We regret we are unable to accommodate pets.

4.96 out of 5 average rating, 127 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

4.96 out of 5 average rating, 161 reviews

Windsor Castle is Waiting for You

Beautiful newly renovated bungalow house one-and-a-half stories. Stay at this beautiful and spacious an open, inviting floor plan cozy castle with a huge kitchen, tower-bedroom, sauna, and all necessities. 3 modern bathrooms. 3 bedrooms with queen size beds. 3 sofa beds in the living room and dine in kitchen. Perfect place for a family or work trip. Located in a quiet neighborhood. (note: respectfully no parties, loud gatherings, or guest with no reviews)

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, 142 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

4.88 out of 5 average rating, 114 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

4.95 out of 5 average rating, 319 reviews

A private outdoor space is highlighted by a hot tub and seating areas, featuring contemporary furniture in neutral tones. Red lounge chairs are positioned on a sandy beach area, with a waterfront view stretching to the horizon, bordered by trees and a pier in the distance.

Cottage in Amherstburg

Year Round Hot Tub, The Beach House

4.88 out of 5 average rating, 209 reviews

The living area features a light gray sectional sofa and a dark coffee table. A dining area is visible with a round table and teal chairs, complemented by a modern chandelier. A large television is positioned on a media console, with natural light streaming through windows.

Home in LaSalle

Year Round Hot Tub at The Gem!

Farm stay in Essex County

5 out of 5 average rating, 189 reviews

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

4.95 out of 5 average rating, 109 reviews

The home's exterior is showcased in the evening, featuring a mix of brick and siding with large windows. Outdoor seating is arranged in a gravel area, illuminated by string lights. A private fenced yard is visible, enhancing the sense of privacy.

Home in Detroit

Centrally located home - Perfect for large groups

An outdoor seating area is surrounded by lush greenery and illuminated by warm string lights. Four black chairs with orange cushions are arranged around a central fire pit. A patterned rug complements the space, creating a cozy ambiance as the sunset casts a warm glow.

4.95 out of 5 average rating, 153 reviews

Hot tub + Fire pit + Luxury cozy home + Game Room

4.85 out of 5 average rating, 110 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

4.82 out of 5 average rating, 175 reviews

A modern kitchen features white cabinetry and a central island with seating for four. Stainless steel appliances, including a refrigerator and dishwasher, are complemented by elegant light fixtures. Natural light filters in through a window, enhancing the functional layout with a dining area in the foreground.

Home in Walkerville

3 Bed | Prime Walkerville | Close to City Center

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

4.96 out of 5 average rating, 172 reviews

Pretty Art and Cinema Reclining Couches

A spacious living area features a dark sectional couch, a white coffee table, and a TV stand with a flat-screen television. Soft lighting is provided by a floor lamp, while wall art and plants add a touch of color and warmth to the neutral-toned walls.

5 out of 5 average rating, 232 reviews

Little House on Laprairie

5 out of 5 average rating, 25 reviews

1 BR Modern Loft Windsor (WEST) by the Bridge

The exterior of a single-story brick house is presented, featuring a small front porch with steps leading to a black railing. A fenced area is visible, with a grassy yard and a paved driveway extending towards the front. Nearby, trash bins are placed along the curb.

4.89 out of 5 average rating, 184 reviews

Full house - 5 bed, 2 bath

Guest suite in Walkerville

4.92 out of 5 average rating, 64 reviews

Bright 2 BDRM | Near Casino, Border & UWindsor

The living area features stylish seating arrangements, including a leather sofa and a light-colored armchair. A round coffee table rests in the center, surrounded by a soft area rug. Natural light enters through the windows, illuminating the neutral-colored walls.

4.92 out of 5 average rating, 155 reviews

Ferndale's Charming Boho style 2bd w/ Fenced Yard

Family-friendly home rentals with a pool

4.83 out of 5 average rating, 101 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

A vibrant outdoor area features a pool surrounded by sun loungers and colorful chairs. String lights adorn the space, enhancing the evening ambiance. A pool table is positioned nearby, offering additional recreational options. The backdrop includes a spacious house with multiple windows reflecting soft twilight.

4.86 out of 5 average rating, 76 reviews

Staycation Windsor

4.8 out of 5 average rating, 140 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

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

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.