Family-friendly holiday rentals in Windsor

4.96 out of 5 average rating, 319 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.

Flat 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.

4.85 out of 5 average rating, 239 reviews

A spacious living area features a comfortable gray sectional sofa adorned with decorative cushions. A wooden coffee table is centered on a soft area rug, while a wall-mounted television and a small dining table for two are visible. Natural light enters through large windows.

Flat in LaSalle

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!

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, 173 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, 168 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.

4.99 out of 5 average rating, 104 reviews

Guest suite in 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.

4.91 out of 5 average rating, 133 reviews

The exterior of a brick bungalow is visible, framed by a variety of lush greenery and colorful flower beds. A small set of steps leads to the entrance, which is accentuated by a welcoming porch and neatly arranged planters.

Guest suite in Windsor

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

4.94 out of 5 average rating, 178 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

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.

4.94 out of 5 average rating, 221 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, 145 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.

4.98 out of 5 average rating, 146 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, 236 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, 132 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

Popular amenities for Windsor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 456 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)

4.87 out of 5 average rating, 225 reviews

Villa in LaSalle

4 Bedroom Waterfront Oasis Getaway with Hot Tub

A wooden deck extends over calm waters, featuring a simple table and seating. The sun sets on the horizon, casting a warm glow across the sky, while reflections shimmer on the water's surface. Trees provide gentle shade along the edge.

4.95 out of 5 average rating, 107 reviews

Lake Louise With hot tub

4.92 out of 5 average rating, 122 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 spacious deck is shown with several comfortable seating options facing the lake. A small table stands in the center, while soft lighting highlights the space. The view showcases a serene sunset over the water, providing a tranquil outdoor experience.

4.84 out of 5 average rating, 133 reviews

BEAUTIFUL WATERFRONT HOME W/ LAKE ST. CLAIR VIEWS!

A spacious outdoor pool is highlighted under clear blue skies. Several lounge chairs are positioned poolside, providing ample seating for relaxation. The surrounding area features well-maintained greenery and a fence that encloses the space.

4.98 out of 5 average rating, 99 reviews

Belanger Air BnB

4.88 out of 5 average rating, 225 reviews

A modern two-story cinder block home is showcased, featuring a vibrant mural on one side. The house is painted in bright blue, accented by red and green elements. A paved pathway leads to the entrance, with grassy areas surrounding the property.

Tiny home in Detroit

The Painted House by Eastern Market ~Boutique B&B~

4.75 out of 5 average rating, 153 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

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 114 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

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.

4.88 out of 5 average rating, 189 reviews

Full house - 5 bed, 2 bath

4.82 out of 5 average rating, 299 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

4.95 out of 5 average rating, 148 reviews

A vibrant space features a colorful hammock perfectly strung across the room. A large projection screen displays a scenic landscape with mountains and skies, while the walls are painted in bright green hues. Natural wood flooring adds a rustic touch to the overall decor.

Barn in Romulus

Vintage Inspired Barn Loft by Maison De LeMade

Flat in Grosse Pointe Park

A modern farmhouse exterior features a combination of dark siding and natural wood accents. Multiple large windows provide ample light, while a covered balcony extends from the upper level. A landscaped yard with green grass and decorative stones surrounds the entrance.

4.99 out of 5 average rating, 101 reviews

Brand new modern farmhouse!

5.0 out of 5 average rating, 240 reviews

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.

Home in Ferndale

Little House on Laprairie

5.0 out of 5 average rating, 16 reviews

2 Beds Comfortable Stay

4.92 out of 5 average rating, 26 reviews

Flat in Walkerville

Walkerville Urban Oasis, Exec. King 2BR W/Parking

Family-friendly home rentals with a pool

4.81 out of 5 average rating, 147 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.

Flat in Detroit

Midtown Gem – Walkable & Bright Hotel Style Unit

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.

4.94 out of 5 average rating, 53 reviews

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

4.88 out of 5 average rating, 91 reviews

The Cedarwood Suite features a modern design with a spacious bed adorned with a patterned coverlet. A flat-screen television is mounted on the wall opposite. Natural light filters through curtains, illuminating a small dining area equipped with a table and chairs.

Guest suite in Tecumseh

Cozy Cedarwood Suite ☆Terrace ☆ heated salt pool

4.98 out of 5 average rating, 50 reviews

Windsor Luxury Stay Oasis

4.66 out of 5 average rating, 41 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

4.79 out of 5 average rating, 14 reviews

A modern kitchen is presented with dark blue cabinetry and a large island featuring seating. Stainless steel appliances, including a refrigerator and microwave, are visible. A sleek chandelier illuminates the space, while natural light enters through a large window.

Home in LaSalle

Spacious home in LaSalle with Pool

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.

4.9 out of 5 average rating, 41 reviews

The Grand River Retreat. Pool/ hot tub avail Sep