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.

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.

4.8 out of 5 average rating, 137 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.

A private outdoor space is highlighted by a covered gazebo, featuring a hot tub and relaxing seating options. Lush greenery surrounds the area, complemented by well-placed planters. Natural light filters through, creating a soothing environment for leisure and relaxation.

4.84 out of 5 average rating, 132 reviews

Couple's Romantic Retreat with hot tub, fire pit.

Romantic & soothing discreet hideaway. Relax, reunite & enjoy the night. Complementary Bathrobe for Sunday to Thursday bookings. 1 for return guests. -private backyard Oasis with Hot tub, Gazebo, outdoor Tv, accent lighting, BBQ and fire pit. -king size bed; -couple's spa shower; -massage table -fully stocked chef's kitchen; -private garage parking; -nearby parks and trails; -plus all of the comforts of being in the city. Everything you need to enjoy a restful and relaxing weekend away.

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.

4.94 out of 5 average rating, 212 reviews

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.

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.

4.97 out of 5 average rating, 133 reviews

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, 135 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.

4.93 out of 5 average rating, 446 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)

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.

4.96 out of 5 average rating, 125 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, 243 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!

Popular amenities for Windsor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.74 out of 5 average rating, 141 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, 113 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, 221 reviews

Villa in LaSalle

4 Bedroom Waterfront Oasis Getaway with Hot Tub

Farm stay in Essex County

5 out of 5 average rating, 188 reviews

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

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, 152 reviews

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

4.94 out of 5 average rating, 197 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

Family- and pet-friendly home rentals

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.

4.82 out of 5 average rating, 175 reviews

3 Bed | Prime Walkerville | Close to City Center

5 out of 5 average rating, 122 reviews

A comfortable living area features a leather sofa and patterned armchairs, with a glass coffee table at the center. A ceiling fan hangs above, and the space is illuminated by recessed lighting. An open kitchen with modern appliances is visible in the background.

Flat in Amherstburg

Navy Yard Flats (Flat A) - Historic Amherstburg

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, 171 reviews

Pretty Art and Cinema Reclining Couches

A comfortable living area features a stylish orange sofa and gray armchair, centered around a round area rug with a modern pattern. Natural light enters through two windows, highlighting a wooden coffee table decorated with a small plant and decorative items. A floor lamp stands nearby.

4.99 out of 5 average rating, 268 reviews

Little Yellow House in Ferndale! Quiet, Cozy 3BR

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, 231 reviews

Little House on Laprairie

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, 182 reviews

Full house - 5 bed, 2 bath

Family-friendly home rentals with a pool

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

4.81 out of 5 average rating, 139 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 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.

4.71 out of 5 average rating, 38 reviews

Architectural Gem | Direct-Entry Pool

4.61 out of 5 average rating, 64 reviews

A spacious bedroom is highlighted by a wooden bed frame with a neatly made comforter, accompanied by two bedside tables with lamps. Natural light enters through sliding glass doors, providing views of the outdoor area. A ceiling fan adds an inviting touch.

Home in Tecumseh

Entire 3 bdrm home on Riverside dr in Tecumseh

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.