Family-friendly holiday rentals in Windsor

4.95 out of 5 average rating, 303 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.

4.9 out of 5 average rating, 281 reviews

A spacious wooden deck extends towards Lake Erie, featuring a grill and two outdoor chairs. The gentle waves can be seen lapping against the rocky shoreline. Lush greenery frames the scene, adding a natural touch to the outdoor space.

Cottage in Kingsville

Lakeview Inn

The Lakeview Inn sits on the North Shore of beautiful Lake Erie. This modern lakehouse is an 8 minute drive to the centre of kingsville where there is multiple breweries and restaurants, a public beach is a 1 minute drive down the road and is right in the centre of Southern Ontario's Wine Country. If you're coming down for a weekend to relax, taste wine or to enjoy the exceptional birding the area has to offer. At the end of your day relax to the sound of the waves brushing up against the shore.

A well-lit bedroom features a queen-sized bed adorned with a textured blanket and decorative pillows. Soft wall colors complement the modern lighting fixture. A window offers a view of the outdoors, while a piece of wall art adds a touch of color.

4.98 out of 5 average rating, 128 reviews

Serenity by the Woods- Elegance with Amenities

Welcome to our secluded and private lower level apartment backing onto a forest. A deer family frequently visits the backyard. We strive to make guests feel at home with tasteful decor & thoughtful amenities. The suite is especially suited to business travelers & small families. Location is central, with 3, 6 & 8 min drives to the grocery store, Walmart and Ambassador bridge. * We are in Canada. You have a fully private floor to yourself, but this is not the full house—we live upstairs.

4.86 out of 5 average rating, 199 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.

Apartment 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!

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.

4.86 out of 5 average rating, 112 reviews

Private/Quiet Perfect for professionals!

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 and Amazon Prime from the cozy sofa or bed. Step into the spacious backyard with a stunning gazebo and elegant seating, ideal for unwinding. Luxury bathroom w/ supplies. Coffee bar! Book your peaceful escape today!

4.97 out of 5 average rating, 137 reviews

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.

Home in Riverside

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

4.94 out of 5 average rating, 116 reviews

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.

Home in South Windsor

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, 108 reviews

An inviting living space features a gas fireplace surrounded by a rustic wooden accent wall. Modern furnishings include a comfortable sofa, an armchair, and a red ottoman. A dining area and updated kitchen are visible, with natural light illuminating the wood floor.

Apartment in Windsor

Victoria Ave - 1 BR apartment w fireplace

Available for monthly rental. Not 420 friendly. No smoking of any kind in apartment or on property. Private, light filled, warm apt in a character home on prestigious Victoria Ave. Furnished in Mid-century modern and Hollywood Regency decor. Includes a queen bed, gas fire place, modern kitchen with wifi and shared laundry room. Easy free street parking. Quick drive to Detroit Tunnel. Perfect for one or two people. A short walk to Hospital - Ouelette Campus - ideal for a daytime rest.

4.93 out of 5 average rating, 110 reviews

A living area is presented with a dark, plush sofa and a low coffee table situated on a textured area rug. A round mirror decorates the wall, reflecting light. A doorway leads to a bedroom space, while a small dining area with bar stools is visible to the side.

Apartment in Walkerville

Walkerville Loft (Main floor unit)

Welcome to our charming loft nestled in the heart of a Walkerville in Windsor. This thoughtfully designed space combines modern comfort with historical 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 vibrant cafes just steps away. Immerse yourself in the city's rich history during the day and unwind in this stylish retreat at night.

4.94 out of 5 average rating, 191 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.

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, 121 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!

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.

4.93 out of 5 average rating, 413 reviews

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.

Popular amenities for Windsor family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 115 reviews

A welcome mat rests at the entrance, displaying the phrase 'WELCOME TO THE LAKE' in bold, black lettering. The mat is set against a backdrop of light-colored decking, inviting guests into the home.

Cottage in Essex

Lakeside Hydeaway Cottage on Lake Erie w/ Hot Tub

4.99 out of 5 average rating, 196 reviews

A modern kitchen features quartz countertops and stainless steel appliances, including a spacious refrigerator and gas stove. An island with seating is situated in the center, while an open design connects to the cozy living area, creating a welcoming and functional space.

Farm stay in Essex

Relax at Bridgewood Farms I Hot Tub & Wine Country

Cottage in Brownstown Charter Township

A tranquil sunset over the water is captured, where warm orange and yellow hues blend into the soft blue of the evening sky. A wooden dock is visible in the foreground, with trees silhouetted along the shoreline, providing a serene backdrop.

4.92 out of 5 average rating, 141 reviews

Waterfront home with amazing views & great fishing

4.97 out of 5 average rating, 178 reviews

A cottage exterior showcases a welcoming front deck with two comfortable chairs beside a small table. Large windows allow natural light to illuminate the interior. A decorative planter, filled with green plants, adorns the base of the windows, enhancing the cottage's charm.

Cottage in Essex

The Mayaswell - All Year - Hot Tub - Lake Views

4.97 out of 5 average rating, 290 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

4.87 out of 5 average rating, 206 reviews

Villa in Windsor

4 Bedroom Waterfront Oasis Getaway with Hot Tub

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.

4.9 out of 5 average rating, 183 reviews

Year Round Hot Tub at The Gem!

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, 171 reviews

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

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 177 reviews

The two-story green house features a generous front porch with seating and is surrounded by a grassy lawn. A detached garage is visible to the right, framed by landscaping. The overall setting is tranquil, with trees lining the background under an overcast sky.

Home in Essex

Shores of Erie Guest House

4.8 out of 5 average rating, 176 reviews

A charming cottage is presented with a welcoming front porch and a neatly paved pathway leading to the entrance. Lush greenery and carefully arranged landscaping surround the home, while a tall chimney adds character. Bright blue skies peek through the trees, creating a serene setting.

Cottage in Essex

Lakeside getaway

4.82 out of 5 average rating, 164 reviews

A modern kitchen space features a large island with wooden stool seating and a light-colored countertop. A designated dining area with a wooden table and chairs is visible in the background, complemented by decorative vase arrangements and soft natural lighting from nearby windows.

Home in Walkerville

3 Bed Bright Modern Home in Heart of Walkerville

5 out of 5 average rating, 117 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.

Apartment in Amherstburg

Navy Yard Flats (Flat A) - Historic Amherstburg

4.91 out of 5 average rating, 231 reviews

The exterior of a two-story brick house is visible, featuring a covered front porch with white railings. Windows are adorned with simple treatments, and a small staircase leads to the main entrance. A wooden fence partially encloses the yard, with greenery enhancing the setting.

Home in River Rouge

3bd House! Driveway! Near I75, Detroit River

Guest suite in Kingsville

A spacious bedroom features a king-size bed with soft linens, placed alongside a decorative fireplace. Natural light enters through two windows, and a green armchair accentuates the space. A colorful area rug and potted plants add warmth and texture to the inviting atmosphere.

4.92 out of 5 average rating, 189 reviews

Main on Main ~ Stylish Studio Downtown Kingsville

A bright living room features two modern sofas facing a coffee table, with a large window dressed in sheer curtains allowing natural light. A functional bar area with stools is visible in the background, connecting to the kitchen, while light wood flooring enhances the space.

4.94 out of 5 average rating, 120 reviews

Family-Sized 3BR • 5 Beds • Near Downtown

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.

4.87 out of 5 average rating, 164 reviews

Full house - 5 bed, 2 bath

Family-friendly home rentals with a pool

4.94 out of 5 average rating, 64 reviews

An outdoor area features a rectangular swimming pool surrounded by a spacious deck. Comfortable seating arrangements consist of dark wicker furniture with soft cushions. A wooden table sits center stage, complemented by a grill nearby. Lush green grass highlights the backyard setting.

Townhouse in Amherstburg

Family Oasis w/ Heated Pool, BBQ and Smoker

4.94 out of 5 average rating, 157 reviews

A spacious living area features a light-colored sectional sofa adorned with dark blue and white blankets. A rustic barn door, made of wood, adds character and leads to the bedroom. Two round mirrors are mounted on the wall, reflecting natural light.

Cottage in Lakeshore

Waterfront Luxurious Cottage in Lakeshore, Ontario

4.99 out of 5 average rating, 118 reviews

Barn in Kingsville

Cozy Forest Retreat • Sauna • Hiking • Event Space

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.

4.88 out of 5 average rating, 88 reviews

Cozy Cedarwood Suite ☆Terrace ☆ heated salt pool

4.83 out of 5 average rating, 107 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, 118 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 Malden

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.

4.64 out of 5 average rating, 22 reviews

Architectural Gem | Direct-Entry Pool