Family-friendly vacation rentals in Windsor

4.95 out of 5 average rating, 294 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, 273 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.

4.98 out of 5 average rating, 126 reviews

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.

Guest suite in Windsor

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.

4.88 out of 5 average rating, 187 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

Private Luxury 1BR Retreat in Prime Location

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!

5 out of 5 average rating, 122 reviews

A spacious bed is adorned with a floral-patterned comforter in shades of yellow and gray. A small decorative pillow adds a touch of comfort. Natural light filters through two windows, illuminating the cozy seating area nearby, which features a chair with dark stripes.

Guest suite in Riverside

Ray's iNN Olde Riverside (all private)

PRIVATE GUEST SUITE with OWN ENTRANCE. Boutique Hotel Suite inspired,offering amenities,privacy & charm.50”Samsung TV+Netflix.This Suite has a KITCHENETTE with SINK also mini-fridge,microwave,toaster-oven,slow-cooker, cooktop,coffee maker,kettle.PRIVATE BATHROOM with stand up shower.Includes dishes, glassware,utensils, towels,linens,coffee.Seasonal PATIO & lovely landscaping. Within Olde Riverside,close to shops,restaurants,grocery,parks, WFCU Centre.Short walk to a beautiful riverfront & trail.

4.93 out of 5 average rating, 106 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.

4.93 out of 5 average rating, 184 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.

4.94 out of 5 average rating, 108 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.

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, 114 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, 222 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 Riverside

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.

4.97 out of 5 average rating, 147 reviews

A modern dining area is highlighted by a wooden table accompanied by four blue upholstered chairs. A minimalist aesthetic is enhanced by a potted plant and wall art featuring colorful portraits. Natural light enters through a window covered by a blind.

Apartment in Walkerville

"The Modern Loft" in Walkerville / 2Bed - 1 Bath

Enjoy a luxury modern experience in the heart of Old Walkerville. This modern 2 bedroom loft is newly renovated with luxury finishes while keeping century old details. Restaurants, pubs, cafes, retail all within a minute walk from this superb location. Stay here and get a taste of what Old Walkerville has to offer. DISTANCES TO: Casino - 2 minutes Downtown - 2 minutes Hospital - 5 minutes Detroit - 10 minutes Ford Field - 12 minutes Little Ceasers Arena - 12 minutes

4.93 out of 5 average rating, 401 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.

Popular amenities for Windsor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 193 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

4.96 out of 5 average rating, 283 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, 203 reviews

A serene view of the river is framed by trees with autumn foliage. The peaceful water reflects the clear sky, while tall grasses and reeds line the riverbank. A wooden fence and steps are visible in the foreground, leading to the water's edge.

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, 173 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, 164 reviews

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

4.98 out of 5 average rating, 190 reviews

A year-round hot tub is positioned under a wooden pergola, with views of a sunset reflecting on the calm waters of Lake Erie. Adirondack chairs are visible nearby, providing a relaxing spot to enjoy the surrounding natural beauty.

Home in Amherstburg

Lake Erie retreat-unwind & explore local wineries

4.95 out of 5 average rating, 127 reviews

A shaded outdoor area features a hot tub under a canopy, surrounded by wooden bar stools. Light beige curtains frame the space, creating a comfortable atmosphere. A wooden table and steps lead to the hot tub, with ample room for relaxation.

Cottage in Essex

Chardonnay Bay- Pet Friendly, beach, hot tub!

Guest suite in Kingsville

A cozy living area features a modern fireplace framed by natural stone. Large windows invite natural light and provide views of the outdoor hot tub on the deck. Comfortable seating arrangements include a white sofa and a light-colored armchair, complemented by a wooden dining table set for two.

4.98 out of 5 average rating, 115 reviews

Lakefront Beautiful Private Vacation Suite

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 170 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

*KID & FAMILY FRIENDLY* Shores of Erie Guest House

4.82 out of 5 average rating, 157 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, 114 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, 161 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.

Cottage in Belle River

2 bedroom Getaway/lake St.Clair/boatslip

4.99 out of 5 average rating, 121 reviews

The living room features a bright blue sofa with yellow accent pillows, complemented by a modern area rug. A multi-functional table sits in front of a stylish armchair. A flat-screen TV is mounted on the wall opposite large windows, adorned with golden drapes, allowing natural light.

Home in Dearborn

3BD Cozy Chic Home Near *Airport*Beaumont*Downtown

4.86 out of 5 average rating, 160 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

4.91 out of 5 average rating, 173 reviews

A charming exterior view of the cottage features a stone and wood facade. A pathway leads to a welcoming front porch, decorated with potted flowers. Adjacent seating areas provide cozy spots for relaxation, framed by a canopy of greenery from a nearby tree.

Cottage in Amherstburg

Sawiak Waterfront Haven

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.

4.91 out of 5 average rating, 180 reviews

Main on Main ~ Stylish Studio Downtown Kingsville

Family-friendly home rentals with a pool

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.

4.58 out of 5 average rating, 31 reviews

Luxury at its finest (Windsor) Swimming Pool

4.94 out of 5 average rating, 154 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, 109 reviews

Barn in Kingsville

Cozy Forest Retreat w/ Sauna + Event Space

4.89 out of 5 average rating, 87 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 Windsor

Cozy Cedarwood Suite ☆Terrace ☆ heated salt pool

4.96 out of 5 average rating, 28 reviews

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.

Home in Riverside

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

5 out of 5 average rating, 5 reviews

A spacious living area features a comfortable sofa and loveseat, complemented by decorative pillows. A wooden coffee table sits in front, with a remote control placed on top. Nearby, a dining table with four chairs is visible, alongside bar stools positioned at a countertop.

Apartment in Tecumseh

Impressive Furnished All-inclusive Apartment

4.91 out of 5 average rating, 117 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.