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Family-friendly holiday rentals in Windsor

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Windsor

  • Total holiday rentals

    Explore 690 holiday rentals in Windsor

  • Nightly prices starting at

    Windsor holiday rentals start at $28 AUD per night before taxes and fees

  • Verified guest reviews

    Over 37,400 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 190 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    430 properties have a dedicated workspace

  • Wi-Fi availability

    680 of Windsor holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Windsor rentals

  • 4.8 Average rating

    Windsor stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Windsor's top spots, include Little Caesars Arena, Comerica Park, and Ford Field

Top-rated family-friendly rentals in Windsor

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite
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.

4.96 out of 5 average rating, 323 reviews
Top Guest favourite
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 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.

4.96 out of 5 average rating, 182 reviews
Top Guest favourite
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, 225 reviews
Guest favourite
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.

4.97 out of 5 average rating, 156 reviews
Top Guest favourite
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.
Home in Windsor

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, 150 reviews
Guest favourite
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.
Home in Windsor

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!

4.81 out of 5 average rating, 242 reviews
Superhost
A living area features a large sectional sofa adorned with decorative pillows, complemented by a wooden coffee table. A stylish armchair and dining table for four are visible. Bright light filters through the blinds covering the windows, highlighting the warm color palette and wooden flooring.
Home in Windsor

Chillin' at Chilver w King Beds

Visit us for a relaxing escape in this spacious & cozy home. Unwind in front of the fireplace. With 2 king beds and 2 queen beds, there’s plenty of space for everyone to sleep comfortably. This property features 2 full bathrooms, a fully stocked kitchen for all your cooking needs, and a finished basement with a quiet office nook and a large family room. Whether you're gathering with loved ones or looking for a getaway, you'll have a great time Chillin' at Chilver!

4.85 out of 5 average rating, 119 reviews
Guest favourite
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, 139 reviews
Superhost
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.
Home in Windsor

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!

4.87 out of 5 average rating, 255 reviews
Top Guest favourite
A spacious living area features a sectional sofa and a coffee table, with soft lighting provided by a pendant light. A dining table with white chairs sits nearby, and an image of a bridge adorns the wall, contributing to a modern and inviting atmosphere.
Home in Windsor

Shalom - Modern Spacious Home, 4BR + 4Beds + 3BA

A beautifully renovated house with a modern finish that lies within Forest Glade, East Windsor Ontario Canada. The 4 bedrooms, 3 bathroom and sofa bed house is plentiful in space for guests and is perfect for families, business travellers, and front line workers. During your stay, we provide the essentials from toilet paper to towels and linens in order for your stay to be as trouble-free as possible. With that being said, we welcome you to come

4.97 out of 5 average rating, 226 reviews
Guest favourite
Villa in LaSalle

4 Bedroom Waterfront Oasis Getaway with Hot Tub

Headline: ♨️ The Ultimate Chill: Hot Tub, Lake Views & Cozy Vibes Embrace the beauty of Windsor at our waterfront home. This is the best time of year to visit! Watch the sun glisten across the waves or unwind after a perfect day with a relaxing dip in our bubbling hot tub. We’ve curated the perfect space for you to disconnect and recharge. Bring a good book, a bottle of local wine, and enjoy the blissful peace of air by the water.

4.87 out of 5 average rating, 231 reviews
Guest favourite
The sleeping area features a spacious, dark wood bed with a neutral plaid comforter. A flat-screen television is mounted on the wall, and a small nightstand is positioned beside the bed. A striped area rug lies on the floor, completing the room's look.
Guest suite in Walkerville

Spacious Wonder

Forget your worries in this spacious and serene space. Free street parking on both Erie and Gladstone. About 7 min from Downtown by car. Entrance is the right side door which is not shared along with everything else to make it completely private for our valued guests! Heaters are provided for guests and thermostat is always on Heat mode for the winter season especially so our guests can feel comfortable!

4.79 out of 5 average rating, 272 reviews

Popular amenities for Windsor family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top Guest favourite
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)

4.93 out of 5 average rating, 462 reviews
Top Guest favourite
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 Windsor

Perfect hideaway with a hot tub and a fireplace

4.98 out of 5 average rating, 179 reviews
Top Guest favourite
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

4.92 out of 5 average rating, 126 reviews
Superhost
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

4.81 out of 5 average rating, 115 reviews
Guest favourite
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.
Home in Belle River

Belanger Air BnB

4.96 out of 5 average rating, 106 reviews
Guest favourite
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~

4.88 out of 5 average rating, 227 reviews
Guest favourite
Home in Detroit

Downtown (5min)Adults Only-Hot Tub (No Parties)

4.91 out of 5 average rating, 127 reviews
Superhost
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 5BR- Hot Tub & Game Room

4.94 out of 5 average rating, 119 reviews

Family- and pet-friendly home rentals

Superhost
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.
Home in Windsor

Family-Sized 3BR • 5 Beds • Near Downtown

4.88 out of 5 average rating, 155 reviews
Guest favourite
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

4.95 out of 5 average rating, 117 reviews
Superhost
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

4.86 out of 5 average rating, 169 reviews
Top Guest favourite
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.
Apartment in Grosse Pointe Park

Brand new modern farmhouse!

4.99 out of 5 average rating, 109 reviews
Top Guest favourite
Home in Walkerville

Windsor Casino and International Swim Meet AirBnb

5.0 out of 5 average rating, 31 reviews
Superhost
Apartment in Windsor

Full 1BR. A short walk to go Eat, Drink, See & Do.

4.8 out of 5 average rating, 5 reviews
Guest favourite
Apartment in Walkerville

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

4.94 out of 5 average rating, 35 reviews
Guest favourite
Guest suite in Walkerville

Bright 2 BDRM | Near Casino, Border & UWindsor

4.92 out of 5 average rating, 90 reviews

Family-friendly home rentals with a pool

Top Guest favourite
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 Lower Level Sport Themed Suite

4.91 out of 5 average rating, 134 reviews
Guest favourite
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

4.95 out of 5 average rating, 183 reviews
Superhost
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

4.82 out of 5 average rating, 152 reviews
Guest favourite
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 Windsor

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

4.93 out of 5 average rating, 57 reviews
Superhost
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

4.67 out of 5 average rating, 45 reviews
Guest favourite
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

4.88 out of 5 average rating, 94 reviews
Superhost
A comfortable seating area is shown with a dark sofa positioned against the wall. A flat-screen television is mounted above a modern kitchenette, which includes a refrigerator. A dining table is set for four, featuring plates and bowls on a textured table runner.
Home in Windsor

South Windsor Spacious Basement + Pool

4.91 out of 5 average rating, 35 reviews
Guest favourite
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.
Home in Belle River

The Grand River Retreat. Pool/ hot tub avail Sep

4.87 out of 5 average rating, 45 reviews

When is the best time to visit Windsor?

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Avg. price$146 AUD$147 AUD$153 AUD$157 AUD$174 AUD$168 AUD$162 AUD$167 AUD$151 AUD$154 AUD$150 AUD$153 AUD
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