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Family-friendly holiday rentals in Windsor

Find and book unique family-friendly homes on Airbnb

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
4.95 out of 5 average rating, 293 reviews

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.

Top Guest favourite
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
4.98 out of 5 average rating, 126 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.

Superhost
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
4.88 out of 5 average rating, 186 reviews

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!

Top Guest favourite
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
5 out of 5 average rating, 122 reviews

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.

Top Guest favourite
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.
Farm stay in Essex County
5 out of 5 average rating, 164 reviews

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

A unique & tranquil wooded getaway nestled on a 16 Acre working Christmas tree farm, 15 mins. from Windsor and surrounding towns. This private lower suite, part of the main house has it's own entrance & space for 4 guests with open concept Kitchen/Living room with electric fireplace,2 futons/double beds with memory foam mattresses, Queen Juno mattress in bedroom and 3 piece bath. Enjoy a covered private furnished patio w/firepit or relax in a private hot tub (netted) at a second enclosed patio

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 Riverside
4.97 out of 5 average rating, 127 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

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 South Windsor
4.93 out of 5 average rating, 106 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.

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
4.93 out of 5 average rating, 184 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.

Guest favourite
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
4.93 out of 5 average rating, 107 reviews

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.

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
4.99 out of 5 average rating, 112 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!

Top Guest favourite
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
4.98 out of 5 average rating, 222 reviews

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.

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 Downtown Windsor
4.9 out of 5 average rating, 213 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
Wi-Fi
Pool
Free parking on premises
Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite
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.
Cottage in Brownstown Charter Township
4.92 out of 5 average rating, 137 reviews

Waterfront home with amazing views & great fishing

Guest favourite
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
4.96 out of 5 average rating, 279 reviews

Year Round Hot Tub, The Beach House

Guest favourite
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
4.89 out of 5 average rating, 201 reviews

4 Bedroom Waterfront Oasis Getaway with Hot Tub

Guest favourite
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.
Home in Windsor
4.9 out of 5 average rating, 173 reviews

Year Round Hot Tub at The Gem!

Guest favourite
A hot tub is positioned in a well-lit corner of an entertainment area. Its water features colorful lighting reflections, creating an inviting ambiance. The surrounding walls are tiled in neutral tones, with a small rug beneath. A towel is neatly hung on a wall-mounted hook.
Home in Detroit
4.95 out of 5 average rating, 171 reviews

Adults-Only Cozy Getaway with Hot Tub (No Parties)

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 Malden
4.91 out of 5 average rating, 116 reviews

The Ambassador Estate Inn

Top Guest favourite
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.
Guest suite in Kingsville
4.98 out of 5 average rating, 115 reviews

Lakefront Beautiful Private Vacation Suite

Top Guest favourite
A spacious living area features a large sectional sofa with decorative pillows, complemented by a ceiling fan above. Natural light floods the room, highlighting the open staircase and modern kitchen visible in the background, creating an inviting atmosphere.
Townhouse in Midtown
4.98 out of 5 average rating, 271 reviews

Bright and spacious centrally located townhouse

Family- and pet-friendly home rentals

Superhost
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.
Home in Walkerville
4.83 out of 5 average rating, 156 reviews

3 Bed Bright Modern Home in Heart of Walkerville

Guest favourite
A spacious living area features wooden paneled walls alongside a comfortable sectional couch, adorned with colorful decorative pillows. A coffee table sits in front, and a modern electric fireplace adds warmth. A wall-mounted TV displays the Netflix logo, creating a cozy entertainment space.
Home in Windsor
4.86 out of 5 average rating, 57 reviews

Spacious 1BD Apartment | Prime Location | Parking

Top Guest favourite
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
5 out of 5 average rating, 113 reviews

Navy Yard Flats (Flat A) - Historic Amherstburg

Guest favourite
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
4.91 out of 5 average rating, 161 reviews

2 bedroom Getaway/lake St.Clair/boatslip

Guest favourite
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
4.86 out of 5 average rating, 160 reviews

Quiet LaSalle Newly Renovated Entire Country Home

Top Guest favourite
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
4.99 out of 5 average rating, 120 reviews

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

Guest favourite
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.
Guest suite in Kingsville
4.91 out of 5 average rating, 179 reviews

Main on Main ~ Stylish Studio Downtown Kingsville

Top Guest favourite
A spacious backyard is surrounded by greenery and trees, featuring a cozy seating area under a gazebo. A fire pit is situated next to a wooden bench, inviting outdoor gatherings. The house's exterior displays a combination of wood and modern finishes, creating an inviting atmosphere.
Home in Spring Garden
5 out of 5 average rating, 63 reviews

Turkey Creek Hideaway

Family-friendly home rentals with a pool

Guest favourite
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
4.94 out of 5 average rating, 154 reviews

Waterfront Luxurious Cottage in Lakeshore, Ontario

Top Guest favourite
Barn in Kingsville
4.99 out of 5 average rating, 105 reviews

Cozy Forest Retreat | Bird watch, Sauna, Hiking

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 Windsor
4.89 out of 5 average rating, 87 reviews

Cozy Cedarwood Suite ☆Terrace ☆ heated salt pool

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 Riverside
4.96 out of 5 average rating, 28 reviews

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

Guest favourite
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
5 out of 5 average rating, 5 reviews

Impressive Furnished All-inclusive Apartment

Superhost
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.
Home in Windsor
4.58 out of 5 average rating, 19 reviews

Architectural Gem | Direct-Entry Pool

Superhost
A spacious living area showcases comfortable seating and a modern kitchen with essential appliances. The outdoor patio features cozy furniture under a large umbrella, perfect for relaxation. Lush greenery surrounds the area, emphasizing the tranquility of the private resort setting.
Place to stay in Belle River
4.83 out of 5 average rating, 54 reviews

Whitty’s at Rochester Boat•Golf •Fish•Swim

Superhost
An aerial view presents a well-maintained raised ranch surrounded by a residential neighborhood. Lush green lawns and various trees create a tranquil setting, while several homes with varied architectural styles can be seen in the background. A driveway leads to the main entrance of the house.
Home in Windsor
4.87 out of 5 average rating, 23 reviews

LaSalle Retreat|Full Home2Suites

When is the best time to visit Windsor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$161 AUD$158 AUD$161 AUD$172 AUD$185 AUD$176 AUD$187 AUD$194 AUD$185 AUD$172 AUD$167 AUD$173 AUD
Avg. temp-3°C-2°C3°C9°C16°C21°C23°C22°C18°C12°C5°C0°C

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

  • Total holiday rentals

    Explore 640 holiday rentals in Windsor

  • Nightly prices starting at

    Windsor holiday rentals start at $30 AUD per night before taxes and fees

  • Verified guest reviews

    Over 33,390 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 170 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    380 properties have a dedicated workspace

  • Wi-Fi availability

    630 of Windsor holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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

Destinations to explore

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