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Family-friendly vacation rentals in Windsor

Find and book unique family-friendly homes on Airbnb

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

  • Total vacation rentals

    Explore 690 vacation rentals in Windsor

  • Nightly prices starting at

    Windsor vacation rentals start at G$4,184 GYD per night before taxes and fees

  • Verified guest reviews

    Over 37,400 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 190 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    430 properties have a dedicated workspace

  • Wi-Fi availability

    680 of Windsor vacation 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 favorite
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
4.96 out of 5 average rating, 322 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.

KitchenFamilyTV

Top guest favorite
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
4.92 out of 5 average rating, 125 reviews

The Ambassador Estate Inn

Welcome home to all our previous guests and greetings to all our new friends across the globe. A luxurious 7 bedroom estate property located on Windsor’s finest golf course and just minutes from both the Ambassador Bridge and the brand new Gordie Howe Bridge International Bridge. With all the amenities of a 5 star resort, yet the privacy and serenity of a large country estate, you need look no further than the Ambassador Estate Inn to make your vacation or business travel a memorable experience!

FamilyIndoor spacesLaundry

Top guest favorite
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
4.96 out of 5 average rating, 180 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.

KitchenIndoor spacesCondition

Top guest favorite
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
4.94 out of 5 average rating, 222 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.

Indoor spacesFamilyComfort

Guest favorite
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
4.97 out of 5 average rating, 154 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.

Indoor spacesKitchenLaundry

Top guest favorite
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
4.98 out of 5 average rating, 150 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!

KitchenFamilyHospitality

Guest favorite
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
4.81 out of 5 average rating, 242 reviews

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!

Indoor spacesKitchenLayout

Top guest favorite
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
4.93 out of 5 average rating, 461 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.

KitchenFamilyNearby

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
4.85 out of 5 average rating, 119 reviews

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!

FamilyIndoor spacesLong stay

Guest favorite
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
4.96 out of 5 average rating, 136 reviews

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

Indoor spacesFamilyCleanliness

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
4.87 out of 5 average rating, 255 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!

Indoor spacesFamilyOutdoor spaces

Guest favorite
Villa in LaSalle
4.87 out of 5 average rating, 231 reviews

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.

Indoor spacesFamilyLong stay

Popular amenities for Windsor family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a pool

Superhost
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
4.91 out of 5 average rating, 134 reviews

Beautiful 2 bdrm Lower Level Sport Themed Suite

FamilyIndoor spacesGetting around

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
4.81 out of 5 average rating, 150 reviews

Midtown Gem – Walkable & Bright Hotel Style Unit

Indoor spacesKitchenSolo travel

Guest favorite
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
4.93 out of 5 average rating, 56 reviews

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

Indoor spacesKitchenBackyard

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
4.67 out of 5 average rating, 45 reviews

Luxury at its finest (Windsor) Swimming Pool

KitchenIndoor spacesHospitality

Guest favorite
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
4.88 out of 5 average rating, 93 reviews

Cozy Cedarwood Suite ☆Terrace ☆ heated salt pool

Indoor spacesKitchenAccuracy

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
4.91 out of 5 average rating, 35 reviews

South Windsor Spacious Basement + Pool

KitchenIndoor spacesParking

Guest favorite
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
4.87 out of 5 average rating, 45 reviews

The Grand River Retreat. Pool/ hot tub avail Sep

Indoor spacesFamilyCleanliness

Top guest favorite
Home in Windsor
4.98 out of 5 average rating, 53 reviews

Windsor Luxury Stay Oasis

KitchenFamilyPool

Family-friendly home rentals with a hot tub

Top guest favorite
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
4.98 out of 5 average rating, 179 reviews

Perfect hideaway with a hot tub and a fireplace

FamilyKitchenDecor

Guest favorite
A wooden deck extends over calm waters, featuring a simple table and seating. The sun sets on the horizon, casting a warm glow across the sky, while reflections shimmer on the water's surface. Trees provide gentle shade along the edge.
Home in Belle River
4.96 out of 5 average rating, 114 reviews

Lake Louise With hot tub

Indoor spacesFamilyAccess

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
4.81 out of 5 average rating, 115 reviews

Breathtaking Waterfront Home

Indoor spacesKitchenLocation

Guest favorite
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
4.96 out of 5 average rating, 105 reviews

Belanger Air BnB

Indoor spacesKitchenBeach

Guest favorite
Home in Detroit
4.91 out of 5 average rating, 126 reviews

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

FamilyIndoor spacesCheck-in

Guest favorite
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
4.88 out of 5 average rating, 227 reviews

The Painted House by Eastern Market ~Boutique B&B~

FamilyIndoor spacesLocation

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
4.94 out of 5 average rating, 118 reviews

Centrally located 5BR- Hot Tub & Game Room

Indoor spacesKitchenValue

Superhost
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
4.86 out of 5 average rating, 126 reviews

Massive Detroit-Themed Stay | HT, Games, Fire Pit

Indoor spacesFamilyCondition

Family-friendly home rentals with air conditioning

Top guest favorite
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
4.97 out of 5 average rating, 226 reviews

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

KitchenIndoor spacesBiking

Guest favorite
A serene lakeside view is captured at dusk, featuring a white navigational beacon standing on green grass. In the background, the calm water reflects the evening sky, while silhouettes of boats and distant lights are visible near the shoreline.
Home in Tecumseh
4.82 out of 5 average rating, 144 reviews

The Lake House 🇨🇦 Tecumseh, Ontario Canada.

Indoor spacesKitchenAccuracy

Superhost
A comfortable seating area features a light-colored sofa and a wooden coffee table atop a textured rug. A brick fireplace serves as the focal point, while a flat-screen television is mounted on the wall, creating a cozy atmosphere in the open space.
Guesthouse in Windsor
4.74 out of 5 average rating, 314 reviews

Cozy 1 Bed Basement Studio Apt

KitchenFamilyHospitality

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 LaSalle
4.83 out of 5 average rating, 248 reviews

The Ambassador’s Stay • Bright 1BR Family Retreat

KitchenIndoor spacesGetting around

Guest favorite
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
4.95 out of 5 average rating, 117 reviews

OldeWalkerville Loft Gem on the River

Indoor spacesKitchenRiver

Top guest favorite
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
4.99 out of 5 average rating, 140 reviews

Serenity by the Woods- Elegance with Amenities

FamilyKitchenValue

Guest favorite
Home in Windsor
4.95 out of 5 average rating, 85 reviews

JP's Dream House

Indoor spacesFamilyParking

Guest favorite
Home in Walkerville
5.0 out of 5 average rating, 30 reviews

Windsor Casino and International Swim Meet AirBnb

KitchenIndoor spacesParking

When is the best time to visit Windsor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$21,755 GYDG$21,964 GYDG$22,801 GYDG$23,428 GYDG$25,938 GYDG$25,102 GYDG$24,265 GYDG$24,892 GYDG$22,591 GYDG$23,010 GYDG$22,382 GYDG$22,801 GYD
Avg. temp-3°C-2°C3°C9°C16°C21°C23°C22°C18°C12°C5°C0°C

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