Family-friendly holiday rentals in Windsor

4.96 out of 5 average rating, 320 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.

KitchenIndoor spacesAccess

4.99 out of 5 average rating, 140 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.

FamilyKitchenDecor

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.

4.98 out of 5 average rating, 178 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

FamilyIndoor spacesComfort

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.

4.95 out of 5 average rating, 174 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.

FamilyIndoor spacesValue

4.99 out of 5 average rating, 105 reviews

Guest suite in Windsor

Modern guest suite downtown

Self contained 1 bedroom suite in the heart of downtown Windsor. This thoughtfully designed space combines both modern comfort and old world charm. Perfect for working professionals, couples or solo travelers. This unit features a separate entrance, stainless steel appliances, an oversized shower, spacious bedroom, a work space, large windows and laundry access. Relax and unwind in the backyard or enjoy the convenience of local shops, cafés, restaurants and vibrant nightlife just steps away.

Indoor spacesFamilyHeating

4.94 out of 5 average rating, 179 reviews

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

Waterfront Modern Executive Cottage with lots of natural light and stunning views. This cottage is a breath of fresh air and provides all of the comforts and conveniences that you need in a luxurious relaxing getaway . The cottage boasts a unique layout that sleeps 4 with a bright fully stocked kitchen and dinette, master bedroom, an eclectic second bedroom, barn doors, Smart TV and plenty of closet space, gas fireplace, swimming pool and giant waterfront backyard with lake access to swim.

Indoor spacesFamilyHiking

4.94 out of 5 average rating, 222 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.

Indoor spacesKitchenHospitality

4.97 out of 5 average rating, 152 reviews

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.

KitchenIndoor spacesNearby

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.

4.98 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!

FamilyKitchenHospitality

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.

4.82 out of 5 average rating, 239 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!

FamilyKitchenAccuracy

4.93 out of 5 average rating, 458 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.

Indoor spacesFamilyValue

4.92 out of 5 average rating, 136 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 - Exclusive Main floor unit

Welcome to our charming main floor private loft in the heart of a Walkerville, Windsor. This space combines modern comfort with some abstract 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 cafes just steps away. Enjoy the city's historic areas during the day and unwind in the unique loft at night.

FamilyKitchenGetting around

Popular amenities for Windsor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.74 out of 5 average rating, 160 reviews

An open-concept living area features a sectional sofa and a modern entertainment unit with a wall-mounted TV. Natural light fills the space, complemented by a decorative area rug. A breakfast bar with gray stools offers additional seating, enhancing the inviting atmosphere.

Home in Dearborn

Top-Rated 4BR Dearborn Oasis | Jacuzzi • Near DTW

FamilyIndoor spacesWi-Fi

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.

4.86 out of 5 average rating, 124 reviews

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

Indoor spacesKitchenCheckout

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.

4.95 out of 5 average rating, 117 reviews

Centrally located home - Perfect for large groups

KitchenIndoor spacesGetting around

An open-concept living area features a modern gas fireplace surrounded by a stylish stone accent wall. Plush couches are arranged on a colorful area rug, with a unique pendant light above. A cozy hanging chair adds an inviting touch, while the kitchen is viewable in the background.

4.93 out of 5 average rating, 104 reviews

The Villa: spa, fire, games-Family/Group Perfect!

Indoor spacesKitchenAir conditioning

4.92 out of 5 average rating, 123 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 LaSalle

The Ambassador Estate Inn

Indoor spacesKitchenView

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.

4.98 out of 5 average rating, 103 reviews

Belanger Air BnB

Indoor spacesKitchenDecor

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.

4.96 out of 5 average rating, 112 reviews

Lake Louise With hot tub

KitchenFamilyCondition

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.

4.82 out of 5 average rating, 114 reviews

Breathtaking Waterfront Home

Indoor spacesKitchenParking

Family- and pet-friendly home rentals

5 out of 5 average rating, 19 reviews

2 Beds Comfortable Stay

FamilyHospitalityLocation

5 out of 5 average rating, 17 reviews

Windsor Gem - Pets, Office, Parking.

KitchenLocationGetting around

4.81 out of 5 average rating, 301 reviews

A bright living area features a blue sectional sofa positioned beside a modern, round coffee table. Natural light enters through large windows, illuminating the space. A sleek fireplace and a mounted television are visible along the white brick wall, creating a cozy gathering spot.

Home in Walkerville

Walkerville Charm Home

KitchenIndoor spacesLong stay

4.94 out of 5 average rating, 32 reviews

Apartment in Walkerville

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

FamilyKitchenAccess

4.87 out of 5 average rating, 167 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

FamilyKitchenValue

4.95 out of 5 average rating, 151 reviews

A vibrant space features a colorful hammock perfectly strung across the room. A large projection screen displays a scenic landscape with mountains and skies, while the walls are painted in bright green hues. Natural wood flooring adds a rustic touch to the overall decor.

Barn in Romulus

Vintage Inspired Barn Loft by Maison De LeMade

FamilyIndoor spacesAccess

4.7 out of 5 average rating, 251 reviews

Apartment in Windsor

AKSUM- Location! Lovely Studio, Ensuite Shower, AC

KitchenIndoor spacesAmenities

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.

4.89 out of 5 average rating, 151 reviews

Family-Sized 3BR • 5 Beds • Near Downtown

KitchenFamilyLong stay

Family-friendly home rentals with a pool

A modern living room features two black leather sofas positioned adjacent to a glass-top coffee table. The space is illuminated by natural light through two windows, accented by light grey walls and a plush area rug underneath.

4.85 out of 5 average rating, 71 reviews

Cute with a pool. 12 mins to Downtown.

Indoor spacesFamilyBarbecue

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.

4.91 out of 5 average rating, 43 reviews

The Grand River Retreat. Pool/ hot tub avail Sep

Indoor spacesKitchenAmenities

5 out of 5 average rating, 44 reviews

Loft in Wyandotte

Penthouse, Queen beds, Pool, Gym, Arcade, Downtown

KitchenIndoor spacesQuiet

4.88 out of 5 average rating, 93 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 Tecumseh

Cozy Cedarwood Suite ☆Terrace ☆ heated salt pool

KitchenIndoor spacesShared spaces

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.

4.93 out of 5 average rating, 56 reviews

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

KitchenIndoor spacesNearby

4.81 out of 5 average rating, 149 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

KitchenIndoor spacesLocation

5 out of 5 average rating, 24 reviews

A circular concrete area is shown, featuring six red Muskoka chairs positioned around a central fire pit. The green grass surrounds the seating area, and a light tree canopy filters sunlight onto the space, creating a relaxed outdoor setting.

Tiny home in Belle River

Cottage-Belle River (Rochester Place #718) WiFi

Indoor spacesKitchenNearby