Family-Friendly Vacation Rentals in Windfields, ON: Compare 10+ Sites & Save

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257 Best Family Vacation Rentals in Windfields (Starting from $80)

Executive Townhome, Bridal Path, Shops at Don Mills
Executive Townhome, Bridal Path, Shops at Don Mills
Apartment
Toronto, Canada
1.2k from Windfields center

Apartments, Accommodations, Parking, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$339
Average price / night
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Newly Renovated 2 Bed/2 Bath 1400 Sq Ft Condo!
Newly Renovated 2 Bed/2 Bath 1400 Sq Ft Condo!
Condo
Toronto, M3B 3N8, Canada
2.4k from Windfields center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
New to Booking
$117
Average price / night
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Luxurious Spa Retreat - Toronto Escape
Luxurious Spa Retreat - Toronto Escape
Apartment
Toronto, Canada
1.7k from Windfields center

Apartments, Accommodations, Parking, Spa, Lodgings, Jacuzzis, Places to stay, Family

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$832
Average price / night
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Toronto Furnished Condo - Modern 1 Bed, 1 Bath Corner Suite. 6 month+ Stays
Toronto Furnished Condo - Modern 1 Bed, 1 Bath Corner Suite. 6 month+ Stays
Condo
Toronto, M2K 0A6, Canada
2.5k from Windfields center

AC, Arcade, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet

1 Bedroom3 Guests
New to Booking
$80
Average price / night
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Immaculate Executive Townhouse 3Br&3Ba at Lawrence Park
Immaculate Executive Townhouse 3Br&3Ba at Lawrence Park
House
Toronto, Canada
3.1k from Windfields center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Self-catering

3 Bedrooms5 Guests
8.7

Fabulous

16 reviews

$334
Average price / night
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Penthouse with swimming pool, saunas, fitness room, BBQ area and indoor carwash.
Penthouse with swimming pool, saunas, fitness room, BBQ area and indoor carwash.
Condo
Toronto, M2J 0B4, Canada
3.4k from Windfields center

AC, Barbecue, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

1 Bedroom3 Guests
New to Booking
$103
Average price / night
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Immaculate Executive Townhouse
Immaculate Executive Townhouse
Villa
Toronto, Canada
3.1k from Windfields center

Balcony/Terrace, Wheelchair Accessible, Parking, Internet, Air Conditioner, Child Friendly

3 Bedrooms5 Guests
New to Booking
$261
Average price / night
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Newly Renovated House in Toronto
Newly Renovated House in Toronto
House
Toronto, M2J 2G6, Canada
3.6k from Windfields center

AC, Barbecue, Dryer, Extra Bed, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms4 Guests
New to Booking
$235
Average price / night
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LARGE 1 bedroom condo great building
LARGE 1 bedroom condo great building
Apartment
Toronto, Canada
3.5k from Windfields center

Air Conditioner, Security/Safety, Parking, Internet, Child Friendly

1 Bedroom2 Guests
New to Booking
$117
Average price / night
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Fully Furnished One Bedroom apartment in the heart of North York
Fully Furnished One Bedroom apartment in the heart of North York
Apartment
North York, M2N 0L1, Canada
3.8k from Windfields center

AC, Balcony, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet

1 Bedroom2 Guests
New to Booking
$248
Average price / night
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Tranquil Toronto Stay - Walk to Shops & Transit
Tranquil Toronto Stay - Walk to Shops & Transit
Villa
Toronto, Canada
3.5k from Windfields center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms8 Guests
New to Booking
$603
Average price / night
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Pivot - 1 Bedroom Apartment North York
Pivot - 1 Bedroom Apartment North York
Apartment
North York, M2N 0L1, Canada
3.8k from Windfields center

AC, Balcony, Crib, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen

1 Bedroom2 Guests
New to Booking
$206
Average price / night
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Lawrence Park Guesthouse
Lawrence Park Guesthouse
House
Toronto, Canada
3.7k from Windfields center

Internet, Air Conditioner, Child Friendly

1 Bedroom4 Guests
New to Booking
$121
Average price / night
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Brand new luxury 1 bedroom 1 bathroom condo in heart of Toronto
Brand new luxury 1 bedroom 1 bathroom condo in heart of Toronto
Apartment
Toronto, M2N 0L7, Canada
4.2k from Windfields center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$141
Average price / night
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Spacious Modern Grand Floor 1, 2 or 3 bedroom (Unit Depending on the number of guests)
Spacious Modern Grand Floor 1, 2 or 3 bedroom (Unit Depending on the number of guests)
Apartment
Toronto, Canada
3.7k from Windfields center

Parking, Child Friendly

3 Bedrooms10 Guests
New to Booking
$261
Average price / night
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Premium one bedroom apartment fully furnished /Northyork
Premium one bedroom apartment fully furnished /Northyork
Condo
Toronto, M2N 0L7, Canada
4.3k from Windfields center

AC, Crib, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom3 Guests
New to Booking
$104
Average price / night
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Sleek 1BR & Sttudy Condo - CN Tower, Skyline view - North York
Sleek 1BR & Sttudy Condo - CN Tower, Skyline view - North York
Apartment
Toronto, Canada
3.7k from Windfields center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Jacuzzis, Places to stay, Family

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$254
Average price / night
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KoHann Design Apartment
KoHann Design Apartment
Apartment
Toronto, M3C 1L4, Canada
4.3k from Windfields center

AC, Balcony, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet

2 Bedrooms4 Guests
New to Booking
$108
Average price / night
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Condo at Yonge-Sheppard Station, North York
Condo at Yonge-Sheppard Station, North York
Apartment
Toronto, Canada
3.7k from Windfields center

Apartments, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Self-catering, Condos

1 Bedroom3 Guests
8.3

Very Good

3 reviews

$199
Average price / night
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Stylish Urban Retreat for Big groups
Stylish Urban Retreat for Big groups
House
Toronto, M4G 2K8, Canada
4.4k from Windfields center

AC, Dryer, Free Parking, Heater, Internet, Laundry, Living Area, Microwave, No Smoking

5 Bedrooms9 Guests
New to Booking
$276
Average price / night
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Cozy 1 BR & Den Condo in North York Free Parking
Cozy 1 BR & Den Condo in North York Free Parking
Apartment
Toronto, Canada
3.7k from Windfields center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay, Condos

1 Bedroom6 Guests
5.0

Review score

2 reviews

$233
Average price / night
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Cozy House,  cottage style in midtown Toronto. Great for Family. Pet friendly
Cozy House, cottage style in midtown Toronto. Great for Family. Pet friendly
House
Toronto, M4G 3N8, Canada
4.5k from Windfields center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
New to Booking
$248
Average price / night
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Quiet Luxury Stay at Prime Location • 2-Min Walk to Leaside Subway• Pet Friendly
Quiet Luxury Stay at Prime Location • 2-Min Walk to Leaside Subway• Pet Friendly
House
Toronto, M4G 2J9, Canada
4.5k from Windfields center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms6 Guests
8.0

Good

1 reviews

$236
Average price / night
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Prime Midtown Toronto Living: Fully Equipped 3-Bedroom & Prime Transit Access
Prime Midtown Toronto Living: Fully Equipped 3-Bedroom & Prime Transit Access
House
Toronto, M4P 1Z8, Canada
4.7k from Windfields center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms5 Guests
New to Booking
$245
Average price / night
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Midtown Victorian Gem
Midtown Victorian Gem
House
Toronto, M4R 1N8, Canada
4.7k from Windfields center

AC, Arcade, Balcony, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms5 Guests
New to Booking
$364
Average price / night
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Victorian Gem - Midtown Toronto
Victorian Gem - Midtown Toronto
House
Toronto, M4R 1N8, Canada
4.7k from Windfields center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$364
Average price / night
Check Availability
Short or Long term stay in Toronto home with family and friends 7 bdr. 6 bath
Short or Long term stay in Toronto home with family and friends 7 bdr. 6 bath
House
North York, M4A 1N6, Canada
4.8k from Windfields center

AC, Arcade, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

6 Bedrooms18 Guests
9.6

Exceptional

15 reviews

$339
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Windfields.

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Windfields Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 257 verified family-friendly vacation rentals in Windfields. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Windfields vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $80 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Windfields offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Windfields are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Windfields often include amenities such as Child Friendly, Wellness Facilities, and Fireplace/Heating. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.