We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Pickering Family & Kid Friendly Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $127 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travelers get your favorite Pickering area vacation rental. You're so close to securing your perfect getaway. Book today.
    20 Matching Rentals in the Pickering AreaView all 26 rentals
    Sort by:
    Default
    Pickering
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Pickering
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Pickering
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Pickering
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Breathe Easy at Chalet Claremont Bed & Breakfast At Chalet Claremont Bed & Breakfast, doing our part to protect the environment – both outdoor and indoor – is extremely important to us. In addition to serving organic food for breakfast, we only use eco-friendly cleaning and laundry products, and...
    View all property information
    Location Information
    Pickering, Ontario L0C 1A0
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Pickering
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Breathe Easy at Chalet Claremont Bed & Breakfast At Chalet Claremont Bed & Breakfast, doing our part to protect the environment – both outdoor and indoor – is extremely important to us. In addition to serving organic food for breakfast, we only use eco-friendly cleaning and laundry products, and...
    View all property information
    Location Information
    Pickering, Ontario L0C 1A0
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Pickering
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Breathe Easy at Chalet Claremont Bed & Breakfast At Chalet Claremont Bed & Breakfast, doing our part to protect the environment – both outdoor and indoor – is extremely important to us. In addition to serving organic food for breakfast, we only use eco-friendly cleaning and laundry products, and...
    View all property information
    Location Information
    Pickering, Ontario L0C 1A0
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    The following rentals are within 15 miles of Pickering.
    A COZY COTTAGE+ HEATED POOL OASIS IN GREATER TORONTO : FREE WIFI,MOVIES, PARKING1 / 78
    (4)Excellent
    Richmond Hill
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 9, 2018
    A great house located on the edge of the City. The house is exceptionally clean in a quiet neighborhood, 30 minutes into Union Station via the GO from Rutherford, the House...
    Reviewed September 17, 2017
    We had a great time in Toronto. Cottage is equipped very well (WIFI and Netflix...) and perfectly located to visit Toronto and surroundings. The owner Jerry was very nice and...
    See all reviews
    About this property
    LOCATION, LOCATION IN GREATER TORONTO AREA(GTA). A rare find .This home has the privacy of a summer cottage oasis and the convenience of a central city location. Nestled in the GTA in the city of Richmond Hill, this 3 bedroom home has a spectacular backyard, perfect for entertaining and family...
    View all property information
    Location Information
    Richmond Hill, Ontario L4C6J1
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    Oshawa
    5 Bedrooms, 2 Bathrooms, Sleeps 20 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront, 5 BR, Spacious, Private, Year Round, Located Close To Lindsay, Hospital, Shopping, Casino, Golfing Etc., Private Beach, Conveniently located, Great Lake View. All amenities of home, swim or fish right off the dock, go for a quiet paddle on the clear lake, or hike the local trails. End...
    View all property information
    Location Information
    Oshawa, Ontario K0M 2C0
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 20
    Make Inquiry
    Ajax
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful one private bedroom available. This is a part of family residence. Washroom is shared with one other person. Access to kitchen, refridgerator and private yard space. this is located in a lovely neighbourhood. Close proximity to Lake Ontario. linens provided. You just need to take...
    View all property information
    Location Information
    Ajax, Ontario L1Z 2C8
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Richmond Hill
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My condo is one bedroom plus den and is located on Yonge Street in the heart of Richmond Hill. Close to parks, great views, restaurants, dining, Hillcrest Mall and groceries. My place is 30 minutes away from Down Town Toronto where you can visit Dundas Square, CN tower, Ripley's aquarium, ROM...
    View all property information
    Location Information
    Richmond Hill, Ontario L4C 1V6
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Inquiry
    Save time - get the best Pickering rentals sent straight to your email!
    Get the List
    Richmond Hill
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A cozy and welcoming 5 bedroom home located in a quiet neighborhood at a very convenient location, minutes (walking) to Yonge St, local restaurants, grocery store and public transportation. Near all the major attractions Canada's Wonderland and Vaughn Mills mall shopping center. Free parking and...
    View all property information
    Location Information
    Richmond Hill, Ontario L4E 4Z6
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Inquiry
    4 BDR FULL HOUSE in RICHMOND HILL1 / 44
    (1)Excellent
    Richmond Hill
    4 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 9, 2016
    We had a large family to stay and the owner was very accommodating to our needs. Home was comfortable and just a place that we needed. Strongly recommend this home to others.
    See all reviews
    About this property
    The kitchen has everything that you will need to prepare a banquet. no party or gathering allowed, only what ever the guest book can stay, or gather, It features high efficiency stainless appliance (fridge, electric stove with oven, dish washer and microwave). Also features with small appliance...
    View all property information
    Location Information
    Richmond Hill, Ontario L4E 4K6
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 15
    Make Inquiry
    Unionville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are located in a safe, quiet neighborhood in Markham. There is easy access to public transportation, shops, schools, churches, shopping malls, parks, recreational areas, etc. All our guests have expressed their appreciation for staying with us....
    View all property information
    Location Information
    Unionville, Markham L3P 4S4
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Richmond Hill
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Balcony
    • Patio
    • Secure Parking
    • Private Yard
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern and contemporary open concept newly renovated house with elegant and spacious 4 rooms & 4 bathrooms, located in a quiet child safe court, in center of Richmond hill area. You will have 3 free parking spots, unlimited WiFi, 50'flat screen TVs , Highest speed internet. Great location! ! ! 5...
    View all property information
    Location Information
    Richmond Hill, Ontario L4S 0B1
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Inquiry
    Richmond Hill
    5 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Secure Parking
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand new multi-million dollar custom home in Richvale (Richmond Hill) Ontario built in the summer 2017. This 6000 sqf home features 5 bedrooms, 6 washrooms, a bar, entertainment room, custom kitchen, an office, 2 in-garage & 3 outdoor private parking. You also enjoy a private backyard with a...
    View all property information
    Location Information
    Richmond Hill, Ontario L4C 6R8
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 13
    Make Inquiry
    Unionville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Private Yard
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are located in a safe, quiet neighborhood in Markham. There is easy access to public transportation, shops, schools, churches, shopping malls, parks, recreational areas, etc. All our guests have expressed their appreciation for staying with us....
    View all property information
    Location Information
    Unionville, Markham L3P 4S4
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Richmond Hill
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Private Yard
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spoil in this luxury living place with extensive space and privacy! The 3400 sqft home is located at a very quiet street in Richmond Hill, north suburban of Toronto. This place is well furnished for rest and comfort with necessary living essentials: 4K smart TV, fast WIFI, charging station,...
    View all property information
    Location Information
    Richmond Hill, Ontario L4E 0T1
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Inquiry
    Unionville
    6 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Big house in the heart of unionville markham, 6 bedrooms. Office , guest room and dinning room Finished basement Hardwood floor in the main floor and carpet in the second floor. Hot tub outside at the backyard Parking for 4 cars Beside Markville mall and unionville area Close to major highways...
    View all property information
    Location Information
    Unionville, Markham L3R6C3
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Inquiry
    Richmond Hill
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Cable/satellite TV
    • Washer
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Absolutely beautiful and cozy walk-out basement apartment, located at center Richmond Hill area, Bayview/Major Mackenzie . This is a self-contained, private with a separate entry with 2 bedrooms, 1 den, newly renovated kitchen with brand new toaster, kettle, coffee maker. Nice living room with...
    View all property information
    Location Information
    Richmond Hill, Ontario L4S 0B1
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Richmond Hill
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This place is located in Mill Pond heritage area, city of Richmond Hill. Steps to the Mill Pond Park, mix of culture and nature. It's perfect for leisure travellers to stay and enjoy in a quite, nice neighbour. Two bedroom are available. Free parking, unlimited wi-fi, full kitchen, living room...
    View all property information
    Location Information
    Richmond Hill, Ontario L4C 4G8
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing

    Additional Pickering Info

    Go to map view
    • Local time: 06:28 PM (EDT)
    • Exchange rate: 1 Canadian Dollars = 0.77 U.S. Dollars
    List your property
    Owner log in