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Airbnb management in Pickering

Frenchman's Bay on one side, the Rouge on the other and a GO train to the city. A home here can earn on the nights you are not using it.

List your property What homes here earn

Who stays here

Weekend visitors to the bay and the casino resort, people working nearby for a few weeks, and families who want a whole house within reach of Toronto.

  • Frenchman's Bay
  • Nautical Village
  • Pickering Casino Resort
  • Pickering Town Centre
  • Pickering GO station
  • Rouge National Urban Park

What homes here earn

A year of bookings, published

Pick the number of bedrooms. These are one data company’s figures for every Airbnb listing in the market, not a promise for your home.

Bedrooms

Two-bedroom homes in Pickering, a year of bookings

to

About CA$1,790 to CA$1,830 a month, before cleaning, booking-site fees, tax and a manager’s fee.

Typical home
Average
Nights booked
Average night

Busiest month across Pickering: August. Quietest: January.

EstimatePublished market figures for 255 Airbnb listings in Pickering, November 2025 to October 2026, from AirROI. Other sources publish different figures. These are not Cloud 9’s results and not a promise of what your home will earn.

Get a figure for your home

Doing it yourself

Hosting is a second job

The listing is the easy part. A week of running it in Pickering looks more like this.

  1. 11:40 pm

    A guest cannot find the key. Your phone is the front desk.

  2. 6:15 am

    Checkout at eleven, the next guests at three, and the cleaner has cancelled.

  3. Tuesday

    The long weekend is priced like any other night. Somebody books it in an hour.

  4. Thursday

    Airbnb and Booking.com both took the same Saturday.

  5. Saturday

    Out of toilet paper, coffee and clean towels, in that order.

  6. Month end

    Which booking paid what, after whose fees, and what is actually left?

With Cloud 9

All of that is ours

You own the home. We do the work that comes with every guest, and show you all of it.

  1. A price for every nightRates follow the season, the day of the week and how full the calendar is. You set the floor and the ceiling.
  2. Three sites, one calendarYour home on Airbnb, Booking.com and VRBO, with one calendar behind all three.
  3. Guests, at any hourWe answer guests before, during and after their stay, so your phone stays quiet.
  4. A clean after every checkoutA cleaner is booked for each one and sends photos when the home is ready.
  5. RestockingWhatever is running low gets reordered before a guest notices.
  6. The numbersA daily update and a profit and loss statement every month, on your phone.

Three things stay in your name

  • The city's registration or licence

    It is issued to you, for your home. We go through what your city asks for with you.

  • Insurance

    Your policy has to cover paying guests. Ask your insurer before the first one arrives.

  • Your tax return

    The income is yours. Your monthly statement gives you or your accountant the numbers.

The paperwork

What the city asks for

The licence, the fee and the tax, in plain words, with the page each comes from.

City of Pickering

The City is still finishing its short-term rental rules. A licence has been proposed.

  • Licence

    The City has consulted on a short-term rental licence. We found no fee and no confirmation that it has been adopted.

  • Accommodation tax

    4% on hotels since 1 June 2025. The City said short-term rentals will be covered once its by-law is adopted.

Which homes qualify, and for how many nights, depends on the home and how you use it. We go through that with you for your address.

Where this comes from

Read on 13 November 2026. Fees and rates change, so check the city’s page for today’s figures.

Sales tax, income tax, condos and insurance are in the owner’s guide.

How it works

Four steps, and the first takes a minute

  1. 1

    Tell us about the home

    Five quick taps: where it is, what kind it is, how many bedrooms. You see what homes like it earn straight away.

  2. 2

    We quote and set it up

    A quote for your home, then listings on the booking sites, nightly prices and a cleaner.

  3. 3

    We run every stay

    Prices, guests, cleaning and restocking, checked again after each checkout.

  4. 4

    You see everything

    Your calendar, a daily update and a monthly statement, on your phone.

Questions from Pickering owners

Straight answers

How much could a Pickering home earn?

The published market figures by number of bedrooms are on this page, with their source. They are estimates for all Pickering listings, not a promise for yours.

Where do Pickering's rules stand?

The City has consulted on a short-term rental licence and we could not confirm that it has been adopted. We go through where it stands with you.

Does the accommodation tax apply to my home?

Pickering's 4% tax has applied to hotels since 1 June 2025. The City said short-term rentals will be covered once its by-law is adopted.

Can you manage it if I live out of town?

Yes. Pricing, guests, cleaning and restocking are run for you and you follow all of it on your phone.

What does Cloud 9 charge?

It depends on the home, so we quote for yours. Answer a few quick questions and we will come back with a figure.

What could yours earn?

Five quick taps about your home, then we send you a figure for it.

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Nearby

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City of Toronto

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