Airbnb Property Management Oakville

Yes, in Oakville, any rental less than 29 days requires a Short-Term Accommodation (STA) Operator Licence, and the host must live at the property (principal residence). Certain housing types are permitted, including up to three units in a B&B setting. Platforms like Airbnb, Vrbo and Booking.com will require any short-term accommodation to have a licence number before renting your property. If you’re exploring long-term rental options, no licensing is required, and the unit does not need to be your primary residence.

In Oakville, a short-term rental is defined as any rental of a property or portion of a property for 29 consecutive days or less. Rentals longer than 30 days are considered long-term and do not fall under the city’s short-term accommodation regulations. To operate legally, the rental must comply with the city’s Short-Term Accommodation (STA) By-law, which includes licensing, insurance, and principal residence requirements. 

A mid-term rental property is a type of furnished accommodation leased for a period longer than a typical short-term rental (like an Airbnb) but shorter than a long-term lease, usually ranging from 29+ days to 6 months. It offers a flexible housing solution for individuals needing temporary housing, such as traveling professionals, students, or those undergoing a life transition. Mid term stays have become quite popular as the rise of remote work has enabled more people to experience living somewhere else for an extended period of time. Some property owners prefer the less turnover that comes with mid term stays and others are not eligible for short term rentals.

Oakville is one of Ontario’s most desirable rental markets, with average nightly rates around CA $142 and seasonal peaks in summer that push occupancy and earnings higher. Well-located, well-presented properties can earn over CA $4,600/month during peak periods, while the median listing earns around CA $1,454/month. Demand is driven by both short weekend stays and longer-term bookings, making it important to set competitive rates based on season, location, and property amenities. Positioning your listing for both leisure and business travellers will maximize returns.

Oakville blends lakeside charm with an upscale, welcoming community atmosphere, attracting a mix of families, business travellers, and weekend vacationers. Visitors are drawn to the Bronte Heritage Waterfront, Bronte Creek Provincial Park, Coronation Park, boutique shopping in Downtown Oakville, and premium retail at Oakville Place. The dining scene is equally enticing and developing at an exciting pace! With fine dining options like Hexagon and Oliver’s Steakhouse, lively venues such as CHOP Steakhouse & Bar, and cozy pubs like The King’s Arms. Its proximity to Toronto and quick access to major highways make Oakville an ideal base for exploring the GTA while enjoying a quieter, more scenic environment.

Oakville’s rental market benefits from a combination of high visitor demand, limited hotel supply, and a growing preference for fully furnished, private accommodations. Guests value the space and amenities offered by modern condos, charming townhouses, and luxury lakefront homes. Specialty features like full kitchens, multiple bedrooms, private outdoor areas, and family-friendly layouts. It has notoriously safe neighbourhoods, excellent schools, and vibrant local culture. This makes Oakville especially appealing for family stays and extended visits, while the upscale dining, arts scene, and waterfront activities attract a steady flow of short-term leisure travellers.

While Oakville has a strong short-term rental market, there is also steady demand for mid-term stays (28–90+ nights), particularly from corporate relocations, visiting professionals, and families between homes. This demand is boosted by Oakville’s reputation for safety, quality of life, and access to both Toronto and the Niagara region. Mid-term rentals are especially appealing to guests seeking a fully furnished, move-in ready space without the commitment of a long lease—creating a niche opportunity for hosts who can cater to this audience.

We take on properties that are going to be attractive to people coming into town for a short term or monthly rental. We try to focus on nicer homes or condos that allow short term rentals or rentals of at least one to three months. A big part of the short term rental guest experience is the condition of the property. Even if a home or condo is in the best location in the city, it’s important that it’s well kept in order to avoid guest issues. Airbnb management is about making guests happy and a great experience is dependent on both a five star service and a great property.

Our clients typically have a long term mindset towards working with us. We’re focused on providing an excellent service managing our clients properties on Airbnb and other short term rental platforms.  Short term rental management is a service that requires a lot of mutual trust, and we want to work with people who want to build a relationship that lasts. 

We’re a local company focused on building lifetime relationships within the community. While we have clients who have been with us over a decade, we also understand people’s situations change and they may need to sell the home or stop renting it out. It’s common for former clients to refer their family or friends or come back after years with a different property. Our mindset is once a client, always a client. While our community of homeowners is local, our community of guests is global. It’s an honor to be able to work with our clients who share their homes with people all over the world and enrich their experiences travelling to the city. 

A big factor when choosing an Airbnb management company in Oakville is that they are local. There are a lot of moving parts to managing a short term rental and for people who want to be hands off it’s important the company they work with has local presence and experience. Many guests who visit Oakville are here on vacation and every detail matters when it comes to their stay. A local company helps ensure that there is that extra level of attention and service to ensure things run smoothly.

There are many different ways a property owner can find someone to manage their property on Airbnb and other short term rental platforms. If you have a friend who works with an Airbnb management company you can ask them if you are happy with their service and ask them to refer you. Some property owners do their research online and find a company that is the best fit for them. Everyone has their own method for selecting a company that is the best fit for their personal goals.

The model for most Airbnb management companies is a commission percentage taken based on each booking. Some companies provide solely online short term rental management services, while others provide a full service model. The full service model is typically more hands on and a higher commission compared to the online model. The online model is great for hosts who want to be actively involved on the ground but need help with generating and optimizing bookings. As a local Airbnb management company in Oakville we provide both full service and online only services depending on our clients needs.

The first step is to create an attractive Airbnb listing you’re proud of on short-term rental platforms. An attractive listing features professional photos and a well written description of the property and the surrounding areas. Next a pricing strategy that factors demand across seasons should be implemented. We do our best to employ a pricing strategy that is a good fit for our clients depending on their goals. Once bookings are coming in, we arrange to ensure the property is clean and well maintained as well as provide guests recommendations to enhance their overall experience.