Mississauga vs. Oakville vs. Burlington: Comparing Short-Term Rental Rules and Returns

Mississauga, Oakville, and Burlington sit within a 30-minute drive of each other along the western GTA/Halton corridor, and investors often treat them as interchangeable. They aren’t. Each municipality runs its own short-term rental licensing regime, with different fees, different caps, and different enforcement postures — and the differences are large enough to change which strategy actually works on a given property. Here’s how the three compare, rule by rule and number by number.

The Rules, Side by Side

Mississauga: By-law 0289-2020

Mississauga was the first of the three to formalize short-term rental licensing, with rules in effect since January 2021. The framework is strict on eligibility and increasingly strict on enforcement:

• Short-term rentals are defined as 30 consecutive days or less, and require an operating licence
• Only a genuine principal residence qualifies — an investment condo or a second property cannot be licensed, no matter the numbers
• The annual licence fee runs $283 as of mid-2026, alongside a required $2 million liability insurance policy naming the City as additional insured, and a criminal record check
• Rentals are capped at 180 nights per year
• Operators collect a 6% Municipal Accommodation Tax plus 13% HST
• The City has been actively cracking down on unlicensed listings, so compliance risk here is real, not theoretical

Oakville: Short-Term Accommodation Operator Licence

Oakville uses a 28-consecutive-day threshold to define a short-term accommodation, slightly different from Mississauga’s 30-day line, and its process is documentation-heavy:

• Principal residence is required — the property must genuinely be where the host lives
• Permitted in most detached, semi-detached, and townhome properties, but not in gated communities or HOA-restricted developments that prohibit it
• Applicants must submit a property maintenance and parking plan, a floor plan, proof of ownership, and an inspection certificate from an Electrical Safety Authority-licensed contractor
• Two licence categories exist — an individual operator licence and a company licence — with Oakville reviewing fee structures for both as recently as its December 2025 council report
• Standard MAT and HST collection applies on top of licensing

Burlington: By-law 01-2025

Burlington is the newest of the three regimes, in effect since May 1, 2025, and it was passed specifically to qualify for federal Short-Term Rental Enforcement Fund money — which tells you how seriously the City is treating enforcement:

• Rentals are capped at 28 consecutive days and a total of 183 days (roughly six months) per year
• Principal residence only, with two narrow exceptions: a seasonal home used part-time, and one unit in a multi-unit property where another unit meets long-term affordability criteria
• The licence fee is $300 annually
• As of Burlington’s own May 2026 council update, the City had already conducted 190 investigations into unlicensed operators, and is weighing whether to layer on a Municipal Accommodation Tax to match its neighbours

Feature	Mississauga	Oakville	Burlington
Governing by-law	0289-2020	STA Operator/Company Licence	01-2025
Short-term threshold	≤30 days	<28 days	≤28 days
Annual night cap	180 nights	Not separately capped	183 nights
Principal residence required	Yes	Yes	Yes (two narrow exceptions)
Licence fee	$283/year	Varies by category	$300/year
In effect since	Jan 2021	In place, being updated	May 2025

The through-line across all three: none of them allow a pure investment-property short-term rental strategy. Every one of these municipalities restricts licensed short-term rentals to a genuine principal residence. For investors who don’t plan to live in the property, that single fact matters more than any revenue projection — and it’s exactly why mid-term rental strategies, which typically fall outside short-term rental bylaws once stays exceed 28–30 days, have become the more workable model for non-owner-occupied investment properties across this corridor.

How the Markets Actually Perform

Regulation aside, the three markets also perform differently on the numbers:

• Mississauga shows some of the strongest headline occupancy of the three, with well-located neighborhoods like City Centre and Port Credit historically posting occupancy in the high 60s to low 70s (percent) and daily rates in the $120–$150 range, driven by proximity to Pearson Airport and downtown Toronto business travel.
• Oakville generates average annual revenue in the low-to-mid $20,000s (CAD) per listing, with a wide spread between top-performing and low-performing properties — high-performing Oakville listings can earn more than double the market average, which points to how much pricing and guest-experience execution matters here.
• Burlington shows a similar pattern to Oakville, with average annual revenue in the high $20,000s to low $30,000s and a comparable gap between top- and bottom-quartile performers. Supply across the combined Burlington–Hamilton–Oakville corridor contracted meaningfully over the past year, which has concentrated remaining demand onto fewer, typically better-managed listings.

The consistent pattern across all three markets is polarization: the difference between a top-quartile listing and a median one is often two to three times the annual revenue. That gap is driven far more by pricing discipline, listing quality, and guest experience than by which of the three cities the property sits in — which is part of why professional management tends to matter more here than the underlying city choice.

Which Market Fits Which Strategy

• Mississauga suits owner-occupiers close to Pearson Airport who want strong short-term occupancy from business and layover travelers, and who are comfortable with the City’s more active enforcement environment.
• Oakville suits owners prioritizing a quieter, higher-end guest profile, with the trade-off of a more document-intensive licensing process up front.
• Burlington, with its newer and still-evolving regime, currently offers a slightly less saturated listing environment relative to demand, though the 190-plus enforcement investigations already logged in its first year signal the City intends to hold the line on unlicensed operators.
• Non-owner-occupied investment properties across all three municipalities are generally better suited to a mid-term rental strategy — furnished 30-to-90-night stays for corporate relocations, healthcare contractors, and remote professionals — since that model typically sits outside each city’s short-term rental bylaw entirely.

The Bigger Picture for Investors

None of these three markets can be evaluated on a spreadsheet alone. A property that pencils out beautifully in Mississauga’s short-term market becomes illegal to operate that way if it’s a second property rather than a principal residence — and the same is true across the border in Oakville or Burlington. Getting the regulatory fit right before you buy, not after, is the difference between a compliant, income-producing asset and a property you can’t legally operate the way you planned.

Bespoke Stays works with investors across Mississauga, Oakville, Burlington, and the wider GTA to match the right property to the right strategy — short-term, mid-term, or a blend of both — before money changes hands. Talk to the Bespoke Stays investment team about which of these markets fits your goals.