How do monthly vacation rentals work in Orlando?

A month or more in Orlando draws a mixed crowd. Snowbirds from the Northeast, the Midwest and Canada trade a winter of shoveling for a heated pool. Remote workers want a home office with palm trees outside the window. Families between homes, or visiting relatives for the season, need more room than a hotel suite. All of them run into rules and costs that a one-week vacation never touches.

Can you rent an Orlando vacation home by the month?

Yes, as long as the home sits in an area where short-term rentals are legal. Under local rules, a stay of one, two or three months is still a short-term rental, not a residential lease.

That matters when you pick an address. In unincorporated Orange County, a short-term rental means any stay of 179 days or less. It is allowed only in commercial and industrial zones and in Planned Developments that expressly permit it. Renting a single-family home for less than 30 days is allowed only in the R-3 district. Everywhere else, both are prohibited. So an ordinary house in a residential Orange County neighborhood does not become a legal rental just because you book it for two months.

Osceola County, home to Kissimmee, keeps a short-term rental overlay map and a zoning district built for this use, the STRPD. Owners have to confirm the property sits inside it before they can get licensed.

That is why the vacation home resort communities south and southwest of the parks work so well for long stays: they were built for exactly this. Our guide to where to stay in Orlando explains the map, and the resorts page lists the communities.

Do monthly rentals in Orlando pay sales tax?

Yes, for any stay of six months or less. Florida taxes the rental of living accommodations for that period, and the state names vacation houses and single-family homes in its list.

The total combines three pieces: the 6% state sales tax, the county surtax and the county tourist development tax (TDT). The state TDT law uses the same six-month line, and Osceola describes it as stays of less than 180 days.

Situation	State tax and surtax	County TDT
Stay of 1 to 6 months	Charged for the whole stay	Charged for the whole stay
More than 6 months, no written lease	Charged for the first 6 months. Exempt from month 7 on, as long as you keep living there continuously	Follows the state exemptions
Bona fide written lease of more than 6 months for continuous residence	Exempt	Follows the state exemptions

Sources: Florida Statutes sections 212.03 and 125.0104, and Florida Department of Revenue brochure GT-800034.

The combined rate depends on the county: 13.5% in Osceola, 12.5% in Orange and 12% in Polk, where Davenport is. For every $1,000 of rent and mandatory fees on a Kissimmee home, that is $135 in tax. Over a month, it becomes one of the biggest lines on the bill.

If your trip is a vacation, even a long one, plan on paying the full tax. The exemption is meant for people signing a lease to live in the property for more than six months, not for a winter getaway. Every piece of the tax is broken down in Orlando vacation rental fees and taxes.

How much does a monthly vacation rental in Orlando cost?

It depends heavily on the month, so the only reliable number is a quote for your dates. Across Orlando Best Place homes, the median nightly rate over the next 12 months, before cleaning and taxes, is $162. The cheapest month is October 2026, at a median of $104 a night, and the most expensive is June 2027, at $192.

Three things change the math on a long stay:

• Cleaning gets spread out. The departure cleaning fee is charged once. Over 30 nights it adds far less per night than it does on a week.
• Tax does not. It is a percentage, and it applies to the whole month, cleaning included.
• Monthly pricing is a conversation. Some managers offer a special rate for long stays and some do not. Ask, and always compare totals with tax.

What an Orlando vacation rental really costs shows how to work out the per night and per person math.

Are utilities and Wi-Fi included in a monthly rental?

In a vacation home, usually yes. It comes furnished and ready, with electricity, water, internet and TV on the home’s account. A traditional lease is different: tenants typically set up utilities in their own name.

On a long stay, still get these answers in writing:

1. Whether electricity and water are included with no cap, or billed above a certain usage.
2. The internet speed, and whether there is a desk and a proper chair. If you work remotely, ask for a recent speed test.
3. Whether pool heat is in the price or charged by the day, which matters for a winter stay.
4. Who services the pool and the yard, and which days they come by.

How long can international visitors stay in the US?

It depends on how you enter. Canadians can usually stay up to six months without a visa. Travelers on ESTA get up to 90 days, with no extension. Visitors on a B-2 tourist visa are admitted for at least six months and up to one year, and the date that counts is on the Form I-94.

How you enter	Permitted stay	Extension?
Canadian citizen, no visa	Usually up to 6 months	Apply to USCIS before your stay expires
ESTA under the Visa Waiver Program (UK, for example)	Up to 90 days	No
B-2 tourist visa	At least 6 months, up to 1 year, per the I-94	Apply to USCIS before your stay expires

Sources: Government of Canada, CBP, Department of Homeland Security, 8 CFR 214.2(b) and USCIS.

The officer at the port of entry sets your admission date, and your visa’s expiration date does not change it. USCIS recommends filing for an extension at least 45 days before your authorized stay ends. The Government of Canada also notes that if officers suspect you spend more time in the US than in Canada, you may have to show you are a temporary visitor.

What changes on a 1 to 3 month stay?

The household routine. A one-week trip needs no upkeep. A month does.

• Mid-stay cleaning. The fee you pay at booking covers the departure clean. Ask whether a mid-stay clean with fresh linens and towels is available, what it costs and how often.
• Trash. Ask for the pickup days and where the bins live. It goes unnoticed on a week. Over a month, it will not.
• Mail. The USPS temporary change of address runs from 15 days up to one year, so bills and prescriptions can follow you south. Check with the manager whether the home accepts packages and which name to use.
• A car. For a month, a rental car is close to essential. Here is why: do you need a car in Orlando.
• Hurricanes. The season runs June 1 to November 30. If your stay overlaps it, read Orlando hurricane season and ask about the cancellation policy.
• Community rules. Ask about parking, guest access and clubhouse use. On a long stay, you will have visitors.

In practice: before you commit to a month, ask for a quote with the full total and the lodging tax on its own line, with the county rate. In the same message, ask for written answers on what is included (utilities, Wi-Fi, pool heat), whether mid-stay cleaning is available and whether the home takes deliveries. If you are visiting from abroad, count your days from your I-94, not from your visa.

Orlando Best Place LLC is a Florida registered company since 2023, with homes in resort communities in Kissimmee, Davenport and Orlando. When you book direct, the final price with cleaning and taxes is shown before payment, with no platform fee, payments are processed by Stripe, and the team answers 24/7 in English, Portuguese and Spanish on WhatsApp at +1 (407) 719-1493. To see the total for your month, start with the vacation home search.