Orlando Getaways: Cite $29,472, Keep Kissimmee Separate

Thomas Garner
16 hours ago
12 min read

Empty Orlando Florida downtown skyline at Lake Eola, no people

Most Orlando listings still get sold as a generic theme-park stay, or worse, as a blended Kissimmee year. Guests who typed Orlando are looking for Lake Eola, downtown, and a real city night. They are not looking for a Kissimmee caption. 4,520 active listings sit on this city extract. Write the stay you can actually host.

The three strongest city months are March, December, and April. March is the busiest. July is the slowest. Occupancy is weakest in July. Most guests arrive from Miami, then Orlando. Stay is 5.1 nights, booked about 53 days ahead. Call Orlando Code Enforcement at 407-246-2686. Home Sharing Registration at orlando.gov. Home share: rental period less than 30 days; one booking at a time; the resident must live on site and be present when hosting; proof of registration on online ads; no more than four unrelated persons in a single booking, or two persons per room, whichever is less; 50 percent or fewer bedrooms devoted to hosting. Annual fee: first year $275; thereafter $100 if the owner lives on the property, $125 if non-owner occupied. Confirm 2026. Entire-home 1-29 day listings are not the Home Share path. Unincorporated Orange County is another hall. Florida DBPR vacation rental licensing is a statewide layer — confirm the current amount at myfloridalicense.com. AirROI's low-regulation label and 0 percent registration evidence are a scrape of listings, not the town file.

Two Cities, Not One Blended Theme-Park Year

Typical Orlando listings earned about $29,472 last year from 4,520 active rentals, AirROI trailing twelve months from August 2025 through July 2026. The average night was $243. Occupancy was 43.8 percent. Revenue per available night was $105. Year over year is plus 14.3 percent. Active supply moved plus 46.9 percent. Write this heading as the stay a host can actually file. Write the city or the satellite the guest typed. Market an Orlando Stay is already live on Crest and Cove. Use it. Do not paste a satellite year into a city tile. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed.

Orlando's Own Extract: $29,472 on 4,520 Listings

4,520 active listings is a real gallery. Superhost share is 51 percent. Professionally managed share is 24.8 percent. Villatel holds 173 listings. Treat $29,472 as evidence for Orlando, not as a corridor dashboard you can paste onto Kissimmee. Write this heading as the stay a host can actually file. Keep $29,472 on 4,520 city listings on its own line. Orlando STR Rules is already live on Crest and Cove. Use it. Do not paste a satellite year into a city tile. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line.

March, December, and April Are the Strong City Months

The three strongest city months are March, December, and April. March is the busiest. July is the slowest revenue month. Occupancy is weakest in July. Stay is 5.1 nights. Lead is 53 days. Most guests arrive from Miami, then Orlando. Write this heading as the stay a host can actually file. March is the city peak. July is the city hole. Orlando Shoulder is already live on Crest and Cove. Use it. Do not paste a satellite year into a city tile. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole.

Kissimmee Is Another Year, Not This Note

Kissimmee listings earned about $35,208 last year from 10,688 active rentals on the current AirROI extract. Keep that stay on its own line. Kissimmee and Osceola County are another hall. A Lake Eola driveway is not a Kissimmee lot. Write this heading as the stay a host can actually file. Call 407-246-2686 before you advertise an Orlando stay. Orlando Remote Stays is already live on Crest and Cove. Use it. Do not paste a satellite year into a city tile. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole.

Winter Park Is Another Year, Not This Note

Winter Park listings earned about $19,847 last year from 130 active rentals on the current AirROI extract. Keep that stay on its own line. Winter Park is another hall. Write this heading as the stay a host can actually file. Home share requires the resident on site. DIY vs Hire in Orlando is already live on Crest and Cove. Use it. Do not paste a satellite year into a city tile. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay.

Lake Eola and Downtown Are Demand, Not Occupancy

Lake Eola, downtown, and convention weeks are visitor demand. Named weekends are demand, not occupancy. Confirm 2026 event dates on the primary page. Do not invent a theme-park date. Write this heading as the stay a host can actually file. Kissimmee is not Lake Eola. Who Books Orlando is already live on Crest and Cove. Use it. Do not paste a satellite year into a city tile. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay.

Year Over Year Is Plus 14.3 Percent on This Pass

Year over year is plus 14.3 percent on the current extract. Supply moved plus 46.9 percent. File both numbers. Write this heading as the stay a host can actually file. Winter Park is not downtown. Buying an Orlando Rental is already live on Crest and Cove. Use it. Do not paste a satellite year into a city tile. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site.

How a Host Should Read This Map

How a host should read this map is to file three occasions. Orlando is Lake Eola, downtown, and city nights. Kissimmee is another city. Winter Park is another city. Keep $243 city ADR off both satellites. Write this heading as the stay a host can actually file. We market. We do not take the lock. Orlando Tourism Data is already live on Crest and Cove. Use it. Do not paste a satellite year into a city tile. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site. Kissimmee is not Lake Eola. Winter Park is not downtown. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole.

Hosts who underwrite Central Florida stays should keep $29,472 on 4,520 city listings, call 407-246-2686, and leave Kissimmee and Winter Park on their own lines. We market. We do not take the lock. Write the city or the satellite the guest typed. Keep $29,472 on 4,520 city listings on its own line. March is the city peak. July is the city hole. Call 407-246-2686 before you advertise an Orlando stay. Home share requires the resident on site.

Frequently Asked Questions

How much did typical Orlando listings earn last year?

AirROI's trailing twelve months, August 2025 through July 2026, put the typical active Orlando listing at about $29,472 across 4,520 rentals, with an average night near $243 and occupancy around 43.8 percent. Revenue per available night landed near $105, active supply rose 46.9 percent year over year, and revenue itself climbed 14.3 percent. Keep Kissimmee and Winter Park on their own lines rather than folding them into this citywide figure.

When is Orlando's strongest month?

March is the busiest revenue month, with December and April close behind as the shoulder strong months. July is both the slowest revenue month and the weakest for occupancy. A listing priced flat across the calendar leaves March upside on the table and overprices the July lull, so treat the two as separate pricing decisions.

Do I need an Orlando short-term rental permit in 2026?

Yes, through Orlando's Home Sharing Registration at orlando.gov: rentals under 30 days require the resident to live on site and be present when hosting, proof of registration on any online ad, no more than four unrelated guests per booking (or two per room, whichever is fewer), and no more than half the home's bedrooms devoted to hosting. The annual fee is $275 the first year, then $100 for an owner-occupied property or $125 for non-owner-occupied. Call Orlando Code Enforcement at 407-246-2686 to confirm current 2026 terms before you advertise.

Is a 30-night minimum the same as occupancy?

No. 1,684 of Orlando's 4,520 active listings, about 37.3 percent, set a 30-night minimum, but that is a platform booking-window setting, not a measure of nights actually filled. The market's typical stay is 5.1 nights with roughly 53 days of lead time, and July remains slow regardless of minimum-stay settings. Write the stay length your own data shows rather than treating a long minimum as proof of a booked month.

Should I hire a property manager in Orlando?

Orlando's professionally managed share sits at 24.8 percent, with Villatel holding the largest footprint at 173 listings. Kissimmee and Winter Park each reward their own city-specific copy rather than one shared pitch, so a manager or marketing approach built for Orlando should not be recycled unedited for a satellite town.

Who books an Orlando short-term rental?

Most guests booking Orlando arrive from Miami, followed by Orlando itself, with an average stay of 5.1 nights and about 53 days of lead time. Urban guests are drawn to Lake Eola and downtown specifically, while Kissimmee and Winter Park each pull a distinct guest base booking a different kind of trip, so listing copy should speak to the actual neighborhood a property sits in.

Can Kissimmee's numbers stand in for Orlando's?

No. Orlando's average night was $243 across 4,520 listings for a typical $29,472 annual figure, while Kissimmee earned about $35,208 across a much larger pool of roughly 10,688 listings. The two markets run at different scale, so keep $29,472 on its own line rather than blending it with Kissimmee's number.

Can I list an entire home for under 30 days in Orlando?

Orlando's Home Share program requires the resident to live on site and be present while hosting, with no more than half the bedrooms devoted to hosting, so an unhosted entire-home listing under 30 days does not fit that path as written. Call Code Enforcement at 407-246-2686 to confirm zoning and current registration terms before listing an entire home short-term.

What should a buyer or lender packet cite for Orlando?

Cite the AirROI figure directly: about $29,472 a year on 4,520 active listings, with supply up 46.9 percent and revenue up 14.3 percent year over year. Keep Kissimmee and Winter Park figures on their own separate lines, and call Orlando Code Enforcement at 407-246-2686 to confirm any permit detail before it goes into a packet.

Where do I confirm Orlando's short-term rental rules directly?

Call Orlando Code Enforcement at 407-246-2686 or review the Home Sharing Registration requirements at orlando.gov, which cover the under-30-day rental period, on-site resident requirement, registration proof on ads, guest caps, and the bedroom-share limit. The annual fee runs $275 the first year and $100 to $125 after that depending on owner occupancy, so confirm current 2026 figures before advertising.

Work with Crest & Cove Creative

A market report that averages Lake Eola condos with a Kissimmee driveway into one blended year hides more than it reveals. The two markets differ in scale by more than double the listing count and should never share a single figure.

Crest & Cove writes market reporting that keeps each town's numbers on its own line instead of one flattened metro average.

Reach out at crestcove.co or (256) 998-7502.