Kissimmee, Florida Short-Term Rental Market
Kissimmee STRs averaged $256/night at 65.5% occupancy in April 2026 across 62,618 tracked listings in the Orlando-Kissimmee market.
Quick Answer: Kissimmee, Florida is an active short-term rental market. average occupancy in the Orlando market area is 62%. average monthly revenue in the Orlando market area is $4,482. average daily rate in the Orlando market area is $267. the top operator in the Orlando market area is Master Vacation Homes with 1,891 listings. market score is 96/100 (grade A).
Market data reflects the Orlando regional market, which includes Kissimmee. Regulations, taxes, and permit details below are specific to Kissimmee.
Market Score Breakdown
Five dimensions StaySTRA evaluates per market.
Market Overview
Kissimmee is the STR capital of Central Florida, marketing itself as the ‘Vacation Home Capital of the World’ with over 30,000 vacation homes operating in the corridor. The city sits within the Orlando-Kissimmee metro STR market, which as of April 2026 shows an average daily rate of $255.89, average occupancy of 65.5%, and RevPAR of $167.47. Revenue per listing averaged $4,444 in April.
The combined market carries 62,618 tracked listings. Entire-place listings dominate at 58,628 (93.6% of total), with private rooms at 3,912 and shared rooms at 78. Channel distribution: 32,063 listings appear on both Airbnb and VRBO, 22,573 are Airbnb-only, and 7,982 are VRBO-only.
Bedroom mix reflects the large-group vacation home model Kissimmee is known for: the 5-plus bedroom segment is the largest at 21,520 listings, followed by 3-bedroom (12,048) and 4-bedroom (11,748) units. One-bedroom units total 10,090 and two-bedroom units 7,112.
Year-over-year performance in April 2026 was positive across all core metrics: occupancy up 1.86 percentage points, ADR up 2.24%, and revenue up 9.75%. The StaySTRA overall market score is 95.64 out of 100, with revenue growth at 93.30 and investability at 87.06.
Seasonal Patterns
| Month | Occupancy |
|---|---|
| Jan | 54% |
| Feb | 70% |
| Mar | 71% |
| Apr | 60% |
| May | 55% |
| Jun | 65% |
| Jul | 66% |
| Aug | 56% |
| Sep | 46% |
| Oct | 56% |
| Nov | 55% |
| Dec | 56% |
Month-by-month nightly rates and revenue figures for Kissimmee are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Top Short-Term Rental Operators in Orlando market area
Ranked by total active listings. Useful for understanding the competitive landscape. Operator data is published for the Orlando market as a whole, which includes Kissimmee, so these counts are not Kissimmee-only figures.
| # | Operator | Listings | Reviews | Rating |
|---|---|---|---|---|
| 1 | Master Vacation Homes | 1,891 | 73,946 | ★ 4.75 |
| 2 | Top Villas | 1,319 | 6,477 | ★ 3.85 |
| 3 | Ohana Vacation | 808 | 3,603 | ★ 4.21 |
| 4 | Vacasa | 762 | 13,386 | ★ 4.38 |
| 5 | RedAwning | 657 | 4,363 | ★ 4.12 |
What Kind of STR Should I Buy in Kissimmee?
Revenue and nightly-rate breakdowns by bedroom count, property tier, and dwelling type for Kissimmee are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 36% |
| vrbo | 12.7% |
| both | 51.2% |
Home Value Trends (Kissimmee)
Typical home values, median sale prices, and the 10-year price trend for Kissimmee are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Insights
Booking-window and length-of-stay analysis for Kissimmee — how far ahead guests book and how to price around it — is available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Short-Term Rental Regulations
Kissimmee’s STR regulatory environment is among the most permissive for a large tourism market. There is no owner-occupancy or primary-residence requirement, meaning investors can operate unhosted entire-home rentals legally.
STRs are legal but geographically restricted: properties must be located in a Short-Term Rental Overlay (STRO) district or specific residential zones (RB-1, RB-2, RC-1, RC-2) that permit short-term use. Standard residential neighborhoods outside these zones prohibit vacation rentals. Two STRO zones exist: a Western District near major attractions and an Eastern District near Florida’s Turnpike. Buyers must verify zoning eligibility before purchase.
Licensing involves three layers: (1) A Florida DBPR Vacation Rental Dwelling License is required statewide for any property rented more than three times per year for stays under 30 days (approximately $170 per year for renewal). (2) A Local Business Tax Receipt (BTR) from Osceola County ($30 per year) and from the City of Kissimmee if within city limits. (3) A Conditional Use Permit may be required in certain residential zones, involving a public hearing process. The initial permit cost in Kissimmee is approximately $200.
Total guest-facing tax burden is 13.5%: Florida state sales tax (6%), Osceola County Tourist Development Tax (6%), and Osceola County discretionary surtax (1.5%). The TDT applies to all stays under 180 days and includes mandatory fees such as cleaning charges in the taxable base.
Enforcement is rated minimal. Governor DeSantis vetoed SB 280 in 2024, keeping Kissimmee’s local STRO framework intact.
Market Comparison
Kissimmee operates within the same StaySTRA market area as Orlando, and the April 2026 metrics of $255.89 ADR and 65.5% occupancy sit well above national STR medians (approximately $220 ADR, 55% occupancy nationally). RevPAR of $167.47 reflects the sustained demand depth from 10.4 million annual Kissimmee visitors and the broader regional draw of 75 million visitors to the metro area.
The StaySTRA total market score of 95.64 out of 100 is among the highest of any large U.S. market. Revenue growth scored 93.30 and investability 87.06. The regulation score of 61.20 reflects constraints within city limits, though Kissimmee’s STRO framework is materially more permissive than the Orlando city-limit ordinance for non-owner-occupied investors.
Professional management is well established. The top five operators are: Master Vacation Homes (1,891 listings, 73,946 reviews, 4.745 average rating), Top Villas (1,319 listings, 6,477 reviews, 3.846 rating), Ohana Vacation (808 listings, 3,603 reviews, 4.210 rating), Vacasa (762 listings, 13,386 reviews, 4.380 rating), and RedAwning (657 listings, 4,363 reviews, 4.124 rating). Master Vacation Homes is the dominant operator by both listing volume and review count.
Kissimmee’s lower home price point ($359,676 typical home value versus $374,302 for Orlando) combined with permissive investor-friendly regulations makes it the more accessible market for investors seeking unhosted entire-home operations.
Frequently Asked Questions About Kissimmee, Florida
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Can investors operate short-term rentals in Kissimmee without living there?
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When is the best time for Kissimmee vacation rental occupancy?
What permits are required to operate a Kissimmee vacation rental?
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