Kissimmee, FL Short Term Rental Properties for Sale

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Updated: Sep 24, 2025

12-Unit Condominium Portfolio

2206 ANTIGUA Place, Kissimmee, FL 34741

$2,250,000

12,004 sqft 0.18 AC lot

12 condominium units totaling 12,004 square feet
Built in 1999 within a larger 35‑acre residential development
Two‑bedroom layouts in every unit; most residences have two bathrooms
Central AC and open floorplans
Two swimming pools and tennis courts

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Updated: Oct 23, 2025

22-Unit Multifamily Portfolio

2218 GRAND CAYMAN COURT, Kissimmee, FL 34741

$3,589,997

20,092 sqft 0.18 AC lot

22‑unit multifamily portfolio
20,092 square feet on 0.18 acres
Short‑term rental approved within Villa del Sol
Community pool, fitness center, playgrounds, tennis court, and car wash area
Built in 1999 with central heating and central air conditioning

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Renovated Six-Unit Apartment Building

1801 DANIELS Street, Kissimmee, FL 34746

$499,999

5,000 sqft 0.36 AC lot

Furnished units offer private entrances, kitchens, bathrooms, laundry, and keyless access within a recently updated property.

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See what stands out in Osceola County

We check every for-sale listing in the county against comparable properties across the country. Most price about where you would expect. A few are worth a second look.

We check every listing here. A few are worth a second look.

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Furnished Short-Term Rental Condo

3151 SUNSET WALK DRIVE #414, Kissimmee, FL 34747

$359,900

1,163 sqft

Fourth-floor unit with a wraparound balcony, resort amenities, and access to nearby dining, entertainment, shopping, and waterpark attractions.

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Furnished Short-Term Rental Condo

3151 SUNSET WALK DRIVE #1507, Kissimmee, FL 34747

$289,000

734 sqft

Top-floor furnished condo with a private balcony and resort amenities.

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Turnkey Furnished Residential Unit

3151 SUNSET WALK DRIVE #116, Kissimmee, FL 34747

$399,900

960 sqft

Fully furnished unit sold ready for immediate use, with access to community amenities in Kissimmee.

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Condo - Hotel

3100 PARKWAY BOULEVARD #728, Kissimmee, FL 34747

$139,900

492 sqft

Short term rental properties · 492 SF

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Kissimmee Condo-Tel Investment Opportunity

5367 W IRLO BRONSON MEMORIAL HWY #1-103, Kissimmee, FL 34746

$59,900

231 sqft

Condo-tel near dining, entertainment, and attractions with community amenities.

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Celebration Condo Hotel Investment Opportunity

225 CELEBRATION Pl 316, Kissimmee, FL 34747

$188,000

0.03 AC lot

Fully furnished condo near Disney World with rental potential.

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Furnished Hotel Condo with Balcony

3151 SUNSET WALK Dr 1507, Kissimmee, FL 34747

$289,000

Fifth-floor resort accommodation with private outdoor space and access to hotel amenities, dining, transportation, and recreation.

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Embassy Suites Condo For Sale

3151 SUNSET WALK Dr 202, Kissimmee, FL 34747

$280,000

0.02 AC lot

Furnished condo at Embassy Suites, prime location, rental income potential.

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Furnished Short-Term Rental Condo

8061 VACATION Ave 2510, Kissimmee, FL 34747

$340,000

Fully furnished residence with pool-facing balcony and access to Embassy Suites amenities in the Sunset Walk district.

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Renovated Six-Unit Apartment Building

1801 Daniels Street, Kissimmee, FL 34746

$499,999

5,000 sqft

Renovated multifamily property with furnished units, individual entrances, and month-to-month occupancy.

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2-Bedroom Short-Term Rental Condo

3151 SUNSET WALK DR #1104, Kissimmee, FL 34747

$549,000

Fully furnished corner residence with a wraparound patio, onsite rental management, and convenient access to resort amenities.

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Furnished Condo Hotel Investment

225 CELEBRATION Pl 526, Kissimmee, FL 34747

$149,999

Turnkey condo near Disney, ideal for short-term rentals.

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Luxury Condo at Sunset Walk

3151 SUNSET WALK Dr 1214, Kissimmee, FL 34747

$399,000

Fully furnished 2-bedroom condo in a premier resort community.

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Furnished Short-Term Rental Condo

8060 VACATION Ave 100, Kissimmee, FL 34747

$484,900

Furnished condo with resort amenities and transportation services to nearby theme parks.

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Windsor Hills Resort Top-Floor Condo

7675 COMROW St 402, Kissimmee, FL 34747

$249,900

Two-bedroom condo in Windsor Hills Resort, near Disney World.

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Furnished Short-Term Rental Condo

3151 SUNSET WALK DR #208, Kissimmee, FL 34747

$404,900

Second-floor vacation condo with resort amenities, shuttle service, and access to dining and entertainment at Sunset Walk.

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AMBAR Orlando Residences Condo-Hotel

3251 SECRET LAKE Dr 1220, Kissimmee, FL 34747

$367,900

Luxury condo-hotel near Orlando theme parks with rental program.

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Furnished 5-Bedroom Rental Townhouse

1800 Tropical Palms Cir, Kissimmee, FL 34747

Contact for pricing

Gated resort townhouse with private heated pool, spa, themed bedrooms, and eligibility for both short- and long-term rentals.

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Remodeled Condo-Hotel Unit Near Parks

3000 MAINGATE Ln 212, Kissimmee, FL 34747

$49,900

Turn-key, renovated condo-hotel unit with amenities and convenient location.

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Remodeled Condo-Hotel Unit Near Parks

3000 MAINGATE Ln 218, Kissimmee, FL 34747

$45,000

Recently remodeled condo-hotel unit with amenities and convenient location.

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Remodeled Condo-Hotel Unit Near Parks

3000 MAINGATE Ln 228, Kissimmee, FL 34747

$47,000

Completely remodeled condo-hotel unit near parks, dining, and entertainment.

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Kissimmee, FL Short Term Rental Properties Market Trends and Statistics

Explore 63 short term rental properties for sale in Kissimmee, FL, showcased through 63 active listings on our real estate platform. These investment opportunities span a total of 45,676 square feet of properties for sale, with an estimated market value of $23,897,394.

Sale prices for short term rental properties in Kissimmee, FL start at $45,000, averaging $405,040, and reaching up to $3,589,997 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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Top Commercial Asset Segments

Commercial property segments ranked by active listings on the market

Demographics Overview

Population 332K

Population Growth (5Y) +17.0%

Median Household Income $64,631

College Educated 28.9%

High-Yield Neighborhoods for Investment

Identify Kissimmee submarkets with the highest inventory density on the market and evaluate the average listing prices of real estate assets

Neighborhood	Average Price
34747	$304.5K
34746	$327.2K
34741	$2.9M

Taxes & Financing

Tax Rate (average for all types) 1.72%

Property Tax per SF $12.40 per SF

Tax Rate vs County Average 0.07 pp below county avg

Average Loan-to-Value 65.0%

Listings Trend

New vs delisted commercial listings in Osceola County

New Delisted

Total CRE Inventory on Market (SF)

Property Size Breakdown

The majority of commercial real estate listings in Kissimmee fall within the 100,000+ square foot range.

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