Short Term Rental

Osceola County, FL Short Term Rental Properties for Sale

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12-Unit Condominium Portfolio
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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22-Unit Multifamily Portfolio
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
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
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
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
Turnkey Furnished Residential Unit

3151 SUNSET WALK DRIVE #116, Kissimmee, FL 34747

$349,900
960 sqft

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

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Turn a Listing Into an Investment Snapshot Cap Rate, Potential NOI, Demand score for every listing. Go To Analytics Center
Condo - Hotel
Condo - Hotel

3100 PARKWAY BOULEVARD #728, Kissimmee, FL 34747

$134,900
492 sqft

Short term rental properties · 492 SF

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Furnished Condo-Hotel Unit
Furnished Condo-Hotel Unit

3000 MAINGATE LANE #317, Kissimmee, FL 34747

$49,000
304 sqft

Renovated vacation accommodation with on-site management, shuttle service, pool access, and a kitchenette.

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Kissimmee Condo-Tel Investment Opportunity
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
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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Celebration Condo Hotel Corner Unit
Celebration Condo Hotel Corner Unit

225 CELEBRATION Pl 117, Celebration, FL 34747

$210,000
0.03 AC lot

Fully furnished 2BR/2BA condo hotel unit in Celebration, Florida.

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Furnished Short-Term Rental Condo
Furnished Short-Term Rental Condo

3100 Parkway Blvd Unit 617, Kissimmee, FL 34747

$130,000

Condominium with resort amenities, included furnishings, and association-covered water and electricity.

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Furnished Hotel Condo with Balcony
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
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
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
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
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
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
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
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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Furnished Three-Bedroom Rental Condo
Furnished Three-Bedroom Rental Condo

2440 Sweetwater Club Cir, Kissimmee, FL 34746

Contact for pricing

Sweetwater Club residence with a private patio, resort amenities, and confirmed future reservations transferring with the sale.

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Furnished Short-Term Rental Condo
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
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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Remodeled Furnished Condo Hotel Studio
Remodeled Furnished Condo Hotel Studio

5367 W Irlo Bronson Memorial Hwy #2-214, Kissimmee, FL 34746

Contact for pricing

Furnished studio with on-site management and included utilities.

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Osceola County, FL Short Term Rental Properties Market Trends and Statistics

Explore 64 short term rental properties for sale in Osceola County, FL, showcased through 64 active listings on our real estate platform. These investment opportunities span a total of 45,980 square feet of properties for sale, with an estimated market value of $23,981,494.

Sale prices for short term rental properties in Osceola County, FL start at $45,000, averaging $393,139, 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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