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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21-Unit Short-Term Rental Portfolio
Updated: Oct 23, 2025
21-Unit Short-Term Rental Portfolio

2218 GRAND CAYMAN COURT, Kissimmee, FL 34741

$3,426,816
20,092 sqft 0.18 AC lot
21‑unit portfolio with 20,092 square feet
Short‑term rentals approved in Villa del Sol
Community amenities include a pool, fitness center, tennis court, playgrounds, and car wash area
Private pool and outdoor kitchen
Built in 1999; reported site area is 0.18 acres
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Short-Term Rental Penthouse
Short-Term Rental Penthouse

7656 WHISPER WAY #402, Kissimmee, FL 34747

$289,000
1,630 sqft

Furnished fourth-floor residence with three ensuite bedrooms and an active Gold Reunion membership that can transfer at closing.

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

3100 PARKWAY BOULEVARD #730, Kissimmee, FL 34747

$140,000
524 sqft

The furnished one-bedroom unit permits short-term rentals and offers resort amenities for guests.

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

2817 ALMATON LOOP #304, Kissimmee, FL 34747

$325,000
1,450 sqft

Residents and guests have access to a water park, lagoon-style pool, fitness center, and gated entry.

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Furnished Two-Bedroom Condo-Hotel
Furnished Two-Bedroom Condo-Hotel

225 CELEBRATION PLACE #212, Kissimmee, FL 34747

$144,500
1,125 sqft

The unit includes a full kitchen and on-site property management, with furnishings and accessories included.

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

8060 VACATION AVENUE #212, Kissimmee, FL 34747

$485,000
1,164 sqft

The corner residence includes a private balcony and resort amenities for guests.

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

3151 SUNSET WALK DRIVE #414, Kissimmee, FL 34747

$309,900
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 Resort Condo
Furnished Resort Condo

8060 VACATION AVENUE #4409, Kissimmee, FL 34747

$179,000
501 sqft

A furnished fourth-floor condo within the Embassy Suites by Hilton at Sunset Walk, with access to the property’s guest amenities.

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

7593 GATHERING DR #706, Kissimmee, FL 34747

$304,900
1,430 sqft

Two bedrooms, two baths, an open living area, and a private balcony create a flexible furnished residence.

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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

$219,900
960 sqft

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

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Renovated Short-Term Rental Property
Renovated Short-Term Rental Property

3100 PARKWAY BOULEVARD #220, Kissimmee, FL 34747

$140,000
524 sqft

The property permits Airbnb and other short-term rental use and can be managed by its owner.

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Hotel Suite with Two Queen Beds
Hotel Suite with Two Queen Beds

3000 MAINGATE LANE #124, Kissimmee, FL 34747

$47,000
304 sqft

The furnished first-floor accommodation participates in the property's required hotel rental program.

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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 Rental Unit
Furnished Condo-Hotel Rental Unit

5245 W IRLO BRONSON MEMORIAL HIGHWAY #203, Kissimmee, FL 34746

$97,995
325 sqft

Renovated, Airbnb-friendly lodging unit with access to hotel amenities, a pool, private security, and included utilities.

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Remodeled Furnished Hotel Suite
Remodeled Furnished Hotel Suite

3000 MAINGATE LANE #219, Kissimmee, FL 34747

$49,000
304 sqft

Turnkey suite with resort amenities, onsite management, and required participation in the rental program.

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First-Floor Condo-Hotel
First-Floor Condo-Hotel

5367 W IRLO BRONSON MEMORIAL HIGHWAY #1-214, Kissimmee, FL 34746

$77,500
231 sqft

An on-site front desk coordinates guest arrival and key handoff for this furnished unit.

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

5245 W IRLO BRONSON MEMORIAL HIGHWAY #121, Kissimmee, FL 34746

$89,000
325 sqft

The condo-hotel offers an Airbnb-friendly policy and access to shared resort amenities.

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Updated Short-Term Rental Studio
Updated Short-Term Rental Studio

5367 W IRLO BRONSON MEMORIAL HIGHWAY #2-225, Kissimmee, FL 34746

$70,000
231 sqft

An open-plan studio with updated finishes is located within a few miles of the area’s theme parks.

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

Explore 77 short term rental properties for sale in Osceola County, FL, showcased through 77 active listings on our real estate platform. These investment opportunities span a total of 49,209 square feet of properties for sale, with an estimated market value of $23,896,210.

Sale prices for short term rental properties in Osceola County, FL start at $41,000, averaging $318,616, and reaching up to $3,426,816 — 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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