Real Estate Investment Properties for Sale in Kissimmee, FL
Looking for investment property in Kissimmee, FL with high ROI ?
Explore a variety of short-term homes & houses in Kissimmee, FL. Invest wisely with VRBO & Kissimmee, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Kissimmee, FL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
4529 ORCHARD GROVE ROADKissimmee, FLWelcome to this beautifully maintained 4-bedroom, 2-bath home in the heart of St. Cloudâ... |
4 beds | 2 baths | 1,707 sq.ft. |
$368,000 |
Airbnb cash on cash: 1.75%
|
2030 CASCADES BOULEVARD 302Kissimmee, FLThis Third Floor 2 bedroom / 2 bathroom is Perfect for an investor or 1st time home buyers... |
2 beds | 2 baths | 1,042 sq.ft. |
$160,000 |
Airbnb cash on cash: 2.31%
|
2730 PARKFIELD ROADKissimmee, FLStep into style and comfort in this modern 5-bedroom, 2.5-bath beautyâa home built to im... |
5 beds | 3 baths | 2,800 sq.ft. |
$465,000 |
Airbnb cash on cash: 1.33%
|
754 CAMEL COURTKissimmee, FLCheck out this incredibly spacious duplex, one of the largest in town! It features 4 bedro... |
6 beds | 4 baths | 3,322 sq.ft. |
$530,000 |
Airbnb cash on cash: 1.96%
|
5006 Laguna Bay Circle unit: 58 #58Kissimmee, FLWelcome to 5006 Laguna Bay Circle #58 in Kissimmee, FL. Well maintained 2 bedroom 2 bath u... |
2 beds | 2 baths | 1,121 sq.ft. |
$207,000 |
Airbnb cash on cash: 0.17%
|
7535 Brooklyn DriveKissimmee, FLTurn key ready Magic Village 2 story 4 bedroom 4.5 bath luxury townhome offering a multitu... |
4 beds | 4 baths | 2,640 sq.ft. |
$470,000 |
Airbnb cash on cash: -1.36%
|
13673 Beauregard PlKissimmee, FL13673 Beauregard Pl, Kissimmee, FL 32837 | Townhouse |
3 beds | 2 baths | 1,604 sq.ft. |
$414,900 |
Airbnb cash on cash: 0.57%
|
0 E25 Princess Way KissimmeKissimmee, FLThe most strategic located townhouses in Kissimmee, Fl. This COMPLEX is the INVESTORS Drea... |
3 beds | 3 baths | N/A |
$593,500 |
Airbnb cash on cash: -1.44%
|
2638 Clarinet DrKissimmee, FL2638 Clarinet Dr, Kissimmee, FL 32837 | Single Family Residential |
4 beds | 2 baths | 2,344 sq.ft. |
$499,990 |
Airbnb cash on cash: 0.31%
|
706 N RENNES COURTKissimmee, FLShort Sale. Third-Party Authorization Required. As you enter, you are greeted by high cei... |
3 beds | 2 baths | 1,395 sq.ft. |
$229,000 |
Airbnb cash on cash: 3.61%
|
12204 Wild Iris Way #109Kissimmee, FL12204 Wild Iris Way #109, Kissimmee, FL 32837 | Condo/Coop |
3 beds | 2 baths | 1,344 sq.ft. |
$271,990 |
Airbnb cash on cash: 0.58%
|
1851 Soaring Heights CirKissimmee, FL1851 Soaring Heights Cir, Kissimmee, FL 32837 | Single Family Residential |
4 beds | 3 baths | 2,768 sq.ft. |
$599,000 |
Airbnb cash on cash: 0.46%
|
13827 Fairway Island Dr #1232Kissimmee, FL13827 Fairway Island Dr #1232, Kissimmee, FL 32837 | Condo/Coop |
2 beds | 2 baths | 1,160 sq.ft. |
$224,900 |
Airbnb cash on cash: -0.29%
|
14238 Fredricksburg Dr #310Kissimmee, FL14238 Fredricksburg Dr #310, Kissimmee, FL 32837 | Condo/Coop |
3 beds | 3 baths | 1,554 sq.ft. |
$275,000 |
Airbnb cash on cash: 0.59%
|
3244 Amaca CirKissimmee, FL3244 Amaca Cir, Kissimmee, FL 32837 | Single Family Residential |
4 beds | 2 baths | 2,660 sq.ft. |
$699,900 |
Airbnb cash on cash: 0.06%
|
14205 Falls Church Dr #2012Kissimmee, FL14205 Falls Church Dr #2012, Kissimmee, FL 32837 | Condo/Coop |
3 beds | 2 baths | 1,491 sq.ft. |
$330,000 |
Airbnb cash on cash: -0.05%
|
2700 CHEROKEE ROADKissimmee, FLWelcome to this one-owner lakefront home on Lake Toho that has been meticulously maintaine... |
4 beds | 3 baths | 2,250 sq.ft. |
$779,000 |
Airbnb cash on cash: 0.62%
|
1574 Derby Glen DrKissimmee, FL1574 Derby Glen Dr, Kissimmee, FL 32837 | Single Family Residential |
3 beds | 2 baths | 1,989 sq.ft. |
$435,000 |
Airbnb cash on cash: 1.3%
|
12107 Poppy Field Ln #110Kissimmee, FL12107 Poppy Field Ln #110, Kissimmee, FL 32837 | Condo/Coop |
1 beds | 1 baths | 858 sq.ft. |
$210,000 |
Airbnb cash on cash: -2.2%
|
14341 Fredricksburg Dr #1010Kissimmee, FL14341 Fredricksburg Dr #1010, Kissimmee, FL 32837 | Condo/Coop |
3 beds | 3 baths | 1,554 sq.ft. |
$254,900 |
Airbnb cash on cash: 0.41%
|
14500 Fox Haven BlvdKissimmee, FL14500 Fox Haven Blvd, Kissimmee, FL 32837 | Single Family Residential |
3 beds | 2 baths | 1,592 sq.ft. |
$369,000 |
Airbnb cash on cash: 1.61%
|
3247 Timucua CirKissimmee, FL3247 Timucua Cir, Kissimmee, FL 32837 | Single Family Residential |
4 beds | 2 baths | 2,154 sq.ft. |
$559,900 |
Airbnb cash on cash: 0.56%
|
4552 Lake Calabay DrKissimmee, FL4552 Lake Calabay Dr, Kissimmee, FL 32837 | Single Family Residential |
5 beds | 4 baths | 3,655 sq.ft. |
$849,900 |
Airbnb cash on cash: 0.08%
|
147 DORCHESTER COURTKissimmee, FLEnjoy this beautifully renovated 4-bedroom, 2-bathroom home nestled on a charming corner l... |
4 beds | 2 baths | 1,748 sq.ft. |
$299,900 |
Airbnb cash on cash: 3.25%
|
2013 Tizewell Cir #1403Kissimmee, FL2013 Tizewell Cir #1403, Kissimmee, FL 32837 | Condo/Coop |
1 beds | 1 baths | 753 sq.ft. |
$175,000 |
Airbnb cash on cash: -1.96%
|
4012 Brookmyra DrKissimmee, FL4012 Brookmyra Dr, Kissimmee, FL 32837 | Single Family Residential |
5 beds | 4 baths | 2,828 sq.ft. |
$795,000 |
Airbnb cash on cash: 0.29%
|
4010 Santa Maria Drive unit: 103 #103Kissimmee, FLWelcome to this beautiful townhouse located at 4010 Santa Maria Dr Unit 103 in Kissimmee, ... |
3 beds | 2 baths | 1,296 sq.ft. |
$229,000 |
Airbnb cash on cash: 3.75%
|
14574 Quail Trail CirKissimmee, FL14574 Quail Trail Cir, Kissimmee, FL 32837 | Single Family Residential |
3 beds | 2 baths | 1,688 sq.ft. |
$424,900 |
Airbnb cash on cash: 1.03%
|
14528 Redmeadow CtKissimmee, FL14528 Redmeadow Ct, Kissimmee, FL 32837 | Single Family Residential |
3 beds | 2 baths | 1,619 sq.ft. |
$429,000 |
Airbnb cash on cash: 1.13%
|
3185 Timucua CirKissimmee, FL3185 Timucua Cir, Kissimmee, FL 32837 | Single Family Residential |
4 beds | 2 baths | 2,063 sq.ft. |
$667,888 |
Airbnb cash on cash: 0.16%
|
14682 Braddock Oak DrKissimmee, FL14682 Braddock Oak Dr, Kissimmee, FL 32837 | Single Family Residential |
5 beds | 4 baths | 3,892 sq.ft. |
$749,900 |
Airbnb cash on cash: 0.29%
|
14609 Quail Trail CirKissimmee, FL14609 Quail Trail Cir, Kissimmee, FL 32837 | Single Family Residential |
4 beds | 2 baths | 1,588 sq.ft. |
$495,900 |
Airbnb cash on cash: 0.87%
|
3447 Amaca CirKissimmee, FL3447 Amaca Cir, Kissimmee, FL 32837 | Single Family Residential |
4 beds | 2 baths | 2,158 sq.ft. |
$590,000 |
Airbnb cash on cash: 0.44%
|
12203 Wild Iris Way #108Kissimmee, FL12203 Wild Iris Way #108, Kissimmee, FL 32837 | Condo/Coop |
1 beds | 1 baths | 790 sq.ft. |
$219,000 |
Airbnb cash on cash: -2.04%
|
2656 Amati Dr #2656Kissimmee, FL3bedroom, 2.5 bath, 2 car garage townhouse located in the Gated community of Tapestry. Cor... |
3 beds | 3 baths | 1,690 sq.ft. |
$329,900 |
Airbnb cash on cash: 0.3%
|
4457 Le Reve courtKissimmee, FLIncome-Producing Modern Townhouse with Private Pool - Prime Location and zoned for short t... |
4 beds | 4 baths | 1,752 sq.ft. |
$474,000 |
Airbnb cash on cash: 0.77%
|
2604 Blowing Breeze AvenueKissimmee, FLWelcome to this beautiful home in Tohoqua! This stunning 5-bed, 3-bath property blends mod... |
5 beds | 3 baths | 2,590 sq.ft. |
$597,000 |
Airbnb cash on cash: 0.77%
|
14420 Hatchee CtKissimmee, FL14420 Hatchee Ct, Kissimmee, FL 32837 | Single Family Residential |
5 beds | 3 baths | 3,132 sq.ft. |
$798,000 |
Airbnb cash on cash: 0.19%
|
14402 Mandolin DrKissimmee, FL14402 Mandolin Dr, Kissimmee, FL 32837 | Single Family Residential |
3 beds | 2 baths | 1,793 sq.ft. |
$469,000 |
Airbnb cash on cash: 0.3%
|
13838 Fairway Island Dr #SKissimmee, FL13838 Fairway Island Dr #S, Kissimmee, FL 32837 | Condo/Coop |
1 beds | 1 baths | 861 sq.ft. |
$170,000 |
Airbnb cash on cash: -2.15%
|
Real Estate investment in Kissimmee, FL
There are 41 properties for sale in the city of Kissimmee . The median list price in Kissimmee is $426,950 and the average price per square foot is $224. In December 2025, the average monthly cash on cash return in Kissimmee is 3.00%. The average monthly rental income in Kissimmee is $2,284.