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 |
|---|---|---|---|
3016 Parkway Blvd #204Kissimmee, FLLocation, Location, Location! 2/2 totally renovated, water view, minutes away from Disney,... |
2 beds | 2 baths | 937 sq.ft. |
$170,000 |
Airbnb cash on cash: 9.06%
|
3101 SHINGLE CREEK CourtKissimmee, FLBoaters and nature enthusiasts-welcome to waterfront living! Situated along Shingle Creek ... |
4 beds | 2 baths | 2,076 sq.ft. |
$529,000 |
Airbnb cash on cash: 6.85%
|
202 WOODSON CourtKissimmee, FLWelcome to this stunning 3,744 square foot residence located on a quiet cul de sac within ... |
5 beds | 4 baths | 3,744 sq.ft. |
$595,000 |
Airbnb cash on cash: N/A
|
255 GARDENIA RoadKissimmee, FLThis wonderful single-family home is located in Osceola County at 255 Gardenia Rd, Kissimm... |
3 beds | 2 baths | 1,168 sq.ft. |
$339,000 |
Airbnb cash on cash: 7.53%
|
225 SOUTHBRIDGE CircleKissimmee, FL225 Southbridge Cir is a 1-story Kissimmee home with an open layout, screened pool, and at... |
3 beds | 2 baths | 1,284 sq.ft. |
$330,000 |
Airbnb cash on cash: 8.13%
|
604 CHADBURY WayKissimmee, FLWelcome to this beautiful LAKEVIEW POOL HOME with 4 bed/3 bath FURNISHED located in Reming... |
4 beds | 3 baths | 1,719 sq.ft. |
$400,900 |
Airbnb cash on cash: 7.66%
|
1122 SPACEPORT CourtKissimmee, FLWHAT A DEAL, BRING YOUR OFFERS! A unique vacation home opportunity that pays for itself, i... |
2 beds | 2 baths | 1,052 sq.ft. |
$275,000 |
Airbnb cash on cash: 2.96%
|
513 HEARTWELL DRKissimmee, FL**SEE VIRTUAL TOUR LINK 1 FOR 3D MATTERPORT VIDEO** Big price improvement on this beautifu... |
2 beds | 2 baths | 1,488 sq.ft. |
$265,000 |
Airbnb cash on cash: 4.36%
|
1958 COMMANDER WayKissimmee, FL1958 Commander Way pairs a covered patio with an open island kitchen and newly installed b... |
3 beds | 2 baths | 1,636 sq.ft. |
$300,000 |
Airbnb cash on cash: 8.71%
|
4647 CUMBRIAN LAKES DriveKissimmee, FLExceptional turnkey opportunity in a highly desirable, gated short-term rental community i... |
4 beds | 4 baths | 1,830 sq.ft. |
$430,000 |
Airbnb cash on cash: 7.46%
|
7664 Comrow St #202Kissimmee, FLWelcome to this beautifully updated 2-bedroom, 2-bath condominium in the highly sought-aft... |
2 beds | 2 baths | 1,081 sq.ft. |
$255,000 |
Airbnb cash on cash: 4.12%
|
8972 Cat Palm RdKissimmee, FLYou can now experience the benefits of a resort and a home together at gated Paradise Palm... |
4 beds | 3 baths | 1,902 sq.ft. |
$334,899 |
Airbnb cash on cash: 8.08%
|
8050 King Palm CirKissimmee, FLWelcome to the Guard gated Windsor Palms Resort style Community to escape to paradise. Thi... |
4 beds | 2 baths | 1,567 sq.ft. |
$495,000 |
Airbnb cash on cash: 4.98%
|
2785 Almaton Loop #303Kissimmee, FL***TURNKEY & THEMED CONDO*** Come see this TASTEFULLY FURNISHED & THEMED condo in beautifu... |
3 beds | 2 baths | 1,246 sq.ft. |
$349,900 |
Airbnb cash on cash: 5.42%
|
2300 EAGLE TALON CourtKissimmee, FLPriced to give the next owner the freedom to walk in and make it exactly what they want, t... |
4 beds | 4 baths | 3,591 sq.ft. |
$447,000 |
Airbnb cash on cash: 6.81%
|
2310 Silver Palm Dr #104Kissimmee, FLPROFESSIONALLY MANAGED with MANY Short Term Rentals! The Royal Retreat at Windsor Palms: Y... |
2 beds | 2 baths | 1,022 sq.ft. |
$234,900 |
Airbnb cash on cash: 5.44%
|
2545 Renshaw StKissimmee, FLPRICE REDUCTION! SELLER IS MOTIVATED! First showing date available October 17th. This town... |
3 beds | 3 baths | 1,440 sq.ft. |
$409,000 |
Airbnb cash on cash: 4.7%
|
2727 Sun Key PlKissimmee, FLDiscover your dream getaway in the stunning Emerald Island Resort! This townhouse is locat... |
3 beds | 2 baths | 1,291 sq.ft. |
$263,000 |
Airbnb cash on cash: 8.09%
|
3004 Parkway Blvd #306Kissimmee, FLJust minutes to restaurants, shops, Celebration, Disney, Disney Springs, Sea World, Univer... |
2 beds | 2 baths | 937 sq.ft. |
$199,000 |
Airbnb cash on cash: 7.33%
|
8474 Crystal Cove LoopKissimmee, FLEasy to fall in love with this gorgeous vacation home near the most famous theme parks whe... |
3 beds | 2 baths | 1,291 sq.ft. |
$237,000 |
Airbnb cash on cash: 9.26%
|
2102 PUTTER PlaceKissimmee, FLLooking for your place in the Florida sunshine? Discover the possibilities at 2102 Putter ... |
4 beds | 3 baths | 2,592 sq.ft. |
$449,000 |
Airbnb cash on cash: 7.15%
|
2634 CORVETTE LaneKissimmee, FL*Discover Your Dream Getaway in Regal Oaks!* This stunning and fully furnished 2-bedroom t... |
2 beds | 3 baths | 1,350 sq.ft. |
$285,000 |
Airbnb cash on cash: 3.92%
|
2918 Sunset Vista BlvdKissimmee, FLCome see this beautiful 4 bedroom, 2 bathroom pool home in a gated community! This home co... |
4 beds | 2 baths | 1,701 sq.ft. |
$399,000 |
Airbnb cash on cash: 8.74%
|
3032 Parkway Blvd #305Kissimmee, FLWelcome to this beautifully remodeled 2-bedroom, 2-bathroom condo at 3032 Parkway Blvd #30... |
2 beds | 2 baths | 937 sq.ft. |
$160,000 |
Airbnb cash on cash: 8.2%
|
225 Celebration Pl #117Kissimmee, FLWelcome to Your Home Away from Home! This perfect retreat is a lovely fully furnished 2 Be... |
2 beds | 2 baths | 1,265 sq.ft. |
$210,000 |
Airbnb cash on cash: 2.53%
|
2971 Banana Palm DrKissimmee, FLPRICED TO SELL! THEMED BEDROOMS AND EXTENDED DECK! Welcome to Paradise Palms Resort! This ... |
4 beds | 3 baths | 1,902 sq.ft. |
$334,900 |
Airbnb cash on cash: 8.06%
|
636 REGENCY WayKissimmee, FLWelcome to 636 Regency Way, a spacious 3-bedroom, 2-bath home offering 1,607 square feet w... |
3 beds | 2 baths | 1,607 sq.ft. |
$280,000 |
Airbnb cash on cash: 9.09%
|
2923 Banana Palm DrKissimmee, FLCompletely Renovated, Professionally Decorated & Beautifully Furnished Home in Paradise Pa... |
4 beds | 3 baths | 1,902 sq.ft. |
$349,000 |
Airbnb cash on cash: 7.66%
|
221 WESTMORELAND CircleKissimmee, FLOVER $50,000 IN UPGRADES! FULLY RENOVATED! GOLF COURSE VIEW! MOVE-IN READY! WHY PAY MORE F... |
4 beds | 2 baths | 1,767 sq.ft. |
$425,000 |
Airbnb cash on cash: 7.24%
|
157 POMPANO BEACH DriveKissimmee, FLThis stunning furnished townhouse features three spacious bedrooms, two full bathrooms, an... |
3 beds | 3 baths | 1,286 sq.ft. |
$290,000 |
Airbnb cash on cash: 7.88%
|
5134 ADELAIDE DriveKissimmee, FLWelcome to 5134 Adelaide Dr, a fully furnished 4-bedroom, 3.5-bathroom private end unit to... |
4 beds | 4 baths | 1,782 sq.ft. |
$375,000 |
Airbnb cash on cash: 8.78%
|
2682 Mayaguana StKissimmee, FLBeautiful end-unit Townhome located in a gated Community just 2.5 miles from Walt Disney W... |
3 beds | 2 baths | 1,595 sq.ft. |
$290,000 |
Airbnb cash on cash: 9.04%
|
146 CLUB VILLAS LaneKissimmee, FLVirtually Staged. Welcome to this beautifully updated villa in the sought-after gated Club... |
2 beds | 2 baths | 1,397 sq.ft. |
$299,900 |
Airbnb cash on cash: 4.29%
|
225 Celebration Pl #427Kissimmee, FL*****NEW UPDATED, MODERN FURNITURE PACKAGE***** This stunning, fully furnished 2-bedroom, ... |
2 beds | 2 baths | 1,206 sq.ft. |
$212,887 |
Airbnb cash on cash: 3.15%
|
3100 Parkway Blvd #728Kissimmee, FLTurnkey Kissimmee Condo Near Disney | Income-Producing Property | $26K-$35K Projected Annu... |
1 beds | 1 baths | 492 sq.ft. |
$134,900 |
Airbnb cash on cash: 5.21%
|
2788 Almaton Loop #102Kissimmee, FLYOUR DISNEY GETAWAY-FULLY FURNISHED, TURNKEY, AND READY FOR FUN! Just 2.5 miles from the D... |
2 beds | 2 baths | 1,081 sq.ft. |
$270,000 |
Airbnb cash on cash: 3.96%
|
3050 Pirates Retreat Ct #207Kissimmee, FLWelcome to your perfect getaway! This beautifully furnished 2-bedroom, 2-bath condo offers... |
2 beds | 2 baths | 1,445 sq.ft. |
$211,000 |
Airbnb cash on cash: 5.69%
|
4340 Summer Breeze WayKissimmee, FLWelcome to an exceptional opportunity where location, accessibility, and the Central Flori... |
4 beds | 3 baths | 3,720 sq.ft. |
$686,900 |
Airbnb cash on cash: 4.11%
|
7681 Sir Kaufmann CtKissimmee, FLImproved price and ready to sell! This beautifully maintained 3-bedroom, 3-bath end-unit t... |
3 beds | 3 baths | 1,440 sq.ft. |
$399,000 |
Airbnb cash on cash: 5.02%
|
Real Estate investment in Kissimmee, FL
There are 1,659 properties for sale in the city of Kissimmee . The median list price in Kissimmee is $349,833 and the average price per square foot is $174. In November 2026, the average monthly cash on cash return in Kissimmee is 3.00%. The average monthly rental income in Kissimmee is $1,960.