Real Estate Investment Properties for Sale in Holiday, FL
Looking for investment property in Holiday, FL with high ROI ?
Explore a variety of short-term homes & houses in Holiday, FL. Invest wisely with VRBO & Holiday, 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 Holiday, FL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
1414 WHITEHALL LANEHOLIDAY, FL-- OWNERS MOTIVATED, LET'S MAKE A DEAL -- **Free 1% one-year interest rate buy down throug... |
3 beds | 2 baths | 1,636 sq.ft. |
$293,990 |
Airbnb cash on cash: 4.78%
|
2228 SOCIETY DRIVEHOLIDAY, FLPrice Improvement! Discover peaceful living in this charming 2-bedroom, 1.5-bath home nest... |
2 beds | 2 baths | 1,039 sq.ft. |
$239,900 |
Airbnb cash on cash: 1.53%
|
2423 TRIGGERFISH COURTHOLIDAY, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. We... |
4 beds | 3 baths | 2,462 sq.ft. |
$500,000 |
Airbnb cash on cash: -1.13%
|
2228 PARROT FISH DRIVEHOLIDAY, FLâDue to seller/investor marketing restrictions, seller is only accepting offers from Own... |
3 beds | 2 baths | 1,876 sq.ft. |
$319,900 |
Airbnb cash on cash: 2.86%
|
3433 TUCKAHOE PLACEHOLIDAY, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. We... |
2 beds | 2 baths | 1,128 sq.ft. |
$240,000 |
Airbnb cash on cash: 2.05%
|
3325 HONEYMOON LANEHOLIDAY, FLWelcome to waterfront living in Holiday! This beautifully maintained 2-bedroom, 2-bath hom... |
2 beds | 2 baths | 1,334 sq.ft. |
$250,000 |
Airbnb cash on cash: 1.82%
|
4345 TAHITIAN GARDENS CIRCLE #CHOLIDAY, FLHello! Welcome to this beautiful 2 -bedroom 1.5-bathroom condo. In the heart of Tahitians ... |
2 beds | 2 baths | 825 sq.ft. |
$143,000 |
Airbnb cash on cash: 2.45%
|
3426 COLDWELL DRIVEHOLIDAY, FLDiscover your Florida retreat in the heart of Holiday Lake Estates! This beautifully refre... |
4 beds | 2 baths | 1,116 sq.ft. |
$275,000 |
Airbnb cash on cash: 0.95%
|
3401 SUPREME DRIVEHOLIDAY, FLWOW! Move in ready and full of potential! This charming home features bright open living... |
2 beds | 2 baths | 1,442 sq.ft. |
$264,000 |
Airbnb cash on cash: 1.49%
|
5828 MARIPOSA DRIVEHOLIDAY, FLWelcome to this beautifully maintained 2-bedroom, 2-bath home located in the heart of Holi... |
2 beds | 2 baths | 973 sq.ft. |
$199,900 |
Airbnb cash on cash: 2.74%
|
2128 SHANNON DRIVEHOLIDAY, FLQuintessential Florida Living in Holiday! Welcome to this charming 2-bedroom, 1-bath, 1-c... |
2 beds | 1 baths | 1,200 sq.ft. |
$214,900 |
Airbnb cash on cash: 2.58%
|
3103 BRIGHT DRIVEHOLIDAY, FLDreaming of being on Holiday, EVERYDAY? Well your search is over and welcome to your new h... |
2 beds | 2 baths | 1,457 sq.ft. |
$328,950 |
Airbnb cash on cash: 0.51%
|
3638 BIGELOW DRIVEHOLIDAY, FLUnder contract-accepting backup offers. CORNER LOT-PRIVACY FENCE-Priced RIGHT!!--No HOA to... |
2 beds | 2 baths | 1,096 sq.ft. |
$214,000 |
Airbnb cash on cash: 2.49%
|
3114 BLUFF BOULEVARDHOLIDAY, FLDiscover the charm of Floridaâs Gulf Coast in this beautifully crafted waterfront home, ... |
3 beds | 3 baths | 3,234 sq.ft. |
$1,265,000 |
Airbnb cash on cash: -0.4%
|
2216 OAK WIND DRIVEHOLIDAY, FLWelcome home to this charming 2 bedroom, 2 bathroom villa in the highly desirable Pinewood... |
2 beds | 2 baths | 1,128 sq.ft. |
$179,900 |
Airbnb cash on cash: 2.17%
|
3706 CHESWICK DRIVEHOLIDAY, FLWelcome to this beautifully maintained property, boasting a fresh interior paint job in a ... |
2 beds | 2 baths | 1,036 sq.ft. |
$198,000 |
Airbnb cash on cash: 2.95%
|
3011 SHADOW OAKS DRIVEHOLIDAY, FLSpacious 3-bedroom, 2-bathroom home featuring laminate flooring throughout with tile in th... |
3 beds | 2 baths | 1,480 sq.ft. |
$329,000 |
Airbnb cash on cash: 4.01%
|
5026 MOOG ROADHOLIDAY, FLCharming Updated Single-Family Home in Holiday with Spacious Fenced Yard. This home has be... |
2 beds | 1 baths | 792 sq.ft. |
$233,500 |
Airbnb cash on cash: 1.58%
|
2406 SOCIETY DRIVEHOLIDAY, FLUnder contract-accepting backup offers. Welcome Home! This beautifully updated home is mov... |
2 beds | 2 baths | 1,198 sq.ft. |
$250,000 |
Airbnb cash on cash: 1.11%
|
3552 BLUEBELL LANEHOLIDAY, FLUnder contract-accepting backup offers. Short Sale. MULTIPLE OFFERS RECEIVED. PLEASE SUBMI... |
2 beds | 2 baths | 900 sq.ft. |
$180,000 |
Airbnb cash on cash: 3.05%
|
2349 HAMA DRIVEHOLIDAY, FLWELCOME HOME to this meticulously maintained 3-bedroom, 2-bath waterfront home in Holiday'... |
3 beds | 2 baths | 1,470 sq.ft. |
$259,900 |
Airbnb cash on cash: 5.61%
|
2146 SOCIETY DRIVEHOLIDAY, FLOne or more photo(s) has been virtually staged. Tucked along the shores of Lake Conley, th... |
2 beds | 2 baths | 1,371 sq.ft. |
$265,000 |
Airbnb cash on cash: 1.43%
|
1313 CHANCELLOR DRIVEHOLIDAY, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. Di... |
2 beds | 2 baths | 953 sq.ft. |
$180,000 |
Airbnb cash on cash: 2.88%
|
1022 BOWSPRIT LANE #1022HOLIDAY, FLGreat location with beautiful pond view from most windows, friendly surroundings, nature a... |
2 beds | 2 baths | 1,114 sq.ft. |
$175,000 |
Airbnb cash on cash: 0.02%
|
2125 BARRACUDA COURTHOLIDAY, FLUnder contract-accepting backup offers. Maintenance Free living, 3-Bedrooms 2.5-Bathrooms,... |
3 beds | 3 baths | 1,740 sq.ft. |
$342,000 |
Airbnb cash on cash: 2.39%
|
3625 Windham DriveHOLIDAY, FLWelcome to 3625 Windham Drive in the heart of Holiday, FL - a charming and move-in-ready 3... |
3 beds | 1 baths | 1,200 sq.ft. |
$225,000 |
Airbnb cash on cash: 6.39%
|
3238 MELA COURTHOLIDAY, FLAmazing Price Reduction in Gated Neighborhood of Vista Lakes at Bailys Bluff - 5 Bedroom,... |
5 beds | 4 baths | 3,198 sq.ft. |
$499,900 |
Airbnb cash on cash: 0.8%
|
4327 BEACON SQUARE DRIVEHOLIDAY, FLWelcome home! This charming Holiday gem is the perfect opportunity for first-time buyers. ... |
3 beds | 1 baths | 1,104 sq.ft. |
$214,000 |
Airbnb cash on cash: 6.95%
|
2945 WOOD POINTE DRIVEHOLIDAY, FLLocated within the 55+ area of the beautiful Key Vista gated community, this move-in-ready... |
2 beds | 2 baths | 1,341 sq.ft. |
$345,000 |
Airbnb cash on cash: -0.14%
|
4102 DARLINGTON ROADHOLIDAY, FLUnder contract-accepting backup offers. Great starter, retirement, or income rental home. ... |
2 beds | 2 baths | 988 sq.ft. |
$190,000 |
Airbnb cash on cash: 2.21%
|
5646 ANDREA DRIVEHOLIDAY, FLPRICE IMPROVEMENT!!! Welcome to your new home! Located in Holiday FL with no Hoa, CDD, and... |
3 beds | 2 baths | 1,522 sq.ft. |
$260,000 |
Airbnb cash on cash: 5.24%
|
3228 ROCK VALLEY DRIVEHOLIDAY, FLWelcome to this charming two bedroom, two bath home with a spacious Florida room that offe... |
2 beds | 2 baths | 1,334 sq.ft. |
$299,000 |
Airbnb cash on cash: 1.38%
|
2907 FEATHERSTONE DRIVEHOLIDAY, FLprice adjustment and a very motived seller,,,Move-in ready and full of potential! This 2-b... |
2 beds | 2 baths | 1,159 sq.ft. |
$194,900 |
Airbnb cash on cash: -0.56%
|
3801 SAILMAKER LANEHOLIDAY, FLWelcome to this well-maintained 2 bedroom, 2 bath condominium in the coastal community of ... |
2 beds | 2 baths | 1,318 sq.ft. |
$166,000 |
Airbnb cash on cash: -1.86%
|
4350 TAHITIAN GARDENS CIRCLE #EHOLIDAY, FLON THE LAKE!!! A RARE FIND, One Bedroom, One Bath CORNER unit that needs a little TLC. Enj... |
1 beds | 1 baths | 600 sq.ft. |
$99,900 |
Airbnb cash on cash: 0.44%
|
4749 SUNNY LOOP #4749HOLIDAY, FLVILLA IS A NON-FLOOD ZONE X!! PERFECT SNOWBIRD VILLA! TURNKEY - FURNISHINGS OPTIONAL! C... |
2 beds | 2 baths | 975 sq.ft. |
$169,900 |
Airbnb cash on cash: -0.32%
|
2817 PLANTAIN DRIVEHOLIDAY, FLUnder contract-accepting backup offers. Welcome home to 2817 Plantain Dr! This beautifully... |
3 beds | 2 baths | 1,683 sq.ft. |
$415,000 |
Airbnb cash on cash: 1.68%
|
3711 ELMWOOD DRIVEHOLIDAY, FLUnder contract-accepting backup offers. Welcome home! This charming and affordable starter... |
2 beds | 2 baths | 1,096 sq.ft. |
$205,000 |
Airbnb cash on cash: 1.69%
|
3320 COLUMBUS DRIVEHOLIDAY, FLUnder contract-accepting backup offers. Looking for a home to entertain family and friends... |
2 beds | 2 baths | 1,289 sq.ft. |
$215,000 |
Airbnb cash on cash: 1.32%
|
2330 SOCIETY DRIVEHOLIDAY, FLUnder contract-accepting backup offers. Welcome to this waterfront pool home in the desira... |
4 beds | 3 baths | 2,418 sq.ft. |
$399,900 |
Airbnb cash on cash: -0.43%
|
Real Estate investment in Holiday, FL
There are 200 properties for sale in the city of Holiday . The median list price in Holiday is $216,888 and the average price per square foot is $165. In June 2026, the average monthly cash on cash return in Holiday is 6.00%. The average monthly rental income in Holiday is $2,033.