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 |
|---|---|---|---|
2228 SOCIETY DRIVEHOLIDAY, FLDiscover peaceful living in this charming 2-bedroom, 1.5-bath home nestled along the banks... |
2 beds | 2 baths | 1,039 sq.ft. |
$254,900 |
Airbnb cash on cash: 4.3%
|
2257 SAND BAY DRIVEHOLIDAY, FLUnder contract-accepting backup offers. Welcome to your entertainerâs dream homeâa stu... |
3 beds | 2 baths | 1,630 sq.ft. |
$459,000 |
Airbnb cash on cash: 3.61%
|
2427 INDIAN KEY DRIVEHOLIDAY, FLOne or more photo(s) has been virtually staged. MOTIVATED ESTATE - HUGE PRICE REDUCTION - ... |
3 beds | 2 baths | 1,758 sq.ft. |
$399,000 |
Airbnb cash on cash: 3.41%
|
2932 WINDRIDGE DRIVEHOLIDAY, FLUnder contract-accepting backup offers. BRAND NEW ROOF INSTALLED (Oct 2025) !! Welcome to ... |
3 beds | 2 baths | 1,662 sq.ft. |
$399,000 |
Airbnb cash on cash: 4.58%
|
2329 BARRACUDA COURTHOLIDAY, FLUnder contract-accepting backup offers. Very well MAINTAINED home priced right for you! Im... |
3 beds | 2 baths | 1,740 sq.ft. |
$339,000 |
Airbnb cash on cash: 3.33%
|
3516 NORLAND COURTHOLIDAY, FLWelcome to this stunning, fully renovated lakefront gem nestled in a peaceful Holiday neig... |
3 beds | 2 baths | 1,334 sq.ft. |
$260,000 |
Airbnb cash on cash: 7.3%
|
1913 BLUE RIVER ROADHOLIDAY, FLLakefront Pool Home in Gated Community â Not in a Flood Zone! Welcome to your private... |
3 beds | 3 baths | 2,202 sq.ft. |
$465,000 |
Airbnb cash on cash: 3.05%
|
2511 INDIAN KEY DRIVEHOLIDAY, FLOne or more photo(s) has been virtually staged. One or more photos have been virtually sta... |
4 beds | 2 baths | 2,027 sq.ft. |
$399,000 |
Airbnb cash on cash: 6.54%
|
2807 BANNER STONE COURTHOLIDAY, FLWelcome to this stunning 4-bedroom, 3-bathroom home located in the desirable Key Vista com... |
4 beds | 3 baths | 2,188 sq.ft. |
$499,000 |
Airbnb cash on cash: 5.14%
|
3426 BLAYTON STREETHOLIDAY, FL$5,000 CREDIT BEING PROVIDED TO BUYER BY SELLER at closing for upgrades or closing costs. ... |
2 beds | 2 baths | 1,164 sq.ft. |
$215,000 |
Airbnb cash on cash: 5.97%
|
4345 TAHITIAN GARDENS CIRCLE #CHOLIDAY, FLJUST REDUCED! This two-bedroom, BATH & HALF condominium located at the back of a cul-de-sa... |
2 beds | 2 baths | 825 sq.ft. |
$143,500 |
Airbnb cash on cash: 8.05%
|
4803 TRAFFORD ROADHOLIDAY, FLThis charming block home features a fenced backyard and a total of 1,402 square feet of li... |
3 beds | 2 baths | 988 sq.ft. |
$239,000 |
Airbnb cash on cash: 8.08%
|
3301 ELKRIDGE DRIVEHOLIDAY, FLWake up to tranquil living ON THE WATER in this spacious 3-bedroom, 2-bathroom home, perfe... |
3 beds | 2 baths | 1,687 sq.ft. |
$282,000 |
Airbnb cash on cash: 6.31%
|
1225 GREENLEA DRIVEHOLIDAY, FLA POOL HOME and NO HOA, NO CDD and is in a NO FLOOD ZONE. It's in the charming Holiday La... |
2 beds | 2 baths | 1,525 sq.ft. |
$366,000 |
Airbnb cash on cash: 2.83%
|
4223 KIBLER LANEHOLIDAY, FLUnder contract-accepting backup offers. Welcome to 4223 Kibler Lane â a charming 2-bedro... |
2 beds | 1 baths | 816 sq.ft. |
$170,000 |
Airbnb cash on cash: 7.3%
|
5828 MARIPOSA DRIVEHOLIDAY, FLWelcome to 5828 Mariposa Drive in Holiday, FL â a charming 2-bedroom, 2-bath home offeri... |
2 beds | 2 baths | 973 sq.ft. |
$216,500 |
Airbnb cash on cash: 5.87%
|
3426 PINON DRHOLIDAY, FLOne or more photo(s) has been virtually staged. Move In Ready in Holiday Lake Estates. Fr... |
3 beds | 1 baths | 884 sq.ft. |
$225,000 |
Airbnb cash on cash: 8.56%
|
3048 HOLIDAY LAKE DRIVEHOLIDAY, FLNO FLOOD ZONE. Lots of Updates. NEW LVP FLOORING throughout 2024. Remodeled Kitchen with N... |
3 beds | 2 baths | 1,504 sq.ft. |
$262,000 |
Airbnb cash on cash: 7.03%
|
2640 ALBION STREETHOLIDAY, FLOne or more photo(s) has been virtually staged. Paradise found at this waterfront home in ... |
3 beds | 2 baths | 1,517 sq.ft. |
$289,000 |
Airbnb cash on cash: 6.3%
|
3114 BLUFF BOULEVARDHOLIDAY, FLLuxury Waterfront Living in Baileyâs Bluff! THIS HOME HAS NEVER EXPERIENCED FLOODING FR... |
3 beds | 3 baths | 3,234 sq.ft. |
$1,450,000 |
Airbnb cash on cash: -0.08%
|
3140 BAHIA AVENUEHOLIDAY, FLBrand-new roof will be installed prior to closing! This updated La Villa Gardens home feat... |
2 beds | 1 baths | 1,134 sq.ft. |
$230,000 |
Airbnb cash on cash: 5.54%
|
5722 MARIPOSA DRIVEHOLIDAY, FLWelcome to your charming POOL home in Holiday, FL! This well maintained two-bedroom, two-b... |
2 beds | 2 baths | 1,338 sq.ft. |
$255,000 |
Airbnb cash on cash: 4.58%
|
3954 SAILMAKER LANEHOLIDAY, FLWelcome to the wonderful Holiday Lake Villas, a desirable and conveniently located 55+ com... |
2 beds | 2 baths | 1,318 sq.ft. |
$149,900 |
Airbnb cash on cash: 8.04%
|
2107 HARRISON DRIVEHOLIDAY, FLPriced to Sell! Here is your chance to stop renting and own a property at an affordable pr... |
2 beds | 2 baths | 1,151 sq.ft. |
$229,000 |
Airbnb cash on cash: 4.46%
|
1629 DARTMOUTH DRIVEHOLIDAY, FLOne or more photo(s) has been virtually staged. Welcome to this beautifully updated 2-bedr... |
2 beds | 2 baths | 1,461 sq.ft. |
$275,000 |
Airbnb cash on cash: 4.52%
|
3518 MOOG RoadHOLIDAY, FLEnjoy Florida living in this updated 3-bedroom, 2-bath home featuring a bright open layout... |
3 beds | 2 baths | 1,514 sq.ft. |
$289,900 |
Airbnb cash on cash: 6.86%
|
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. |
$289,900 |
Airbnb cash on cash: 6.96%
|
5021 PHOENIX AVENUEHOLIDAY, FLUnder contract-accepting backup offers. Location truly is everything with this well-mainta... |
2 beds | 2 baths | 1,295 sq.ft. |
$250,000 |
Airbnb cash on cash: 4.85%
|
2735 PLANTAIN DRIVEHOLIDAY, FLWelcome to Key Vista Villas, a premier gated 55+ community where low-maintenance living me... |
2 beds | 2 baths | 1,555 sq.ft. |
$329,900 |
Airbnb cash on cash: 2.42%
|
4731 AEGEAN AVENUEHOLIDAY, FLOne or more photo(s) has been virtually staged. Welcome to this charming Holiday home feat... |
3 beds | 1 baths | 1,104 sq.ft. |
$242,500 |
Airbnb cash on cash: 8.73%
|
1313 CHANCELLOR DRIVEHOLIDAY, FLBring all your outdoor toys to 1313 Chancellor Drive! Plenty of RV and boat/other parking ... |
2 beds | 2 baths | 953 sq.ft. |
$209,900 |
Airbnb cash on cash: 5.86%
|
1023 ORCA COURTHOLIDAY, FLUnder contract-accepting backup offers. GORGEOUS! GORGEOUS! GORGEOUS! Welcome to the Highl... |
3 beds | 2 baths | 1,740 sq.ft. |
$379,300 |
Airbnb cash on cash: 3.15%
|
2016 GULFVIEW DRIVEHOLIDAY, FLSpectacular waterfront living in the highly sought-after Baileyâs Bluff community! REMOD... |
3 beds | 2 baths | 2,723 sq.ft. |
$1,459,000 |
Airbnb cash on cash: 0.41%
|
3238 MELA COURTHOLIDAY, FL5 Bedroom, 3.5 Bath, 2 Story home located in the Gated Community of Vista Lakes, perfectl... |
5 beds | 4 baths | 3,198 sq.ft. |
$575,000 |
Airbnb cash on cash: 6.77%
|
4102 DARLINGTON ROADHOLIDAY, FLGreat starter home or retirement home. This comfortable home has 2 bedrooms, 2 bathrooms, ... |
2 beds | 2 baths | 988 sq.ft. |
$215,000 |
Airbnb cash on cash: 5.28%
|
3138 DEERGRASS COURTHOLIDAY, FLShort Sale. Welcome to 3138 Deergrass Ct, nestled in the charming Glenwood of Gulf Trace n... |
4 beds | 3 baths | 2,525 sq.ft. |
$480,000 |
Airbnb cash on cash: 4.97%
|
3217 ROCK VALLEY DRIVEHOLIDAY, FLFULLY FURNISHED! Perfect for snowbirds or rental investment opportunity, rent as soon as y... |
4 beds | 2 baths | 1,600 sq.ft. |
$325,000 |
Airbnb cash on cash: 8.93%
|
4706 DARLINGTON ROADHOLIDAY, FLWell-kept home in Holiday with fast access to US19. Shopping and beaches close by. No floo... |
2 beds | 2 baths | 816 sq.ft. |
$199,900 |
Airbnb cash on cash: 6.07%
|
2909 FEATHERSTONE DRIVEHOLIDAY, FLTurnkey 2-Bed, 2-Bath Home with Premium Amenities â Minutes from Top Destinations Own... |
2 beds | 2 baths | 1,232 sq.ft. |
$254,900 |
Airbnb cash on cash: 2.45%
|
5657 OCEANIC ROADHOLIDAY, FLWelcome to your dream home! This 4-bedroom, 3.5-bath home offers the perfect blend of comf... |
4 beds | 4 baths | 3,553 sq.ft. |
$649,900 |
Airbnb cash on cash: 4.58%
|
Real Estate investment in Holiday, FL
There are 218 properties for sale in the city of Holiday . The median list price in Holiday is $247,999 and the average price per square foot is $185. In October 2025, the average monthly cash on cash return in Holiday is 6.00%. The average monthly rental income in Holiday is $2,015.