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 |
|---|---|---|---|
3520 OVERLAND DRIVEHOLIDAY, FLUnder contract-accepting backup offers. Welcome to your own slice of Gulf Coast waterfront... |
2 beds | 2 baths | 1,068 sq.ft. |
$269,000 |
Airbnb cash on cash: 9.46%
|
2228 PARROT FISH DRIVEHOLIDAY, FLBeautiful Must See Vylla. HIgh & Dry Villa makes this the Perfect Florida Home. Enter your... |
3 beds | 2 baths | 1,876 sq.ft. |
$319,900 |
Airbnb cash on cash: 6.92%
|
1028 ORCA COURTHOLIDAY, FLUnder contract-accepting backup offers. BRAND NEW ROOF (5/2025) | NEVER FLOODED | MOVE-IN ... |
3 beds | 2 baths | 1,740 sq.ft. |
$329,900 |
Airbnb cash on cash: 8.61%
|
1225 GREENLEA DRIVEHOLIDAY, FLUnder contract-accepting backup offers. Spacious POOL HOME with a new pump and filter syst... |
2 beds | 2 baths | 1,525 sq.ft. |
$333,000 |
Airbnb cash on cash: 7.23%
|
5313 BOARDWALK STREETHOLIDAY, FLOne or more photo(s) has been virtually staged. Welcome to 5313 Boardwalk Street â a bea... |
3 beds | 3 baths | 1,848 sq.ft. |
$444,000 |
Airbnb cash on cash: 7%
|
3645 OVERLAND DRIVEHOLIDAY, FLOne or more photo(s) has been virtually staged. THIS RESIDENCE IS A 2/3/2 with an oversize... |
2 beds | 3 baths | 1,416 sq.ft. |
$284,900 |
Airbnb cash on cash: 8.78%
|
3114 BLUFF BOULEVARDHOLIDAY, FLDiscover the charm of Floridaâs Gulf Coast in this beautifully crafted waterfront home, ... |
3 beds | 3 baths | 3,234 sq.ft. |
$1,295,000 |
Airbnb cash on cash: 1.29%
|
3309 JACKSON DRIVEHOLIDAY, FLWelcome to 3309 Jackson Dr., Holiday, FL â A Charming Pool Home in the Tahitian Developm... |
2 beds | 1 baths | 1,140 sq.ft. |
$259,999 |
Airbnb cash on cash: 9.31%
|
3147 MELA COURTHOLIDAY, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. Ne... |
3 beds | 2 baths | 1,483 sq.ft. |
$375,000 |
Airbnb cash on cash: 8.44%
|
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: N/A
|
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: 5.91%
|
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: 8.35%
|
5657 OCEANIC ROADHOLIDAY, FLWelcome to 5657 Oceanic Rd in Holiday, Florida a quiet, well-established neighborhood with... |
4 beds | 4 baths | 3,553 sq.ft. |
$629,900 |
Airbnb cash on cash: 8.9%
|
2817 PLANTAIN DRIVEHOLIDAY, FLWelcome home to 2817 Plantain Dr! This beautifully maintained home, located inside the gat... |
3 beds | 2 baths | 1,683 sq.ft. |
$415,000 |
Airbnb cash on cash: 6.96%
|
2216 PARROT FISH DRIVEHOLIDAY, FLUnder contract-accepting backup offers. *NEW PRICE!* This is a great find! This Beautifull... |
3 beds | 2 baths | 1,740 sq.ft. |
$340,000 |
Airbnb cash on cash: 8.83%
|
2906 WINDRIDGE DRIVEHOLIDAY, FLWelcome to 2906 Windridge Drive a large lake front lot where peace of mind meets luxury li... |
3 beds | 2 baths | 1,647 sq.ft. |
$375,000 |
Airbnb cash on cash: 8.32%
|
3127 DOLE STREETHOLIDAY, FLWelcome to this beautifully updated 2-bedroom, 2-bath, 2-car garage home offering 1,184 sq... |
2 beds | 2 baths | 1,184 sq.ft. |
$299,900 |
Airbnb cash on cash: 7.69%
|
3406 PALOMA DRIVEHOLIDAY, FLWelcome home to this beautifully updated 2-bedroom, 2-bath home offering comfort, style, a... |
2 beds | 2 baths | 1,310 sq.ft. |
$255,000 |
Airbnb cash on cash: 9.03%
|
2012 FERN RIDGE COURTHOLIDAY, FLUnder contract-accepting backup offers. Located in the gated community of Key Vista, this ... |
4 beds | 3 baths | 2,768 sq.ft. |
$490,000 |
Airbnb cash on cash: 9.73%
|
3409 SPRINGFIELD DRIVEHOLIDAY, FLLovely setting on a spring-fed lake. Enjoy the spectacular sunsets and cool evening breeze... |
2 beds | 2 baths | 1,519 sq.ft. |
$349,900 |
Airbnb cash on cash: 6.29%
|
2126 PARROT FISH DRIVEHOLIDAY, FLWelcome home to this exceptional 3 bedroom, 2 bath villa with a 2 car garage, located in t... |
3 beds | 2 baths | 1,740 sq.ft. |
$353,999 |
Airbnb cash on cash: 8.41%
|
2211 BARRACUDA COURTHOLIDAY, FLWelcome to 2211 Barracuda Ct, Holiday, FL 34691 â a beautifully maintained turn-key home... |
3 beds | 2 baths | 1,876 sq.ft. |
$320,000 |
Airbnb cash on cash: 8.75%
|
2529 SANDY HILL COURTHOLIDAY, FLWhere else can you find a like-new home in a gated community just a short walk from the Gu... |
2 beds | 2 baths | 1,555 sq.ft. |
$379,000 |
Airbnb cash on cash: 4.85%
|
5311 BOARDWALK STREETHOLIDAY, FLWelcome to 5311 Boardwalk St, a rare opportunity to own a beautifully updated waterfront t... |
3 beds | 3 baths | 1,848 sq.ft. |
$449,900 |
Airbnb cash on cash: 7.9%
|
5930 DELLA DRIVEHOLIDAY, FLUnder contract-accepting backup offers. Tucked away in a quiet, peaceful neighborhood, thi... |
2 beds | 2 baths | 1,125 sq.ft. |
$265,000 |
Airbnb cash on cash: 9.12%
|
1414 GRAND BOULEVARDHOLIDAY, FLNEW ROOF JUST PUT ON AUGUST 2025,NEW FANS, AND THE INSIDE PAINTED! NEWER ELECTRIC, WINDOWS... |
2 beds | 2 baths | 2,278 sq.ft. |
$349,999 |
Airbnb cash on cash: 6.86%
|
1102 SPRINGTIME DRIVEHOLIDAY, FLUnder contract-accepting backup offers. Pool Home Under $400K The One Buyers Have Been Wai... |
3 beds | 2 baths | 1,930 sq.ft. |
$379,900 |
Airbnb cash on cash: 9.04%
|
3257 MASONVILLE LOOPHOLIDAY, FLWelcome to this beautifully updated 2 bedroom, 1-bathroom, single-family home, offering bo... |
2 beds | 1 baths | 1,134 sq.ft. |
$259,000 |
Airbnb cash on cash: 9.08%
|
2627 CHARLAN COURTHOLIDAY, FLWelcome to effortless living in Holidayâperfectly positioned between the historic charm ... |
2 beds | 3 baths | 1,541 sq.ft. |
$280,000 |
Airbnb cash on cash: 7.24%
|
3222 JACKSON DRIVEHOLIDAY, FLImagine waking up to the gentle sounds of nature and enjoying a stunning lake view every m... |
2 beds | 2 baths | 1,126 sq.ft. |
$339,000 |
Airbnb cash on cash: 6.57%
|
3237 SANFORD DRIVEHOLIDAY, FLUnder contract-accepting backup offers. Welome to 3237 Sanford Drive in Holiday, Florida â... |
2 beds | 2 baths | 1,246 sq.ft. |
$259,998 |
Airbnb cash on cash: 9.57%
|
3143 PINEVIEW DRIVEHOLIDAY, FLWelcome to your dream waterfront estate in the sought-after Baileys Bluff community! This ... |
4 beds | 4 baths | 4,204 sq.ft. |
$1,449,000 |
Airbnb cash on cash: 2.87%
|
2211 PLEASANT HILL LANEHOLIDAY, FLWelcome to Key Vista, one of Holidayâs most desirable 55+ gated communities, where comfo... |
2 beds | 2 baths | 1,500 sq.ft. |
$315,000 |
Airbnb cash on cash: 7.15%
|
2743 BIG PINE DRIVEHOLIDAY, FLWelcome to this beautifully maintained three bedroom, two bath, plus a den, pool home in t... |
3 beds | 2 baths | 1,758 sq.ft. |
$415,000 |
Airbnb cash on cash: 7.89%
|
2453 PLEASANT HILL LANEHOLIDAY, FLWelcome to one of Holidayâs most sought after 55+ gated communities, where privacy, comf... |
2 beds | 2 baths | 1,555 sq.ft. |
$300,000 |
Airbnb cash on cash: 7.56%
|
3149 ROCK VALLEY DRIVEHOLIDAY, FLThis property truly stands out from the rest! Boasting rich, bold colors, gorgeous styling... |
2 beds | 2 baths | 1,519 sq.ft. |
$309,500 |
Airbnb cash on cash: 8.24%
|
1734 RUMAR LANEHOLIDAY, FLTake advantage of a unique opportunity to own an expansive duplex that includes both units... |
6 beds | N/A baths | 3,384 sq.ft. |
$610,000 |
Airbnb cash on cash: 2.84%
|
5199 FORUM BOULEVARDHOLIDAY, FL2% towards closing cost/ rate buy down with preferred lender! Also available for Rent! Wel... |
2 beds | 3 baths | 1,541 sq.ft. |
$268,000 |
Airbnb cash on cash: 7.55%
|
5904 SPRINGRUN COURTHOLIDAY, FLA Private, Park-Like Oasis with Unmatched Amenities Awaits! Discover an unparalleled ret... |
3 beds | 2 baths | 2,284 sq.ft. |
$463,000 |
Airbnb cash on cash: 7.32%
|
3340 WILSON DRIVEHOLIDAY, FLOne or more photo(s) has been virtually staged. HUGE PRICE ADJUSTMENT. This charming 2-bed... |
2 beds | 2 baths | 1,268 sq.ft. |
$264,900 |
Airbnb cash on cash: 9.27%
|
Real Estate investment in Holiday, FL
There are 64 properties for sale in the city of Holiday . The median list price in Holiday is $240,000 and the average price per square foot is $177. In April 2026, the average monthly cash on cash return in Holiday is 7.00%. The average monthly rental income in Holiday is $2,060.