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 |
|---|---|---|---|
1023 VIKING DriveHOLIDAY, FLWelcome home to this charming 2-bedroom, 1.5-bath house offering comfort, convenience, and... |
2 beds | 2 baths | 1,097 sq.ft. |
$215,000 |
Airbnb cash on cash: 2.94%
|
2228 SOCIETY DriveHOLIDAY, FLWake Up on the Water, Every Single Day, coffee in hand, mist rising off Lake Conley, and a... |
2 beds | 2 baths | 1,039 sq.ft. |
$240,000 |
Airbnb cash on cash: 1.82%
|
3431 OVERLAND DriveHOLIDAY, FLMOVE-IN READY! Welcome home to this charming 3-bedroom, 2-bathroom home featuring a desira... |
3 beds | 2 baths | 1,236 sq.ft. |
$239,900 |
Airbnb cash on cash: 4.26%
|
2228 PARROT FISH DriveHOLIDAY, FLAuction Property. This Villa can be a "dream home" again. With a bit of thoughtful plannin... |
3 beds | 2 baths | 1,876 sq.ft. |
$269,900 |
Airbnb cash on cash: 2.35%
|
1056 TAMARAC DriveHOLIDAY, FLVirtually Staged. Spacious, move-in ready home with fully fenced front and back yards-perf... |
2 beds | 2 baths | 1,272 sq.ft. |
$239,916 |
Airbnb cash on cash: 2.42%
|
3400 BAINBRIDGE DriveHOLIDAY, FLVirtually Staged. Imagine 3400 Bainbridge Dr, recently refreshed with fresh exterior paint... |
2 beds | 2 baths | 1,051 sq.ft. |
$212,000 |
Airbnb cash on cash: 2.85%
|
1031 CONOLEY LaneHOLIDAY, FLWelcome to 1031 Conoley Ln, a beautifully maintained and thoughtfully updated 3-bedroom, 1... |
3 beds | 1 baths | 1,004 sq.ft. |
$230,000 |
Airbnb cash on cash: 5.45%
|
4345 TAHITIAN GARDENS Circle #CHOLIDAY, FLWelcome to Tahitian Gardens, a gated 55+ condominium community in Holiday, FL! This mostly... |
2 beds | 2 baths | 825 sq.ft. |
$135,000 |
Airbnb cash on cash: 3.06%
|
3225 HEARTHSTONE CourtHOLIDAY, FLBeautifully Updated 3-Bedroom Home on an Oversized Cul-de-Sac Lot Welcome home! This beaut... |
3 beds | 2 baths | 2,011 sq.ft. |
$459,500 |
Airbnb cash on cash: 1.65%
|
3128 HARVARDSTON LoopHOLIDAY, FLVirtually Staged. Welcome to your beautifully updated Florida retreat in the heart of Holi... |
3 beds | 2 baths | 1,048 sq.ft. |
$279,900 |
Airbnb cash on cash: 4.24%
|
3419 PALOMA DriveHOLIDAY, FLWelcome to this beautifully maintained home both inside and out with great landscaping bot... |
2 beds | 2 baths | 1,070 sq.ft. |
$253,000 |
Airbnb cash on cash: 2.36%
|
3011 SHADOW OAKS DriveHOLIDAY, FLBeautiful 3-bedroom, 2-bath home situated on a fully fenced 1/4-acre corner lot with a pea... |
3 beds | 2 baths | 1,480 sq.ft. |
$319,000 |
Airbnb cash on cash: 3.14%
|
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. |
$235,000 |
Airbnb cash on cash: 4.91%
|
1166 CHANCELLOR DriveHOLIDAY, FLWelcome to true waterfront living in this beautifully remodeled 4-bedroom, 3-bath home wit... |
4 beds | 3 baths | 1,761 sq.ft. |
$459,900 |
Airbnb cash on cash: -1%
|
2146 SOCIETY DriveHOLIDAY, FLVirtually Staged. OPPORTUNITY knocks!! Back on market due to buyers inability to perform. ... |
2 beds | 2 baths | 1,371 sq.ft. |
$259,000 |
Airbnb cash on cash: 1.74%
|
3221 ROXBURY DriveHOLIDAY, FLSummer may almost be over, but it's still not too late to own a pool home and enjoy the Fl... |
2 beds | 2 baths | 1,136 sq.ft. |
$252,000 |
Airbnb cash on cash: 2.25%
|
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: 0.38%
|
3238 MELA CourtHOLIDAY, FLUnder contract-accepting backup offers. Amazing Price Reduction in Gated Neighborhood of V... |
5 beds | 4 baths | 3,198 sq.ft. |
$499,900 |
Airbnb cash on cash: 0.77%
|
4327 BEACON SQUARE DriveHOLIDAY, FLSELLER IS MOTIVATED! Eligible buyers may be able to purchase this home with NO MONEY DOWN ... |
3 beds | 1 baths | 1,104 sq.ft. |
$213,000 |
Airbnb cash on cash: 5.46%
|
2222 ARCADIA RoadHOLIDAY, FLVirtually Staged. Welcome to this move-in ready 2-bedroom, 2-bath home with flexible livin... |
2 beds | 2 baths | 1,088 sq.ft. |
$247,500 |
Airbnb cash on cash: 2.17%
|
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. |
$289,000 |
Airbnb cash on cash: 1.69%
|
1050 DEAL LaneHOLIDAY, FLTurn-Key 3 bedroom home with Dual Primary Suites-Ideal for Multi-Generational Living or In... |
3 beds | 3 baths | 1,667 sq.ft. |
$305,000 |
Airbnb cash on cash: 2.63%
|
3029 HUNTINGTON RoadHOLIDAY, FLVirtually Staged. Welcome to 3029 Huntington Road, a well-maintained 3-bedroom, 2-bath hom... |
3 beds | 2 baths | 1,486 sq.ft. |
$272,500 |
Airbnb cash on cash: 3.4%
|
3124 LECANTO StreetHOLIDAY, FLWelcome home to this beautifully updated residence featuring modern finishes and a bright,... |
2 beds | 1 baths | 1,104 sq.ft. |
$205,000 |
Airbnb cash on cash: 2.03%
|
3849 LUMA DriveHOLIDAY, FLWelcome home to this move-in-ready 3-bedroom, 2-bathroom home in the established community... |
3 beds | 2 baths | 1,076 sq.ft. |
$239,000 |
Airbnb cash on cash: 5.47%
|
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. |
$160,000 |
Airbnb cash on cash: -1.49%
|
2030 GULFVIEW DriveHOLIDAY, FL"Gulf Access Waterfront Home in Historic Baileys Bluff Estates" A rare opportunity to own ... |
2 beds | 2 baths | 2,280 sq.ft. |
$799,000 |
Airbnb cash on cash: -1.07%
|
3020 SHEPPARDS CROOK CourtHOLIDAY, FL"Luxury Living in an Exclusive Gated Community" Experience coastal elegance in this custom... |
3 beds | 4 baths | 2,367 sq.ft. |
$579,000 |
Airbnb cash on cash: 0.01%
|
3547 WILSON DriveHOLIDAY, FL-PROPERTY HIGHLIGHTS: Large corner lot with NO HOA. Fully fenced backyard with double-gate... |
2 beds | 1 baths | 984 sq.ft. |
$199,900 |
Airbnb cash on cash: 2.4%
|
2332 CHANCERY DriveHOLIDAY, FLBeautifully updated throughout, this 3-bedroom, 2-bathroom home with a 1-car garage offers... |
3 beds | 2 baths | 1,151 sq.ft. |
$274,900 |
Airbnb cash on cash: 3.36%
|
3313 BRIAR CLIFF DriveHOLIDAY, FLWelcome to 3313 Briar Cliff Dr! This 3/2/1 BLOCK home sits high & dry in a non-flood zone.... |
3 beds | 2 baths | 1,417 sq.ft. |
$239,900 |
Airbnb cash on cash: 4.16%
|
3920 BEACON SQUARE DriveHOLIDAY, FLNEW PRICE + A RARE 3.625% ASSUMABLE FHA MORTGAGE OPPORTUNITY! Qualified buyers could have ... |
2 beds | 2 baths | 992 sq.ft. |
$239,900 |
Airbnb cash on cash: 1.92%
|
1817 DARTMOUTH DriveHOLIDAY, FLDon't miss out on this 3-bedroom 2-bath home just 2.5 miles from the BEACH and the Ancloe ... |
3 beds | 2 baths | 1,457 sq.ft. |
$249,000 |
Airbnb cash on cash: 3.63%
|
Real Estate investment in Holiday, FL
There are 208 properties for sale in the city of Holiday . The median list price in Holiday is $224,865 and the average price per square foot is $165. In September 2026, the average monthly cash on cash return in Holiday is 6.00%. The average monthly rental income in Holiday is $2,074.