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.

Sugarloaf Investment Property for Sale in Holiday, FL

Search for Sugarloaf Investment Property for Sale in Holiday, Florida. Browse all of Mashvisor’s Sugarloaf Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 200 Sugarloaf Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
5309 BOARDWALK STREET HOLIDAY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. FI...	3 beds \| 3 baths \| 1,848 sq.ft.	$449,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 4.61% Airbnb Rental Income: $3151 Traditional Rental Income: $2848 Airbnb ROI: 3.63% Traditional ROI: 4.61%
3520 OVERLAND DRIVE HOLIDAY, FL Welcome to your own slice of Gulf Coast waterfront living. This beautifully updated pool h...	2 beds \| 2 baths \| 1,068 sq.ft.	$269,000	Airbnb cash on cash: 4.49% Traditional cash on cash: 7.49% Airbnb Rental Income: $2176 Traditional Rental Income: $2387 Airbnb ROI: 4.49% Traditional ROI: 7.49%
3142 MERITA DRIVE HOLIDAY, FL Under contract-accepting backup offers. This 3 bedroom, 1 bathroom home offers flexibility...	3 beds \| 1 baths \| 1,356 sq.ft.	$235,000	Airbnb cash on cash: 9.08% Traditional cash on cash: 8.13% Airbnb Rental Income: $3151 Traditional Rental Income: $2226 Airbnb ROI: 9.08% Traditional ROI: 8.13%
2228 SOCIETY DRIVE HOLIDAY, FL Price 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: 4.62% Traditional cash on cash: 5.53% Airbnb Rental Income: $2176 Traditional Rental Income: $1831 Airbnb ROI: 4.62% Traditional ROI: 5.53%
2228 PARROT FISH DRIVE HOLIDAY, FL Surrounded by Nature in this Spacious HIgh & Dry Villa makes this the Perfect Florida Home...	3 beds \| 2 baths \| 1,876 sq.ft.	$319,900	Airbnb cash on cash: 4.76% Traditional cash on cash: 5.82% Airbnb Rental Income: $3151 Traditional Rental Income: $2755 Airbnb ROI: 4.76% Traditional ROI: 5.82%
2150 PARROT FISH DRIVE HOLIDAY, FL Under contract-accepting backup offers. PRICED BELOW MARKET VALUE! Welcome to your Florida...	3 beds \| 2 baths \| 1,740 sq.ft.	$334,900	Airbnb cash on cash: 3.5% Traditional cash on cash: 3.03% Airbnb Rental Income: $3151 Traditional Rental Income: $2289 Airbnb ROI: 3.5% Traditional ROI: 3.03%
3543 HOOVER DRIVE HOLIDAY, FL 3.5% DOWN PAYMENT ASSISTANCE AVAILABLE THROUGH PREFERRED LENDER FOR QUALIFIED BUYERS!!!!! ...	2 beds \| 2 baths \| 1,096 sq.ft.	$215,000	Airbnb cash on cash: 5.87% Traditional cash on cash: 6.71% Airbnb Rental Income: $2176 Traditional Rental Income: $1794 Airbnb ROI: 5.87% Traditional ROI: 6.71%
3249 EISENHOWER DRIVE HOLIDAY, FL WOW! This bright open spacious floor plan and meticulous well-maintained home is a MUST SE...	2 beds \| 2 baths \| 1,216 sq.ft.	$219,900	Airbnb cash on cash: 5.81% Traditional cash on cash: 7.89% Airbnb Rental Income: $2176 Traditional Rental Income: $2057 Airbnb ROI: 5.81% Traditional ROI: 7.89%
1028 ORCA COURT HOLIDAY, FL Under 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: 3.76% Traditional cash on cash: 5.92% Airbnb Rental Income: $3151 Traditional Rental Income: $3106 Airbnb ROI: 3.76% Traditional ROI: 5.92%
1225 GREENLEA DRIVE HOLIDAY, FL Under 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: 3.2% Traditional cash on cash: 5.91% Airbnb Rental Income: $2176 Traditional Rental Income: $2474 Airbnb ROI: 3.2% Traditional ROI: 5.91%
3524 CHESWICK DRIVE HOLIDAY, FL Under contract-accepting backup offers. Well-maintained 3-bedroom, 2-bath home with a 1-ca...	3 beds \| 2 baths \| 1,258 sq.ft.	$235,000	Airbnb cash on cash: 8.3% Traditional cash on cash: 7.53% Airbnb Rental Income: $3151 Traditional Rental Income: $2266 Airbnb ROI: 8.3% Traditional ROI: 7.53%
5828 MARIPOSA DRIVE HOLIDAY, FL Welcome to 5828 Mariposa Drive in Holiday, FL â a charming 2-bedroom, 2-bath home offeri...	2 beds \| 2 baths \| 973 sq.ft.	$203,000	Airbnb cash on cash: 6.32% Traditional cash on cash: 7.6% Airbnb Rental Income: $2176 Traditional Rental Income: $1872 Airbnb ROI: 6.32% Traditional ROI: 7.6%
2128 SHANNON DRIVE HOLIDAY, FL Quintessential Florida Living in Holiday! Welcome to this charming 2-bedroom, 1-bath, 1-c...	2 beds \| 1 baths \| 1,200 sq.ft.	$249,900	Airbnb cash on cash: 5.06% Traditional cash on cash: 5.7% Airbnb Rental Income: $2176 Traditional Rental Income: $1776 Airbnb ROI: 5.06% Traditional ROI: 5.7%
5313 BOARDWALK STREET HOLIDAY, FL One or more photo(s) has been virtually staged. Welcome to 5313 Boardwalk Street â a bea...	3 beds \| 3 baths \| 1,848 sq.ft.	$449,999	Airbnb cash on cash: 3.33% Traditional cash on cash: 3.73% Airbnb Rental Income: $3151 Traditional Rental Income: $2606 Airbnb ROI: 3.33% Traditional ROI: 3.73%
3529 GARFIELD DRIVE HOLIDAY, FL NEW PRICE! Extremely well maintained and move-in ready, this charming 2 bedroom, 2 full b...	2 beds \| 2 baths \| 1,096 sq.ft.	$240,000	Airbnb cash on cash: 5.18% Traditional cash on cash: 6.28% Airbnb Rental Income: $2176 Traditional Rental Income: $1873 Airbnb ROI: 5.18% Traditional ROI: 6.28%
3426 PINON DR HOLIDAY, FL One or more photo(s) has been virtually staged. Move In Ready in Holiday Lake Estates. Fr...	3 beds \| 1 baths \| 884 sq.ft.	$219,900	Airbnb cash on cash: 8.77% Traditional cash on cash: 5.97% Airbnb Rental Income: $3151 Traditional Rental Income: $1854 Airbnb ROI: 8.77% Traditional ROI: 5.97%
3048 HOLIDAY LAKE DRIVE HOLIDAY, FL Under contract-accepting backup offers. NO FLOOD ZONE. Lots of Updates. NEW LVP FLOORING t...	3 beds \| 2 baths \| 1,504 sq.ft.	$249,900	Airbnb cash on cash: 7.29% Traditional cash on cash: 5.21% Airbnb Rental Income: $3151 Traditional Rental Income: $1945 Airbnb ROI: 7.29% Traditional ROI: 5.21%
3645 OVERLAND DRIVE HOLIDAY, FL One 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: 4.08% Traditional cash on cash: 5.77% Airbnb Rental Income: $2176 Traditional Rental Income: $2078 Airbnb ROI: 4.08% Traditional ROI: 5.77%
3638 BIGELOW DRIVE HOLIDAY, FL CORNER LOT-PRIVACY FENCE-Priced RIGHT!!--No HOA to worry about in this open floor plan hom...	2 beds \| 2 baths \| 1,096 sq.ft.	$214,000	Airbnb cash on cash: 5.94% Traditional cash on cash: 6.7% Airbnb Rental Income: $2176 Traditional Rental Income: $1777 Airbnb ROI: 5.94% Traditional ROI: 6.7%
4375 TAHITIAN GARDENS CIRCLE #B HOLIDAY, FL Under contract-accepting backup offers. Welcome to this beautifully maintained 2-bedroom, ...	2 beds \| 1 baths \| 825 sq.ft.	$127,900	Airbnb cash on cash: 8.8% Traditional cash on cash: 7.67% Airbnb Rental Income: $2176 Traditional Rental Income: $1485 Airbnb ROI: 8.8% Traditional ROI: 7.67%
3707 PINEHURST DRIVE HOLIDAY, FL Under contract-accepting backup offers. Unaffected by recent storm activity and located in...	3 beds \| 2 baths \| 1,534 sq.ft.	$279,800	Airbnb cash on cash: 6.52% Traditional cash on cash: 5.79% Airbnb Rental Income: $3151 Traditional Rental Income: $2244 Airbnb ROI: 6.52% Traditional ROI: 5.79%
3706 CHESWICK DRIVE HOLIDAY, FL Welcome 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: 6.67% Traditional cash on cash: 7.95% Airbnb Rental Income: $2176 Traditional Rental Income: $1864 Airbnb ROI: 6.67% Traditional ROI: 7.95%
5026 MOOG ROAD HOLIDAY, FL Charming Updated Single-Family Home in Holiday with Spacious Fenced Yard. This home has be...	2 beds \| 1 baths \| 792 sq.ft.	$239,000	Airbnb cash on cash: 4.62% Traditional cash on cash: 4.42% Airbnb Rental Income: $2176 Traditional Rental Income: $1580 Airbnb ROI: 4.62% Traditional ROI: 4.42%
3954 SAILMAKER LANE HOLIDAY, FL Under contract-accepting backup offers. Welcome to the wonderful Holiday Lake Villas, a de...	2 beds \| 2 baths \| 1,318 sq.ft.	$125,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 10% Airbnb Rental Income: $2176 Traditional Rental Income: $2286 Airbnb ROI: 4.51% Traditional ROI: 10%
2107 HARRISON DRIVE HOLIDAY, FL Under contract-accepting backup offers. Priced to Sell! Here is your chance to stop rentin...	2 beds \| 2 baths \| 1,151 sq.ft.	$219,000	Airbnb cash on cash: 4.7% Traditional cash on cash: 4.86% Airbnb Rental Income: $2176 Traditional Rental Income: $1657 Airbnb ROI: 4.7% Traditional ROI: 4.86%
3552 BLUEBELL LANE HOLIDAY, FL Short Sale. Pre-Foreclosure. INVESTOR SPECIAL! Welcome to this 2-bedroom, 2-bathroom, 1-ca...	2 beds \| 2 baths \| 900 sq.ft.	$180,000	Airbnb cash on cash: 7.13% Traditional cash on cash: 10.18% Airbnb Rental Income: $2176 Traditional Rental Income: $2146 Airbnb ROI: 7.13% Traditional ROI: 10.18%
3309 JACKSON DRIVE HOLIDAY, FL Welcome 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: 4.16% Traditional cash on cash: 5.92% Airbnb Rental Income: $2176 Traditional Rental Income: $2056 Airbnb ROI: 4.16% Traditional ROI: 5.92%
2349 HAMA DRIVE HOLIDAY, FL WELCOME HOME to this meticulously maintained 3-bedroom, 2-bath waterfront home in Holiday'...	3 beds \| 2 baths \| 1,470 sq.ft.	$279,900	Airbnb cash on cash: 7.24% Traditional cash on cash: 8.55% Airbnb Rental Income: $3151 Traditional Rental Income: $2782 Airbnb ROI: 7.24% Traditional ROI: 8.55%
1313 CHANCELLOR DRIVE HOLIDAY, FL One or more photo(s) has been virtually staged. Discover the charm of the Forest Hills nei...	2 beds \| 2 baths \| 953 sq.ft.	$180,000	Airbnb cash on cash: 6.97% Traditional cash on cash: 7.66% Airbnb Rental Income: $2176 Traditional Rental Income: $1743 Airbnb ROI: 6.97% Traditional ROI: 7.66%
3147 MELA COURT HOLIDAY, FL Under 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: 4.17% Traditional cash on cash: 4.54% Airbnb Rental Income: $3151 Traditional Rental Income: $2566 Airbnb ROI: 4.17% Traditional ROI: 4.54%
3625 Windham Drive HOLIDAY, FL Welcome 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: 8.97% Traditional cash on cash: 6.51% Airbnb Rental Income: $3151 Traditional Rental Income: $1912 Airbnb ROI: 8.97% Traditional ROI: 6.51%
3238 MELA COURT HOLIDAY, FL 5 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% Traditional cash on cash: 4.23% Airbnb Rental Income: $6270 Traditional Rental Income: $3671 Airbnb ROI: 6.77% Traditional ROI: 4.23%
3844 REDWOOD DRIVE HOLIDAY, FL Under contract-accepting backup offers. DOWN PAYMENT ASSISTANCE AVAILABLE â NO INCOME LI...	2 beds \| 2 baths \| 948 sq.ft.	$219,000	Airbnb cash on cash: 5.48% Traditional cash on cash: 6.21% Airbnb Rental Income: $2176 Traditional Rental Income: $1776 Airbnb ROI: 5.48% Traditional ROI: 6.21%
4102 DARLINGTON ROAD HOLIDAY, FL Great starter,retiremen, or income rental home. This comfortable home has 2 bedrooms, 2 ba...	2 beds \| 2 baths \| 988 sq.ft.	$185,000	Airbnb cash on cash: 6.27% Traditional cash on cash: 7.11% Airbnb Rental Income: $2176 Traditional Rental Income: $1773 Airbnb ROI: 6.27% Traditional ROI: 7.11%
3138 DEERGRASS COURT HOLIDAY, FL Short Sale. Welcome to 3138 Deergrass Ct, nestled in the charming Glenwood of Gulf Trace n...	4 beds \| 3 baths \| 2,525 sq.ft.	$425,000	Airbnb cash on cash: 5.73% Traditional cash on cash: 6.39% Airbnb Rental Income: $4419 Traditional Rental Income: $3754 Airbnb ROI: 5.73% Traditional ROI: 6.39%
3525 EMORY DRIVE HOLIDAY, FL Public facing remarks - Beautifully renovated clean home that features a brand new white k...	3 beds \| 2 baths \| 1,283 sq.ft.	$239,900	Airbnb cash on cash: 7.71% Traditional cash on cash: 5.97% Airbnb Rental Income: $3151 Traditional Rental Income: $2041 Airbnb ROI: 7.71% Traditional ROI: 5.97%
3228 ROCK VALLEY DRIVE HOLIDAY, FL Welcome 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: 3.87% Traditional cash on cash: 5.39% Airbnb Rental Income: $2176 Traditional Rental Income: $2052 Airbnb ROI: 3.87% Traditional ROI: 5.39%
2907 FEATHERSTONE DRIVE HOLIDAY, FL Move-in ready and full of potential! This 2-bedroom, 2-bath home features an open floorpla...	2 beds \| 2 baths \| 1,159 sq.ft.	$194,900	Airbnb cash on cash: 3.22% Traditional cash on cash: 4.99% Airbnb Rental Income: $2176 Traditional Rental Income: $1952 Airbnb ROI: 3.22% Traditional ROI: 4.99%
2909 FEATHERSTONE DRIVE HOLIDAY, FL Price adjustment very motivated seller ...Own this beautifully maintained partially furnis...	2 beds \| 2 baths \| 1,232 sq.ft.	$239,900	Airbnb cash on cash: 2.66% Traditional cash on cash: 4.41% Airbnb Rental Income: $2176 Traditional Rental Income: $2022 Airbnb ROI: 2.66% Traditional ROI: 4.41%
5657 OCEANIC ROAD HOLIDAY, FL Welcome 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: 4.75% Traditional cash on cash: 6.57% Airbnb Rental Income: $4419 Traditional Rental Income: $4562 Airbnb ROI: 4.75% Traditional ROI: 6.57%

Your search for investment property begins and ends here

Sugarloaf Investment Property for Sale in Holiday, FL

5309 BOARDWALK STREET

HOLIDAY, FL

3 beds | 3 baths | 1,848 sq.ft.

$449,000

Airbnb cash on cash: 3.63%

Traditional cash on cash: 4.61%

Airbnb Rental Income: $3151

Traditional Rental Income: $2848

Airbnb ROI: 3.63%

Traditional ROI: 4.61%

3520 OVERLAND DRIVE

HOLIDAY, FL

2 beds | 2 baths | 1,068 sq.ft.

$269,000

Airbnb cash on cash: 4.49%

Traditional cash on cash: 7.49%

Airbnb Rental Income: $2176

Traditional Rental Income: $2387

Airbnb ROI: 4.49%

Traditional ROI: 7.49%

3142 MERITA DRIVE

HOLIDAY, FL

3 beds | 1 baths | 1,356 sq.ft.

$235,000

Airbnb cash on cash: 9.08%

Traditional cash on cash: 8.13%

Airbnb Rental Income: $3151

Traditional Rental Income: $2226

Airbnb ROI: 9.08%

Traditional ROI: 8.13%

2228 SOCIETY DRIVE

HOLIDAY, FL

2 beds | 2 baths | 1,039 sq.ft.

$239,900

Airbnb cash on cash: 4.62%

Traditional cash on cash: 5.53%

Airbnb Rental Income: $2176

Traditional Rental Income: $1831

Airbnb ROI: 4.62%

Traditional ROI: 5.53%

2228 PARROT FISH DRIVE

HOLIDAY, FL

3 beds | 2 baths | 1,876 sq.ft.

$319,900

Airbnb cash on cash: 4.76%

Traditional cash on cash: 5.82%

Airbnb Rental Income: $3151

Traditional Rental Income: $2755

Airbnb ROI: 4.76%

Traditional ROI: 5.82%

2150 PARROT FISH DRIVE

HOLIDAY, FL

3 beds | 2 baths | 1,740 sq.ft.

$334,900

Airbnb cash on cash: 3.5%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $3151

Traditional Rental Income: $2289

Airbnb ROI: 3.5%

Traditional ROI: 3.03%

3543 HOOVER DRIVE

HOLIDAY, FL

2 beds | 2 baths | 1,096 sq.ft.

$215,000

Airbnb cash on cash: 5.87%

Traditional cash on cash: 6.71%

Airbnb Rental Income: $2176

Traditional Rental Income: $1794

Airbnb ROI: 5.87%

Traditional ROI: 6.71%

3249 EISENHOWER DRIVE

HOLIDAY, FL

2 beds | 2 baths | 1,216 sq.ft.

$219,900

Airbnb cash on cash: 5.81%

Traditional cash on cash: 7.89%

Airbnb Rental Income: $2176

Traditional Rental Income: $2057

Airbnb ROI: 5.81%