Real Estate Investment Properties for Sale in South Pasadena, FL

Looking for investment property in South Pasadena, FL with high ROI ?

Explore a variety of short-term homes & houses in South Pasadena, FL. Invest wisely with VRBO & South Pasadena, 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 South Pasadena, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
7700 SUN ISLAND DRIVE S #105C SOUTH PASADENA, FL Welcome to waterfront living at its finest in Bay Islands â a vibrant 55+ gated communit...	2 beds \| 2 baths \| 1,235 sq.ft.	$418,000	Airbnb cash on cash: 4.2% Traditional cash on cash: 3.84% Airbnb Rental Income: $3577 Traditional Rental Income: $2651 Airbnb ROI: 4.2% Traditional ROI: 3.84%
7645 SUN ISLAND DRIVE S #304 SOUTH PASADENA, FL Welcome to your coastal retreat in the highly desirable 55+ gated community of Bay Island,...	1 beds \| 1 baths \| 600 sq.ft.	$165,000	Airbnb cash on cash: 7.7% Traditional cash on cash: 7.56% Airbnb Rental Income: $2431 Traditional Rental Income: $1815 Airbnb ROI: 7.7% Traditional ROI: 7.56%
7930 SUN ISLAND DRIVE S #305 SOUTH PASADENA, FL Under contract-accepting backup offers. This stunning condo has just been REDUCED. Whethe...	1 beds \| 2 baths \| 940 sq.ft.	$247,900	Airbnb cash on cash: 3.61% Traditional cash on cash: 4.86% Airbnb Rental Income: $2431 Traditional Rental Income: $2130 Airbnb ROI: 3.61% Traditional ROI: 4.86%
7902 SAILBOAT KEY BOULEVARD S #206 SOUTH PASADENA, FL Imagine watching breathtaking sunsets from your private, west-facing balcony after a livel...	2 beds \| 2 baths \| 1,145 sq.ft.	$625,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 0.95% Airbnb Rental Income: $3577 Traditional Rental Income: $2514 Airbnb ROI: 1.42% Traditional ROI: 0.95%
1898 SHORE DRIVE S #311 SOUTH PASADENA, FL AMAZING VIEWS!! Enjoy breathtaking water and sunset views from 3rd floor of this beautiful...	2 beds \| 2 baths \| 1,260 sq.ft.	$267,500	Airbnb cash on cash: 4.76% Traditional cash on cash: 4.46% Airbnb Rental Income: $3577 Traditional Rental Income: $2714 Airbnb ROI: 4.76% Traditional ROI: 4.46%
1893 SHORE DRIVE S #208 SOUTH PASADENA, FL *Motivated Seller* Welcome to your own slice of coastal paradise in Shore Plaza, a pea...	2 beds \| 1 baths \| 840 sq.ft.	$230,000	Airbnb cash on cash: 8.21% Traditional cash on cash: 4.25% Airbnb Rental Income: $3577 Traditional Rental Income: $1931 Airbnb ROI: 8.21% Traditional ROI: 4.25%
7600 SUN ISLAND DRIVE S #107 SOUTH PASADENA, FL *ABSOLUTELY BREATHTAKING!!!* Enjoy the Spectacular Water Views of Boca Ciega Bay and t...	1 beds \| 2 baths \| 925 sq.ft.	$239,999	Airbnb cash on cash: 5.49% Traditional cash on cash: 5.56% Airbnb Rental Income: $2431 Traditional Rental Income: $1852 Airbnb ROI: 5.49% Traditional ROI: 5.56%
7405 BAY ISLAND DRIVE S #220 SOUTH PASADENA, FL NEW PRICE & SELLER IS PAYING 3 MONTHS OF HOA FEES! Whether you are looking for a new full ...	2 beds \| 2 baths \| 1,110 sq.ft.	$255,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 1.69% Airbnb Rental Income: $3577 Traditional Rental Income: $2467 Airbnb ROI: 3.04% Traditional ROI: 1.69%
7700 SUN ISLAND DRIVE S #107 SOUTH PASADENA, FL Experience the ultimate waterfront lifestyle in this stunning, ground-floor retreat 2nd to...	1 beds \| 2 baths \| 940 sq.ft.	$359,999	Airbnb cash on cash: 2.35% Traditional cash on cash: 3.45% Airbnb Rental Income: $2431 Traditional Rental Income: $2211 Airbnb ROI: 2.35% Traditional ROI: 3.45%
1115 RUE DES CHATEAUX #2A SOUTH PASADENA, FL Location! Location! Location! Priced to sell! 1.6 miles to St. Pete Beach or 7 miles to do...	1 beds \| 1 baths \| 741 sq.ft.	$145,000	Airbnb cash on cash: 4.95% Traditional cash on cash: 5.24% Airbnb Rental Income: $2431 Traditional Rental Income: $1878 Airbnb ROI: 4.95% Traditional ROI: 5.24%
7300 SUN ISLAND DRIVE S #202 SOUTH PASADENA, FL Under contract-accepting backup offers. PRICED TO SELL! This beautifully remodeled waterf...	1 beds \| 2 baths \| 1,120 sq.ft.	$285,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 4% Airbnb Rental Income: $2431 Traditional Rental Income: $2010 Airbnb ROI: 3.35% Traditional ROI: 4%
7645 SUN ISLAND DRIVE S #201 SOUTH PASADENA, FL Beautifully renovated Water View condo in the lovely gated community of Bay Island - on th...	2 beds \| 2 baths \| 1,385 sq.ft.	$395,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 0.83% Airbnb Rental Income: $3577 Traditional Rental Income: $2839 Airbnb ROI: 0.7% Traditional ROI: 0.83%
7932 SAILBOAT KEY BOULEVARD S #806 SOUTH PASADENA, FL Beautiful 8th floor penthouse corner unit condo with incredible views of the Gulf, the In...	2 beds \| 2 baths \| 1,300 sq.ft.	$849,900	Airbnb cash on cash: 0.75% Traditional cash on cash: 0.63% Airbnb Rental Income: $3577 Traditional Rental Income: $2696 Airbnb ROI: 0.75% Traditional ROI: 0.63%
7400 SUN ISLAND DRIVE S #407 SOUTH PASADENA, FL Get ready to experience the perks of St. Pete Beach living without the hassle in this Bay ...	1 beds \| 2 baths \| 1,035 sq.ft.	$240,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 0.48% Airbnb Rental Income: $2431 Traditional Rental Income: $1759 Airbnb ROI: 0.82% Traditional ROI: 0.48%
7979 SAILBOAT KEY BOULEVARD S #202 SOUTH PASADENA, FL Updated Waterfront Condo in Harbourside ~~~LOW HOA's!~~~ Resort-Style Island Living with ...	2 beds \| 2 baths \| 1,145 sq.ft.	$625,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 0.42% Airbnb Rental Income: $3577 Traditional Rental Income: $2280 Airbnb ROI: 1.3% Traditional ROI: 0.42%
7400 SUN ISLAND DRIVE S #603 SOUTH PASADENA, FL Florida resort style living at its best! Your spacious 2 bedroom, 2 full bathroom home has...	2 beds \| 2 baths \| 1,230 sq.ft.	$319,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 3.7% Airbnb Rental Income: $3577 Traditional Rental Income: $2732 Airbnb ROI: 3.9% Traditional ROI: 3.7%
7300 SUN ISLAND DRIVE S #1602 SOUTH PASADENA, FL One or more photo(s) has been virtually staged. *Price Improvement - Motivated Seller*...	1 beds \| 2 baths \| 1,120 sq.ft.	$299,900	Airbnb cash on cash: 2.83% Traditional cash on cash: 4.75% Airbnb Rental Income: $2431 Traditional Rental Income: $2379 Airbnb ROI: 2.83% Traditional ROI: 4.75%
7625 SUN ISLAND DRIVE S #304 SOUTH PASADENA, FL Waterfront Condo in Bay Island â Ideal for Boaters and Outdoor Enthusiasts Welcom...	1 beds \| 1 baths \| 855 sq.ft.	$249,900	Airbnb cash on cash: 0.56% Traditional cash on cash: 0.86% Airbnb Rental Income: $2431 Traditional Rental Income: $1908 Airbnb ROI: 0.56% Traditional ROI: 0.86%
1847 SHORE DRIVE S #316 SOUTH PASADENA, FL Charming Waterfront Condo Nestled in the heart of South Pasadena, this inviting 2-bedro...	2 beds \| 2 baths \| 1,274 sq.ft.	$299,500	Airbnb cash on cash: 7.77% Traditional cash on cash: 7.39% Airbnb Rental Income: $3577 Traditional Rental Income: $2685 Airbnb ROI: 7.77% Traditional ROI: 7.39%
7400 SUN ISLAND DRIVE S #104 SOUTH PASADENA, FL This is your opportunity to have a condo in Bay Island's Ambassador building with a pool, ...	2 beds \| 2 baths \| 1,230 sq.ft.	$399,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 2.85% Airbnb Rental Income: $3577 Traditional Rental Income: $2646 Airbnb ROI: 3.24% Traditional ROI: 2.85%
7892 SAILBOAT KEY BOULEVARD S #307 SOUTH PASADENA, FL Welcome to Island Place at Harbourside, 7892 building 4. The unit faces west and has a pri...	2 beds \| 2 baths \| 1,145 sq.ft.	$699,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 0.1% Airbnb Rental Income: $3577 Traditional Rental Income: $2467 Airbnb ROI: 0.6% Traditional ROI: 0.1%
7645 SUN ISLAND DRIVE S #207 SOUTH PASADENA, FL FULLY FURNISHED, TURNKEY CONDO ON THE WATER located in the popular gated, active 55+ commu...	1 beds \| 1 baths \| 600 sq.ft.	$160,000	Airbnb cash on cash: 5.63% Traditional cash on cash: 4.47% Airbnb Rental Income: $2431 Traditional Rental Income: $1661 Airbnb ROI: 5.63% Traditional ROI: 4.47%
7872 SAILBOAT KEY BOULEVARD S #306 SOUTH PASADENA, FL This end unit is light and bright and has beautiful views of Boca Ciega Bay and intracoast...	2 beds \| 2 baths \| 1,300 sq.ft.	$775,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 0.03% Airbnb Rental Income: $3577 Traditional Rental Income: $2716 Airbnb ROI: 0.14% Traditional ROI: 0.03%
7300 SUN ISLAND DRIVE S #706 SOUTH PASADENA, FL One or more photo(s) has been virtually staged. Welcome to refined coastal living in the h...	2 beds \| 2 baths \| 1,375 sq.ft.	$549,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 2.92% Airbnb Rental Income: $3577 Traditional Rental Income: $2845 Airbnb ROI: 2.82% Traditional ROI: 2.92%
1859 SHORE DRIVE S #202 SOUTH PASADENA, FL PRICE REDUCED. FULLY FURNISHED (OPTIONAL) WATERFRONT CONDO! REMODELED AND NESTLED ON BOCA ...	1 beds \| 1 baths \| 670 sq.ft.	$195,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 4.13% Airbnb Rental Income: $2431 Traditional Rental Income: $1715 Airbnb ROI: 4.79% Traditional ROI: 4.13%
7922 SAILBOAT KEY BOULEVARD S #608 SOUTH PASADENA, FL Welcome to Beach living at its best in this amazing 6th floor end unit Penthouse located i...	2 beds \| 2 baths \| 1,300 sq.ft.	$799,900	Airbnb cash on cash: -0.56% Traditional cash on cash: -0.42% Airbnb Rental Income: $3577 Traditional Rental Income: $2895 Airbnb ROI: -0.56% Traditional ROI: -0.42%
7050 SUNSET DRIVE S #415 SOUTH PASADENA, FL Incredible Waterviews ..... Endless Sunsets .... ! Open floor plan with recent updates, ma...	1 beds \| 2 baths \| 850 sq.ft.	$295,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 5.45% Airbnb Rental Income: $2431 Traditional Rental Income: $2074 Airbnb ROI: 4.59% Traditional ROI: 5.45%
7903 SAILBOAT KEY BOULEVARD S #401 SOUTH PASADENA, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Be...	2 beds \| 2 baths \| 1,445 sq.ft.	$449,000	Airbnb cash on cash: 4.26% Traditional cash on cash: 4.48% Airbnb Rental Income: $3577 Traditional Rental Income: $2886 Airbnb ROI: 4.26% Traditional ROI: 4.48%
1425 COREY WAY S SOUTH PASADENA, FL LOCATION, LOCATION, LOCATION!!! The first three rules in buying Real Estate. This Home sit...	2 beds \| 2 baths \| 1,247 sq.ft.	$975,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 1.17% Airbnb Rental Income: $3577 Traditional Rental Income: $2517 Airbnb ROI: 1.48% Traditional ROI: 1.17%
7910 SUN ISLAND DRIVE S #301 SOUTH PASADENA, FL Big Price Reduction! Great Opportunity for Discerning Buyer! Beautiful two-bedroom, two-ba...	2 beds \| 2 baths \| 1,170 sq.ft.	$450,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 0.8% Airbnb Rental Income: $3577 Traditional Rental Income: $2774 Airbnb ROI: 0.85% Traditional ROI: 0.8%
1868 SHORE DRIVE S #410 SOUTH PASADENA, FL Water Views ... EVERY Window .... Awesome Sunsets ....! Welcome to this 2 Bed 2 FULL Bath...	2 beds \| 2 baths \| 1,100 sq.ft.	$299,000	Airbnb cash on cash: 7.42% Traditional cash on cash: 5.46% Airbnb Rental Income: $3577 Traditional Rental Income: $2239 Airbnb ROI: 7.42% Traditional ROI: 5.46%
7600 SUN ISLAND DRIVE S #804 SOUTH PASADENA, FL Open the door to luxury living in this 2535 sq ft penthouse condo located at 7600 Sun Isla...	3 beds \| 4 baths \| 2,535 sq.ft.	$875,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 0.6% Airbnb Rental Income: $5039 Traditional Rental Income: $4156 Airbnb ROI: 0.43% Traditional ROI: 0.6%
7465 BAY ISLAND DRIVE S #213 SOUTH PASADENA, FL Short Sale. Lovely 2 bedroom waterfront condo at a newly improved price, you won't find a ...	2 beds \| 2 baths \| 1,050 sq.ft.	$194,000	Airbnb cash on cash: 8.39% Traditional cash on cash: 3.11% Airbnb Rental Income: $3577 Traditional Rental Income: $1819 Airbnb ROI: 8.39% Traditional ROI: 3.11%
1750 HARBOR PLACE S #103 SOUTH PASADENA, FL Experience the charm of coastal living in this delightful 1-bedroom, 1.5-bathroom condo si...	1 beds \| 2 baths \| 920 sq.ft.	$215,000	Airbnb cash on cash: 7.27% Traditional cash on cash: 8.32% Airbnb Rental Income: $2431 Traditional Rental Income: $2051 Airbnb ROI: 7.27% Traditional ROI: 8.32%
7037 SUNSET DRIVE S #205 SOUTH PASADENA, FL MOTIVATED SELLER, seller is paying special assessment at closing!!! Location Location and ...	2 beds \| 2 baths \| 1,390 sq.ft.	$329,900	Airbnb cash on cash: 3.48% Traditional cash on cash: 1.72% Airbnb Rental Income: $3577 Traditional Rental Income: $2248 Airbnb ROI: 3.48% Traditional ROI: 1.72%
7176 S SHORE DRIVE SOUTH PASADENA, FL Under Construction. This stunning 5-bedroom, 5 full & 2 half-bathroom estate located in th...	5 beds \| 7 baths \| 4,434 sq.ft.	$3,495,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 1.41% Airbnb Rental Income: $7736 Traditional Rental Income: $8745 Airbnb ROI: 0.64% Traditional ROI: 1.41%
6925-a AVENUE DES PALAIS #1A SOUTH PASADENA, FL Very nice Condo complex located in the heart of South Pasadena. This is a bright and spaci...	1 beds \| 1 baths \| 720 sq.ft.	$150,000	Airbnb cash on cash: 9.42% Traditional cash on cash: 7.71% Airbnb Rental Income: $2431 Traditional Rental Income: $1592 Airbnb ROI: 9.42% Traditional ROI: 7.71%
1324 PASADENA AVENUE S #501 SOUTH PASADENA, FL Under contract-accepting backup offers. Fully Renovated Corner Unit with Boca Ciega Bay Vi...	2 beds \| 2 baths \| 1,170 sq.ft.	$400,000	Airbnb cash on cash: 5.84% Traditional cash on cash: 5.4% Airbnb Rental Income: $3577 Traditional Rental Income: $2627 Airbnb ROI: 5.84% Traditional ROI: 5.4%
1847 SHORE DRIVE S #509 SOUTH PASADENA, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Hu...	1 beds \| 1 baths \| 1,068 sq.ft.	$189,999	Airbnb cash on cash: 4.24% Traditional cash on cash: 3.92% Airbnb Rental Income: $2431 Traditional Rental Income: $1778 Airbnb ROI: 4.24% Traditional ROI: 3.92%
7400 SUN ISLAND DRIVE S #802 SOUTH PASADENA, FL Welcome to this PENTHOUSE, CORNER UNIT, a stunning 3 BEDROOM, 3.5 BATH residence in the hi...	3 beds \| 4 baths \| 2,435 sq.ft.	$640,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 2.29% Airbnb Rental Income: $5039 Traditional Rental Income: $5012 Airbnb ROI: 0.62% Traditional ROI: 2.29%

Real Estate investment in South-pasadena, FL

There are 77 properties for sale in the city of South Pasadena . The median list price in South Pasadena is $312,000 and the average price per square foot is $255. In September 2025, the average monthly cash on cash return in South Pasadena is 4.00%. The average monthly rental income in South Pasadena is $2,384.

South-pasadena, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 77 investment properties available for sale in South-pasadena.

In 2025, the best neighborhood to buy investment property is SOUTH PASADENA.

The ROI for Short-Term is higher than the Long-Term in South-pasadena with average rental income of $3,577.

Your search for investment property begins and ends here

Investment Property for Sale in South Pasadena, FL

7700 SUN ISLAND DRIVE S #105C

SOUTH PASADENA, FL

2 beds | 2 baths | 1,235 sq.ft.

$418,000

Airbnb cash on cash: 4.2%

Traditional cash on cash: 3.84%

Airbnb Rental Income: $3577

Traditional Rental Income: $2651

Airbnb ROI: 4.2%

Traditional ROI: 3.84%

7645 SUN ISLAND DRIVE S #304

SOUTH PASADENA, FL

1 beds | 1 baths | 600 sq.ft.

$165,000

Airbnb cash on cash: 7.7%

Traditional cash on cash: 7.56%

Airbnb Rental Income: $2431

Traditional Rental Income: $1815

Airbnb ROI: 7.7%

Traditional ROI: 7.56%

7930 SUN ISLAND DRIVE S #305

SOUTH PASADENA, FL

1 beds | 2 baths | 940 sq.ft.

$247,900

Airbnb cash on cash: 3.61%

Traditional cash on cash: 4.86%

Airbnb Rental Income: $2431

Traditional Rental Income: $2130

Airbnb ROI: 3.61%

Traditional ROI: 4.86%

7902 SAILBOAT KEY BOULEVARD S #206

SOUTH PASADENA, FL

2 beds | 2 baths | 1,145 sq.ft.

$625,000

Airbnb cash on cash: 1.42%

Traditional cash on cash: 0.95%

Airbnb Rental Income: $3577

Traditional Rental Income: $2514

Airbnb ROI: 1.42%

Traditional ROI: 0.95%

1898 SHORE DRIVE S #311

SOUTH PASADENA, FL

2 beds | 2 baths | 1,260 sq.ft.

$267,500

Airbnb cash on cash: 4.76%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $3577

Traditional Rental Income: $2714

Airbnb ROI: 4.76%

Traditional ROI: 4.46%

1893 SHORE DRIVE S #208

SOUTH PASADENA, FL

2 beds | 1 baths | 840 sq.ft.

$230,000

Airbnb cash on cash: 8.21%

Traditional cash on cash: 4.25%

Airbnb Rental Income: $3577

Traditional Rental Income: $1931

Airbnb ROI: 8.21%

Traditional ROI: 4.25%

7600 SUN ISLAND DRIVE S #107

SOUTH PASADENA, FL

1 beds | 2 baths | 925 sq.ft.

$239,999

Airbnb cash on cash: 5.49%

Traditional cash on cash: 5.56%

Airbnb Rental Income: $2431

Traditional Rental Income: $1852

Airbnb ROI: 5.49%

Traditional ROI: 5.56%

7405 BAY ISLAND DRIVE S #220

SOUTH PASADENA, FL

2 beds | 2 baths | 1,110 sq.ft.

$255,000

Airbnb cash on cash: 3.04%

Traditional cash on cash: 1.69%

Airbnb Rental Income: $3577

Traditional Rental Income: $2467

Airbnb ROI: 3.04%