Real Estate Investment Properties for Sale in Summerland Key, FL

Looking for investment property in Summerland Key, FL with high ROI ?

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
701 Spanish Main Dr #536 Summerland Key, FL Welcome to your slice of the Florida Keys lifestyle! This charming beach-themed retreat is...	2 beds \| 1 baths \| 726 sq.ft.	$350,000	Airbnb cash on cash: 4.92% Traditional cash on cash: 4.99% Airbnb Rental Income: $3768 Traditional Rental Income: $2971 Airbnb ROI: 4.92% Traditional ROI: 4.99%
24840 Park Drive Summerland Key, FL Hard to find a home in a Park like setting with a boat ramp right out the back door! 3 bed...	3 beds \| 2 baths \| 1,565 sq.ft.	$950,000	Airbnb cash on cash: -1.54% Traditional cash on cash: 3.32% Airbnb Rental Income: $364 Traditional Rental Income: $4413 Airbnb ROI: -1.54% Traditional ROI: 3.32%
23950 Overseas Highway Summerland Key, FL Welcome to Pink Sands, a Glenn Gray-designed waterfront retreat where the vibrant colors a...	5 beds \| 4 baths \| 3,886 sq.ft.	$2,999,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.91% Airbnb Rental Income: $null Traditional Rental Income: $6030 Airbnb ROI: N/A Traditional ROI: 0.91%
Melody Summerland Key, FL An unparalleled opportunity to own your own private island in the Florida Keys. Melody Key...	3 beds \| 4 baths \| 2,851 sq.ft.	$7,000,000	Airbnb cash on cash: -1.27% Traditional cash on cash: -0.01% Airbnb Rental Income: $364 Traditional Rental Income: $8258 Airbnb ROI: -1.27% Traditional ROI: -0.01%
24347 W Caribbean Drive Summerland Key, FL Welcome to Summerland Key Cove! This beautifully home is perfectly situated on a deep-wate...	3 beds \| 2 baths \| 1,232 sq.ft.	$1,199,000	Airbnb cash on cash: -1.67% Traditional cash on cash: 1.94% Airbnb Rental Income: $364 Traditional Rental Income: $4135 Airbnb ROI: -1.67% Traditional ROI: 1.94%
96 John Street Summerland Key, FL Well-maintained 3-bedroom, 2-bath home offering 1,120 square feet of comfortable living sp...	3 beds \| 2 baths \| 1,120 sq.ft.	$535,000	Airbnb cash on cash: -1.71% Traditional cash on cash: 3.27% Airbnb Rental Income: $364 Traditional Rental Income: $2607 Airbnb ROI: -1.71% Traditional ROI: 3.27%
25361 1st Street Summerland Key, FL Experience the pinnacle of Florida Keys waterfront living in this exceptional 3-bedroom, 3...	3 beds \| 3 baths \| 2,535 sq.ft.	$3,500,000	Airbnb cash on cash: -1.41% Traditional cash on cash: 0.15% Airbnb Rental Income: $364 Traditional Rental Income: $5161 Airbnb ROI: -1.41% Traditional ROI: 0.15%
860 Lagoon Drive Summerland Key, FL This stately concrete home has all the best of everything on one of the best boating areas...	3 beds \| 3 baths \| 1,797 sq.ft.	$1,950,000	Airbnb cash on cash: -1.58% Traditional cash on cash: 1.34% Airbnb Rental Income: $364 Traditional Rental Income: $5397 Airbnb ROI: -1.58% Traditional ROI: 1.34%
23940 Overseas Highway Summerland Key, FL Bring your water toys & experience island living in this newly built waterfront home in Su...	3 beds \| 2 baths \| 1,242 sq.ft.	$899,000	Airbnb cash on cash: -1.74% Traditional cash on cash: 1.81% Airbnb Rental Income: $364 Traditional Rental Income: $3079 Airbnb ROI: -1.74% Traditional ROI: 1.81%
361 Avenue D Summerland Key, FL Beach House Paradise in Summerland Key. Nestled in one of the Lower Keys' most desirable o...	2 beds \| 3 baths \| 1,819 sq.ft.	$3,100,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 0% Airbnb Rental Income: $3768 Traditional Rental Income: $3756 Airbnb ROI: -0.28% Traditional ROI: 0%
24923 Park Drive Summerland Key, FL Tropical Waterfront Living in the Florida Keys! Welcome to 24923 Park Drive in beautiful S...	2 beds \| 1 baths \| 902 sq.ft.	$950,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 2.5% Airbnb Rental Income: $3768 Traditional Rental Income: $3720 Airbnb ROI: 1.63% Traditional ROI: 2.5%
701 Spanish Main Drive #265 Summerland Key, FL This Truly Spectacular Oceanfront Property offers the ultimate waterfront lifestyle and is...	2 beds \| 2 baths \| 816 sq.ft.	$879,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 1.47% Airbnb Rental Income: $3768 Traditional Rental Income: $3376 Airbnb ROI: 0.95% Traditional ROI: 1.47%
22865 Redfish Lane Summerland Key, FL The Best Boating Access in the Lower Keys, hands down!!! The 'Island Life' awaits you in t...	3 beds \| 2 baths \| 1,667 sq.ft.	$1,575,000	Airbnb cash on cash: -1.22% Traditional cash on cash: 2.12% Airbnb Rental Income: $364 Traditional Rental Income: $4999 Airbnb ROI: -1.22% Traditional ROI: 2.12%
701 Spanish Main Drive #495 Summerland Key, FL Spectacular peekaboo open water views abound with this updated 2 bed/2 bath canal front ho...	2 beds \| 2 baths \| 864 sq.ft.	$639,000	Airbnb cash on cash: 2% Traditional cash on cash: 0.85% Airbnb Rental Income: $3768 Traditional Rental Income: $2264 Airbnb ROI: 2% Traditional ROI: 0.85%
701 Spanish Main Drive #639 Summerland Key, FL Enjoy the Salty Air from this Key Lime Gem in the Florida Keys! This furnished, 2 bedroom,...	2 beds \| 1 baths \| 748 sq.ft.	$425,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 0.81% Airbnb Rental Income: $3768 Traditional Rental Income: $1737 Airbnb ROI: 3.86% Traditional ROI: 0.81%
94 Sacarma Drive Summerland Key, FL Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys, with SELLER...	5 beds \| 3 baths \| 1,978 sq.ft.	$2,060,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.12% Airbnb Rental Income: $null Traditional Rental Income: $2399 Airbnb ROI: N/A Traditional ROI: -0.12%
23057 Bluegill Lane Summerland Key, FL Look no further--this exceptional property truly has it all. This beautifully maintained C...	3 beds \| 2 baths \| 1,270 sq.ft.	$1,349,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 1.24% Airbnb Rental Income: $364 Traditional Rental Income: $3188 Airbnb ROI: -1.21% Traditional ROI: 1.24%
22970 Gasparilla Lane Summerland Key, FL OPEN WATER VIEWS - BRAND NEW CUSTOM WATERFRONT HOME - DOUBLE LOT & MOVE IN READY. This ELE...	3 beds \| 2 baths \| 2,050 sq.ft.	$1,799,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 1.7% Airbnb Rental Income: $364 Traditional Rental Income: $4773 Airbnb ROI: -1.09% Traditional ROI: 1.7%
22832 John Silver Lane Summerland Key, FL CUDJOE KEY CANALFRONT SPECIAL - LOWEST PRICED HOME IN CUTTHROAT HARBOR ESTATES. ASSUMABLE ...	3 beds \| 3 baths \| 1,800 sq.ft.	$849,000	Airbnb cash on cash: -1.78% Traditional cash on cash: 3.92% Airbnb Rental Income: $364 Traditional Rental Income: $4625 Airbnb ROI: -1.78% Traditional ROI: 3.92%

Real Estate investment in Summerland-key, FL

There are 21 properties for sale in the city of Summerland Key . The median list price in Summerland Key is $950,000 and the average price per square foot is $638. In September 2026, the average monthly cash on cash return in Summerland Key is 1.00%. The average monthly rental income in Summerland Key is $2,290.

Summerland-key, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 21 investment properties available for sale in Summerland-key.

In 2026, the best neighborhood to buy investment property is Summerland Key.

The ROI for Long-Term is higher than the Short-Term in Summerland-key with average rental income of $2,290.

Your search for investment property begins and ends here

Investment Property for Sale in Summerland Key, FL

701 Spanish Main Dr #536

Summerland Key, FL

2 beds | 1 baths | 726 sq.ft.

$350,000

Airbnb cash on cash: 4.92%

Traditional cash on cash: 4.99%

Airbnb Rental Income: $3768

Traditional Rental Income: $2971

Airbnb ROI: 4.92%

Traditional ROI: 4.99%

24840 Park Drive

Summerland Key, FL

3 beds | 2 baths | 1,565 sq.ft.

$950,000

Airbnb cash on cash: -1.54%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $364

Traditional Rental Income: $4413

Airbnb ROI: -1.54%

Traditional ROI: 3.32%

23950 Overseas Highway

Summerland Key, FL

5 beds | 4 baths | 3,886 sq.ft.

$2,999,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.91%

Airbnb Rental Income: $null

Traditional Rental Income: $6030

Airbnb ROI: N/A

Traditional ROI: 0.91%

Melody

Summerland Key, FL

3 beds | 4 baths | 2,851 sq.ft.

$7,000,000

Airbnb cash on cash: -1.27%

Traditional cash on cash: -0.01%

Airbnb Rental Income: $364

Traditional Rental Income: $8258

Airbnb ROI: -1.27%

Traditional ROI: -0.01%

24347 W Caribbean Drive

Summerland Key, FL

3 beds | 2 baths | 1,232 sq.ft.

$1,199,000

Airbnb cash on cash: -1.67%

Traditional cash on cash: 1.94%

Airbnb Rental Income: $364

Traditional Rental Income: $4135

Airbnb ROI: -1.67%

Traditional ROI: 1.94%

96 John Street

Summerland Key, FL

3 beds | 2 baths | 1,120 sq.ft.

$535,000

Airbnb cash on cash: -1.71%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $364

Traditional Rental Income: $2607

Airbnb ROI: -1.71%

Traditional ROI: 3.27%

25361 1st Street

Summerland Key, FL

3 beds | 3 baths | 2,535 sq.ft.

$3,500,000

Airbnb cash on cash: -1.41%

Traditional cash on cash: 0.15%

Airbnb Rental Income: $364

Traditional Rental Income: $5161

Airbnb ROI: -1.41%

Traditional ROI: 0.15%

860 Lagoon Drive

Summerland Key, FL

3 beds | 3 baths | 1,797 sq.ft.

$1,950,000

Airbnb cash on cash: -1.58%

Traditional cash on cash: 1.34%

Airbnb Rental Income: $364

Traditional Rental Income: $5397

Airbnb ROI: -1.58%