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
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: 2.69% Traditional cash on cash: 3.32% Airbnb Rental Income: $4854 Traditional Rental Income: $4413 Airbnb ROI: 2.69% Traditional ROI: 3.32%
1331 Hudgins Drive Summerland Key, FL Construction Location Orientation. A Beautifully Appointed Canal Front Fortress All Concre...	2 beds \| 2 baths \| 1,060 sq.ft.	$1,119,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 2.36% Airbnb Rental Income: $5495 Traditional Rental Income: $3840 Airbnb ROI: 2.89% Traditional ROI: 2.36%
94 Sacarma Drive Summerland Key, FL Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys. Welcome to ...	5 beds \| 3 baths \| 1,978 sq.ft.	$2,089,000	Airbnb cash on cash: 5.33% Traditional cash on cash: -0.12% Airbnb Rental Income: $15807 Traditional Rental Income: $2399 Airbnb ROI: 5.33% Traditional ROI: -0.12%
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: -0.69% Traditional cash on cash: -0.01% Airbnb Rental Income: $4854 Traditional Rental Income: $8258 Airbnb ROI: -0.69% Traditional ROI: -0.01%
701 Spanish Main Drive #411 Summerland Key, FL Affordable waterfront Living in the Lower Keys! This waterfront 2-bedroom, 2-bath mobile h...	2 beds \| 2 baths \| 618 sq.ft.	$499,000	Airbnb cash on cash: 7.37% Traditional cash on cash: 2.58% Airbnb Rental Income: $5495 Traditional Rental Income: $2154 Airbnb ROI: 7.37% Traditional ROI: 2.58%
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: 2.71% Traditional cash on cash: 1.47% Airbnb Rental Income: $5495 Traditional Rental Income: $3376 Airbnb ROI: 2.71% 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: 1.33% Traditional cash on cash: 2.12% Airbnb Rental Income: $4854 Traditional Rental Income: $4999 Airbnb ROI: 1.33% Traditional ROI: 2.12%
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: 0.49% Traditional cash on cash: 1.34% Airbnb Rental Income: $4854 Traditional Rental Income: $5397 Airbnb ROI: 0.49% Traditional ROI: 1.34%
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: 5.38% Traditional cash on cash: 1.81% Airbnb Rental Income: $5495 Traditional Rental Income: $2264 Airbnb ROI: 5.38% Traditional ROI: 1.81%
715 E Caribbean Drive Summerland Key, FL Experience the ultimate Florida Keys lifestyle at 715 Caribbean Drive East in Summerland K...	3 beds \| 2 baths \| 1,544 sq.ft.	$1,150,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 2.62% Airbnb Rental Income: $4854 Traditional Rental Income: $4612 Airbnb ROI: 1.91% Traditional ROI: 2.62%
24225 W Caribbean Drive Summerland Key, FL Sailor's Dream -- waterfront living at its best! Beautifully maintained tropical home with...	3 beds \| 2 baths \| 1,056 sq.ft.	$999,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 1.37% Airbnb Rental Income: $4854 Traditional Rental Income: $2782 Airbnb ROI: 2.52% Traditional ROI: 1.37%
701 Spanish Main Drive lot: 49 Summerland Key, FL ******Nightly Licensed Transient Rental!!!****** This amazing, two bedroom / one bathr...	2 beds \| 1 baths \| 806 sq.ft.	$887,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 0.82% Airbnb Rental Income: $5495 Traditional Rental Income: $2241 Airbnb ROI: 3.42% Traditional ROI: 0.82%
23941 Henry Street Summerland Key, FL Beach House Oceanfront retreat with protected dockage & direct access to both the Ocean & ...	3 beds \| 2 baths \| 2,232 sq.ft.	$2,775,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 0.86% Airbnb Rental Income: $4854 Traditional Rental Income: $5517 Airbnb ROI: 0.21% Traditional ROI: 0.86%
701 Spanish Main Drive #51 Summerland Key, FL Panoramic Ocean Views W/ Transient Rental License! This beautifully updated and well-maint...	2 beds \| 2 baths \| 888 sq.ft.	$899,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 0.81% Airbnb Rental Income: $5495 Traditional Rental Income: $2211 Airbnb ROI: 3.41% Traditional ROI: 0.81%
290 46th Street Summerland Key, FL Pilots, this is a great opportunity to build your dream home with access to Summerland Key...	2 beds \| 1 baths \| 1,184 sq.ft.	$425,000	Airbnb cash on cash: 9.59% Traditional cash on cash: 4.66% Airbnb Rental Income: $5495 Traditional Rental Income: $2430 Airbnb ROI: 9.59% Traditional ROI: 4.66%
701 Spanish Main Drive #444 Summerland Key, FL Affordable piece of paradise! Fully furnished, move in ready, open concept, bright and air...	2 beds \| 2 baths \| 861 sq.ft.	$575,000	Airbnb cash on cash: 6.03% Traditional cash on cash: 1.99% Airbnb Rental Income: $5495 Traditional Rental Income: $2222 Airbnb ROI: 6.03% Traditional ROI: 1.99%
1163 De Lussan Lane Summerland Key, FL Are you dreaming of your own personal paradise? Look no further than this stunning propert...	2 beds \| 2 baths \| 1,344 sq.ft.	$1,650,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 1.74% Airbnb Rental Income: $5495 Traditional Rental Income: $4337 Airbnb ROI: 1.77% Traditional ROI: 1.74%
701 Spanish Main Drive #140 Summerland Key, FL This charming and meticulously maintained property is perfect for anyone looking to start ...	2 beds \| 1 baths \| 833 sq.ft.	$399,900	Airbnb cash on cash: 9.89% Traditional cash on cash: 6.53% Airbnb Rental Income: $5495 Traditional Rental Income: $3134 Airbnb ROI: 9.89% Traditional ROI: 6.53%
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.	$375,000	Airbnb cash on cash: 8.62% Traditional cash on cash: 4.59% Airbnb Rental Income: $5495 Traditional Rental Income: $2971 Airbnb ROI: 8.62% Traditional ROI: 4.59%
701 Spanish Main Drive #97 Summerland Key, FL Luxurious Waterfront Living - Welcome to your perfect coastal oasis in the sought-after co...	2 beds \| 2 baths \| 640 sq.ft.	$799,000	Airbnb cash on cash: 4.11% Traditional cash on cash: 1.11% Airbnb Rental Income: $5495 Traditional Rental Income: $2154 Airbnb ROI: 4.11% Traditional ROI: 1.11%

Real Estate investment in Summerland-key, FL

There are 25 properties for sale in the city of Summerland Key . The median list price in Summerland Key is $937,500 and the average price per square foot is $721. In June 2026, the average monthly cash on cash return in Summerland Key is 1.00%. The average monthly rental income in Summerland Key is $2,410.

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

There are 25 investment properties available for sale in Summerland-key.

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

The ROI for Short-Term is higher than the Long-Term in Summerland-key with average rental income of $4,854.

Your search for investment property begins and ends here

Investment Property for Sale in Summerland Key, FL

24840 Park Drive

Summerland Key, FL

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

$950,000

Airbnb cash on cash: 2.69%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $4854

Traditional Rental Income: $4413

Airbnb ROI: 2.69%

Traditional ROI: 3.32%

1331 Hudgins Drive

Summerland Key, FL

2 beds | 2 baths | 1,060 sq.ft.

$1,119,000

Airbnb cash on cash: 2.89%

Traditional cash on cash: 2.36%

Airbnb Rental Income: $5495

Traditional Rental Income: $3840

Airbnb ROI: 2.89%

Traditional ROI: 2.36%

94 Sacarma Drive

Summerland Key, FL

5 beds | 3 baths | 1,978 sq.ft.

$2,089,000

Airbnb cash on cash: 5.33%

Traditional cash on cash: -0.12%

Airbnb Rental Income: $15807

Traditional Rental Income: $2399

Airbnb ROI: 5.33%

Traditional ROI: -0.12%

Melody

Summerland Key, FL

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

$7,000,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: -0.01%

Airbnb Rental Income: $4854

Traditional Rental Income: $8258

Airbnb ROI: -0.69%

Traditional ROI: -0.01%

701 Spanish Main Drive #411

Summerland Key, FL

2 beds | 2 baths | 618 sq.ft.

$499,000

Airbnb cash on cash: 7.37%

Traditional cash on cash: 2.58%

Airbnb Rental Income: $5495

Traditional Rental Income: $2154

Airbnb ROI: 7.37%

Traditional ROI: 2.58%

701 Spanish Main Drive #265

Summerland Key, FL

2 beds | 2 baths | 816 sq.ft.

$879,000

Airbnb cash on cash: 2.71%

Traditional cash on cash: 1.47%

Airbnb Rental Income: $5495

Traditional Rental Income: $3376

Airbnb ROI: 2.71%

Traditional ROI: 1.47%

22865 Redfish Lane

Summerland Key, FL

3 beds | 2 baths | 1,667 sq.ft.

$1,575,000

Airbnb cash on cash: 1.33%

Traditional cash on cash: 2.12%

Airbnb Rental Income: $4854

Traditional Rental Income: $4999

Airbnb ROI: 1.33%

Traditional ROI: 2.12%

860 Lagoon Drive

Summerland Key, FL

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

$1,950,000

Airbnb cash on cash: 0.49%

Traditional cash on cash: 1.34%

Airbnb Rental Income: $4854

Traditional Rental Income: $5397

Airbnb ROI: 0.49%