Airbnb Properties for Sale in Summerland Key, FL

Looking for a vacation rental investment in Summerland Key, FL with high ROI ?

Explore a range of newly added short-term rental homes in Summerland Key, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Summerland Key, FL

Q: How to get Summerland-key, FL Airbnb data?

Airbnb data on vacation rentals in Summerland-key, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Summerland-key, FL market insights, guest information and booking details, seasonality trends and historical Summerland-key, FL Airbnb performance data .

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
21855 & 21865 Spain Boulevard Summerland Key, FL Majestically positioned at the end of Spain Blvd, within the Prestigious Cudjoe Acres neig...	3 beds \| 2 baths \| 1,467 sq.ft.	$1,500,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 0.98% Airbnb Rental Income: $4854 Traditional Rental Income: $3225 Airbnb ROI: 1.43% Traditional ROI: 0.98%
701 Spanish Main Drive #UNIT 635 Summerland Key, FL Vacation Rental Property with Transient Rentals Allowed! Welcome to the epitome of comfort...	2 beds \| 2 baths \| 864 sq.ft.	$425,000	Airbnb cash on cash: 7.55% Traditional cash on cash: 2.45% Airbnb Rental Income: $5495 Traditional Rental Income: $2357 Airbnb ROI: 7.55% Traditional ROI: 2.45%
701 Spanish Main Drive #UNIT 51 Summerland Key, FL Panoramic Ocean Views W/ Transient Rental License! This beautifully updated and well-maint...	2 beds \| 2 baths \| 888 sq.ft.	$985,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 0.42% Airbnb Rental Income: $5495 Traditional Rental Income: $2560 Airbnb ROI: 2.42% Traditional ROI: 0.42%
701 Spanish Main Drive #UNIT 495 Summerland Key, FL Welcome to this completely remodeled, direct canal front cottage located at 701 Spanish Ma...	2 beds \| 2 baths \| 816 sq.ft.	$625,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 2.37% Airbnb Rental Income: $5495 Traditional Rental Income: $2586 Airbnb ROI: 5.46% Traditional ROI: 2.37%
701 Spanish Main Drive #UNIT 221 Summerland Key, FL Enjoy open water views and instant boating access from this transiently licensed, turn-key...	2 beds \| 2 baths \| 864 sq.ft.	$995,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 0.56% Airbnb Rental Income: $5495 Traditional Rental Income: $2635 Airbnb ROI: 2.46% Traditional ROI: 0.56%
701 Spanish Main Drive #UNIT 49 Summerland Key, FL ******Nightly Licensed Transient Rental!!!******This amazing, two bedroom / one bathro...	2 beds \| 1 baths \| 806 sq.ft.	$925,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 0.16% Airbnb Rental Income: $5495 Traditional Rental Income: $2305 Airbnb ROI: 2.58% Traditional ROI: 0.16%
701 Spanish Main Drive #UNIT 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.	$839,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 1.13% Airbnb Rental Income: $5495 Traditional Rental Income: $2394 Airbnb ROI: 3.69% Traditional ROI: 1.13%
701 Spanish Main Drive #UNIT 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: 5.73% Traditional cash on cash: 1.71% Airbnb Rental Income: $5495 Traditional Rental Income: $2232 Airbnb ROI: 5.73% Traditional ROI: 1.71%
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 be...	3 beds \| 2 baths \| 1,565 sq.ft.	$999,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 1.78% Airbnb Rental Income: $4854 Traditional Rental Income: $3180 Airbnb ROI: 2.51% Traditional ROI: 1.78%
1331 Hudgins Drive Summerland Key, FL Location, Location and Location Enter the Palm Tree Stained-glass Impact door to 24-inch T...	2 beds \| 2 baths \| 1,060 sq.ft.	$1,150,000	Airbnb cash on cash: 2.78% Traditional cash on cash: 1.21% Airbnb Rental Income: $5495 Traditional Rental Income: $2715 Airbnb ROI: 2.78% Traditional ROI: 1.21%
1147 Flagship Drive Summerland Key, FL Located on the highly desired Flagship Drive in Summerland Cove Isles, this stunning 3 bed...	3 beds \| 2 baths \| 2,058 sq.ft.	$2,650,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 0% Airbnb Rental Income: $4854 Traditional Rental Income: $3818 Airbnb ROI: 0.01% Traditional ROI: 0%
270 S Airport Drive Summerland Key, FL A rare aviation-and-waterfront opportunity in the private Summerland Key Airport community...	3 beds \| 3 baths \| 1,275 sq.ft.	$1,999,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 0.31% Airbnb Rental Income: $4854 Traditional Rental Income: $3236 Airbnb ROI: 0.64% Traditional ROI: 0.31%
195 W Shore Drive Summerland Key, FL Welcome to a truly unique aviation property in the heart of Summerland Key! Located at the...	3 beds \| 2 baths \| 1,500 sq.ft.	$925,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 1.92% Airbnb Rental Income: $4854 Traditional Rental Income: $3189 Airbnb ROI: 2.69% Traditional ROI: 1.92%
25368 2nd Street Summerland Key, FL Experience the perfect blend of character, durability, and Keys style at this quintessenti...	2 beds \| 2 baths \| 1,392 sq.ft.	$1,595,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 0.68% Airbnb Rental Income: $5495 Traditional Rental Income: $3468 Airbnb ROI: 1.3% Traditional ROI: 0.68%
466 W Shore Drive Summerland Key, FL Welcome to 466 W Shore Dr in prestigious Summerland Key. This 2 bedroom concrete home is s...	2 beds \| 2 baths \| 1,364 sq.ft.	$1,250,000	Airbnb cash on cash: 2.66% Traditional cash on cash: 1.73% Airbnb Rental Income: $5495 Traditional Rental Income: $3317 Airbnb ROI: 2.66% Traditional ROI: 1.73%
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: 0.23% Airbnb Rental Income: $4854 Traditional Rental Income: $3393 Airbnb ROI: 0.49% Traditional ROI: 0.23%
219 E Caribbean Drive Summerland Key, FL Waterfront Home in Summerland Key. Quick access to both Ocean & Gulf. Partial open water v...	2 beds \| 1 baths \| 960 sq.ft.	$799,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 1.56% Airbnb Rental Income: $5495 Traditional Rental Income: $2308 Airbnb ROI: 4.36% Traditional ROI: 1.56%
56 Colson Dr Summerland Key, FL Exceptional waterfront living awaits at 56 Colson Drive in Cudjoe Gardens on Cudjoe Key--a...	3 beds \| 2 baths \| 1,645 sq.ft.	$1,599,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 0.82% Airbnb Rental Income: $4854 Traditional Rental Income: $3694 Airbnb ROI: 0.93% Traditional ROI: 0.82%
21250 Conch Dr Summerland Key, FL Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe...	3 beds \| 2 baths \| 1,508 sq.ft.	$1,599,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 0.73% Airbnb Rental Income: $4854 Traditional Rental Income: $3577 Airbnb ROI: 0.92% Traditional ROI: 0.73%
153 Peg Leg Ln Summerland Key, FL Super quick ocean access and 60' of concrete dockage from this 3 Bedroom 2 Bath canal fron...	3 beds \| 2 baths \| 1,203 sq.ft.	$899,000	Airbnb cash on cash: 3% Traditional cash on cash: 1.99% Airbnb Rental Income: $4854 Traditional Rental Income: $3016 Airbnb ROI: 3% Traditional ROI: 1.99%
701 Spanish Main Dr #140 Summerland Key, FL This charming and meticulously maintained property is perfect for anyone looking to start ...	1 beds \| 1 baths \| 833 sq.ft.	$419,000	Airbnb cash on cash: 4.84% Traditional cash on cash: 3.16% Airbnb Rental Income: $3458 Traditional Rental Income: $2033 Airbnb ROI: 4.84% Traditional ROI: 3.16%
1163 De Lussan Ln 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.	$1,749,900	Airbnb cash on cash: 1.54% Traditional cash on cash: 0.86% Airbnb Rental Income: $5495 Traditional Rental Income: $3249 Airbnb ROI: 1.54% Traditional ROI: 0.86%
701 Spanish Main Dr #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: 0.4% Airbnb Rental Income: $5495 Traditional Rental Income: $2494 Airbnb ROI: 2.71% Traditional ROI: 0.4%

Vacation Rentals in Summerland Key

There are 34 vacation rental properties available for sale in the city of Summerland Key . The median list price of Airbnb properties available for sale in Summerland Key is $1,150,000 and the average price per square foot is $835. The cash on cash return on vacation rentals in Summerland Key is 3.00%. The average monthly short term rental income in Summerland Key is $4,854.

Summerland Key, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 34 Airbnb properties available for sale in Summerland Key.

In 2026, the best neighborhood to buy short term rental property is Summerland Key.

In February 2026, the average Airbnb occupancy rate in Summerland Key is 65%.

Airbnb data on vacation rentals in Summerland Key, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Summerland Key, FL market insights, guest information and booking details, seasonality trends and historical Summerland Key, FL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Summerland Key, FL

21855 & 21865 Spain Boulevard

Summerland Key, FL

3 beds | 2 baths | 1,467 sq.ft.

$1,500,000

Airbnb cash on cash: 1.43%

Traditional cash on cash: 0.98%

Airbnb Rental Income: $4854

Traditional Rental Income: $3225

Airbnb ROI: 1.43%

Traditional ROI: 0.98%

701 Spanish Main Drive #UNIT 635

Summerland Key, FL

2 beds | 2 baths | 864 sq.ft.

$425,000

Airbnb cash on cash: 7.55%

Traditional cash on cash: 2.45%

Airbnb Rental Income: $5495

Traditional Rental Income: $2357

Airbnb ROI: 7.55%

Traditional ROI: 2.45%

701 Spanish Main Drive #UNIT 51

Summerland Key, FL

2 beds | 2 baths | 888 sq.ft.

$985,000

Airbnb cash on cash: 2.42%

Traditional cash on cash: 0.42%

Airbnb Rental Income: $5495

Traditional Rental Income: $2560

Airbnb ROI: 2.42%

Traditional ROI: 0.42%

701 Spanish Main Drive #UNIT 495

Summerland Key, FL

2 beds | 2 baths | 816 sq.ft.

$625,000

Airbnb cash on cash: 5.46%

Traditional cash on cash: 2.37%

Airbnb Rental Income: $5495

Traditional Rental Income: $2586

Airbnb ROI: 5.46%

Traditional ROI: 2.37%

701 Spanish Main Drive #UNIT 221

Summerland Key, FL

2 beds | 2 baths | 864 sq.ft.

$995,000

Airbnb cash on cash: 2.46%

Traditional cash on cash: 0.56%

Airbnb Rental Income: $5495

Traditional Rental Income: $2635

Airbnb ROI: 2.46%

Traditional ROI: 0.56%

701 Spanish Main Drive #UNIT 49

Summerland Key, FL

2 beds | 1 baths | 806 sq.ft.

$925,000

Airbnb cash on cash: 2.58%

Traditional cash on cash: 0.16%

Airbnb Rental Income: $5495

Traditional Rental Income: $2305

Airbnb ROI: 2.58%

Traditional ROI: 0.16%

701 Spanish Main Drive #UNIT 97

Summerland Key, FL

2 beds | 2 baths | 640 sq.ft.

$839,000

Airbnb cash on cash: 3.69%

Traditional cash on cash: 1.13%

Airbnb Rental Income: $5495

Traditional Rental Income: $2394

Airbnb ROI: 3.69%

Traditional ROI: 1.13%

701 Spanish Main Drive #UNIT 444

Summerland Key, FL

2 beds | 2 baths | 861 sq.ft.

$575,000

Airbnb cash on cash: 5.73%

Traditional cash on cash: 1.71%

Airbnb Rental Income: $5495

Traditional Rental Income: $2232

Airbnb ROI: 5.73%