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
165 Cutlass Lane Summerland Key, FL Discover Your Dream Waterfront Home in the Florida Keys! This stunning canal-front residen...	4 beds \| 3 baths \| 2,448 sq.ft.	$1,175,000	Airbnb cash on cash: 9.29% Traditional cash on cash: 2.51% Airbnb Rental Income: $14473 Traditional Rental Income: $4464 Airbnb ROI: 9.29% Traditional ROI: 2.51%
701 Spanish Main Drive #UNIT 154 Summerland Key, FL Transient 1 Day Rentals Allowed! Welcome to your tropical paradise! This charming 2 bedroo...	2 beds \| 2 baths \| 836 sq.ft.	$549,900	Airbnb cash on cash: 5.45% Traditional cash on cash: 1.49% Airbnb Rental Income: $5495 Traditional Rental Income: $2359 Airbnb ROI: 5.45% Traditional ROI: 1.49%
554 W Shore Drive Summerland Key, FL Experience waterfront living at its finest at 554 W Shore Drive in Summerland Key. This el...	3 beds \| 2 baths \| 1,407 sq.ft.	$899,000	Airbnb cash on cash: 2.79% Traditional cash on cash: 2.07% Airbnb Rental Income: $4854 Traditional Rental Income: $3257 Airbnb ROI: 2.79% Traditional ROI: 2.07%
22464 La Fitte Drive Summerland Key, FL Cudjoe Key Canal Front Living -- Newly renovated home with covered carport, custom master ...	2 beds \| 2 baths \| 860 sq.ft.	$799,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 3.3% Airbnb Rental Income: $5495 Traditional Rental Income: $3842 Airbnb ROI: 4.04% Traditional ROI: 3.3%
22961 John Avery Lane Summerland Key, FL Boater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!Bring yo...	3 beds \| 3 baths \| 960 sq.ft.	$989,999	Airbnb cash on cash: 2.4% Traditional cash on cash: 0.81% Airbnb Rental Income: $4854 Traditional Rental Income: $2387 Airbnb ROI: 2.4% Traditional ROI: 0.81%
22815 Port Royal Lane Summerland Key, FL DIRECT OCEAN FRONT 323FT of Water Frontage- BOATERS PARADISE FOUND with room for 3 Boats o...	4 beds \| 5 baths \| 3,228 sq.ft.	$3,750,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 0.2% Airbnb Rental Income: $14473 Traditional Rental Income: $6465 Airbnb ROI: 1.75% Traditional ROI: 0.2%
22865 Redfish Lane Summerland Key, FL The 'Island Life' awaits you in this stunning well thought out custom designed canal front...	3 beds \| 2 baths \| 1,667 sq.ft.	$1,699,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 1.02% Airbnb Rental Income: $4854 Traditional Rental Income: $3610 Airbnb ROI: 1.18% Traditional ROI: 1.02%
4500 Filer Cove Road Summerland Key, FL Picture perfect Sunset Views over the open water at this 12-Acre waterfront compound locat...	4 beds \| 4 baths \| 4,315 sq.ft.	$5,999,000	Airbnb cash on cash: 0.98% Traditional cash on cash: -0.2% Airbnb Rental Income: $14473 Traditional Rental Income: $5317 Airbnb ROI: 0.98% Traditional ROI: -0.2%
76 W Shore Drive Summerland Key, FL Discover the ultimate boaters retreat in beautiful Summerland Key! This stilted canal-fron...	3 beds \| 2 baths \| 1,028 sq.ft.	$979,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 1.09% Airbnb Rental Income: $4854 Traditional Rental Income: $2502 Airbnb ROI: 2.57% Traditional ROI: 1.09%
701 Spanish Main Drive #UNIT 30 Summerland Key, FL Welcome to a stunning brand-new construction in the sought-after Venture Out community on ...	2 beds \| 2 baths \| 840 sq.ft.	$649,999	Airbnb cash on cash: 4.73% Traditional cash on cash: 1.08% Airbnb Rental Income: $5495 Traditional Rental Income: $2174 Airbnb ROI: 4.73% Traditional ROI: 1.08%
701 Spanish Main Drive #UNIT 444 Summerland Key, FL Affordable piece of paradise! Move in ready, open concept, bright and airy, and freshly pa...	2 beds \| 2 baths \| 861 sq.ft.	$625,000	Airbnb cash on cash: 5.29% Traditional cash on cash: 1.59% Airbnb Rental Income: $5495 Traditional Rental Income: $2232 Airbnb ROI: 5.29% Traditional ROI: 1.59%
1151 Ocean Drive Summerland Key, FL Trophy Oceanfront Estate in THE PRIME location on Ocean Dr Summerland Key - surrounded by ...	5 beds \| 6 baths \| 3,952 sq.ft.	$6,995,000	Airbnb cash on cash: 0.41% Traditional cash on cash: -0.38% Airbnb Rental Income: $15807 Traditional Rental Income: $7876 Airbnb ROI: 0.41% Traditional ROI: -0.38%
22837 CALICO JACK Circle Summerland Key, FL SELLER SAYS BRING OFFERS! Open Water Views & Sunset Skies with great boating access descri...	2 beds \| 2 baths \| 1,008 sq.ft.	$1,135,000	Airbnb cash on cash: 2.19% Traditional cash on cash: 0.61% Airbnb Rental Income: $5495 Traditional Rental Income: $2724 Airbnb ROI: 2.19% Traditional ROI: 0.61%
951 LAGOON Drive Summerland Key, FL Need space for family and friends? Come see this 4 bedroom Summerland Cove Isles beautiful...	4 beds \| 3 baths \| 1,704 sq.ft.	$1,599,900	Airbnb cash on cash: 6.78% Traditional cash on cash: 1.39% Airbnb Rental Income: $14473 Traditional Rental Income: $3861 Airbnb ROI: 6.78% Traditional ROI: 1.39%
22852 John Silver Lane Summerland Key, FL Paradise Awaits on Cudjoe KeyDiscover 22852 John Silver Lane, a rare A-frame waterfront re...	2 beds \| 2 baths \| 1,620 sq.ft.	$949,000	Airbnb cash on cash: 3.52% Traditional cash on cash: 2.67% Airbnb Rental Income: $5495 Traditional Rental Income: $3641 Airbnb ROI: 3.52% Traditional ROI: 2.67%
701 Spanish Main Drive #UNIT 49 Summerland Key, FL Nightly Licensed Transient Rental!!!This amazing, two bedroom / one bathroom, open water f...	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 369, 370 Drive #UNIT 369 Summerland Key, FL Boater's Paradise with Expansive Waterfront Views!Rare opportunity to own one of only thre...	2 beds \| 2 baths \| 840 sq.ft.	$999,965	Airbnb cash on cash: 2.02% Traditional cash on cash: -0.11% Airbnb Rental Income: $5495 Traditional Rental Income: $2409 Airbnb ROI: 2.02% Traditional ROI: -0.11%
701 Spanish Main Drive #UNIT 635 Summerland Key, FL Transient Rental License! Welcome to the epitome of comfort and convenience in this Palm H...	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 234 Summerland Key, FL Transient Rental License. Beautiful updated 2bed/2bath, fully furnished, canal front home ...	2 beds \| 2 baths \| 604 sq.ft.	$499,000	Airbnb cash on cash: 6.3% Traditional cash on cash: 1.68% Airbnb Rental Income: $5495 Traditional Rental Income: $2236 Airbnb ROI: 6.3% Traditional ROI: 1.68%
701 Spanish Main Drive #UNIT 29 Summerland Key, FL Welcome to a stunning brand-new construction in the sought-after Venture Out community on ...	2 beds \| 2 baths \| 840 sq.ft.	$659,999	Airbnb cash on cash: 4.65% Traditional cash on cash: 1.46% Airbnb Rental Income: $5495 Traditional Rental Income: $2427 Airbnb ROI: 4.65% Traditional ROI: 1.46%
701 Spanish Main Drive #UNIT 51 Summerland Key, FL Panoramic Ocean Views With Transient Rental License! This beautifully updated and well-mai...	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%
715 E Caribbean Dr E Summerland Key, FL Take advantage of a rare lease-to-own opportunity! Experience the ultimate boaterâs lif...	3 beds \| 2 baths \| 1,544 sq.ft.	$1,150,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 1.72% Airbnb Rental Income: $4854 Traditional Rental Income: $3613 Airbnb ROI: 1.95% Traditional ROI: 1.72%
142 Peg Leg Ln Summerland Key, FL Welcome to your dream coastal retreat! This newer 4-bedroom, 3-bath luxury home offers the...	4 beds \| 3 baths \| 2,136 sq.ft.	$1,599,999	Airbnb cash on cash: 6.74% Traditional cash on cash: 1.72% Airbnb Rental Income: $14473 Traditional Rental Income: $4414 Airbnb ROI: 6.74% Traditional ROI: 1.72%
22846 Port Royal Lane Summerland Key, FL Stunning open-water views, unforgettable sunsets over the bay, and direct ocean access fro...	2 beds \| 2 baths \| 1,086 sq.ft.	$998,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 1.35% Airbnb Rental Income: $5495 Traditional Rental Income: $2812 Airbnb ROI: 3.05% Traditional ROI: 1.35%
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.	$1,750,000	Airbnb cash on cash: 1.09% Traditional cash on cash: 0.7% Airbnb Rental Income: $4854 Traditional Rental Income: $3225 Airbnb ROI: 1.09% Traditional ROI: 0.7%
558 E Shore Drive Summerland Key, FL Single-family property on a dry lot in Summerland Key. This property features 3 bedrooms ...	2 beds \| 2 baths \| 1,392 sq.ft.	$735,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 2.61% Airbnb Rental Income: $5495 Traditional Rental Income: $3048 Airbnb ROI: 4.56% Traditional ROI: 2.61%
22954 Buccaneer Lane Summerland Key, FL Welcome to 22954 Buccaneer Ln, a quintessential Florida Keys waterfront escape. Perfectly ...	3 beds \| 2 baths \| 1,400 sq.ft.	$999,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 2.34% Airbnb Rental Income: $4854 Traditional Rental Income: $3506 Airbnb ROI: 2.72% Traditional ROI: 2.34%
27314 Saint Lucie Lane Summerland Key, FL Brand new concrete waterfront pool home on a corner canal lot with an exceptional 204' of ...	3 beds \| 2 baths \| 1,666 sq.ft.	$1,699,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 1.1% Airbnb Rental Income: $4854 Traditional Rental Income: $3643 Airbnb ROI: 1.23% Traditional ROI: 1.1%
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.	$650,000	Airbnb cash on cash: 5.88% Traditional cash on cash: 4.78% Airbnb Rental Income: $5495 Traditional Rental Income: $3720 Airbnb ROI: 5.88% Traditional ROI: 4.78%

Vacation Rentals in Summerland Key

There are 29 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 $999,483 and the average price per square foot is $604. The cash on cash return on vacation rentals in Summerland Key is 2.00%. 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 29 Airbnb properties available for sale in Summerland Key.

In 2025, the best neighborhood to buy short term rental property is Summerland Key.

In September 2025, 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

165 Cutlass Lane

Summerland Key, FL

4 beds | 3 baths | 2,448 sq.ft.

$1,175,000

Airbnb cash on cash: 9.29%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $14473

Traditional Rental Income: $4464

Airbnb ROI: 9.29%

Traditional ROI: 2.51%

701 Spanish Main Drive #UNIT 154

Summerland Key, FL

2 beds | 2 baths | 836 sq.ft.

$549,900

Airbnb cash on cash: 5.45%

Traditional cash on cash: 1.49%

Airbnb Rental Income: $5495

Traditional Rental Income: $2359

Airbnb ROI: 5.45%

Traditional ROI: 1.49%

554 W Shore Drive

Summerland Key, FL

3 beds | 2 baths | 1,407 sq.ft.

$899,000

Airbnb cash on cash: 2.79%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $4854

Traditional Rental Income: $3257

Airbnb ROI: 2.79%

Traditional ROI: 2.07%

22464 La Fitte Drive

Summerland Key, FL

2 beds | 2 baths | 860 sq.ft.

$799,000

Airbnb cash on cash: 4.04%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $5495

Traditional Rental Income: $3842

Airbnb ROI: 4.04%

Traditional ROI: 3.3%

22961 John Avery Lane

Summerland Key, FL

3 beds | 3 baths | 960 sq.ft.

$989,999

Airbnb cash on cash: 2.4%

Traditional cash on cash: 0.81%

Airbnb Rental Income: $4854

Traditional Rental Income: $2387

Airbnb ROI: 2.4%

Traditional ROI: 0.81%

22815 Port Royal Lane

Summerland Key, FL

4 beds | 5 baths | 3,228 sq.ft.

$3,750,000

Airbnb cash on cash: 1.75%

Traditional cash on cash: 0.2%

Airbnb Rental Income: $14473

Traditional Rental Income: $6465

Airbnb ROI: 1.75%

Traditional ROI: 0.2%

22865 Redfish Lane

Summerland Key, FL

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

$1,699,000

Airbnb cash on cash: 1.18%

Traditional cash on cash: 1.02%

Airbnb Rental Income: $4854

Traditional Rental Income: $3610

Airbnb ROI: 1.18%

Traditional ROI: 1.02%

4500 Filer Cove Road

Summerland Key, FL

4 beds | 4 baths | 4,315 sq.ft.

$5,999,000

Airbnb cash on cash: 0.98%

Traditional cash on cash: -0.2%

Airbnb Rental Income: $14473

Traditional Rental Income: $5317

Airbnb ROI: 0.98%