Real Estate Investment Properties for Sale in Plantation Key, FL

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
88500 Overseas Highway #UNIT 501 Plantation Key, FL This stunning 3-bedroom, 2 bath, fully furnished penthouse Condominium with private roof t...	3 beds \| 2 baths \| 1,567 sq.ft.	$725,000	Airbnb cash on cash: 2.85% Traditional cash on cash: 1.16% Airbnb Rental Income: $6224 Traditional Rental Income: $3854 Airbnb ROI: 2.85% Traditional ROI: 1.16%
88547 Old Highway Plantation Key, FL Open Oceanfront Estate with Deep Water Dockage on 1.5 Acres on Millionaires' Row... Islamo...	4 beds \| 3 baths \| 4,103 sq.ft.	$7,500,000	Airbnb cash on cash: -0.28% Traditional cash on cash: -0.61% Airbnb Rental Income: $8621 Traditional Rental Income: $4739 Airbnb ROI: -0.28% Traditional ROI: -0.61%
88500 Overseas Highway #UNIT 233 Plantation Key, FL Charming Studio in Desirable Summer Sea - Islamorada, the Fishing Capital of the World!Enj...	1 beds \| 1 baths \| 398 sq.ft.	$290,000	Airbnb cash on cash: 6.28% Traditional cash on cash: 1.65% Airbnb Rental Income: $3833 Traditional Rental Income: $1742 Airbnb ROI: 6.28% Traditional ROI: 1.65%
117 Leoni Drive Plantation Key, FL Welcome to paradise at 117 Leoni Drive in the exclusive Venetian Shores neighborhood! This...	5 beds \| 6 baths \| 4,100 sq.ft.	$4,950,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.92% Airbnb Rental Income: $null Traditional Rental Income: $9849 Airbnb ROI: N/A Traditional ROI: 0.92%
88500 Overseas Highway #UNIT 428 Plantation Key, FL Tavernier beauty, Summer Sea Condo sits on MM 88.5 right on the Bay - waterfront building ...	2 beds \| 2 baths \| 794 sq.ft.	$449,000	Airbnb cash on cash: 2.63% Traditional cash on cash: 1.49% Airbnb Rental Income: $3788 Traditional Rental Income: $2488 Airbnb ROI: 2.63% Traditional ROI: 1.49%
88500 Overseas Highway #UNIT 422 Plantation Key, FL Significant reduction in price!!! Check this one out!!! Incredible Panoramic Bay View, Spe...	2 beds \| 2 baths \| 794 sq.ft.	$649,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 0.13% Airbnb Rental Income: $3788 Traditional Rental Income: $2244 Airbnb ROI: 1.32% Traditional ROI: 0.13%
40 High Point Road #UNIT F106 Plantation Key, FL Clean, fresh and move-in ready, ground level, 1 bedroom, 1 bath condo with new kitchen, ne...	1 beds \| 1 baths \| 895 sq.ft.	$260,000	Airbnb cash on cash: 6.03% Traditional cash on cash: 1.73% Airbnb Rental Income: $3833 Traditional Rental Income: $1950 Airbnb ROI: 6.03% Traditional ROI: 1.73%
87200 Overseas Highway #UNIT V9 Plantation Key, FL All NEW NEXT TO MARINA & POOL Stunning Islamorada 3 full bedrooms 2 brand new bathrooms pl...	3 beds \| 2 baths \| 1,355 sq.ft.	$685,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 1.07% Airbnb Rental Income: $6224 Traditional Rental Income: $3224 Airbnb ROI: 3.84% Traditional ROI: 1.07%
200 Wrenn Street #UNIT 404 Plantation Key, FL This unit at Sea Gulls Condominium is more than just a home; it's an invitation to a lifes...	2 beds \| 2 baths \| 1,179 sq.ft.	$425,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 4.96% Airbnb Rental Income: $3788 Traditional Rental Income: $2944 Airbnb ROI: 5.02% Traditional ROI: 4.96%
88181 Old Highway #UNIT 21H Plantation Key, FL Welcome to Boater's Paradise, featuring a 30' deeded boat slip! Immerse yourself in breath...	2 beds \| 2 baths \| 1,672 sq.ft.	$935,000	Airbnb cash on cash: -1.3% Traditional cash on cash: -0.48% Airbnb Rental Income: $3788 Traditional Rental Income: $3687 Airbnb ROI: -1.3% Traditional ROI: -0.48%
406 S Coconut Palm Boulevard Plantation Key, FL BRAND NEW DOCKAGE COMING SOON!! UPDATED PICTURES ONCE COMPLETED!! Discover coastal luxury ...	4 beds \| 4 baths \| 4,144 sq.ft.	$4,440,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 0.29% Airbnb Rental Income: $8621 Traditional Rental Income: $7258 Airbnb ROI: 0.22% Traditional ROI: 0.29%
87455 Old Highway #UNIT 237 Plantation Key, FL Islamorada townhouse in Plantation by the Sea. Offering 2 bedrooms/ 1.5 baths, furnished, ...	2 beds \| 2 baths \| 989 sq.ft.	$395,000	Airbnb cash on cash: 3.59% Traditional cash on cash: 2.48% Airbnb Rental Income: $3788 Traditional Rental Income: $2553 Airbnb ROI: 3.59% Traditional ROI: 2.48%
136 Aregood Lane #UNIT 2A Plantation Key, FL Coastal Living Redefined: Your Port of Call Oasis--Where Sunrises Paint the Sky and Salty ...	2 beds \| 3 baths \| 1,152 sq.ft.	$950,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 1.7% Airbnb Rental Income: $3788 Traditional Rental Income: $3102 Airbnb ROI: 1.54% Traditional ROI: 1.7%
164 Plantation Shores Drive Plantation Key, FL EXQUISITE OCEAN VIEW POOL HOME! Welcome to Tut's Cay, a luxurious 4 bedroom, 5 bathroom, ...	4 beds \| 5 baths \| 2,970 sq.ft.	$2,995,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 2.29% Airbnb Rental Income: $8621 Traditional Rental Income: $10529 Airbnb ROI: 1.01% Traditional ROI: 2.29%
162 Azalea Street Plantation Key, FL OWNER FINANCING-Plantation Key Colony - Completely UPDATED-Like New - 2/1 up and 1/1 dow...	3 beds \| 2 baths \| 1,740 sq.ft.	$1,599,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 0.94% Airbnb Rental Income: $6224 Traditional Rental Income: $4103 Airbnb ROI: 1.54% Traditional ROI: 0.94%
132 Gardenia Street Plantation Key, FL Here's your chance for a Key's Life Getaway! Located in the desirable Tavernier neighborh...	3 beds \| 3 baths \| 1,360 sq.ft.	$1,295,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 1.37% Airbnb Rental Income: $6224 Traditional Rental Income: $3917 Airbnb ROI: 2.27% Traditional ROI: 1.37%
282 S Coconut Palm Boulevard Plantation Key, FL Experience the lifestyle of waterfront living in this quintessential Islamorada home. Feat...	3 beds \| 3 baths \| 2,100 sq.ft.	$1,850,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 0.91% Airbnb Rental Income: $6224 Traditional Rental Income: $4708 Airbnb ROI: 1.08% Traditional ROI: 0.91%
88181 Old Highway #UNIT 2A Plantation Key, FL Calling all Anglers. Coral Harbor Club is located in Islamorada, Florida, the only comple...	3 beds \| 2 baths \| 1,553 sq.ft.	$899,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 1.78% Airbnb Rental Income: $6224 Traditional Rental Income: $3786 Airbnb ROI: 3.23% Traditional ROI: 1.78%
200 Wrenn Street #UNIT PH 701 Plantation Key, FL OCEANFRONT PENTHOUSE - STRONG RENTAL INCOME. Welcome to PH701 at Sea Gulls, a rare and inc...	3 beds \| 2 baths \| 2,137 sq.ft.	$999,988	Airbnb cash on cash: 3.47% Traditional cash on cash: 2.4% Airbnb Rental Income: $6224 Traditional Rental Income: $4008 Airbnb ROI: 3.47% Traditional ROI: 2.4%
87851 Old Highway #UNIT M3 Plantation Key, FL Experience the relaxed lifestyle of Islamorada at its finest, Ocean Harbor Condominiums. T...	2 beds \| 2 baths \| 1,536 sq.ft.	$1,095,000	Airbnb cash on cash: -0.87% Traditional cash on cash: -0.04% Airbnb Rental Income: $3788 Traditional Rental Income: $3814 Airbnb ROI: -0.87% Traditional ROI: -0.04%
157 Caloosa Street Plantation Key, FL This is it!! Your Florida Key Oasis! Quintessentially Key-z, this home has it all ... and ...	3 beds \| 3 baths \| 1,769 sq.ft.	$1,537,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 1.62% Airbnb Rental Income: $6224 Traditional Rental Income: $4675 Airbnb ROI: 1.85% Traditional ROI: 1.62%
163 Fontaine Drive Plantation Key, FL Custom Waterfront Pool Home! Offering teak wood floors and doors, 16' vaulted ceilings, cu...	3 beds \| 2 baths \| 2,669 sq.ft.	$1,985,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 1.28% Airbnb Rental Income: $6224 Traditional Rental Income: $5329 Airbnb ROI: 1.1% Traditional ROI: 1.28%
87851 Old Highway #UNIT M26 Plantation Key, FL Experience resort-style living in this 3-bedroom, 2-bathroom corner unit in the highly sou...	3 beds \| 2 baths \| 1,800 sq.ft.	$1,425,000	Airbnb cash on cash: 0.32% Traditional cash on cash: -0.35% Airbnb Rental Income: $6224 Traditional Rental Income: $4112 Airbnb ROI: 0.32% Traditional ROI: -0.35%
160 E Ridge Road Plantation Key, FL Prime Islamorada Location - Across from Founders Park!Spacious 3 bed, 3 bath CBS ground-le...	3 beds \| 3 baths \| 2,034 sq.ft.	$950,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 5.8% Airbnb Rental Income: $6224 Traditional Rental Income: $6806 Airbnb ROI: 3.76% Traditional ROI: 5.8%
115 Fontaine Drive Plantation Key, FL Charming Home in a desirable Plantation Key Subdivision!This well-maintained Sheffield Ste...	2 beds \| 2 baths \| 864 sq.ft.	$685,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 1.86% Airbnb Rental Income: $3788 Traditional Rental Income: $2312 Airbnb ROI: 2.89% Traditional ROI: 1.86%
118 Spoonbill Road Plantation Key, FL OPEN HOUSE! AUG 21ST, 10AM to 12pm! This canal-front pool home is an absolute show-stopper...	4 beds \| 3 baths \| 3,482 sq.ft.	$3,199,000	Airbnb cash on cash: 0.77% Traditional cash on cash: -0.44% Airbnb Rental Income: $8621 Traditional Rental Income: $3401 Airbnb ROI: 0.77% Traditional ROI: -0.44%
87465 Old Highway #UNIT 106 Plantation Key, FL Welcome to Plantation by the Sea! This beautifully remodeled 2 bedroom, 2 bathroom condo ...	2 beds \| 2 baths \| 976 sq.ft.	$479,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 3.38% Airbnb Rental Income: $3788 Traditional Rental Income: $3263 Airbnb ROI: 2.72% Traditional ROI: 3.38%
125 S Rolling Hill Road Plantation Key, FL Move-In Ready Islamorada Home Well-kept 2-bedroom, 2-bath home on a spacious corner lot in...	2 beds \| 2 baths \| 1,120 sq.ft.	$785,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 1.3% Airbnb Rental Income: $3788 Traditional Rental Income: $2392 Airbnb ROI: 2.08% Traditional ROI: 1.3%
124 Venetian Way Plantation Key, FL Island Living in Prestigious Venetian Shores!Welcome to this newly custom-built four bedro...	4 beds \| 3 baths \| 2,096 sq.ft.	$1,625,000	Airbnb cash on cash: 2.93% Traditional cash on cash: 1.43% Airbnb Rental Income: $8621 Traditional Rental Income: $4736 Airbnb ROI: 2.93% Traditional ROI: 1.43%
154 Redwing Road Plantation Key, FL Unobstructed SUNSET/BAY views. Tucked away on a secluded point in the prestigious 'Sunshin...	4 beds \| 5 baths \| 2,320 sq.ft.	$3,899,999	Airbnb cash on cash: 0.74% Traditional cash on cash: 0.5% Airbnb Rental Income: $8621 Traditional Rental Income: $6108 Airbnb ROI: 0.74% Traditional ROI: 0.5%
301 Woods Avenue Plantation Key, FL Enter the Islamorada waterfront game with this fantastic ground level 3-bedroom home, perf...	3 beds \| 2 baths \| 1,376 sq.ft.	$1,150,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 2.77% Airbnb Rental Income: $6224 Traditional Rental Income: $4568 Airbnb ROI: 3.17% Traditional ROI: 2.77%
140 Gardenia St Plantation Key, FL DOUBLE LOT! FUNKY KEYS PRIVATE WATERFRONT HIDEOUT -enjoy/rebuild on GIANT 12,500 sqft ...	2 beds \| 1 baths \| 978 sq.ft.	$1,540,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 0.06% Airbnb Rental Income: $3788 Traditional Rental Income: $2576 Airbnb ROI: 0.33% Traditional ROI: 0.06%
87950 Overseas Highway Plantation Key, FL Tired of waiting on Uber or Freebee? Why not make this stunning bayfront estate your own p...	5 beds \| 3 baths \| 2,464 sq.ft.	$3,800,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.08% Airbnb Rental Income: $null Traditional Rental Income: $4694 Airbnb ROI: N/A Traditional ROI: -0.08%
260 Plantation Avenue Plantation Key, FL ''Sunset Haven'' This absolutely delightful and serene Florida bayfront beauty will take y...	3 beds \| 4 baths \| 2,459 sq.ft.	$6,500,000	Airbnb cash on cash: -0.51% Traditional cash on cash: -0.27% Airbnb Rental Income: $6224 Traditional Rental Income: $6432 Airbnb ROI: -0.51% Traditional ROI: -0.27%
88181 Old Highway #UNIT 1G Plantation Key, FL Florida Keys Living at Its Finest - Stunning Ground-Floor Condo at Coral Harbour Club. Thi...	3 beds \| 2 baths \| 1,593 sq.ft.	$668,800	Airbnb cash on cash: 5.83% Traditional cash on cash: 7.21% Airbnb Rental Income: $6224 Traditional Rental Income: $5858 Airbnb ROI: 5.83% Traditional ROI: 7.21%
87200 Overseas Highway #UNIT H4 Plantation Key, FL MOTIVATED SELLER! Are you Ready for a lift style change? We have just the place for you, w...	2 beds \| 2 baths \| 1,359 sq.ft.	$749,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 0.18% Airbnb Rental Income: $3788 Traditional Rental Income: $2811 Airbnb ROI: 0.41% Traditional ROI: 0.18%
126 Villa Bella Drive Plantation Key, FL Welcome to your Keys escape -- a fresh, modern coastal home with 100 feet of dockage, just...	3 beds \| 3 baths \| 2,088 sq.ft.	$3,995,000	Airbnb cash on cash: -0.08% Traditional cash on cash: -0.1% Airbnb Rental Income: $6224 Traditional Rental Income: $4903 Airbnb ROI: -0.08% Traditional ROI: -0.1%
155 Fontaine Drive Plantation Key, FL Welcome to your elevated retreat in the heart of Plantation Key--where island living and t...	5 beds \| 4 baths \| 2,492 sq.ft.	$1,299,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.13% Airbnb Rental Income: $null Traditional Rental Income: $5466 Airbnb ROI: N/A Traditional ROI: 3.13%
87200 Overseas Highway #UNIT S8 Plantation Key, FL No spiral stairs here! They have been replaced and it's so much easier to walk up the sta...	2 beds \| 2 baths \| 1,365 sq.ft.	$590,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 0.67% Airbnb Rental Income: $3788 Traditional Rental Income: $2811 Airbnb ROI: 0.96% Traditional ROI: 0.67%
140 Aregood Lane #UNIT C2 Plantation Key, FL Welcome to Port of Call, an exclusive low-density, private community nestled on the ocean ...	2 beds \| 3 baths \| 1,248 sq.ft.	$882,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 1.12% Airbnb Rental Income: $3788 Traditional Rental Income: $3300 Airbnb ROI: 0.71% Traditional ROI: 1.12%

Real Estate investment in Plantation-key, FL

There are 85 properties for sale in the city of Plantation Key . The median list price in Plantation Key is $1,239,000 and the average price per square foot is $674. In September 2025, the average monthly cash on cash return in Plantation Key is 1.00%. The average monthly rental income in Plantation Key is $3,826.

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

There are 85 investment properties available for sale in Plantation-key.

In 2025, the best neighborhood to buy investment property is Plantation Key.

The ROI for Short-Term is higher than the Long-Term in Plantation-key with average rental income of $6,224.

Your search for investment property begins and ends here

Investment Property for Sale in Plantation Key, FL

88500 Overseas Highway #UNIT 501

Plantation Key, FL

3 beds | 2 baths | 1,567 sq.ft.

$725,000

Airbnb cash on cash: 2.85%

Traditional cash on cash: 1.16%

Airbnb Rental Income: $6224

Traditional Rental Income: $3854

Airbnb ROI: 2.85%

Traditional ROI: 1.16%

88547 Old Highway

Plantation Key, FL

4 beds | 3 baths | 4,103 sq.ft.

$7,500,000

Airbnb cash on cash: -0.28%

Traditional cash on cash: -0.61%

Airbnb Rental Income: $8621

Traditional Rental Income: $4739

Airbnb ROI: -0.28%

Traditional ROI: -0.61%

88500 Overseas Highway #UNIT 233

Plantation Key, FL

1 beds | 1 baths | 398 sq.ft.

$290,000

Airbnb cash on cash: 6.28%

Traditional cash on cash: 1.65%

Airbnb Rental Income: $3833

Traditional Rental Income: $1742

Airbnb ROI: 6.28%

Traditional ROI: 1.65%

117 Leoni Drive

Plantation Key, FL

5 beds | 6 baths | 4,100 sq.ft.

$4,950,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.92%

Airbnb Rental Income: $null

Traditional Rental Income: $9849

Airbnb ROI: N/A

Traditional ROI: 0.92%

88500 Overseas Highway #UNIT 428

Plantation Key, FL

2 beds | 2 baths | 794 sq.ft.

$449,000

Airbnb cash on cash: 2.63%

Traditional cash on cash: 1.49%

Airbnb Rental Income: $3788

Traditional Rental Income: $2488

Airbnb ROI: 2.63%

Traditional ROI: 1.49%

88500 Overseas Highway #UNIT 422

Plantation Key, FL

2 beds | 2 baths | 794 sq.ft.

$649,000

Airbnb cash on cash: 1.32%

Traditional cash on cash: 0.13%

Airbnb Rental Income: $3788

Traditional Rental Income: $2244

Airbnb ROI: 1.32%

Traditional ROI: 0.13%

40 High Point Road #UNIT F106

Plantation Key, FL

1 beds | 1 baths | 895 sq.ft.

$260,000

Airbnb cash on cash: 6.03%

Traditional cash on cash: 1.73%

Airbnb Rental Income: $3833

Traditional Rental Income: $1950

Airbnb ROI: 6.03%

Traditional ROI: 1.73%

87200 Overseas Highway #UNIT V9

Plantation Key, FL

3 beds | 2 baths | 1,355 sq.ft.

$685,000

Airbnb cash on cash: 3.84%

Traditional cash on cash: 1.07%

Airbnb Rental Income: $6224

Traditional Rental Income: $3224

Airbnb ROI: 3.84%