The Florida Keys have proven time and time again to be a great investment destination. Over time our property values continue to increase making long term gains quite substantial. 

Monroe County, or the Florida Keys in general have a robust ordinance restricting homes to a 28 day minimum rental period due to Hurricane evacuation time periods and the balance of vacation homes to workforce housing.  There are exceptions to this rule, which you will find on this page. 

It is advised to speak with a Better Homes and Gardens Real Estate Destinations agent and other well versed professionals to ensure you understand the rules and regulations surrounding the property you intend to purchase. It differs from one property to the next. Due diligence is key. 

This search includes all Florida Keys homes, condominiums and any other property type that allows rentals of 7 nights or less. With such flexible rental restrictions these properties rent throughout the year and often have a profitable income revenue stream. 

Rental Investments

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New
440 Pattison Drive, Cudjoe

$1,869,000

440 Pattison Drive, Cudjoe

3 Beds 3 Baths 1,827 SqFt Residential MLS® # 610904

Berkshire Hathaway Knight & Gardner

New
122 Court Contessa, ISLAMORADA

$3,495,000

122 Court Contessa, ISLAMORADA

3 Beds 3 Baths 2,374 SqFt Residential MLS® # 610903

Coldwell Banker Schmitt Islamorada

New
30919 Edward Road A, Big Pine

$889,000

30919 Edward Road A, Big Pine

3 Beds 2 Baths 1,414 SqFt Residential MLS® # 610902

Ocean Sotheby's International Realty

New
27417 Cayman Lane, Ramrod

$975,000

27417 Cayman Lane, Ramrod

2 Beds 1 Bath 1,085 SqFt Residential MLS® # 610901

Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

New
522 Elizabeth Street, KEY WEST

$5,999,999

522 Elizabeth Street, KEY WEST

6 Beds 7 Baths 3,209 SqFt Residential MLS® # 610898

Brenda Donnelly Real Estate LLC

New
137 E Caribbean Drive, Summerland

$1,329,000

137 E Caribbean Drive, Summerland

2 Beds 2 Baths 1,120 SqFt Residential MLS® # 610897

Keller Williams Key West Compass Realty

New
73 Coral Lane, KEY COLONY

$725,000

73 Coral Lane, KEY COLONY

2 Beds 2 Baths 1,290 SqFt Residential MLS® # 610895

Elite Realty International Co.

New
2751 Yellowtail Drive, MARATHON

$2,999,999

2751 Yellowtail Drive, MARATHON

4 Beds 3 Baths 1,950 SqFt Residential MLS® # 610892

BYOWNER.COM

New
1015 Eaton Street, KEY WEST

$2,600,000

1015 Eaton Street, KEY WEST

4 Beds 3 Baths 1,738 SqFt Residential MLS® # 610891

Brenda Donnelly Real Estate LLC

New
1211 Knowles Lane, KEY WEST

$1,800,000

1211 Knowles Lane, KEY WEST

2 Beds 3 Baths 1,042 SqFt Residential MLS® # 610890

Saltwater Real Estate Florida Keys, Inc

New
17129 Amberjack Lane, Sugarloaf

$5,250,000

17129 Amberjack Lane, Sugarloaf

6 Beds 7 Baths 4,200 SqFt Residential MLS® # 610889

Ocean Sotheby's International Realty

New
79901 Overseas Highway 404, ISLAMORADA

$599,900

79901 Overseas Highway 404, ISLAMORADA

2 Beds 2 Baths 981 SqFt Residential MLS® # 610888

Realty One Group Engage the Keys

In addition to short term rentals there is a tremendous opportunity to purchase multi-family homes or single family homes tapping into the long term rental market. 

This search includes all multi-family rental properties listed for sale on the Florida Keys MLS, or multiple listing service. Contact your Better Homes and Gardens Real Estate Destinations agent for more information on any property including rental histories or projections. Our sister company Star Properties Destinations is available to help determine if the property would be a desirable rental property and what to consider improving  to increase revenue. 

Multi-family Homes

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New
1409 4th Street, KEY WEST

$1,795,000

1409 4th Street, KEY WEST

4 Beds 3 Baths 2,004 SqFt Residential MLS® # 610831

Ocean Sotheby's International Realty

1320 Johnson Street, KEY WEST

$2,436,000

1320 Johnson Street, KEY WEST

3 Beds 4 Baths 2,436 SqFt Residential MLS® # 610821

Berkshire Hathaway Knight & Gardner

1297/1299 73rd Street Ocean, MARATHON

$1,098,000

1297/1299 73rd Street Ocean, MARATHON

4 Beds 2 Baths 1,536 SqFt Residential MLS® # 610715

Ocean Sotheby's International Realty

105 N Anglers Drive A, MARATHON

$1,800,000

105 N Anglers Drive A, MARATHON

4 Beds 4 Baths 2,752 SqFt Residential MLS® # 610669

Key to the Keys Real Estate, Inc

53 Coral Lane, KEY COLONY

$1,199,000

53 Coral Lane, KEY COLONY

3 Beds 3 Baths 1,428 SqFt Residential MLS® # 610653

Walker Reid Realty

1320 6th Street, KEY WEST

$2,450,000

1320 6th Street, KEY WEST

5 Beds 5 Baths 1,856 SqFt Residential MLS® # 610618

Keller Williams Key West Compass Realty

400 Aronovitz Lane, KEY WEST

$3,750,000

400 Aronovitz Lane, KEY WEST

5 Beds 6 Baths 3,665 SqFt Residential MLS® # 610578

Berkshire Hathaway Knight & Gardner

901 Eisenhower Drive, KEY WEST

$4,975,000

901 Eisenhower Drive, KEY WEST

6 Beds 5 Baths 3,788 SqFt Residential MLS® # 610558

Berkshire Hathaway Knight & Gardner

21540 21470 Overseas Highway, Cudjoe

$14,495,000

21540 21470 Overseas Highway, Cudjoe

31 Beds 19 Baths 0 SqFt Residential MLS® # 610484

Select Properties of NWFL

2421 Fogarty Avenue 1 &2, KEY WEST

$695,000

↓ $100,000

2421 Fogarty Avenue 1 &2, KEY WEST

4 Beds 2 Baths 1,594 SqFt Residential MLS® # 610466

Coldwell Banker Schmitt Real Estate Co. (KW)

528 Grinnell Street, KEY WEST

$1,599,000

528 Grinnell Street, KEY WEST

3 Beds 2 Baths 2,280 SqFt Residential MLS® # 610346

Keller Williams Key West Compass Realty

23930 Overseas Highway, Summerland

$845,000

↓ $4,000

23930 Overseas Highway, Summerland

3 Beds 3 Baths 1,360 SqFt Residential MLS® # 610335

Expert Realty LLC


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Pink sunset over waterfront with pier in the Florida Keys

What's my Florida Keys home worth?

Use our Home Evaluation tool to get a free estimated market value of your Florida Keys home. We'll calculate a home valuation based on similar properties in your area.

Complete the form below to connect with a Better Homes and Gardens Real Estate Destinations agent for more information and a detailed analysis on your desired vacation rental property from our sister company, Star Properties Destinations a Florida Keys vacation rental management company. 

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