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

Click the links below to sort results by price range.

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New
1207 Mockingbird Road, KEY LARGO

$2,250,000

1207 Mockingbird Road, KEY LARGO

4 Beds 5 Baths 2,324 SqFt Residential MLS® # 609873

Compass Florida LLC

1330 Ocean Drive, Summerland

$1,699,000

1330 Ocean Drive, Summerland

2 Beds 2 Baths 1,144 SqFt Residential MLS® # 604706

Coldwell Banker Schmitt Lower Keys (KW)

New
1012 Varela Street 2, KEY WEST

$545,000

1012 Varela Street 2, KEY WEST

0 Beds 1 Bath 241 SqFt Residential MLS® # 609872

Douglas Elliman Florida, LLC

New
3930 S 3930 Roosevelt Boulevard S204, KEY WEST

$419,000

3930 S 3930 Roosevelt Boulevard S204, KEY WEST

1 Bed 1 Bath 478 SqFt Residential MLS® # 609871

RE/MAX Keys Connection (KW)

New
314 E Seaview Drive, Duck

$4,250,000

314 E Seaview Drive, Duck

4 Beds 4 Baths 3,295 SqFt Residential MLS® # 609870

Ocean Sotheby's International Realty

New
1314 Johnson Street, KEY WEST

$1,050,000

1314 Johnson Street, KEY WEST

3 Beds 1 Bath 1,305 SqFt Residential MLS® # 609869

Coldwell Banker Schmitt Real Estate Co. (KW)

New
2601 S Roosevelt Boulevard 505b, KEY WEST

$1,895,000

2601 S Roosevelt Boulevard 505b, KEY WEST

5 Beds 2 Baths 2,207 SqFt Residential MLS® # 609867

Coastal Collection Real Estate Inc.

New
101551 Overseas Highway 113, KEY LARGO

$420,000

101551 Overseas Highway 113, KEY LARGO

2 Beds 1 Bath 684 SqFt Residential MLS® # 609866

RE/MAX All Keys Real Estate

New
1904 Staples Avenue, KEY WEST

$835,000

1904 Staples Avenue, KEY WEST

3 Beds 3 Baths 1,160 SqFt Residential MLS® # 609865

Lokation Real Estate

New
1500 Atlantic Boulevard 409, KEY WEST

$3,550,000

1500 Atlantic Boulevard 409, KEY WEST

3 Beds 3 Baths 2,038 SqFt Residential MLS® # 609863

Berkshire Hathaway Knight & Gardner

New
81801 Overseas Highway 712, ISLAMORADA

$725,000

81801 Overseas Highway 712, ISLAMORADA

1 Bed 1 Bath 550 SqFt Residential MLS® # 609862

Coldwell Banker Schmitt Islamorada

New
44 Palmetto Drive, Big Coppitt

$1,450,000

44 Palmetto Drive, Big Coppitt

3 Beds 3 Baths 1,817 SqFt Residential MLS® # 609861

Expert Realty LLC (HQ)

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
237 Atlantic Boulevard, KEY LARGO

$2,699,000

237 Atlantic Boulevard, KEY LARGO

7 Beds 4 Baths 3,164 SqFt Residential MLS® # 609804

Ocean Sotheby's International Realty

New
303 Sombrero Beach Road, MARATHON

$1,995,000

303 Sombrero Beach Road, MARATHON

4 Beds 4 Baths 2,114 SqFt Residential MLS® # 609802

Ocean Sotheby's International Realty

New
411 & 415 1st Street, Big Coppitt

$1,400,000

411 & 415 1st Street, Big Coppitt

6 Beds 5 Baths 2,377 SqFt Residential MLS® # 609794

Keller Williams Key West Compass Realty

904 Truman Avenue, KEY WEST

$1,495,000

904 Truman Avenue, KEY WEST

3 Beds 3 Baths 1,150 SqFt Residential MLS® # 609787

Key West Luxury Real Estate Inc (KW)

500 22nd Street Ocean 1-4, MARATHON

$1,599,000

500 22nd Street Ocean 1-4, MARATHON

8 Beds 4 Baths 2,780 SqFt Residential MLS® # 609777

Coldwell Banker Schmitt Real Estate Co.

1205 11th Street, KEY WEST

$1,675,000

1205 11th Street, KEY WEST

4 Beds 3 Baths 1,778 SqFt Residential MLS® # 609691

Bascom Grooms Real Estate (KW)

29528 Constitution Avenue, Big Pine

$1,100,000

29528 Constitution Avenue, Big Pine

4 Beds 4 Baths 1,568 SqFt Residential MLS® # 609612

KeyIsle Realty

1500 Patricia Street, KEY WEST

$1,589,000

1500 Patricia Street, KEY WEST

4 Beds 3 Baths 2,240 SqFt Residential MLS® # 609591

Berkshire Hathaway Knight & Gardner

1101 W Ocean Drive 14, KEY COLONY

$349,000

1101 W Ocean Drive 14, KEY COLONY

2 Beds 2 Baths 990 SqFt Residential MLS® # 609514

Ocean Sotheby's International Realty

329 William Street, KEY WEST

$4,199,000

329 William Street, KEY WEST

6 Beds 7 Baths 2,294 SqFt Residential MLS® # 609512

Island Home Realty Inc.

530 65th Street, MARATHON

$595,000

530 65th Street, MARATHON

4 Beds 2 Baths 1,800 SqFt Residential MLS® # 609490

Coastal Collection Real Estate Inc.

1304 Elizabeth Street, KEY WEST

$1,675,000

↓ $125,000

1304 Elizabeth Street, KEY WEST

6 Beds 4 Baths 2,050 SqFt Residential MLS® # 609428

Berkshire Hathaway Knight & Gardner


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Pink sunset over waterfront with pier in the Florida Keys

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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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