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
100 Villa Bella Drive, ISLAMORADA

$2,150,000

100 Villa Bella Drive, ISLAMORADA

3 Beds 2 Baths 1,583 SqFt Residential MLS® # 610054

Coldwell Banker Schmitt Islamorada

New
1500 Seminary Street 5a, KEY WEST

$599,000

1500 Seminary Street 5a, KEY WEST

1 Bed 1 Bath 525 SqFt Residential MLS® # 610053

Coastal Collection Real Estate Inc.

New
1708 Duncan Street, KEY WEST

$1,649,000

1708 Duncan Street, KEY WEST

3 Beds 3 Baths 1,708 SqFt Residential MLS® # 610049

American Caribbean Real Estate, Christie's International Real Estate

New
861 12th Street, KEY COLONY

$5,150,000

861 12th Street, KEY COLONY

4 Beds 3 Baths 5,186 SqFt Residential MLS® # 610048

Coldwell Banker Schmitt Real Estate Co.

94 Sirius Lane, Geiger

$699,000

94 Sirius Lane, Geiger

2 Beds 2 Baths 756 SqFt Residential MLS® # 610047

Saltwater Real Estate Florida Keys, Inc

New
107 Point Pleasant Drive, KEY LARGO

$1,999,999

107 Point Pleasant Drive, KEY LARGO

5 Beds 4 Baths 2,957 SqFt Residential MLS® # 610046

Ocean Sotheby's International Realty

New
201 Coppitt Road 101b, Big Coppitt

$365,000

201 Coppitt Road 101b, Big Coppitt

1 Bed 1 Bath 536 SqFt Residential MLS® # 610043

Century 21 Circle

New
29115 Allamanda Lane, Big Pine

$1,275,000

29115 Allamanda Lane, Big Pine

3 Beds 2 Baths 1,039 SqFt Residential MLS® # 610042

Keller Williams Realty Premier Properties

New
7951 Gulfstream Boulevard, MARATHON

$775,000

7951 Gulfstream Boulevard, MARATHON

3 Beds 1 Bath 1,538 SqFt Residential MLS® # 610041

Coldwell Banker Schmitt Real Estate Co.

New
21025 Hamilton Avenue, Cudjoe

$1,799,900

21025 Hamilton Avenue, Cudjoe

6 Beds 4 Baths 4,060 SqFt Residential MLS® # 610039

Internet Realty of the Florida Keys

New
701 Spanish Main Drive 30, Cudjoe

$749,900

701 Spanish Main Drive 30, Cudjoe

2 Beds 2 Baths 865 SqFt Residential MLS® # 610036

Berkshire Hathaway Knight & Gardner

New
1210 Virginia Street, KEY WEST

$1,269,000

1210 Virginia Street, KEY WEST

3 Beds 3 Baths 1,740 SqFt Residential MLS® # 610034

Keller Williams Key West Compass Realty

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
1210 Virginia Street, KEY WEST

$1,269,000

1210 Virginia Street, KEY WEST

3 Beds 3 Baths 1,740 SqFt Residential MLS® # 610034

Keller Williams Key West Compass Realty

New
29654 Constitution Avenue, Big Pine

$799,000

29654 Constitution Avenue, Big Pine

4 Beds 2 Baths 1,547 SqFt Residential MLS® # 609978

Ocean Sotheby's International Realty

New
1724 Bahama Drive, KEY WEST

$1,299,000

1724 Bahama Drive, KEY WEST

4 Beds 4 Baths 1,725 SqFt Residential MLS® # 609972

Saltwater Real Estate Florida Keys, Inc

2514 Staples Avenue, KEY WEST

$1,350,000

2514 Staples Avenue, KEY WEST

4 Beds 2 Baths 2,174 SqFt Residential MLS® # 609960

Expert Realty LLC (HQ)

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

303 Sombrero Beach Road, MARATHON

$1,950,000

↓ $45,000

303 Sombrero Beach Road, MARATHON

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

Ocean Sotheby's International Realty

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

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


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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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