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
59720 Overseas Highway 12, MARATHON

$3,600,000

59720 Overseas Highway 12, MARATHON

5 Beds 5 Baths 3,011 SqFt Residential MLS® # 609662

Internet Realty of the Florida Keys Inc

New
300 Duck Key Drive 12, Duck

$399,000

300 Duck Key Drive 12, Duck

1 Bed 1 Bath 510 SqFt Residential MLS® # 609661

Ocean Sotheby's International Realty

New
1015 Angela Street, KEY WEST

$1,100,000

1015 Angela Street, KEY WEST

1 Bed 1 Bath 673 SqFt Residential MLS® # 609658

Berkshire Hathaway Knight & Gardner

New
1615 United Street, KEY WEST

$1,499,000

1615 United Street, KEY WEST

3 Beds 3 Baths 1,788 SqFt Residential MLS® # 609657

Coldwell Banker Schmitt Real Estate Co. (KW)

New
500 Burton Drive 4201, Tavernier

$759,000

500 Burton Drive 4201, Tavernier

2 Beds 2 Baths 916 SqFt Residential MLS® # 609655

American Caribbean Real Estate, Christie's International Real Estate

New
477 Barracuda Boulevard, KEY LARGO

$839,000

477 Barracuda Boulevard, KEY LARGO

3 Beds 2 Baths 1,598 SqFt Residential MLS® # 609653

The Keyes Company

New
59 W Plaza Del Sol, ISLAMORADA

$3,125,000

59 W Plaza Del Sol, ISLAMORADA

5 Beds 3 Baths 2,922 SqFt Residential MLS® # 609650

Coldwell Banker Schmitt Islamorada

New
421 W Indies, Ramrod

$1,295,000

421 W Indies, Ramrod

2 Beds 2 Baths 1,124 SqFt Residential MLS® # 609649

Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

New
701 Spanish Main Drive 390, Cudjoe

$699,999

701 Spanish Main Drive 390, Cudjoe

2 Beds 2 Baths 828 SqFt Residential MLS® # 609648

Coldwell Banker Schmitt RE Co. Lower Keys Office

New
105 Front Street 119, KEY WEST

$2,395,000

105 Front Street 119, KEY WEST

2 Beds 3 Baths 1,210 SqFt Residential MLS® # 609647

Keller Williams Key West Compass Realty

New
30889 Minorca Drive, Big Pine

$955,000

30889 Minorca Drive, Big Pine

3 Beds 2 Baths 1,486 SqFt Residential MLS® # 609646

Keller Williams Key West Compass Realty

New
1032 Adams Drive, KEY LARGO

$1,800,000

1032 Adams Drive, KEY LARGO

3 Beds 2 Baths 1,680 SqFt Residential MLS® # 609645

Keller Williams Capital 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
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

New
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

$1,800,000

1304 Elizabeth Street, KEY WEST

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

Berkshire Hathaway Knight & Gardner

1716 Washington Street 1 & 2, KEY WEST

$1,499,000

↓ $100,000

1716 Washington Street 1 & 2, KEY WEST

3 Beds 3 Baths 1,785 SqFt Residential MLS® # 609263

Beach Club Brokers (KW)

580 & 590 10th Street, KEY COLONY

$3,980,000

580 & 590 10th Street, KEY COLONY

7 Beds 7 Baths 4,478 SqFt Residential MLS® # 609274

Berkshire Hathaway HomeServices Keys Real Estate

10703-05 2nd Avenue Gulf, MARATHON

$450,000

10703-05 2nd Avenue Gulf, MARATHON

2 Beds 2 Baths 916 SqFt Residential MLS® # 609228

Berkshire Hathaway HomeServices Keys Real Estate

1216 Virginia Street, KEY WEST

$2,200,000

1216 Virginia Street, KEY WEST

4 Beds 5 Baths 1,944 SqFt Residential MLS® # 609213

Truman & Co. (KW)

58234 Overseas Highway, MARATHON

$1,800,000

58234 Overseas Highway, MARATHON

7 Beds 7 Baths 2,190 SqFt Residential MLS® # 609161

Coldwell Banker Schmitt Real Estate Co.

11283 4th Ave Ocean 1, MARATHON

$1,720,000

11283 4th Ave Ocean 1, MARATHON

3 Beds 3 Baths 1,878 SqFt Residential MLS® # 609104

Shilalis Real Estate


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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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