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
1302 11th Street, KEY WEST

$975,000

1302 11th Street, KEY WEST

3 Beds 3 Baths 1,616 SqFt Residential MLS® # 613325

Ocean Sotheby's International Realty

New
1126 Grand Street, KEY LARGO

$999,000

1126 Grand Street, KEY LARGO

2 Beds 1 Bath 1,000 SqFt Residential MLS® # 613324

RE/MAX All Keys Real Estate

New
135 Coco Plum Drive 1a, MARATHON

$799,000

135 Coco Plum Drive 1a, MARATHON

2 Beds 2 Baths 1,280 SqFt Residential MLS® # 613323

Coldwell Banker Schmitt Real Estate Co.

New
183 Azalea Street, Tavernier

$1,775,000

183 Azalea Street, Tavernier

3 Beds 3 Baths 2,048 SqFt Residential MLS® # 613322

Coldwell Banker Schmitt Islamorada

New
201 E Ocean Drive 106, KEY COLONY

$619,000

201 E Ocean Drive 106, KEY COLONY

2 Beds 2 Baths 1,034 SqFt Residential MLS® # 613321

Coldwell Banker Schmitt Real Estate Co.

New
35250 Sw 177th Court 156, Homestead

$159,900

35250 Sw 177th Court 156, Homestead

2 Beds 2 Baths 850 SqFt Residential MLS® # 613320

RE/MAX All Keys Real Estate

New
188 Indian Mound Trail, Tavernier

$3,950,000

188 Indian Mound Trail, Tavernier

3 Beds 3 Baths 2,250 SqFt Residential MLS® # 613317

Ocean Sotheby's International Realty

New
22879 Blackbeard Lane, Cudjoe

$995,000

22879 Blackbeard Lane, Cudjoe

3 Beds 2 Baths 1,344 SqFt Residential MLS® # 613315

Island Welcome Real Estate

New
28 Bonefish Avenue, KEY LARGO

$925,000

28 Bonefish Avenue, KEY LARGO

4 Beds 3 Baths 2,092 SqFt Residential MLS® # 613314

Lokation Real Estate - Tavernier

New
200 Wrenn Street 203, Tavernier

$329,000

200 Wrenn Street 203, Tavernier

1 Bed 1 Bath 756 SqFt Residential MLS® # 613313

American Caribbean Real Estate, Christie's International Real Estate

New
1616 Atlantic Boulevard 18, KEY WEST

$1,625,000

1616 Atlantic Boulevard 18, KEY WEST

2 Beds 3 Baths 2,016 SqFt Residential MLS® # 613312

Suzanne Moore Real Estate

New
101 11th Street 2, MARATHON

$599,000

101 11th Street 2, MARATHON

2 Beds 2 Baths 960 SqFt Residential MLS® # 613310

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

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
107 Carroll Street All Units, ISLAMORADA

$1,350,000

107 Carroll Street All Units, ISLAMORADA

4 Beds 3 Baths 1,459 SqFt Residential MLS® # 613294

Coldwell Banker Schmitt Islamorada

New
1626 Sirugo Avenue, KEY WEST

$2,800,000

1626 Sirugo Avenue, KEY WEST

5 Beds 3 Baths 2,730 SqFt Residential MLS® # 613185

Keys Atlantic Realty

34 Atlantic Drive, KEY LARGO

$2,199,999

34 Atlantic Drive, KEY LARGO

5 Beds 4 Baths 1,440 SqFt Residential MLS® # 613125

RE/MAX All Keys Real Estate

1409 Truman Avenue, KEY WEST

$1,599,000

↓ $100,000

1409 Truman Avenue, KEY WEST

3 Beds 5 Baths 1,932 SqFt Residential MLS® # 613108

Truman & Co. (KW)

405 Petronia Street, KEY WEST

$2,999,999

405 Petronia Street, KEY WEST

2 Beds 4 Baths 1,596 SqFt Residential MLS® # 613064

Saltwater Real Estate Florida Keys, Inc

928 Truman Avenue 101, KEY WEST

$1,800,000

928 Truman Avenue 101, KEY WEST

8 Beds 5 Baths 1,830 SqFt Residential MLS® # 613024

Preferred Properties (KW)

225 Pescayo Avenue, MARATHON

$936,000

225 Pescayo Avenue, MARATHON

6 Beds 2 Baths 2,072 SqFt Residential MLS® # 613021

Coldwell Banker Schmitt Real Estate Co.

85 Coco Plum Drive, MARATHON

$936,000

85 Coco Plum Drive, MARATHON

6 Beds 4 Baths 2,027 SqFt Residential MLS® # 613002

Coldwell Banker Schmitt Real Estate Co.

83 Coco Plum Drive, MARATHON

$936,000

83 Coco Plum Drive, MARATHON

6 Beds 4 Baths 2,072 SqFt Residential MLS® # 612991

Coldwell Banker Schmitt Real Estate Co.

737 Olivia Street, KEY WEST

$1,650,000

737 Olivia Street, KEY WEST

3 Beds 3 Baths 1,860 SqFt Residential MLS® # 612943

Berkshire Hathaway Knight & Gardner

82 N Conch Avenue, Conch

$900,000

82 N Conch Avenue, Conch

6 Beds 4 Baths 2,704 SqFt Residential MLS® # 612942

Coco Plum Real Estate

1621 Josephine Street, KEY WEST

$1,701,000

1621 Josephine Street, KEY WEST

8 Beds 4 Baths 3,200 SqFt Residential MLS® # 612909

Key West Realty, LLC (KW)


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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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