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
31256 Avenue H, Big Pine

$655,000

31256 Avenue H, Big Pine

3 Beds 2 Baths 1,144 SqFt Residential MLS® # 615160

Coldwell Banker Schmitt RE Co. Lower Keys Office

New
74 Ed Swift Road, Big Coppitt

$699,000

74 Ed Swift Road, Big Coppitt

3 Beds 2 Baths 1,132 SqFt Residential MLS® # 615159

Robert Slack LLC

New
3314 Northside Drive 31, KEY WEST

$474,900

3314 Northside Drive 31, KEY WEST

2 Beds 2 Baths 920 SqFt Residential MLS® # 615158

Sunshine State Realty Services

New
640 Carolyn Avenue, Little Torch

$775,000

640 Carolyn Avenue, Little Torch

2 Beds 2 Baths 848 SqFt Residential MLS® # 615157

Coastal Collection Real Estate Inc.

New
105 Avenue D 101, MARATHON

$559,000

105 Avenue D 101, MARATHON

2 Beds 2 Baths 925 SqFt Residential MLS® # 615156

Coldwell Banker Schmitt Real Estate Co.

New
711 W Indies Drive, Ramrod

$2,499,000

711 W Indies Drive, Ramrod

4 Beds 3 Baths 2,000 SqFt Residential MLS® # 615155

Internet Realty of the Florida Keys

New
15 Garden Cove Drive, KEY LARGO

$750,000

15 Garden Cove Drive, KEY LARGO

3 Beds 2 Baths 1,196 SqFt Residential MLS® # 615153

RE/MAX All Keys Real Estate

New
3312 Northside Drive 407, KEY WEST

$455,000

3312 Northside Drive 407, KEY WEST

2 Beds 2 Baths 696 SqFt Residential MLS® # 615152

Berkshire Hathaway HomeServices Knight & Gardner Realty

New
1025 Elgin Lane, KEY WEST

$1,199,000

1025 Elgin Lane, KEY WEST

2 Beds 2 Baths 1,110 SqFt Residential MLS® # 615151

Island Life Realty Experts

New
75 Pelayo Avenue, OTHER

$2,999,999

75 Pelayo Avenue, OTHER

5 Beds 6 Baths 3,074 SqFt Residential MLS® # 615149

Berkshire Hathaway HomeServices Knight & Gardner Realty

New
577 Boyd Drive, KEY LARGO

$695,000

577 Boyd Drive, KEY LARGO

3 Beds 3 Baths 1,608 SqFt Residential MLS® # 615150

Coldwell Banker Schmitt Key Largo

New
872 La Paloma Road, KEY LARGO

$890,000

872 La Paloma Road, KEY LARGO

3 Beds 2 Baths 1,704 SqFt Residential MLS® # 615148

Ocean Sotheby's International 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
N/A,

$2,200,000

N/A,

4 Beds 4 Baths 3,017 SqFt Residential MLS® # 615113

Engel & Volkers Marathon

New
2394 Coco Plum Drive, MARATHON

$11,000,000

2394 Coco Plum Drive, MARATHON

18 Beds 21 Baths 12,198 SqFt Residential MLS® # 615103

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

620 White Street, KEY WEST

$1,199,000

620 White Street, KEY WEST

3 Beds 2 Baths 1,421 SqFt Residential MLS® # 614993

Berkshire Hathaway HomeServices Knight & Gardner Realty

1030 James Street, KEY WEST

$1,750,000

1030 James Street, KEY WEST

3 Beds 3 Baths 1,700 SqFt Residential MLS® # 614957

Berkshire Hathaway HomeServices Knight & Gardner Realty

5669 Man O War Drive, MARATHON

$2,499,000

5669 Man O War Drive, MARATHON

4 Beds 3 Baths 2,312 SqFt Residential MLS® # 614953

Coldwell Banker Schmitt Real Estate Co.

5331 5th Avenue, KEY WEST

$2,999,000

5331 5th Avenue, KEY WEST

1 Bed 1 Bath 1,200 SqFt Residential MLS® # 614930

ICAMCO Realty LLC, dba Cosgrove Realty

1430 Vernon Avenue, KEY WEST

$12,888,000

1430 Vernon Avenue, KEY WEST

3 Beds 2 Baths 2,071 SqFt Residential MLS® # 614801

Keys Top Realty LLC

708 William Street, KEY WEST

$2,495,000

↓ $204,000

708 William Street, KEY WEST

4 Beds 4 Baths 1,967 SqFt Residential MLS® # 614772

Ocean Sotheby's International Realty

3848 No Name Road, Big Pine

$1,050,000

3848 No Name Road, Big Pine

5 Beds 2 Baths 1,887 SqFt Residential MLS® # 614750

LoKation Real Estate

1205 11th Street, KEY WEST

$1,399,000

↓ $51,000

1205 11th Street, KEY WEST

4 Beds 3 Baths 1,778 SqFt Residential MLS® # 614708

Bascom Grooms Real Estate (KW)

1916 Seidenberg Avenue, KEY WEST

$1,169,900

↓ $25,100

1916 Seidenberg Avenue, KEY WEST

6 Beds 2 Baths 1,694 SqFt Residential MLS® # 614599

Coldwell Banker Realty - Aventura

1821 Harris Avenue, KEY WEST

$1,995,000

↓ $105,000

1821 Harris Avenue, KEY WEST

9 Beds 7 Baths 3,687 SqFt Residential MLS® # 614598

Coldwell Banker Realty - Aventura


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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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