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
316 E Seaview Drive, Duck

$2,499,000

316 E Seaview Drive, Duck

4 Beds 3 Baths 2,378 SqFt Residential MLS® # 618203

All American Realty LLC

New
1998 Overseas Highway A22, MARATHON

$861,000

1998 Overseas Highway A22, MARATHON

3 Beds 2 Baths 1,650 SqFt Residential MLS® # 618201

Coldwell Banker Schmitt RE Co.

New
166 Airstream Lane, Tavernier

$879,000

166 Airstream Lane, Tavernier

2 Beds 2 Baths 1,220 SqFt Residential MLS® # 618200

Coldwell Banker Schmitt Islamorada

New
79901 Overseas Highway 204, ISLAMORADA

$590,000

79901 Overseas Highway 204, ISLAMORADA

2 Beds 2 Baths 981 SqFt Residential MLS® # 618199

Venture Realty Group

New
304 Melaleuca Street, Duck

$14,975,000

304 Melaleuca Street, Duck

5 Beds 6 Baths 6,391 SqFt Residential MLS® # 618198

Florida Keys Real Estate Group

New
3605 Eagle Avenue, KEY WEST

$2,395,000

3605 Eagle Avenue, KEY WEST

4 Beds 4 Baths 2,390 SqFt Residential MLS® # 618197

Ocean Sotheby's International Realty

New
200 5th Street, KEY COLONY

$1,590,000

200 5th Street, KEY COLONY

3 Beds 4 Baths 2,400 SqFt Residential MLS® # 618196

Berkshire Hathaway HomeServices Keys Real Estate

New
317 E Seaview Drive 1, Duck

$2,400,000

317 E Seaview Drive 1, Duck

4 Beds 4 Baths 3,172 SqFt Residential MLS® # 618195

Trustpoint Realty, LLC

New
1113 Watson Street, KEY WEST

$1,455,000

1113 Watson Street, KEY WEST

5 Beds 4 Baths 1,819 SqFt Residential MLS® # 618193

Lokation Real Estate

New
24 Tamarind Drive, Big Coppitt

$1,399,999

24 Tamarind Drive, Big Coppitt

2 Beds 2 Baths 1,275 SqFt Residential MLS® # 618192

Internet Realty of the Florida Keys

New
1113 Watson Street, KEY WEST

$1,455,000

1113 Watson Street, KEY WEST

5 Beds 4 Baths 1,819 SqFt Residential MLS® # 618191

Lokation Real Estate

New
114 Mockingbird Lane, MARATHON

$1,749,000

114 Mockingbird Lane, MARATHON

3 Beds 2 Baths 1,462 SqFt Residential MLS® # 618189

FlatFee.com

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
1113 Watson Street, KEY WEST

$1,455,000

1113 Watson Street, KEY WEST

5 Beds 4 Baths 1,819 SqFt Residential MLS® # 618191

Lokation Real Estate

New
1306 &1308 51st Street Gulf, MARATHON

$1,050,000

1306 &1308 51st Street Gulf, MARATHON

4 Beds 2 Baths 1,568 SqFt Residential MLS® # 618176

Coldwell Banker Schmitt Real Estate Co.

New
1614 Dennis Street, KEY WEST

$1,499,000

1614 Dennis Street, KEY WEST

7 Beds 4 Baths 2,699 SqFt Residential MLS® # 618151

Ocean Sotheby's International Realty

New
908 66th Street, MARATHON

$785,000

908 66th Street, MARATHON

4 Beds 3 Baths 2,074 SqFt Residential MLS® # 618129

American Caribbean Real Estate, Christie's International Real Estate

668 & 670 89th Street Ocean, MARATHON

$1,750,000

668 & 670 89th Street Ocean, MARATHON

4 Beds 4 Baths 2,016 SqFt Residential MLS® # 618025

Lokation Real Estate

500 22nd St Ocean 1-4, MARATHON

$1,249,000

500 22nd St Ocean 1-4, MARATHON

8 Beds 4 Baths 2,780 SqFt Residential MLS® # 618043

Coldwell Banker Schmitt Real Estate Co.

621 Elizabeth Street, KEY WEST

$1,699,000

621 Elizabeth Street, KEY WEST

3 Beds 2 Baths 1,594 SqFt Residential MLS® # 618032

Truman & Co. (KW)

3707 Paula Avenue, KEY WEST

$950,000

3707 Paula Avenue, KEY WEST

3 Beds 3 Baths 1,552 SqFt Residential MLS® # 617985

Robert H Cardenas Jr., PA

31034 Hollerich Drive, Big Pine

$899,000

31034 Hollerich Drive, Big Pine

4 Beds 2 Baths 1,460 SqFt Residential MLS® # 617907

Action Keys Realty of the Lower FL Keys LLC

574-576 99th Street, MARATHON

$1,700,000

574-576 99th Street, MARATHON

4 Beds 4 Baths 1,854 SqFt Residential MLS® # 617878

Continental Real Estate Group, Inc.

114 N North Mrytle Street 32948, OTHER

$565,000

114 N North Mrytle Street 32948, OTHER

2 Beds 2 Baths 3,038 SqFt Residential MLS® # 617858

Lokation Real Estate

1209 Pearl Street, KEY WEST

$1,249,000

1209 Pearl Street, KEY WEST

3 Beds 2 Baths 1,395 SqFt Residential MLS® # 617855

Berkshire Hathaway HomeServices Knight & Gardner Realty


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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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