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
97652 Overseas Highway Hh31, Key Largo

$1,599,000

97652 Overseas Highway Hh31, Key Largo

3 Beds 2 Baths 1,685 SqFt Residential MLS® # 621549

LoKation Real Estate

New
10881 7th Avenue Gulf, Marathon

$1,200,000

10881 7th Avenue Gulf, Marathon

4 Beds 4 Baths 1,888 SqFt Residential MLS® # 621548

Coldwell Banker Schmitt Real Estate Co.

New
5405 3rd Avenue, Stock Island

$469,000

5405 3rd Avenue, Stock Island

3 Beds 3 Baths 1,312 SqFt Residential MLS® # 621546

Coldwell Banker Schmitt Lower Keys (KW)

New
206 Pimlico Lane, Key Largo

$1,300,000

206 Pimlico Lane, Key Largo

3 Beds 2 Baths 1,677 SqFt Residential MLS® # 621545

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

New
1311 Truman Avenue, Key West

$6,449,000

1311 Truman Avenue, Key West

7 Beds 8 Baths 4,306 SqFt Residential MLS® # 621544

Suzanne Moore Real Estate

New
473 W 105th Street Ocean, Marathon

$499,000

473 W 105th Street Ocean, Marathon

2 Beds 2 Baths 1,120 SqFt Residential MLS® # 621543

Island Life Realty Experts

New
107 Azalea Street, Plantation Key

$2,800,000

107 Azalea Street, Plantation Key

5 Beds 3 Baths 1,950 SqFt Residential MLS® # 621542

Still Water Properties

New
1129 Pebble Beach Lane Apt 11, Duck Key

$275,000

1129 Pebble Beach Lane Apt 11, Duck Key

2 Beds 2 Baths 860 SqFt Residential MLS® # 621540

Florida Keys Real Estate Group

New Open House
150 Sabal Avenue, Key Largo

$875,000

150 Sabal Avenue, Key Largo

2 Beds 2 Baths 1,152 SqFt Residential MLS® # 621539

Coldwell Banker Schmitt Key Largo

New
1153 70th Street Gulf, Marathon

$14,999,000

1153 70th Street Gulf, Marathon

6 Beds 7 Baths 6,661 SqFt Residential MLS® # 621538

Coldwell Banker Schmitt Real Estate Co

New
597 Ne 5th Place, Other

$5,000

597 Ne 5th Place, Other

4 Beds 3 Baths 1,700 SqFt Residential MLS® # 621537

Jamie Boone, LLC

New
48 S Andros Road, Key Largo

$3,100,000

48 S Andros Road, Key Largo

4 Beds 1 Bath 3,024 SqFt Residential MLS® # 621536

Centennial Realty Group, LLC

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
10881 7th Avenue Gulf, Marathon

$1,200,000

10881 7th Avenue Gulf, Marathon

4 Beds 4 Baths 1,888 SqFt Residential MLS® # 621548

Coldwell Banker Schmitt Real Estate Co.

New
6415 2nd Terrace, Stock Island

$749,000

6415 2nd Terrace, Stock Island

4 Beds 2 Baths 1,304 SqFt Residential MLS® # 621519

Suzanne Moore Real Estate

New
6359 Hera Street B, Other

$369,999

6359 Hera Street B, Other

4 Beds 4 Baths 1,918 SqFt Residential MLS® # 621505

Delphi Investment Realty

New
1112 Sw 11th Avenue 0, Other

$1,199,000

1112 Sw 11th Avenue 0, Other

5 Beds 3 Baths 1,980 SqFt Residential MLS® # 621503

Delphi Investment Realty

New
5 Hilton Haven Drive, Key West

$1,695,000

5 Hilton Haven Drive, Key West

4 Beds 5 Baths 2,027 SqFt Residential MLS® # 621480

Coldwell Banker Schmitt Real Estate Co. (KW)

New
723 Eaton Street, Key West

$6,450,000

723 Eaton Street, Key West

7 Beds 9 Baths 3,739 SqFt Residential MLS® # 621458

Truman & Co. (KW)

New
646 William Street, Key West

$1,400,000

646 William Street, Key West

3 Beds 2 Baths 1,780 SqFt Residential MLS® # 621406

Coldwell Banker Schmitt Real Estate Co. (KW)

Open House
1030 Snapper Lane, Key Largo

$659,000

↓ $90,000

1030 Snapper Lane, Key Largo

2 Beds 2 Baths 936 SqFt Residential MLS® # 621389

LoKation Real Estate

New
3962-3964 No Name Road, Big Pine Key

$925,000

3962-3964 No Name Road, Big Pine Key

4 Beds 2 Baths 1,536 SqFt Residential MLS® # 621284

Island Real Estate Company Florida Keys

New
220 Angela Street A&b, Key West

$1,999,999

220 Angela Street A&b, Key West

4 Beds 4 Baths 2,342 SqFt Residential MLS® # 621502

USA Trust Realty, Inc.

New
75433 Overseas Highway, Lower Matecumbe

$3,999,000

75433 Overseas Highway, Lower Matecumbe

4 Beds 4 Baths 2,624 SqFt Residential MLS® # 621270

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

Open House
709 Olivia Street, Key West

$1,395,000

709 Olivia Street, Key West

2 Beds 4 Baths 1,092 SqFt Residential MLS® # 621159

Bascom Grooms Real Estate (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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