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
1511 Johnson Street, KEY WEST

$3,245,000

1511 Johnson Street, KEY WEST

3 Beds 3 Baths 1,615 SqFt Residential MLS® # 616872

Ocean Sotheby's International Realty

New
1625 Patricia Street, KEY WEST

$2,050,000

1625 Patricia Street, KEY WEST

3 Beds 3 Baths 1,839 SqFt Residential MLS® # 616870

Coldwell Banker Schmitt Real Estate Co. (KW)

New
5070 Sunset Village Drive, Duck

$642,000

5070 Sunset Village Drive, Duck

2 Beds 2 Baths 900 SqFt Residential MLS® # 616868

RE/MAX All Keys Real Estate

New
211 120th Street Gulf B, MARATHON

$525,000

211 120th Street Gulf B, MARATHON

2 Beds 1 Bath 728 SqFt Residential MLS® # 616867

Ocean Sotheby's International

New
75433 Overseas Highway, ISLAMORADA

$4,189,000

75433 Overseas Highway, ISLAMORADA

4 Beds 4 Baths 2,024 SqFt Residential MLS® # 616866

FlatFee.com

New
1616 Bertha Street 2, KEY WEST

$1,149,000

1616 Bertha Street 2, KEY WEST

2 Beds 2 Baths 802 SqFt Residential MLS® # 616865

Berkshire Hathaway HomeServices Knight & Gardner Realty

New
808 Virginia Street 4, KEY WEST

$1,150,000

808 Virginia Street 4, KEY WEST

2 Beds 2 Baths 896 SqFt Residential MLS® # 616864

RE/MAX Keys Connection (KW)

New
3312 Northside Drive 707, KEY WEST

$519,000

3312 Northside Drive 707, KEY WEST

2 Beds 2 Baths 696 SqFt Residential MLS® # 616863

Ocean Sotheby's International Realty

New
614 R Santa Anita Lane, KEY LARGO

$1,399,000

614 R Santa Anita Lane, KEY LARGO

3 Beds 3 Baths 1,708 SqFt Residential MLS® # 616862

Century 21 Circle- Islamorada

New
104500 Overseas Highway B102, KEY LARGO

$785,000

104500 Overseas Highway B102, KEY LARGO

2 Beds 2 Baths 1,282 SqFt Residential MLS® # 616861

Coldwell Banker Schmitt Islamorada

New
83201 Old Highway 405, ISLAMORADA

$1,199,000

83201 Old Highway 405, ISLAMORADA

2 Beds 2 Baths 1,275 SqFt Residential MLS® # 616860

Coastal Realty of the Florida Keys

New
153 Apache Street, Tavernier

$699,000

153 Apache Street, Tavernier

2 Beds 2 Baths 1,250 SqFt Residential MLS® # 616859

Palm House Real Estate

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
75433 Overseas Highway, ISLAMORADA

$4,189,000

75433 Overseas Highway, ISLAMORADA

4 Beds 4 Baths 2,024 SqFt Residential MLS® # 616866

FlatFee.com

New
190 & 192 Harborview Drive, Tavernier

$2,650,000

190 & 192 Harborview Drive, Tavernier

2 Beds 1 Bath 776 SqFt Residential MLS® # 616856

Cornell Commercial Real Estate, Inc.

New
3711 Eagle Avenue, KEY WEST

$859,500

3711 Eagle Avenue, KEY WEST

2 Beds 2 Baths 1,464 SqFt Residential MLS® # 616790

Truman & Co. (KW)

New
1011 Truman Avenue, KEY WEST

$1,825,000

1011 Truman Avenue, KEY WEST

2 Beds 3 Baths 1,959 SqFt Residential MLS® # 616774

Berkshire Hathaway HomeServices Knight & Gardner Realty

405 Petronia Street, KEY WEST

$2,999,999

405 Petronia Street, KEY WEST

2 Beds 4 Baths 1,596 SqFt Residential MLS® # 616727

RE/MAX Keys Connection (KW)

1409 Truman Avenue, KEY WEST

$1,299,000

1409 Truman Avenue, KEY WEST

3 Beds 4 Baths 1,932 SqFt Residential MLS® # 613108

Truman & Co. (KW)

251 2nd St, KEY COLONY

$550,000

↓ $25,000

251 2nd St, KEY COLONY

2 Beds 1 Bath 750 SqFt Residential MLS® # 616639

Keller Williams Capital Realty

219 Preston Street, ISLAMORADA

$1,250,000

219 Preston Street, ISLAMORADA

4 Beds 3 Baths 1,766 SqFt Residential MLS® # 616583

Coldwell Banker Schmitt Islamorada

1877-1875 107th Street Gulf, MARATHON

$450,000

1877-1875 107th Street Gulf, MARATHON

4 Beds 2 Baths 1,656 SqFt Residential MLS® # 616478

Truman & Co. (KW)

1433 Sunset Road, Big Pine

$849,000

1433 Sunset Road, Big Pine

4 Beds 3 Baths 1,924 SqFt Residential MLS® # 616469

Action Keys Realty of the Lower FL Keys LLC

1022 Fleming Street, KEY WEST

$2,100,000

1022 Fleming Street, KEY WEST

4 Beds 2 Baths 2,016 SqFt Residential MLS® # 616423

Ocean Sotheby's International Realty

1612 Washington Street, KEY WEST

$1,575,000

1612 Washington Street, KEY WEST

4 Beds 2 Baths 1,760 SqFt Residential MLS® # 616392

Bascom Grooms Real Estate (KW)


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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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