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

Click the links below to sort results by price range.

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New
29859 Overseas Highway A-8, Big Pine

$265,000

29859 Overseas Highway A-8, Big Pine

1 Bed 1 Bath 396 SqFt Residential MLS® # 609762

Coldwell Banker Schmitt RE Co. Lower Keys Office

New
3015 Riviera Drive, KEY WEST

$949,000

3015 Riviera Drive, KEY WEST

3 Beds 3 Baths 1,596 SqFt Residential MLS® # 609763

Expert Realty LLC (HQ)

571 8th Street, KEY COLONY

$2,399,000

571 8th Street, KEY COLONY

5 Beds 4 Baths 2,218 SqFt Residential MLS® # 606381

Coldwell Banker Schmitt Real Estate Co.

New
4 Avenue F, MARATHON

$2,995,000

4 Avenue F, MARATHON

3 Beds 3 Baths 2,177 SqFt Residential MLS® # 609756

Ocean Sotheby's International Realty

New
66 Colson Drive, Cudjoe

$1,495,000

66 Colson Drive, Cudjoe

3 Beds 2 Baths 1,764 SqFt Residential MLS® # 609755

Keller Williams Key West Compass Realty

New
201 Humpty Dumpty Drive, KEY LARGO

$800,000

201 Humpty Dumpty Drive, KEY LARGO

2 Beds 2 Baths 670 SqFt Residential MLS® # 609754

Island Equity Real Estate

New
65821 Overseas Highway 232, Long Key

$395,000

65821 Overseas Highway 232, Long Key

2 Beds 1 Bath 460 SqFt Residential MLS® # 609753

Venture Realty Group

New
1001 W Ocean Drive 1-202, KEY COLONY

$1,095,000

1001 W Ocean Drive 1-202, KEY COLONY

3 Beds 2 Baths 1,352 SqFt Residential MLS® # 609752

Berkshire Hathaway HomeServices Keys Real Estate

New
115 Azalea Street, Tavernier

$2,499,999

115 Azalea Street, Tavernier

5 Beds 3 Baths 2,450 SqFt Residential MLS® # 609751

Golden International Realty

New
103 Azalea Street, Tavernier

$2,499,999

103 Azalea Street, Tavernier

5 Beds 3 Baths 2,450 SqFt Residential MLS® # 609750

Golden International Realty

New
325 Calusa Street 489, KEY LARGO

$1,399,000

325 Calusa Street 489, KEY LARGO

5 Beds 4 Baths 2,134 SqFt Residential MLS® # 609749

RE/MAX All Keys Real Estate

New
1709 Washington Street, KEY WEST

$1,500,000

1709 Washington Street, KEY WEST

2 Beds 2 Baths 1,038 SqFt Residential MLS® # 609748

Preferred Properties (KW)

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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571 8th Street, KEY COLONY

$2,399,000

571 8th Street, KEY COLONY

5 Beds 4 Baths 2,218 SqFt Residential MLS® # 606381

Coldwell Banker Schmitt Real Estate Co.

1205 11th Street, KEY WEST

$1,675,000

1205 11th Street, KEY WEST

4 Beds 3 Baths 1,778 SqFt Residential MLS® # 609691

Bascom Grooms Real Estate (KW)

29528 Constitution Avenue, Big Pine

$1,100,000

29528 Constitution Avenue, Big Pine

4 Beds 4 Baths 1,568 SqFt Residential MLS® # 609612

KeyIsle Realty

1500 Patricia Street, KEY WEST

$1,589,000

1500 Patricia Street, KEY WEST

4 Beds 3 Baths 2,240 SqFt Residential MLS® # 609591

Berkshire Hathaway Knight & Gardner

1101 W Ocean Drive 14, KEY COLONY

$349,000

1101 W Ocean Drive 14, KEY COLONY

2 Beds 2 Baths 990 SqFt Residential MLS® # 609514

Ocean Sotheby's International Realty

329 William Street, KEY WEST

$4,199,000

329 William Street, KEY WEST

6 Beds 7 Baths 2,294 SqFt Residential MLS® # 609512

Island Home Realty Inc.

530 65th Street, MARATHON

$595,000

530 65th Street, MARATHON

4 Beds 2 Baths 1,800 SqFt Residential MLS® # 609490

Coastal Collection Real Estate Inc.

1304 Elizabeth Street, KEY WEST

$1,800,000

1304 Elizabeth Street, KEY WEST

6 Beds 4 Baths 2,050 SqFt Residential MLS® # 609428

Berkshire Hathaway Knight & Gardner

1716 Washington Street 1 & 2, KEY WEST

$1,499,000

↓ $100,000

1716 Washington Street 1 & 2, KEY WEST

3 Beds 3 Baths 1,785 SqFt Residential MLS® # 609263

Beach Club Brokers (KW)

580 & 590 10th Street, KEY COLONY

$3,980,000

580 & 590 10th Street, KEY COLONY

7 Beds 7 Baths 4,478 SqFt Residential MLS® # 609274

Berkshire Hathaway HomeServices Keys Real Estate

10703-05 2nd Avenue Gulf, MARATHON

$450,000

10703-05 2nd Avenue Gulf, MARATHON

2 Beds 2 Baths 916 SqFt Residential MLS® # 609228

Berkshire Hathaway HomeServices Keys Real Estate

1216 Virginia Street, KEY WEST

$2,200,000

1216 Virginia Street, KEY WEST

4 Beds 5 Baths 1,944 SqFt Residential MLS® # 609213

Truman & Co. (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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