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
101 E Ocean Drive C402, KEY COLONY

$1,950,000

101 E Ocean Drive C402, KEY COLONY

3 Beds 2 Baths 1,716 SqFt Residential MLS® # 609907

Lokation Real Estate

New
589 Powell Avenue, Little Torch

$955,000

589 Powell Avenue, Little Torch

4 Beds 2 Baths 1,568 SqFt Residential MLS® # 609906

Expert Realty LLC (HQ)

New
101 Gulfview Drive 102, ISLAMORADA

$1,100,000

101 Gulfview Drive 102, ISLAMORADA

2 Beds 2 Baths 1,473 SqFt Residential MLS® # 609905

Coldwell Banker Schmitt Islamorada

New
589 Powell Avenue, Little Torch

$1,299,000

589 Powell Avenue, Little Torch

4 Beds 2 Baths 1,568 SqFt Residential MLS® # 609904

Expert Realty LLC (HQ)

New
70 Avenue D, KEY LARGO

$774,900

↑ $200,000

70 Avenue D, KEY LARGO

2 Beds 2 Baths 924 SqFt Residential MLS® # 609902

Ocean Sotheby's International Realty

New
600 12th Street, KEY COLONY

$2,100,000

600 12th Street, KEY COLONY

4 Beds 3 Baths 1,860 SqFt Residential MLS® # 609901

Coldwell Banker Schmitt Real Estate Co.

New
119 W Plaza Del Lago, ISLAMORADA

$4,000,000

119 W Plaza Del Lago, ISLAMORADA

4 Beds 3 Baths 3,000 SqFt Residential MLS® # 609900

Coldwell Banker Schmitt Islamorada

New
30876 Malaga Lane, Big Pine

$695,000

30876 Malaga Lane, Big Pine

2 Beds 2 Baths 1,080 SqFt Residential MLS® # 609894

FlatFee.com

New
21 Riviera Drive, Big Coppitt

$449,000

21 Riviera Drive, Big Coppitt

3 Beds 2 Baths 1,104 SqFt Residential MLS® # 609892

Coastal Collection Real Estate Inc.

New
1001 W Ocean Drive 2-106, KEY COLONY

$695,000

1001 W Ocean Drive 2-106, KEY COLONY

2 Beds 2 Baths 1,352 SqFt Residential MLS® # 609890

Berkshire Hathaway HomeServices Keys Real Estate

New
32029 Marginella Drive, Big Pine

$3,500,000

32029 Marginella Drive, Big Pine

3 Beds 1 Bath 1,020 SqFt Residential MLS® # 609891

Berkshire Hathaway Knight & Gardner

New
616 Caroline Street 6, KEY WEST

$925,000

616 Caroline Street 6, KEY WEST

1 Bed 2 Baths 650 SqFt Residential MLS® # 609889

Bascom Grooms Real Estate (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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New
237 Atlantic Boulevard, KEY LARGO

$2,699,000

237 Atlantic Boulevard, KEY LARGO

7 Beds 4 Baths 3,164 SqFt Residential MLS® # 609804

Ocean Sotheby's International Realty

New
303 Sombrero Beach Road, MARATHON

$1,950,000

↓ $45,000

303 Sombrero Beach Road, MARATHON

4 Beds 4 Baths 2,114 SqFt Residential MLS® # 609802

Ocean Sotheby's International Realty

411 & 415 1st Street, Big Coppitt

$1,400,000

411 & 415 1st Street, Big Coppitt

6 Beds 5 Baths 2,377 SqFt Residential MLS® # 609794

Keller Williams Key West Compass Realty

904 Truman Avenue, KEY WEST

$1,495,000

904 Truman Avenue, KEY WEST

3 Beds 3 Baths 1,150 SqFt Residential MLS® # 609787

Key West Luxury Real Estate Inc (KW)

500 22nd Street Ocean 1-4, MARATHON

$1,599,000

500 22nd Street Ocean 1-4, MARATHON

8 Beds 4 Baths 2,780 SqFt Residential MLS® # 609777

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

$1,675,000

↓ $125,000

1304 Elizabeth Street, KEY WEST

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

Berkshire Hathaway Knight & Gardner


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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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