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
17054 Coral Drive, Sugarloaf

$2,350,000

17054 Coral Drive, Sugarloaf

4 Beds 3 Baths 2,422 SqFt Residential MLS® # 609922

Truman & Co. (KW)

New
92 Coral Way, KEY LARGO

$899,000

92 Coral Way, KEY LARGO

2 Beds 2 Baths 826 SqFt Residential MLS® # 609920

American Caribbean Real Estate, Christie's International Real Estate

New
2000 Coco Plum Drive 806, MARATHON

$775,000

2000 Coco Plum Drive 806, MARATHON

2 Beds 2 Baths 1,056 SqFt Residential MLS® # 609919

Coldwell Banker Schmitt Real Estate Co.

New
96000 Overseas Highway P4, KEY LARGO

$879,900

96000 Overseas Highway P4, KEY LARGO

2 Beds 2 Baths 1,229 SqFt Residential MLS® # 609918

American Caribbean Real Estate, Christie's International Real Estate

New
500 Burton Drive 3314, Tavernier

$759,000

500 Burton Drive 3314, Tavernier

2 Beds 2 Baths 841 SqFt Residential MLS® # 609917

American Caribbean Real Estate, Christie's International Real Estate

New
174 Westminster Drive, Tavernier

$1,989,000

174 Westminster Drive, Tavernier

3 Beds 2 Baths 1,648 SqFt Residential MLS® # 609916

American Caribbean Real Estate, Christie's International Real Estate

New
325 Calusa Street 94, KEY LARGO

$439,900

325 Calusa Street 94, KEY LARGO

2 Beds 2 Baths 315 SqFt Residential MLS® # 609915

TruRes Real Estate, Inc.

New
873 Hawksbill Lane, Sugarloaf

$999,999

873 Hawksbill Lane, Sugarloaf

3 Beds 2 Baths 1,467 SqFt Residential MLS® # 609912

Sunshine State Realty Services

220 8th Street, KEY COLONY

$640,000

220 8th Street, KEY COLONY

2 Beds 2 Baths 1,144 SqFt Residential MLS® # 609345

Coldwell Banker Schmitt Real Estate Co.

New
920 S Silver Circle, KEY LARGO

$495,000

920 S Silver Circle, KEY LARGO

2 Beds 2 Baths 1,076 SqFt Residential MLS® # 609911

Lokation Real Estate - Tavernier

New
30958 Nathalie Road, Big Pine

$350,000

30958 Nathalie Road, Big Pine

2 Beds 1 Bath 384 SqFt Residential MLS® # 609910

Keys Realty Redefined LLC

New
121 Gulfwinds Lane, MARATHON

$1,675,000

121 Gulfwinds Lane, MARATHON

3 Beds 2 Baths 1,685 SqFt Residential MLS® # 609909

Coldwell Banker Schmitt RE Co. Lower Keys Office

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

Sort by:
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

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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