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
219 Treasure Harbor Drive, ISLAMORADA

$929,000

219 Treasure Harbor Drive, ISLAMORADA

3 Beds 2 Baths 1,176 SqFt Residential MLS® # 610789

Still Water Properties

3922 Gordon Road, Big Pine

$783,000

3922 Gordon Road, Big Pine

2 Beds 2 Baths 1,040 SqFt Residential MLS® # 608032

Coldwell Banker Schmitt RE Co. Lower Keys Office

New
87200 Overseas Highway N9, ISLAMORADA

$679,000

87200 Overseas Highway N9, ISLAMORADA

2 Beds 2 Baths 1,355 SqFt Residential MLS® # 610788

Century 21 Circle

New
19749 Date Palm Drive, Sugarloaf

$1,649,000

19749 Date Palm Drive, Sugarloaf

0 Beds 3 Baths 2,464 SqFt Residential MLS® # 610786

Brightwild Real Estate

New
45 Coral Way, KEY WEST

$840,000

45 Coral Way, KEY WEST

2 Beds 3 Baths 1,094 SqFt Residential MLS® # 610785

Coldwell Banker Schmitt Real Estate Co. (KW)

New
9 Sombrero Boulevard 202, MARATHON

$499,000

9 Sombrero Boulevard 202, MARATHON

2 Beds 2 Baths 1,001 SqFt Residential MLS® # 610783

Ocean Sotheby's International Realty

New
180 15th Circle, KEY COLONY

$1,200,000

180 15th Circle, KEY COLONY

3 Beds 2 Baths 1,296 SqFt Residential MLS® # 610782

Ocean Sotheby's International Realty

New
11340 6th Avenue Ocean, MARATHON

$1,280,000

11340 6th Avenue Ocean, MARATHON

2 Beds 2 Baths 1,400 SqFt Residential MLS® # 610779

Berkshire Hathaway HomeServices Keys Real Estate

New
88547 Old Highway, Tavernier

$6,500,000

88547 Old Highway, Tavernier

4 Beds 3 Baths 4,103 SqFt Residential MLS® # 610778

Coldwell Banker Schmitt Islamorada

190 Biscayne Boulevard #, ISLAMORADA

$3,600,000

190 Biscayne Boulevard #, ISLAMORADA

3 Beds 2 Baths 2,872 SqFt Residential MLS® # 608307

Coldwell Banker - Pinecrest

New
921 Whitehead Street, KEY WEST

$3,095,000

921 Whitehead Street, KEY WEST

4 Beds 4 Baths 3,009 SqFt Residential MLS® # 610776

Coldwell Banker Schmitt Real Estate Co. (KW)

New
3930 S Roosevelt Boulevard W404, KEY WEST

$620,000

3930 S Roosevelt Boulevard W404, KEY WEST

3 Beds 2 Baths 1,070 SqFt Residential MLS® # 610774

Keller Williams Key West Compass Realty

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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1297/1299 73rd Street Ocean, MARATHON

$1,098,000

1297/1299 73rd Street Ocean, MARATHON

4 Beds 2 Baths 1,536 SqFt Residential MLS® # 610715

Ocean Sotheby's International Realty

105 N Anglers Drive A, MARATHON

$1,800,000

105 N Anglers Drive A, MARATHON

4 Beds 4 Baths 2,752 SqFt Residential MLS® # 610669

Key to the Keys Real Estate, Inc

53 Coral Lane, KEY COLONY

$1,199,000

53 Coral Lane, KEY COLONY

3 Beds 3 Baths 1,428 SqFt Residential MLS® # 610653

Walker Reid Realty

1320 6th Street, KEY WEST

$2,450,000

1320 6th Street, KEY WEST

5 Beds 5 Baths 1,856 SqFt Residential MLS® # 610618

Keller Williams Key West Compass Realty

400 Aronovitz Lane, KEY WEST

$3,750,000

400 Aronovitz Lane, KEY WEST

5 Beds 6 Baths 3,665 SqFt Residential MLS® # 610578

Berkshire Hathaway Knight & Gardner

901 Eisenhower Drive, KEY WEST

$4,975,000

901 Eisenhower Drive, KEY WEST

6 Beds 5 Baths 3,788 SqFt Residential MLS® # 610558

Berkshire Hathaway Knight & Gardner

21540 21470 Overseas Highway, Cudjoe

$14,495,000

21540 21470 Overseas Highway, Cudjoe

31 Beds 19 Baths 0 SqFt Residential MLS® # 610484

Select Properties of NWFL

2421 Fogarty Avenue 1 &2, KEY WEST

$795,000

2421 Fogarty Avenue 1 &2, KEY WEST

4 Beds 2 Baths 1,594 SqFt Residential MLS® # 610466

Coldwell Banker Schmitt Real Estate Co. (KW)

528 Grinnell Street, KEY WEST

$1,599,000

528 Grinnell Street, KEY WEST

3 Beds 2 Baths 2,280 SqFt Residential MLS® # 610346

Keller Williams Key West Compass Realty

23930 Overseas Highway, Summerland

$845,000

↓ $4,000

23930 Overseas Highway, Summerland

3 Beds 3 Baths 1,360 SqFt Residential MLS® # 610335

Expert Realty LLC

235 Antigua Road, KEY LARGO

$475,000

235 Antigua Road, KEY LARGO

5 Beds 4 Baths 3,000 SqFt Residential MLS® # 610294

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

116 N Indies Drive, Duck

$2,095,000

116 N Indies Drive, Duck

4 Beds 4 Baths 2,108 SqFt Residential MLS® # 610110

Florida Keys Real Estate Group


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Pink sunset over waterfront with pier in the Florida Keys

What's my Florida Keys home worth?

Use our Home Evaluation tool to get a free estimated market value of your Florida Keys home. We'll calculate a home valuation based on similar properties in your area.

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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