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
1901 S Roosevelt Boulevard 101s, KEY WEST

$900,000

1901 S Roosevelt Boulevard 101s, KEY WEST

2 Beds 2 Baths 1,099 SqFt Residential MLS® # 610029

Coldwell Banker Schmitt Real Estate Co. (KW)

15800 Old State Road 4a Road 4a, Sugarloaf

$2,499,000

15800 Old State Road 4a Road 4a, Sugarloaf

2 Beds 3 Baths 1,548 SqFt Residential MLS® # 607547

Expert Realty LLC (HQ)

New
3312 Northside Drive 513, KEY WEST

$545,000

3312 Northside Drive 513, KEY WEST

2 Beds 1 Bath 736 SqFt Residential MLS® # 610027

Coastal Collection Real Estate Inc.

New
61 Jean La Fitte Drive, KEY LARGO

$1,249,900

61 Jean La Fitte Drive, KEY LARGO

3 Beds 2 Baths 1,744 SqFt Residential MLS® # 610026

Coldwell Banker Schmitt Key Largo

New
1596 Buttonwood Drive, Big Pine

$775,000

1596 Buttonwood Drive, Big Pine

2 Beds 2 Baths 951 SqFt Residential MLS® # 610025

Berkshire Hathaway Knight & Gardner

New
132 E Cahill Court, Big Pine

$1,130,000

132 E Cahill Court, Big Pine

3 Beds 2 Baths 1,388 SqFt Residential MLS® # 610023

Coldwell Banker Schmitt RE Co. Lower Keys Office

New
46 Mutiny Place, KEY LARGO

$925,000

46 Mutiny Place, KEY LARGO

3 Beds 2 Baths 1,418 SqFt Residential MLS® # 610022

American Caribbean Real Estate, Christie's International Real Estate

New
153 Venetian Way, ISLAMORADA

$1,375,000

153 Venetian Way, ISLAMORADA

4 Beds 3 Baths 2,304 SqFt Residential MLS® # 610021

American Caribbean Real Estate, Christie's International Real Estate

New
325 Calusa Street 122, KEY LARGO

$349,000

325 Calusa Street 122, KEY LARGO

2 Beds 1 Bath 300 SqFt Residential MLS® # 610019

RE/MAX All Keys Real Estate

New
88500 Overseas Highway 326, Tavernier

$725,000

88500 Overseas Highway 326, Tavernier

2 Beds 2 Baths 1,148 SqFt Residential MLS® # 610018

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

New
11600 1st Ave Gulf 23, MARATHON

$1,150,000

11600 1st Ave Gulf 23, MARATHON

3 Beds 3 Baths 1,600 SqFt Residential MLS® # 610017

Coco Plum Real Estate

New
206 Southard Street 8, KEY WEST

$799,000

206 Southard Street 8, KEY WEST

1 Bed 1 Bath 513 SqFt Residential MLS® # 610015

Expert Realty LLC (HQ)

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
29654 Constitution Avenue, Big Pine

$799,000

29654 Constitution Avenue, Big Pine

4 Beds 2 Baths 1,547 SqFt Residential MLS® # 609978

Ocean Sotheby's International Realty

New
1724 Bahama Drive, KEY WEST

$1,299,000

1724 Bahama Drive, KEY WEST

4 Beds 4 Baths 1,725 SqFt Residential MLS® # 609972

Saltwater Real Estate Florida Keys, Inc

New
2514 Staples Avenue, KEY WEST

$1,350,000

2514 Staples Avenue, KEY WEST

4 Beds 2 Baths 2,174 SqFt Residential MLS® # 609960

Expert Realty LLC (HQ)

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


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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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