This page is dedicated to Florida Keys homes, condominiums and any other property type that allows rentals of less 7 nights or less. With such flexible rental restrictions these properties rent throughout the year and often have a profitable income revenue stream. 

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. 

Rental Investments

Click the links below to sort results by price range.

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• Under $100,000
• $100,000 - $200,000
• $200,000 - $300,000
• $300,000 - $400,000
• $400,000 - $500,000
• $500,000 - $600,000
• $600,000 - $700,000
• $700,000 - $800,000
• $800,000 - $900,000
• $900,000 - $1,000,000
• Over $1,000,000

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$29,750,000

141 Cortez Drive, ISLAMORADA

10 Beds 11 Baths 3,772 SqFt Residential MLS® # 604054

Ocean Sotheby's International Realty

$20,000,000

1565 Ocean Bay Drive, KEY LARGO

3 Beds 3 Baths 1,849 SqFt Residential MLS® # 607064

Ocean Sotheby's International Realty

$19,990,000

87429 Old Highway, ISLAMORADA

6 Beds 7 Baths 6,602 SqFt Residential MLS® # 607350

The Firm Realty Group

$19,200,000

2405 Coco Plum Drive, MARATHON

6 Beds 7 Baths 18,763 SqFt Residential MLS® # 606843

M & M Realty Investors LLC

$19,000,000

180 Galleon Road, ISLAMORADA

6 Beds 9 Baths 7,160 SqFt Residential MLS® # 607298

Coldwell Banker Schmitt Islamorada

$17,999,900

1300 Sunset Boulevard, Summerland

6 Beds 8 Baths 7,720 SqFt Residential MLS® # 605262

Truman & Co. (KW)

$17,999,000

57 Garden Cove Drive, KEY LARGO

5 Beds 6 Baths 5,113 SqFt Residential MLS® # 606406

Ocean Sotheby's International Realty

$15,000,000

21540 21470 Overseas Highway, Cudjoe

31 Beds 19 Baths 0 SqFt Residential MLS® # 605173

Select Properties of NWFL

$14,500,000

87895 Old Highway, ISLAMORADA

5 Beds 8 Baths 9,011 SqFt Residential MLS® # 606146

Coldwell Banker Schmitt Real Estate Co.

$14,000,000

83283 Old Highway, ISLAMORADA

7 Beds 9 Baths 6,696 SqFt Residential MLS® # 606946

Coldwell Banker Schmitt Islamorada

$13,895,000

10001 Gulf Of Mexico Boulevard, MARATHON

5 Beds 7 Baths 4,187 SqFt Residential MLS® # 604560

Premiere Plus Realty Company

$11,900,000

89401 Old Highway, ISLAMORADA

8 Beds 8 Baths 6,500 SqFt Residential MLS® # 603960

American Caribbean Real Estate, Christie's International Real Estate

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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.