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