The Vacation Rental Management Companies listed below know Islamorada Area, typically have access to dozens of vacation properties, and can assist you in finding the right rental for your vacation.

Not only can you RENT with confidence from these property managers but if you are a property owner these professional companies can MANAGE your property.

In addition, many of these property managers are licensed brokers and real estate agents and can help you BUY and/or SELL a vacation property.

Florida Keys Vacation Rentals
Find Rentals Member Since 2011

Florida Keys Vacation Rentals is one of the largest rental management companies in the Florida Keys and we're dedicated to helping guests find the best vacation home or condo rentals in the Florida Keys. We first help you find your ideal vacation rental property and then ensure that you’ll spend yo...

Vacation Rentals from Florida Keys Vacation Rentals

4BR / 3BA

2BR / 2BA

3BR / 2BA

4BR / 3BA

3BR / 2BA

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292 Rentals Available

Schwartz Vacations
Find Rentals Member Since 2018

The Fabulous Florida Keys -- An Island Paradise You Can Drive To! If you're looking for a quality vacation rental property in the Lower Florida Keys, look no further! Schwartz Vacation Rentals has what you need to ensure a stress-free visit to the Florida Keys: a clean, comfortable rental home or c...

Vacation Rentals from Schwartz Vacations

Cudjoe Key, FL 3 bedroom pet friendly vacation home with pool

3BR / 2BA

2BR / 2BA

3BR / 2BA

2BR / 2BA

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14 Rentals Available

Florida Keys Luxury Rentals
Find Rentals Member Since 2018

Our Luxury Upscale Vacation Rentals includes only the best Accommodations in the Upper Florida Keys. Our inventory includes only the best properties the Upper Florida Keys have to offer. We will do everything to make your luxury vacation relaxing and comfortable. Call or email us with any questi...

Vacation Rentals from Florida Keys Luxury Rentals

5BR / 5BA

3BR / 3BA

4BR / 4BA

5BR / 6BA

4BR / 5BA

3BR / 4BA

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15 Rentals Available

Keys Holiday Rentals
Find Rentals Member Since 2010

Welcome to Keys Holiday Rentals. Established in 2007 we have grown our vacation rental management business due to our reputation for guest satisfaction. The properties we represent offer a variety of amenities in a variety of price ranges. We have experienced rental specialists who know Islamor...

Vacation Rentals from Keys Holiday Rentals

2BR / 2BA

2BR / 2BA

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51 Rentals Available
1 Reviews

Rent My Island
Find Rentals Member Since 2018

Rent My Island has offered vacation rentals to over 25,000 satisfied guests since the 1980's. We offer vacation destinations in the Middle Florida Keys, Florida. Our friendly and knowledgeable Customer Service staff will assist you in selecting the best home for your needs. Waterfront Vacation Hom...

Vacation Rentals from Rent My Island

1BR / 1BA

2BR / 1BA

3BR / 2BA

4BR / 3BA

3BR / 2BA

4BR / 2BA

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21 Rentals Available

Island Villa
Find Rentals Member Since 2018

For more than fifteen years, Island Villa Rentals—with Patti Stanley charting its course—has been the trusted source for Islamorada luxury vacation rentals, Tavernier and Key Largo rentals and destination wedding properties. Known as the "sport fishing capital of the world", Islamorada is a haven f...

Vacation Rentals from Island Villa