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Florida Keys

Vacation Home Rentals


Welcome to the Private Home Collection, where your dream island vacation becomes a reality. Our luxury Florida Keys vacation rentals are located throughout the most fabulous island destinations, including Key Largo, Islamorada, Duck Key, and Marathon.

Each of these stunning locations offers its own unique charm, from the vibrant coral reefs in Key Largo to the world-class sport fishing in Islamorada. Duck Key provides serene environments for a peaceful retreat, while Marathon boasts beautiful beaches and family-friendly attractions.

Whether you’re seeking adventure, relaxation, or a bit of both, our exquisite homes ensure an unforgettable experience for every type of traveler. Enjoy breathtaking sunsets, crystal-clear waters, and the ultimate in comfort and style.

Special Offers

At KeysCaribbean, we believe that luxury should be accessible. That’s why we offer flexible booking options, whether planning a weekend retreat or a long-term stay, to suit your needs. Take advantage of our special offers and discover how to enjoy a premium vacation without breaking the bank. From advance booking discounts to last-minute deals, we have options that cater to every traveler’s budget.

Book Now, Pay Later

Available any time of year

Reserve the dates of your vacation in advance with a minimal deposit.


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Extend Your Stay at Shady Palms – 50% OFF the 7th Night

Available any time of year

Extend your stay for less with savings of half off the 7th night of your stay!


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Last-Minute Booking Discount – 15% OFF

Available April 12th – May 12th, 2024

Enjoy savings of 15% off your last-minute Florida Keys getaway.


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90-Day Advance Purchase Rate Discount – 15% OFF

Available January 1st – 31st, 2024

Book 90+ days in advance and enjoy savings of 15% off your FL Keys getaway.


Offer Details

Vacation Rentals

Our Florida Keys vacation rentals are designed to provide the ultimate comfort and privacy. Forget the cramped and noisy hotel experience—our homes offer spacious living areas, fully equipped kitchens, and private bedrooms that make you feel right at home. Imagine waking up to the sound of the ocean, enjoying your morning coffee on a private balcony, and ending your day in a cozy, well-appointed bedroom.

Each home offers a unique combination of premium amenities, making it easy to find the ideal home. Whether you prefer a private swimming pool, communal pool and beach access, boat dockage, or luxurious Jacuzzi tubs, we have the perfect property to match your desires.

Enjoy a swim in your private pool, dock your boat just steps from your home, or unwind in a Jacuzzi tub after a thrilling day of island adventures. With such premium amenities, every day of your vacation is filled with opportunities for leisure and enjoyment.

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3BR/3BA Key largo Cottage by the Sea

Sleeps 8 | Weekly Rental

Rates from $1269

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1BR/2BA Key Largo Cottage on the Bay

Sleeps 2 | Monthly Rental

Rates from $250

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2BR/1BA Cottage in Islamorada

Sleeps 4 | Nightly Rental

Rates from $259

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3BR/3BA Duck Key Vacation Home

Sleeps 6 | Monthly Rental

Rates from $165

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3BR/2BA Key Colony Beach Home

Sleeps 8 | Weekly Rental

Rates from $269

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6BR/5BA Pelican’s Nest in Marathon

Sleeps 14 | Weekly Rental

Rates from $849

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3BR/2BA Canalside Home in Marathon

Sleeps 8 | Weekly Rental

Rates from $299

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Frequently Asked Questions

We understand that planning a vacation can come with many questions. That’s why we’ve compiled a list of FAQs to make your experience seamless from start to finish. Our FAQ section covers topics ranging from supplies during your stay to connecting to the private Wi-Fi.