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Florida Keys

Vacation Home Rentals

Florida Keys Vacation Rentals

Introducing a stunning collection of select Florida Keys vacation rentals! We have beautiful rental homes in the Upper & Middle Keys, including Key Largo, Islamorada, Duck Key, and Marathon. Discover your ideal home, whether it’s a waterfront condo, a charming cottage, or a lavish seaside estate. We offer many options to cater to your desires and surpass your expectations.

Excellent Choice of Amenities

You’ll find a variety of indulgent and lavish amenities to enjoy during your stay at our rental houses. Wake up to the ocean at your bedside, cool off in the freeform swimming pool, and warm back up in the Jacuzzi. Many of our homes also feature water sports equipment, like kayaks and paddle boards, as well as bicycles. Find the perfect vacation rental with amenities like boat dockage, a private putting course, or exclusive beach access.

Vacation Homes For Any Number of Guests

Our homes can accommodate almost any group size. It doesn’t matter if it’s just you and your partner or your whole family for a reunion. Our Florida Keys rentals feature up to an impressive six bedrooms to ensure your privacy and comfort.

Unbeatable Island Locations

Our island locations are second to none. The Florida Keys boasts many unique attractions, such as the only living coral reef in North America. We also have winding waterways through mangrove channels and lush forests with hardwood hammock trees. In addition, there are sandbars close to the shore, perfect for a unique beach-esque experience.

The Florida Keys offers endless exploration opportunities, attracting repeat visitors seeking relaxation and a taste of island living. You can enjoy incredible diving and fishing in Key Largo and Islamorada. Our Duck Key vacation homes offer luxurious stays in a secluded location. Additionally, Marathon Key provides convenient access to popular activities and attractions throughout the island chain.

Regardless of how you prefer to spend your vacation, the Florida Keys are the ideal vacation destination. Picture an afternoon relaxing poolside under the shade of palm-leaf cabanas. You might also enjoy an action-packed day of exciting activities like parasailing or deep-sea fishing.

Special Offers

Seize your chance now to save on an unbeatable vacation experience that you can only have in the Florida Keys!

Discover luxury private homes with KeysCaribbean in the most incredible island locations. Enjoy exclusive amenities and excellent service that goes beyond a typical hotel stay.

Book Now, Pay Later

Available any time of year

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

Offer Details

Last-Minute Booking Discount – 10% OFF

Available November 14th – December 23rd, 2023

Enjoy savings of 10% off your last-minute Florida Keys getaway.

Offer Details

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

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Vacation Rentals

Enjoy a secluded luxury stay at any of our Florida Keys vacation rentals. You’ll find all the comforts of home and more, with private bedrooms, full kitchens, dining areas, and spacious living rooms.

In our Private Home Collection, you can find Florida Keys rentals with fantastic amenities. These include private pools, boat docks, water sports equipment such as kayaks or paddle boards, and more! Find your new second home in the stunning Florida Keys today and see the beauty of the island chain firsthand.


3BR/3BA Key largo Cottage by the Sea

Sleeps 8 | Weekly Rental

Rates from $819

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2BR/1BA Cottage in Islamorada

Sleeps 4 | Nightly Rental

Rates from $269

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3BR/3BA Duck Key Vacation Home

Sleeps 6 | Monthly Rental

Rates from $250.50

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6BR/5BA Pelican’s Nest in Marathon

Sleeps 12 | Weekly Rental

Rates from $1,149

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3BR/2BA Canalside Home in Marathon

Sleeps 6 | Weekly Rental

Rates from $339

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Frequently Asked Questions

Click here to view Frequently Asked Questions & Answers for the Private Home Collection.