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Florida Keys

Vacation Home Rentals

Florida Keys Vacation Rentals

Introducing a stunning collection of select Florida Keys vacation rentals! Our spectacular rental homes are located throughout the Upper & Middle Keys, including Key Largo, Tavernier, Islamorada, Duck Key, and Marathon. Our island locations are home to an incredibly diverse environment, including North America’s only living coral reef, curving waterways through lush mangrove barriers, hardwood hammock forests, sandbars just a short distance offshore, and more marvelous natural features to discover. It’s no wonder why travelers return every year for a taste of the island life and a moment to de-stress. Enjoy world-class diving and sportfishing in Key Largo and Islamorada, a secluded and upscale stay at our Duck Key vacation homes, or a central location to top-rated activities and attractions from Marathon Key. Whether it’s relaxing poolside under the shade of the palm-leaf cabanas or adventurous activities such as deep-sea fishing or parasailing, our Florida Keys rentals are the ideal vacation destination with an abundance of activities to choose from and are sure to satisfy every member of the family. 

There are an exceptional variety of indulgent and lavish amenities to enjoy during your stay at our Florida Keys vacation rentals, such as waterfront views, freeform swimming pools, Jacuzzi tubs, kayaks and paddle boards, deep-water dockage, and more. Whether it’ll just be you and your significant other or you need space for the annual family reunion, our homes come in various sizes to comfortably accommodate all your guests. From waterfront one-bedroom condos and two-bedroom classical Keys cottages to boastful six-bedroom seaside properties with the finest amenities, you will find a holiday home that satisfies all your desires and exceeds your expectations within our Private Home Collection.

Special Offers

Don’t miss your chance to save! Take advantage of one of our limited-time special offers and enjoy an unparalleled vacation experience only found in the Florida Keys. Discover deluxe private home accommodations in the most incredible locations with lavish amenities and outstanding service guaranteed to outshine any traditional 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

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

Last-Minute Booking Discount – 10% OFF

Available July 14th – September 30th, 2023

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

Offer Details

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Vacation Rentals

Enjoy a secluded luxury stay at any of our Florida Keys vacation rentals. Stay comfortably with all the conveniences of home and more, including private bedrooms, full-sized kitchens and dining, and spacious living areas. Within our Private Home Collection, discover an exceptional array of Florida Keys rentals featuring superb amenities such as private swimming pools, boat dockage, watersports equipment including kayaks or paddle boards, or even a private putting course! Discover your new home away from home in the fabulous Florida Keys today and witness the beauty of the island chain for yourself.

Frequently Asked Questions

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