Luxury Vacation Rentals with a Private Pool in Grassy Key

Discover effortless island living with Wander on tranquil Grassy Key. Our collection of luxury private pool vacation rentals in Grassy Key blends the polish of a five-star hotel with the space and privacy of a coastal home. What you see in the photos is exactly what awaits on arrival.

Unwind beside your own temperature-controlled pool, framed by tropical landscaping and generous sun decks. Many homes offer waterfront settings, outdoor lounges, and breezy balconies for golden-hour views. Expect designer kitchens, plush linens, smart-home ease, and dedicated work-friendly spaces that let you toggle between focus and downtime.

Every stay includes pristine cleaning, ultra fast WiFi, and 24/7 concierge support, so you can simply settle in and enjoy.

Set between Marathon and Long Key, Grassy Key feels like a hidden lane in the Middle Keys, where clear shallows meet swaying pines and endless sky. Sunsets melt into Florida Bay, while sunrise lights the Atlantic a few steps the other way. The vibe is unrushed, salt aired, and wonderfully private.

Days here invite time on the water, from the calm flats and mangrove backcountry to nearby reef access for unforgettable boat days. Explore Curry Hammock State Park’s shoreline, visit the Dolphin Research Center, or cross the Seven Mile Bridge for a scenic drive and big-open-water views.

With natural beauty, easy access, and rare quiet, this is why Wander's luxury private pool vacation rentals in Grassy Key are the perfect choice, whether you're traveling for work or leisure.