Luxury Vacation Rentals with a Private Pool in Islamorada
Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 4 private pool vacation rentals – enter your dates for availability.
Welcome to private poolside luxury in Islamorada
Sink into island living with Wander’s luxury private-pool vacation rentals in Islamorada, Florida. Our handpicked waterfront homes pair crystal-clear views with stunning pools designed for all-day lounging, from lap lanes for morning swims to tropical lagoons framed by palms.
Each residence is operated with hotel-level precision. Expect immaculate housekeeping, 24/7 concierge, ultra fast WiFi, smart-home controls, and spa-grade linens. Slide open glass walls to expansive sun decks, grill at outdoor kitchens, then cool off in your heated pool under starlit skies.
Many homes feature private docks and panoramic terraces, creating a seamless backdrop for work, wellness, and unhurried time together. What you see in the photos is exactly what awaits.
IT'S A VACATION HOME, BUT BETTER
The Wander difference
Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.
All homes in Islamorada
Discover more beyond the pool in Islamorada
Islamorada strings together six storied islands between the Atlantic and Florida Bay, where teal flats meet living coral and sunsets paint the horizon. Snorkel near Alligator Reef Lighthouse, drift over the famed Islamorada Sandbar, kayak to Indian Key, or wander the fossilized coral formations at Windley Key.
Evenings bring a calm rhythm and salt-tinged breezes, with artful touches along Morada Way and a horizon that glows long after dusk. Central to the Upper and Middle Keys, it delivers easy access without losing its intimate, barefoot-elegant spirit. This is why Wander’s luxury vacation rentals in Islamorada, Florida are the perfect choice, whether you’re traveling for work or leisure.