Southwind Islamorada

Southwind Islamorada is a private beachfront estate on the Atlantic Ocean in the Florida Keys, offering five bedrooms, six full bathrooms and one half bathroom, and accommodations for up to ten guests. Each bedroom has its own ensuite bathroom and private balcony, giving couples and multigenerational families comfortable spaces to gather and privacy to unwind.

Luxury comforts include hypoallergenic linens on every bed, plus Dyson hair dryers, Molton Brown bath amenities, and Frette towels in each bathroom. A whole-house Sonos sound system lets you enjoy your favorite music, while a poolside TV makes it easy to catch a game or enjoy a show outdoors.

The fully equipped kitchen features high-end appliances, a wine refrigerator, and generous supplies of cookware, serving pieces, and tableware for more than ten. Enjoy leisurely breakfasts, family dinners, and outdoor meals overlooking the ocean.

Outside, enjoy a private beach, oceanfront infinity pool and spa, fishing pier, pickleball, mini golf, Pop-A-Shot basketball, ping-pong, kayaks, and bikes. Spend your days playing together, relaxing by the water, or exploring Islamorada’s fishing, snorkeling, and waterfront dining.

Families traveling with little ones will find a crib, Pack ’n Play, high chair, baby gates, baby bath, and baby monitor provided. A dedicated property manager is available throughout your stay whenever assistance is needed.

Southwind requires a minimum stay of seven nights. The private pier is primarily for fishing; boat access is limited by shallow water and tides. Guests planning to bring a boat should discuss arrangements with us before booking.