Fall & Early Winter Escape
November 1 – December 15, 2026
Seven nights for approximately $12,000
Thanksgiving stays approximately $14,000
Taxes and cleaning included. Your private beachfront week awaits.
Seven-night minimum. Subject to availability. Pet fees additional.
Thanksgiving pricing applies November 21–29. Mixed-date stays vary; your exact total is shown when you select dates.
Southwind Islamorada - Private Beachfront Vacation Home
Southwind Islamorada is a private beachfront estate on the Atlantic Ocean in the Florida Keys, accommodating up to ten guests in five bedrooms, each with its own ensuite bathroom and private balcony. The home has six full bathrooms and one half bathroom, an oceanfront infinity pool and spa, a private fishing pier, and spacious outdoor gathering areas.
Enjoy luxury hypoallergenic bed linens, Frette towels, Molton Brown bath amenities, and Dyson hair dryers. A whole-house Sonos sound system, poolside TV, and fully equipped kitchen with high-end appliances and a wine refrigerator bring added comfort to your stay.
From pickleball, mini golf, kayaks, and bikes to thoughtful baby essentials, Southwind welcomes couples and multigenerational families with activities and conveniences for every age. A dedicated property manager is available throughout your stay whenever assistance is needed.
Explore photos, guest reviews, rates, and availability, then book directly with us. Seven-night minimum stay.