Southwind: Beachfront Islamorada Estate | Pool, Spa & Private Beach

Welcome to Southwind, a private beachfront estate in Islamorada designed for families and groups who want the space and amenities of a private resort. Set directly on the Atlantic in Lower Matecumbe Key, this five-bedroom, 6.5-bath home accommodates up to 10 guests and combines panoramic water views with an exceptional collection of indoor and outdoor amenities.

Each of the five bedrooms has its own ensuite bath and private balcony, giving guests both privacy and space to gather. The sleeping layout includes two king bedrooms, one queen bedroom, one room with two twin beds, and one bedroom with two twin beds plus two full bunks.

Outside is where Southwind really stands apart. Spend the day around the infinity pool and spa, relax on the private beach, launch a kayak or paddleboard, or enjoy the many recreation areas throughout the property. Guests also have access to pickleball, a putting and chipping green, mini golf, Pop-A-Shot basketball, ping-pong, cornhole, bicycles, hammocks, a fire pit, and an outdoor shower.

The outdoor entertaining areas are designed for long Florida Keys days and evenings, with an outdoor bar, multiple seating areas, and dining space for up to 12. Large balconies and water views throughout the home make it easy to enjoy the setting whether you are gathering with everyone or finding a quiet place to relax.
Southwind also has a private pier extending into the shallow Atlantic-side water. Please note that the pier is not suitable for docking larger boats. Guests bringing a boat should plan to use a nearby marina or launch facility; Caloosa Cove Marina is approximately two miles away.

The location offers the best of the Upper Keys while still feeling private. Restaurants, fishing, boating, snorkeling, diving and Islamorada attractions are all within easy reach, yet once you return to Southwind, the home feels like its own private resort.

Highlights include:
- Private Atlantic beachfront
- Infinity pool and spa
- 5 bedrooms / 6.5 baths
- Sleeps up to 10 guests
- Ensuite bath and balcony for every bedroom
- Kayaks and stand-up paddleboards
- Pickleball
- Putting and chipping green
- Mini golf
- Pop-A-Shot basketball
- Ping-pong and cornhole
- Bicycles
- Outdoor bar and dining for 12
- Fire pit and hammocks
- Outdoor shower
- Gated property
- Parking for up to six vehicles plus a boat trailer
- One dog permitted with prior approval and applicable fee
Important booking information: Southwind has a 7-night minimum stay. Maximum occupancy is 10 guests. The primary renter must be at least 25 years old. No parties or events are permitted.

Southwind is best suited for guests looking for a high-end Islamorada vacation home where the property itself is part of the vacation—not simply a place to sleep.

Area Information

Southwind is located on Lower Matecumbe Key in Islamorada, one of the most sought-after destinations in the Florida Keys. Known as the “Sportfishing Capital of the World,” Islamorada combines exceptional boating, fishing, snorkeling and diving with excellent restaurants, galleries and a relaxed Keys atmosphere.

The home’s Atlantic-side location offers a peaceful residential setting while keeping guests within easy reach of Islamorada’s restaurants, marinas and attractions. Spend the day snorkeling or diving the nearby reefs, book an offshore or backcountry fishing charter, paddle through the mangroves, or simply explore the islands at an unhurried pace.

Popular nearby experiences include feeding the tarpon at Robbie’s, visiting the History of Diving Museum, exploring local art galleries, enjoying fresh seafood and sunset dining, and taking a boat excursion to the reefs and surrounding waters. Islamorada is also known for its small local restaurants, waterfront bars and laid-back live music.

For guests bringing a boat, Caloosa Cove Marina is approximately two miles from Southwind and offers convenient access to local launching and marina services.
Southwind’s location works especially well for guests who want to enjoy everything Islamorada has to offer during the day, then return to a private beachfront home where the pool, beach and outdoor spaces become the evening’s destination.