Black Friday sale for 2026 bookings! Ending soon!

We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! See below for more details!

Black Friday Sale! Save on your 2026 reservation when you book during Black Friday weekend!
Escape to paradise at Four Winds D-08, a newly renovated condo in a beautifully maintained oceanfront community. Inside, we provide everything you need for a relaxing stay, a fully stocked kitchen, fresh linens, new furnishings, and charming coastal decor. Step outside to enjoy the pools and quiet walking paths, challenge your group to a friendly match of tennis or pickleball or a game of shuffleboard or basketball. Just a few steps away is your private access to the incredibly soft white sands of Crescent Beach, where you are sure to enjoy the natural dunes, wildlife, surf, and wide spaces to walk, play, or just relax in the sun with family and friends.

The layout is perfect for creating memories together while still having plenty of space. The main floor features an open layout where your group will enjoy delicious meals and great conversation gathered around the dining table, relax on the brand new sofa as you enjoy your favorite shows and movies on the smart TV. Step outside onto your private balcony to sip your morning coffee, breathe in the fresh ocean air, and dine al fresco on the brand new patio furniture. There is a half bathroom and full size washer and dryer conveniently located on the first floor. Upstairs, relaxation awaits in the master suite, which features a king size bed, incredible views, and an attached full bathroom. Down the hall, you will find a full bathroom with a shower tub combo and a second bedroom outfitted with two full size beds.

After enjoying the beach, take in a little history during your stay as all of the sights and activities of Historic St. Augustine are located within a 20 minute drive of the condo. Also, just a few minutes away, enjoy fishing or swimming in the beautiful Matanzas Inlet, take a free water taxi ride to the Matanzas fort on the intracoastal, or spend a day exploring Marineland and Washington Oaks Gardens State Park, one of Florida's hidden treasures of history and nature!

Amenities and Features:

- Fully stocked kitchen

- Dining table

- Smart TVs

- High-Speed WiFi

- Private balcony

- Intracoastal views from entry balcony

- Ocean front pool

- Tennis, basketball, pickleball, shuffleboard (equipment available in the community office)

- Beach towels and chairs

- Full size washer and dryer

- Private beach access

- Free parking

- Keyless entry

Proximity to Area Attractions:

-Downtown St. Augustine 12.8 miles

-St. Augustine Amphitheatre, Alligator Farm, Pier 10.5 miles

-Daytona International Speedway 43.6 miles

-TPC Sawgrass 41.4 miles

-Disney World 116 miles

-Marineland 5.2 miles


Let iTrip help you make the most of your vacation!

Ride the Old Towne Trolley around the area and take in the historic beauty of Downtown St. Augustine! Explore the oldest fort in the continental United States, the Castillo San Marcos, and stroll down colorful St. George Street filled with shops and restaurants of irresistible local flare. You might even spot a Pirate or Spanish Conquistador in period attire! Breathe in the warm, salty air as you enjoy a romantic walk along the waterfront as the sun sets, casting its final rays on the sparkling water, the drifting boats, and the picturesque Bridge of Lions. But don’t forget to make good use of the night by experiencing the Ghost train or Haunted House tour. Enjoy the endless variety of restaurants, coffee shops, ice cream, art, bookstores and more just a short drive away from your front door.
FREE FUN! Each booking will include one free entry per attraction each day of your stay! The following attractions are included:

- St. Augustine Alligator Farm

- St. Augustine Pirate & Treasure Museum

- Old Town Trolley One Day Tour

- Royal St. Augustine Golf & Country Club Course

- Yoga Bohemia St. Augustine: Beach Yoga

Additional attractions may be available, so feel free to reach out with any questions!



NOTE: $500 cancellation fee applies to all bookings 27 days or more.

Startup bathroom, kitchen, and laundry supplies are provided with each booking.

25 year age requirement to book and stay: Tenant must be at least twenty-five (25) years of age (an "adult") and will be an occupant of the unit during the entire reserved dates.

Noise Ordinance: The city of St. Augustine has a noise ordinance that prohibits noise between the hours of 10:00pm-6:00am Sunday-Thursday, and 11:00pm-7:00am Friday-Saturday. Violations can result in a $500 fee.

No smoking or vaping on the property. $500 fine for rule violation.