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, A Pirate’s Paradise, a beachfront retreat ideally situated where the Atlantic Ocean meets the St. Augustine Inlet. Your beach dreams are sure to come true here, where the fun and adventure of the ocean waves coexist with the calm waters of the Inlet. Imagine sipping your coffee as you watch the sunrise each morning, spending the afternoons lounging around the private dipping pool, and the evenings stargazing from the spacious balconies - be on the lookout for dolphins splashing by in the distant glow of the St. Augustine Lighthouse and you may even experience a rocket launch.

You are sure to rest well in the five spacious bedrooms, including two king suites, both of which have full en suite bathrooms, and one is also equipped with a kitchenette and desk. Gather together to prepare your favorite meals in the fully stocked kitchen and enjoy them seated at one of the dining tables. Grab a cozy seat and enjoy your favorite shows and movies on the large smart TV in the living room. The four and a half bathrooms provide plenty of storage space and are equipped with soft white towels. The elevator makes moving through the spacious home a breeze.

Key Features:
- Beachfront home
- Ideally located where the waves of the ocean meet the calm inlet waters
- Short walk to restaurants, shopping, bars, and more
- Stunning views
- Private dipping pool - a small pool, ideal for cooling off in the warm Florida sun
- Two spacious balconies
- Fully stocked kitchen
- Full size washer and dryer
- Elevator access
- TVs in the living room and bedrooms
- WiFi
- Propane grill
- Parking for 6 vehicles

Located on breathtaking wide Vilano Beach where the ocean meets the St. Augustine Inlet and you can view historic downtown from the beach. This area is perfect for surfing, swimming, and exploring the natural surroundings. Just a short walk away, stroll down palm tree lined Vilano Road along sea colored sidewalk pavers to the Vilano Pier, which offers beautiful sunset views across the river to Historic St. Augustine. You can also fish off the Pier. On your way back through the Art Deco Florida Vernacular styled Vilano Beach Town Center, stop in for a great meal at one of five local restaurants ranging from pizza to Chinese to Italian to seafood. Or pick up everything you need to prepare meals at home at the Publix Grocery, which includes a deli, liquor store, and a pharmacy.

This stunning home is new to iTrip St. Augustine, but it is not new to the rental market. For a limited time, guests who have stayed at this home in the past 2 years can enjoy 10% off their next stay when booking again! Check out what past guests have loved about their stay:

Leigh C. - May 2025
We loved the location and beautiful views of this house! It's so nice to stay on the beach, but only be 10 minutes away from historic downtown! It's the best of both worlds....the beach and historic St. Augustine! This was the perfect house for a large family plus a few friends. The kitchen and seating areas were very accommodating. The beds were all very comfortable. It was also a huge plus to have an elevator!!!

Ryan S. - April 2025
Great location and clean home.

Sheryl T. - Dec 2024
This was our second visit to Pirate’s Paradise. We had a wonderful time. Beach is out the front door, porches to watch the sun rise or a rocket launch, more than enough room for all of us. Great vaca!!!

Ashley A. - Oct 2024
The pictures do not do justice. This home was absolutely gorgeous. Just steps from with beach with easy access. Very large home. We had 7 in our group and could have easily had more guests.

Alison V. - Aug 2024
This is our second time staying at this home and we LOVE it! From the view, beach access, the pool and super comfy beds and pillows. We hope to save up and be able to stay again next year!

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For safety and security purposes this property is equipped with a cameras in the front yard overlooking the driveway, under the home where cars are parked, on the second-story balcony overlooking the driveway, front yard, and door access points, and on the third-floor balcony overlooking the front yard and door access points.

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While in St. Augustine, enjoy all of the attractions the area has to offer, and take advantage of free tickets included with this rental. Ride the Old Town 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 galleries and bookstores just a few miles from your front door!

Let iTrip help you make the most of your vacation.
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.