Four Winds H8
Ocean Views, Easy Beach Access, Private Balcony, Two Heated Pools, Tennis, Basketball, Free Tickets!
About
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!
**New photos coming November 2026!**
Enjoy the best of coastal living at Four Winds, a welcoming oceanfront community nestled along the beautiful shores of Crescent Beach! Whether you're planning a family beach vacation, a getaway with friends, or a relaxing escape by the sea, this two-bedroom condo offers a comfortable home base for enjoying everything St. Augustine has to offer. Spend your days exploring the beach, lounging by the community pools, or taking advantage of the many recreational amenities just outside your door.
Inside, you'll find a thoughtfully arranged two-story layout with inviting spaces to relax and spend quality time together. The main level features a comfortable living area, a dining space for sharing meals, and a kitchen where you can prepare anything from a quick breakfast before heading to the beach to a homemade dinner after a day of exploring. A convenient half bathroom and an in-unit washer and dryer add to the ease of your stay. Upstairs, you'll find two bedrooms that offer a peaceful place to unwind after sun-filled days, along with two full bathrooms to help make getting ready a breeze.
There's no shortage of ways to enjoy the outdoors at Four Winds! Take a refreshing dip in one of the community's swimming pools, wander along the peaceful walking paths, or challenge your travel companions to a game of tennis, pickleball, basketball, or shuffleboard. When you're ready for some sand between your toes, head through the community's private beach access to Crescent Beach. Known for its soft white sand, natural dunes, and beautiful Atlantic shoreline, it's the perfect place to spend a sunny afternoon swimming, beachcombing, building sandcastles, or simply listening to the waves roll in.
Beyond the beach, you'll find plenty of opportunities to explore the area's unique coastal charm. Historic downtown St. Augustine is approximately a 20-minute drive away, where you can discover centuries of history, browse local boutiques, enjoy waterfront dining, and experience the city's lively atmosphere. Closer to the condo, Matanzas Inlet offers a beautiful setting for fishing, swimming, and enjoying the natural scenery. You can also take a complimentary water taxi across the Intracoastal Waterway to visit historic Fort Matanzas or spend an afternoon exploring the fascinating marine life at Marineland and the scenic grounds of Washington Oaks Gardens State Park.
From peaceful mornings by the shore to afternoons filled with adventure, this Four Winds getaway makes it easy to slow down, soak up the sunshine, and create lasting memories on Florida's beautiful coast. We look forward to welcoming you!
Amenities and Features:
- Fully stocked kitchen
- Dining table
- Smart TVs
- High-Speed WiFi
- Private balcony
- Intracoastal views from entry balcony
- Two heated pools
- 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
-The Fountain of Youth
Additional attractions may be available, so feel free to reach out with any questions!
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. *Decibel levels are monitored at this property to abide by city and county noise ordinances.
No smoking or vaping on the property. $500 fine for rule violation.
Sleeping Arrangements
Bathroom Configuration
Property Rules
Amenities
Map
Frequently Asked Questions
We hope you enjoyed your stay! Check Out Time is at 10:00 AM! But before you leave, be sure to:
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Please empty the refrigerator.
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Place all dirty dishes in the dishwasher and start the cleaning cycle.
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Please do not strip sheets but leave beds unmade.
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Pile all dirty towels in the bathroom or laundry room.
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If you have rearranged any furniture or placed any items out of sight, please put them back as they were when you arrived.
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Please be sure to collect all of your belongings.
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Please remove all trash and place it in the respective trash recepticle.
*Please be considerate of the check out time since the cleaners need to get in to prepare the property for the next guests. A delay in check out will result in a charge of additional fees. Thanks so much and we hope you will come again soon!
Minimum $500 Fee for House Rule Violations
MAINTENANCE
Please report any maintenance needs for the premises to the us and we will respond as quickly as possible. Refunds will not be made for maintenance issues including, but not limited to heating and air conditioning, appliances, televisions, and stereos. Check out instructions as provided must be complied with.
HOLD HARMLESS
Tenant and all other occupants willingly occupy these premises. In exchange for being allowed to occupy the premises, Tenant, on behalf of himself, his heirs, assigns, and descendants, agrees to the fullest extent permitted by law, to release and forever discharge iTrip or the Owner from any and all injuries, costs, damages, loss, death, or other claim or injury suffered of any nature whatsoever arising out of Tenant’s own negligence or gross negligence; the negligence or gross negligence of the Owner or iTrip or any of its employees, managers, principals, owners, representatives, agents, authorities, leaders, or other person affiliated with it in any way; and the negligence or gross negligence of any other occupant in connection with the stay whether that be prior to, during, or immediately after the stay. By agreeing to these terms, and in exchange for being allowed to stay on the premises, you further agree that you will indemnify iTrip and the Owner and hold iTrip and the Owner harmless for any and all injuries, costs, damages, loss, or other claims made by all other occupants other than yourself arising out of or in any way caused by your actions undertaken in the course of your stay on the premises. Tenant understands that he/she does not have to stay on the premises and that without agreeing to these terms whereby he/she chooses voluntarily to waive any liability of iTrip and the Owner under the above terms, he/she will not be allowed to stay on the premises.
Common Areas and Shared Spaces
If your property shares a common indoor or outdoor space, please be respectful of the other tennants in conduct and language.
SUSCRIBE TO TEXT COMMUNICATION
Clicking the box below provides consent to receive text communication from iTrip St. Augustine relating to your reservation. Guests can opt out of this text communication at any time by following specified opt out procedures.
There will also be a $500 fine for smoking or vaping in the home.
Please keep these house rules in mind, thank you!
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Phone (904) 824-9974