Four Winds vacation rentals

We found 14 vacation rentals — enter your dates for availability

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Four Winds

Why visit Four Winds

  • Beautiful Beaches: Enjoy relaxing days on stunning beaches, perfect for sunbathing and water activities.
  • Rich History: Explore historic buildings and charming neighborhoods that showcase St. Augustine's storied past.
  • Outdoor Experiences: Discover nearby national parks offering hiking, wildlife viewing, and scenic landscapes.
  • Family-Friendly Atmosphere: Engage in activities suitable for all ages, making it ideal for family vacations.
  • Diverse Accommodations: Choose from a variety of vacation rentals, including oceanfront homes and cozy condos.

Popular types of accommodation around Four Winds

Four Winds offers a variety of vacation rental options tailored to your needs. Whether you prefer the spaciousness of houses, the convenience of condos, or the comfort of apartments, we have you covered. Popular choices include oceanfront rentals and townhouse condos, ensuring you enjoy beachfront access and stunning views. Discover the perfect accommodation for your getaway and experience the best that Four Winds has to offer.

  • Houses: The top choice for visitors in Four Winds, offering spacious accommodations perfect for families or groups seeking privacy and comfort.
  • Condos: A popular option, these modern units provide amenities and proximity to the beach, ideal for those who enjoy convenience.
  • Apartments: Great for solo travelers or couples, these cozy spaces offer all the essentials for a comfortable stay.
  • Cottages: Charming and often quaint, cottages provide a unique, homey feel for those wishing to escape the hustle and bustle.
  • Villas: Luxurious and spacious, villas are perfect for travelers looking to indulge in a premium vacation experience.**

Top attractions near Four Winds

Whether you're seeking a relaxing beach day, exploring historic buildings, or enjoying the beauty of a national park, Four Winds in St. Augustine offers a diverse range of attractions. This vibrant area is perfect for travelers looking to immerse themselves in culture and outdoor experiences, making it an ideal destination for both adventure and leisure.

  • St. Augustine Beach: A picturesque beach located 7 miles away, St. Augustine Beach boasts soft sands and vibrant beach vibes. It's perfect for sunbathing, swimming, and enjoying water sports.
  • Matanzas Inlet: Only 2 miles from Four Winds, Matanzas Inlet is a scenic bay offering stunning outdoor views. Ideal for kayaking, fishing, and picnicking, it’s a serene spot to connect with nature.
  • Fort Matanzas National Monument: Just 1 mile away, this historic fort showcases the area's rich culture and history. Visitors can explore its preserved structures and enjoy guided tours of this significant landmark.

Things to do recommended for couples

For a romantic getaway near Four Winds, consider a playful round at Fiesta Falls Mini-Golf, only 8 miles away. Enjoy a wine tasting at the charming San Sebastian Winery, 12 miles away, or embark on an adventurous sea excursion with Sea Love Charters, just 11 miles from your stay.

Things to do recommended for families

Your family vacation in St. Augustine will be filled with fun at Bing's Landing for relaxation, Palm Coast Lanes for arcade adventures, and a sweet treat experience at Whetstone Chocolate Factory. Each location offers a unique atmosphere perfect for creating lasting memories together.

Things to do recommended for groups

Your group can enjoy a round of golf at St. Augustine Shores Golf Club, just 6 miles from Four Winds. Experience live performances at the Saint Augustine Amphitheatre, 10 miles away, and indulge in tastings at the St. Augustine Distillery, located 12 miles from your stay.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Four Winds

When traveling with a group, family, or pets, or if you're seeking extended stays, be sure to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Four Winds with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Four Winds with young kids: Traveling with young kids can be a bit demanding. It's important to prioritize their comfort and safety, along with having suitable amenities, like a private pool. Additionally, it's wise to think about how close you are to attractions that are fun for families.
  • Taking your pets with you to Four Winds: For many families, a trip wouldn't feel complete without their furry companion along for the adventure. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Four Winds: If you're in search of vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Four Winds

Exploring Four Winds in St. Augustine offers a delightful mix of family-friendly vibes and rich history. Just a short walk away, you'll find beautiful beaches perfect for relaxation and fun. The south end of the area boasts charming neighborhoods that reflect the city's storied past, while the historic district invites you to wander through time. Enjoy friendly locals and budget-friendly options as you make unforgettable memories in this enchanting destination.

  • St. Augustine: As the oldest city in the United States, St. Augustine offers a rich tapestry of history, culture, and coastal beauty. Nestled near Four Winds, this vibrant city is perfect for families seeking outdoor adventures and beach experiences. Visitors can explore the historic district, including landmarks like the Castillo de San Marcos and the iconic lighthouse. Enjoy numerous resorts and golf courses, catering to various tastes, while basking in the sun on its beautiful family-friendly beaches. The town's charming neighborhoods invite leisurely strolls, dining, and shopping, making it a must-visit destination.
  • St. Augustine Beach: Located 8 miles from Four Winds, St. Augustine Beach is a picturesque village that promises an unforgettable beach getaway. Known for its stunning coastline and outdoor recreational opportunities, visitors can indulge in sunbathing, swimming, and beach volleyball. The area is dotted with resorts and shopping venues that enhance the city-themed experience. St. Augustine Beach provides a perfect backdrop for families looking to create lasting memories, with its inviting atmosphere and vibrant local community. Don't miss the chance to explore the charming beachside restaurants and shops that add to the local flavor.
  • Crescent Beach: Crescent Beach, a serene neighborhood adjacent to Four Winds, is an ideal destination for those craving a laid-back beach experience. With its inviting sandy shores and outdoor activities, visitors can enjoy everything from sun-soaked relaxation to recreational sports like kayaking and paddleboarding. The area boasts access to resorts and golf options for a leisurely retreat. Its family-friendly beaches and tranquil neighborhoods create a welcoming ambiance, making Crescent Beach a perfect spot for both adventure seekers and those looking to unwind in a peaceful coastal setting.

Best time to go to Four Winds

If you're planning a trip to Four Winds, it's a good idea to check both the weather and property rates. The warmest months are July and August. Peak season runs in March and June to July, while off-peak times, like September to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January58.1°F (14.5°C)Light RainMostly SunnyAverageSlightly Low
February61.0°F (16.1°C)Light RainMostly SunnyAverageSlightly Low
March64.6°F (18.1°C)Light RainMostly SunnyModerately HighSlightly Low
April69.8°F (21.0°C)Light RainMostly SunnyAverageAverage
May75.0°F (23.9°C)Light RainMostly SunnyAverageAverage
June79.9°F (26.6°C)Light RainMostly SunnyModerately HighSlightly High
July81.7°F (27.6°C)Light RainMostly SunnyModerately HighSlightly High
August81.7°F (27.6°C)Light RainMostly SunnyAverageSlightly High
September79.5°F (26.4°C)Light RainMostly SunnyModerately LowAverage
October73.9°F (23.3°C)Light RainMostly SunnyModerately LowAverage
November66.7°F (19.3°C)Light RainMostly SunnyModerately LowAverage
December62.4°F (16.900000000000002°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming travel plans? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that meets your budget, utilize our filters to narrow down your search by price, location, and type of rental. We're here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner truly has its advantages. When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's user-friendly Trip Board offers you a convenient way to plan new trips, pick up right where you left off, or keep track of your travel arrangements. You can easily find the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, just visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

More Vacation Ideas