Tradewinds vacation rentals

We found 20 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 Tradewinds

Why visit Tradewinds

  • Beautiful Beaches: Enjoy stunning beach views and soft white sands at the picturesque Crescent Beach, perfect for relaxation.
  • Outdoor Adventures: Explore nearby national and state parks, offering exciting opportunities for hiking and scenic coastal views.
  • Rich History: Discover historic houses and cultural sites that reflect the area's vibrant heritage and history.
  • Family-Friendly Atmosphere: Experience a welcoming environment ideal for solo travelers, families, and groups alike.
  • Diverse Accommodation: Choose from a variety of vacation rentals, including cozy oceanfront condos and spacious homes.

Popular types of accommodation around Tradewinds

Tradewinds offers a fantastic selection of vacation rentals, including houses, condos, and apartments. Whether you're seeking a cozy oceanfront condo or a spacious Tradewinds condominium, we have options to suit every traveler's needs. Our platform provides transparent information, ensuring you find the perfect Tradewinds vacation rental for a memorable getaway. Explore your choices and discover the ideal spot for your next adventure.

  • Houses: The top choice for visitors in Tradewinds, ideal for families or groups seeking a spacious and comfortable stay.
  • Condos: A popular option for those wanting modern amenities and a community feel, often located near the beach.
  • Apartments: A great selection for solo travelers or couples, offering convenience and easy access to local attractions.
  • Cottages: Charming and cozy, these rentals provide a quaint atmosphere perfect for a relaxing getaway.
  • Villas: Luxurious and spacious, villas are perfect for travelers looking for upscale accommodations with plenty of privacy.**

Top attractions near Tradewinds

Tradewinds, St. Augustine offers a delightful mix of attractions for every type of traveler. From beautiful beaches to the nearby national and state parks, you can enjoy outdoor adventures and stunning coastal views. History enthusiasts will appreciate the historic houses that reflect the area's rich culture. Whether you're traveling solo, with family, or in a group, there's plenty to explore to make your visit memorable.

  • St. Augustine Beach: A beautiful stretch of sandy shore, perfect for sunbathing and swimming. Enjoy the vibrant beach vibes while savoring fresh seafood at nearby restaurants. It’s only 6 miles from Tradewinds, making it an easy and relaxing getaway.
  • Matanzas Inlet: A picturesque bay offering stunning views and outdoor activities. Located 3 miles away, it’s ideal for kayaking, fishing, and enjoying the scenic beauty of the coastline.
  • Anastasia State Park: A stunning national park 9 miles from Tradewinds, featuring diverse wildlife, hiking trails, and beautiful beaches. Perfect for adventure seekers wanting to explore the great outdoors.

Things to do recommended for couples

Looking for a romantic getaway in St. Augustine? Enjoy a fun round at Fiesta Falls Mini-Golf, sip fine wines at San Sebastian Winery, or embark on an adventurous Sea Love Charter. These local experiences will surely create unforgettable memories for you and your partner.

Things to do recommended for families

Families will love exploring Bing's Landing, just 9 miles from Tradewinds, for a relaxing day outdoors. Enjoy arcade fun at Palm Coast Lanes, located 13 miles away, or indulge in sweet treats at the Whetstone Chocolate Factory, only 11 miles from your stay.

Things to do recommended for groups

Enjoy a round of golf at St. Augustine Shores Golf Club, just 5 miles away, or immerse yourselves in culture at the Saint Augustine Amphitheatre, 9 miles from Tradewinds. For a unique experience, visit the St. Augustine Distillery, located 11 miles away, and savor local spirits.

*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 Tradewinds

If you're traveling with friends, family, your pets, or planning an extended stay, it's important to prioritize your needs when searching. Here are some helpful Vrbo booking tips for you.

  • Traveling to Tradewinds with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group activities. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Tradewinds with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with having suitable amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly activities.
  • Taking your pets with you to Tradewinds: For many families, a vacation wouldn't feel complete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Tradewinds: If you're in search of vacation rentals offering discounts 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 rental options. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay near Tradewinds

Tradewinds, St. Augustine, Florida, offers a delightful vacation experience with its stunning beach views and beautiful white sands. Travelers can enjoy a relaxing atmosphere in family-friendly neighborhoods, perfect for a memorable getaway. Explore the charming local sites, indulge in the beach experience, and stay in cozy vacation homes. The picturesque Crescent Beach is just a stone's throw away, providing a serene backdrop for relaxation and fun in the sun.

  • St. Augustine: As the oldest city in the United States, St. Augustine is rich in history and charm. Located directly in St. Augustine, Tradewinds offers easy access to this vibrant city filled with family-friendly activities and outdoor adventures. Visitors can explore historic sites like the Castillo de San Marcos, enjoy the beautiful beaches, and indulge in local cuisine at various restaurants. The area is also known for its golf courses and resorts, making it a perfect destination for a leisurely vacation.
  • St. Augustine Beach: Just 7 miles from Tradewinds, St. Augustine Beach is a delightful village perfect for beach lovers. This area is known for its stunning coastline and outdoor recreational opportunities. Visitors can bask in the sun on the sandy shores, partake in water sports, or explore the local shopping areas. The vibrant atmosphere and variety of resorts make it an ideal spot for families and those seeking a relaxing city-themed beach experience.
  • Crescent Beach: Nestled within the Crescent Beach neighborhood, which encompasses Tradewinds, this area boasts a quieter, more laid-back beach experience. Travelers flock here for its pristine beaches and outdoor activities. Popular venues include recreational areas and resorts, perfect for unwinding or enjoying a round of golf. Crescent Beach offers a serene atmosphere while still being close to family-friendly attractions, making it a great spot to explore during your vacation.

Best time to go to Tradewinds

If you're planning a trip to Tradewinds, 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 journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to enjoy even greater savings. To discover a Vrbo property that aligns with your budget, simply utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit for your needs.

Vrbo Trips: Effortless planning

Vrbo's Trip Board is designed to help you plan your travels effortlessly. You can easily create new trips, refine your current plans, or review and manage your bookings all in one place. The properties you’ve saved or booked are conveniently categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

More Vacation Ideas