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Discover Your Perfect St. Augustine Winter Rental

St. Augustine Winter Rental

More Top-Rated Winter Rental in St. Augustine Area

Why Choose Rent By Owner for your St. Augustine Winter Rental?

What makes our Winter Rental special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for St. Augustine Winter Rental

Where are the best neighborhoods to stay in St. Augustine?

When choosing a neighborhood to stay in St. Augustine, you can enjoy the historic charm and vibrant local culture that define this charming city. The downtown area offers close proximity to cultural sites and lively dining options, making it ideal for exploring on foot. Alternatively, beachfront neighborhoods provide a tranquil retreat with stunning ocean views, perfect for relaxing winter getaways.

St. Augustine Historic District

In this area, you can immerse yourself in the charming atmosphere of one of the most historic neighborhoods, offering a perfect setting for winter rentals that combine cultural richness with easy access to local sights.

View 1419+ Rentals in St. Augustine Historic District

Crescent Beach

This seaside neighborhood provides tranquil beachfront settings ideal for winter rentals, allowing you to enjoy scenic ocean views and relaxing strolls along the coast during your stay.

View 697+ Rentals in Crescent Beach

Vilano Beach

Known for its quiet beaches and laid-back vibe, Vilano Beach offers cozy winter rental options that place you close to beautiful shores and outdoor activities.

View 468+ Rentals in Vilano Beach

Downtown Historic District

The vibrant hub of the region, this district features charming streets and historic sites, making it an excellent choice for winter rentals immersed in local culture and entertainment.

View 1849+ Rentals in Downtown Historic District

Butler Beach

A peaceful coastal neighborhood, Butler Beach offers inviting winter rentals with direct access to pristine sands and gentle surf, perfect for a relaxed seaside retreat.

View 1314+ Rentals in Butler Beach

Saint Augustine Shores

Ideal for those seeking a quiet residential area, this neighborhood provides comfortable winter rentals set amid lush landscapes and close-knit communities.

View 25+ Rentals in Saint Augustine Shores

Old Town

Centering around historic charm, Old Town delivers an authentic experience with charming streets and historic architecture, making it a great location for cozy winter rentals.

View 2672+ Rentals in Old Town

St. Augustine South

Offering a suburban ambiance, this area features affordable winter rentals near local parks and amenities, ideal for a comfortable and convenient stay.

View 46+ Rentals in St. Augustine South

Best Times to Visit St. Augustine

When should you plan your Winter Rental stay?

Choosing the right time to visit here can enhance your experience, especially if you're seeking pleasant winter weather and fewer crowds, making it an ideal destination for your winter rentals in this charming region.

Peak Season Highlights

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Spring (March to May)

During the spring months, the area experiences warm weather ideal for outdoor activities, attracting many visitors seeking a vibrant atmosphere and pleasant temperatures.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

Autumn offers mild temperatures and fewer crowds, making it an excellent time to enjoy the region's historic charm and scenic beauty.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Summer (June to August)

The summer months bring hot weather and higher humidity, often resulting in fewer visitors who prefer cooler, more temperate times of year.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 70°F to 75°F
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Winter (December to February)

Winter is considered off-peak, with cooler temperatures that attract those looking for cozy winter rentals and a quieter vacation experience.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 45°F to 55°F

Weekly Weather Forecast for St. Augustine

How to Book Your St. Augustine Winter Rental

What's our booking process?

Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in St. Augustine

More Top-Rated Winter Rental in St. Augustine Area

Common Winter Rental Amenities

What amenities can you expect?

Our Winter Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy private outdoor spaces such as patios or decks to unwind after a day exploring the region.
  • Take advantage of lush gardens or landscaped yards that surround your winter rental for relaxing strolls.
  • Make the most of outdoor dining areas, perfect for enjoying meals in the fresh air under the sun or stars.
  • Relax by a private pool or hot tub, offering a refreshing retreat during the cooler winter months.
  • Benefit from outdoor grilling stations to prepare delicious barbecues with family and friends.
  • Utilize outdoor fire pits for cozy evenings, ideal for storytelling and warmth in the evenings.
  • Explore nearby walking trails or nature paths accessible directly from your vacation home for outdoor adventures.

Top Attractions Around St. Augustine

What attractions are nearby?

During your stay in this destination, you can enjoy a variety of nearby activities such as exploring historic sites, relaxing on scenic beaches, and discovering charming local shops, all within easy reach of your chosen winter rentals in the region.

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Family Activities

  • St. Augustine Historic Tour: Explore the area's rich history and charming architecture on a guided family-friendly tour through this destination's historic district.
  • Marine Science Center: Visit this engaging center where your family can learn about local marine life and enjoy hands-on exhibits that bring the region’s coastal environment to life.
  • Fountain of Youth Archaeological Park: Discover the legends and explore the archaeological sites that highlight the region’s storied past, offering interactive experiences for all ages.
  • Beaches and Water Activities: Relax and have fun at the nearby beaches, where you can build sandcastles or try water sports suitable for the entire family in this popular coastal area.
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Adult Activities

  • Historic Old Town Tour: Explore the charming streets and Spanish colonial architecture that define this area, offering an enriching experience for history enthusiasts.
  • St. Augustine Lighthouse & Maritime Museum: Climb to the top of the lighthouse for panoramic views and learn about the region’s maritime history at the museum nearby.
  • Ghost Tours: Discover the spooky side of the destination with guided ghost tours that delve into its haunted past and legendary local lore.
  • Beach Relaxation: Spend your days unwinding on the sandy shores along here’s coastline, perfect for sunbathing, swimming, or enjoying a seaside stroll.

Other Places to Stay in St. Augustine, FL

St. Johns County
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Anastasia Island
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Downtown Historic District
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St. Augustine Historic District
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Butler Beach
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St. Augustine Beach
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Coquina Gables
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Crescent Beach
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Vilano Beach
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Lincolnville
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Putnam County
Explore 274 Properties
Crescent City
Explore 51 Properties
More Places to Stay Near St. Augustine

St. Augustine Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead Secure your winter rentals early to ensure you have access to the best properties available in this historic destination.
  • Explore Local Cuisine Take time to indulge in the region's culinary offerings, which highlight the area's unique cultural heritage.
  • Visit Historical Sites Incorporate visits to iconic landmarks to enrich your understanding of the area's rich history and architecture.
  • Enjoy the Coastal Atmosphere Spend leisurely days on nearby beaches or waterfront areas to truly experience the region’s scenic beauty.

Transportation Options

  • Rental Cars: Renting a car provides the most flexibility for exploring this destination at your own pace, with numerous local agencies offering convenient options.
  • Public Transit: The area's public transit system includes buses that connect key attractions and neighborhoods, making it an economical choice for getting around.
  • Taxi and Rideshare Services: Taxis and rideshare services like Uber and Lyft operate extensively here, offering quick and reliable transportation for short trips or when traveling without a car.
  • Biking and Walking: Exploring on foot or by bike is a popular way to experience the charm of this region, especially in its historic districts and scenic waterfront areas.

Local Customs Options

  • Greetings and Respectful Addressing: In this destination, it is customary to greet others with a warm smile and a friendly nod, reflecting the area's welcoming spirit.
  • Dress Code for Religious and Historic Sites: When visiting local landmarks or places of worship, modest attire is appreciated, showing respect for the area's rich cultural heritage.
  • Dining Etiquette: At local dining establishments, it is common to wait for the host or hostess to start the meal, and tipping generously is appreciated for good service in this region.
  • Celebration and Festival Participation: Engaging in community festivals and events offers an authentic experience, as participation often involves embracing local traditions and customs.

St. Augustine Winter Rental Frequently Asked Questions

1. What are the top Winter Rentals in St. Augustine?

There are a lot of options in St. Augustine. If you plan on staying in the St. Augustine area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in St. Augustine:

2. How many Winter Rentals are available in St. Augustine?

Currently, the total number of properties listed by RBO in 2026 is over 3684 in the St. Augustine area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in St. Augustine. 

3. What is the cancellation policy for winter rentals in this area?

Cancellation policies vary by property. Please review the specific listing details or contact the owner directly to understand the terms and any applicable fees for cancellations.

4. Are utilities like heating and internet included in the booking price?

Utility inclusion depends on the individual property. Check the listing description or reach out to the host to confirm which utilities are covered during your stay.

5. How do I secure my booking for a winter rental in this destination?

Booking procedures are outlined in the listing, typically requiring a reservation deposit or full payment. For precise steps, refer to the property's booking instructions or contact the owner directly.

6. Is there a minimum stay requirement during the winter season?

Minimum stay requirements depend on the property. Please review the listing details or contact the host to verify the length of stay needed for your reservation.

7. What amenities can I expect at a winter rental here?

Amenities vary among properties but often include essential comforts such as heating, Wi-Fi, and kitchen facilities. For exact amenities offered, consult the individual listing or speak with the property owner.

More Rentals You May Like Near St. Augustine

More Top-Rated Winter Rental in St. Augustine Area