1. USA
  2. Florida
  3. St. Augustine
  4. Winter Rental

Top Rated Activities & Tours in St. Augustine

Medieval Torture Museum with Ghost Hunting and Tiny Art Gallery
Medieval Torture Museum with Ghost Hunting and Tiny Art Gallery
10
Excellent
2011 Reviews
5 star rating Recommendation
From
US $25 Per Person
Reserve
St. Augustine's Wine, Cocktail and Food Experience
St. Augustine's Wine, Cocktail and Food Experience
10
Excellent
1247 Reviews
5 star rating Recommendation
From
US $159 Per Person
Reserve
Sunset Cruise of St. Augustine
Sunset Cruise of St. Augustine
10
Excellent
1232 Reviews
5 star rating Recommendation
From
US $43 Per Person
Reserve
See More Activities & Tours in St. Augustine

St. Augustine Winter Rentals & Holiday Homes

Discover winter rentals St. Augustine - We found 3757 exact matches

About St. Augustine Winter Rental on Varoom

Planning on a winter vacation and need a place to stay in St. Augustine? Discover 3757 places to stay in St. Augustine, for those traveling with their family, friends, or in large groups.

At Varoom, we feature a wide range of listings for accommodations in St. Augustine, FL that are perfect for your winter trip or seasonal escape. Our listings include hotels, private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. Varoom winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Whether you are escaping the snow, or running to it, Varoom can connect you to the best cabins, bungalows, and rent by owner homes as well as best places to stay in both sun and ski resorts. Varoom will make your winter trip memorable.

Varoom offers a great deal for travelers planning on renting a place in St. Augustine, to enjoy these benefits and to book your winter vacation homes, go to Varoom filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around St. Augustine and unlock even more amazing deals.

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Frequently Asked Questions About St. Augustine Winter Rentals

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:

The average cost for winter rentals in St. Augustine is $377 per night. Varoom has a wide list of great winter places to stay near St. Augustine that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in St. Augustine that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in St. Augustine on Varoom

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in St. Augustine to find what works for you.
As of 2026, the data from Varoom shows that there are over 3757 private swimming pools or indoor pools accommodations near St. Augustine along with other great amenities.

About 3757 holiday rentals in St. Augustine boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in St. Augustine for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near St. Augustine with all the best amenities for your next trip.