House
10.0(477 Reviews)
2 Bedrooms
5 Guests
Parking
Ocean View
Balcony/Terrace
View
US $500/Night
7 Nights - US $3,500
St. Augustine Winter Rentals & Holiday Homes
Discover winter rentals St. Augustine - We found 4066 exact matches
- Up-front pricing
- No markup
- Trusted partners
Compare Winter Rental in St. Augustine
10.0
House
10.0(6 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
Air Conditioner
US $444/Night
7 Nights - US $3,105
House
4 Bedrooms
14 Guests
US $537/Night
7 Nights - US $3,760
House
10.0(437 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $182/Night
7 Nights - US $1,275
US $437/Night
7 Nights - US $3,059
House
10.0(332 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $214/Night
7 Nights - US $1,497
Apartment
10.0(3 Reviews)
3 Bedrooms
6 Guests
Oceanfront
Hot Tub- Parking
- Ocean View
US $892/Night
7 Nights - US $6,241
Condo
10.0(305 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
Pool- Ocean View
US $202/Night
7 Nights - US $1,417
House
10.0(3 Reviews)
7 Bedrooms
14 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- View
US $844/Night
7 Nights - US $5,910
Villa
10.0(235 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $207/Night
7 Nights - US $1,451
House
10.0(3 Reviews)
1 Bedroom
10 Guests
Private Beach- Oceanfront
- Parking
- Pool
US $441/Night
7 Nights - US $3,089
House
10.0(229 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $294/Night
7 Nights - US $2,060
House
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $229/Night
7 Nights - US $1,603
Condo
10.0(211 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $306/Night
7 Nights - US $2,142
Apartment
10.0(202 Reviews)
1 Bedroom
4 Guests
- Parking
Kitchen- Air Conditioner
Internet
US $308/Night
7 Nights - US $2,157
Condo
10.0(194 Reviews)
2 Bedrooms
4 Guests
Private Pool- Oceanfront
- Parking
- Pool
US $276/Night
7 Nights - US $1,929
![Ocean View Unit 3305 - Ocean & Racquet Resort [20% DISCOUNT ON 7+ NIGHT STAYS]](https://imgservice.bedroomvillas.com/640x287/ocean-view-u-us-st-augustine-beach-ha-3212175711-0.jpg)
Condo
10.0(194 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $167/Night
7 Nights - US $1,166
Condo
10.0(193 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $276/Night
7 Nights - US $1,932
Apartment
10.0(182 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $158/Night
7 Nights - US $1,103
Apartment
10.0(181 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $401/Night
7 Nights - US $2,808
Apartment
10.0(181 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $315/Night
7 Nights - US $2,206
Apartment
10.0(177 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- View
- Kitchen
US $123/Night
7 Nights - US $864
Condo
10.0(170 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $283/Night
7 Nights - US $1,980
Cottage
10.0(160 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $162/Night
7 Nights - US $1,131
About St. Augustine Winter Rental on BedroomVillas
At BedroomVillas, 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 travelers are sure to love. BedroomVillas 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, BedroomVillas helps connect you to the best cabins, bungalows, lodges, and villas, as well as the best places to stay in both sun and ski resorts. BedroomVillas will make your winter getaway an unforgettable experience.
BedroomVillas offers luxury finds for travelers planning on renting a place in St. Augustine, to enjoy these benefits and to book your winter vacation homes, go to the BedroomVillas filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of incredible winter vacation rentals without hassle. Our interactive map is also available, so you can view destinations spanning the globe or around St. Augustine and unlock even more amazing deals. Relax with BedroomVillas.
Winter Rental: Explore Top Destinations
Frequently Asked Questions About St. Augustine Winter Rentals
What are the top rated 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:
- A WOW! Pristine, private oceanfront. Luxury 7 unit boutique bldg. St Aug close
- Oceanfront Luxury Next To St Augustine Center - Quiet Vilano Beach, Dogs Welcome
- GOIN COASTAL Beach House, 3/2, Sleeps 10, 3 min Walk To The Beach
- Spacious and up to date - Flexible dates and prices!
- Gorgeous Direct OCEANFRONT Home - Straight Out of Pottery Barn - 3 Decks/Pool Table - Amazing Views
- Oceanfront Home with Best Views & NEW Pool on the Beach
- 💲Historic Lady💲2 Block Stroll to DT- 3Mi to Beach - Optional Guesthouse
- St Augustine, Remodeled Oceanfront 3-Bedroom with Beautiful Views. Great Deal
- Luxury 8BR Ocean Views, Pool & Heated Spa, Walk to the Beach! 360 Views from Top
- Oceanfront - 3 Bedroom Renovated 1,800 sq ft. + Huge Balcony - Casual Elegance
How much does it cost to rent a place to stay near St. Augustine in the wintertime?
The average cost for winter rentals in St. Augustine is $397 per night. BedroomVillas 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.
Are there any winter cottages/chalets in St. Augustine that allow pets?
Yes, here are the top cottage/chalet rentals in St. Augustine that allow you to bring your pet or dog:
- ~Sea Salt Sanctuary~Plush Beach Refuge~Bikes Kayaks SUPs Fire Pit~
- The Moody Manor -Luxurious Home Recently Renovated Close to Beach and Downtown
- Private Beach Access, Beautiful Ocean Views, Balcony, Brand New Furnishings, $300 in Free Tickets!
- HARBOR ISLAND - A GEM IN THE HISTORIC DISTRICT.
See all pet-friendly vacation rentals in St. Augustine on BedroomVillas
Do you have any winter rentals in St. Augustine that are suitable for families?
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.
Are there winter accommodations in St. Augustine that have indoor swimming pools?
As of 2026, the data from BedroomVillas shows that there are over 4066 private swimming pools or indoor pools accommodations near St. Augustine along with other great amenities.
Do any winter holiday rentals in St. Augustine have hot tubs?
About 4066 holiday rentals in St. Augustine boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in St. Augustine?
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.
