St. Thomas Winter Rentals & Holiday Homes

Discover winter rentals St. Thomas - We found 22 exact matches

Designer Penthouse - Amazing Views & Location
10.0 (51 Reviews)
3 Bedrooms 6 Guests
Annwin Annex
FromUS $90 per night
|
9.8 (16 Reviews)
1 Bedroom 2 Guests
Beach View
FromUS $225 per night
|
9.6 (423 Reviews)
1 Bedroom 2 Guests
Elegant West Coast Townhouse - Private Pool - Ocean Views
8.8 (25 Reviews)
2 Bedrooms 4 Guests
Country Bliss
FromUS $30 per night
7.0 (2 Reviews)
1 Bedroom 2 Guests
Villas & Suites at Beach View
FromUS $432 per night
|
10.0 (25 Reviews)
1 Bedroom 2 Guests
Free loaner car…Paradise get away near beach.
8.0 (2 Reviews)
3 Bedrooms 6 Guests
Coral Lane Beach Apartments
FromUS $136 per night
8.4 (107 Reviews)
1 Bedroom 2 Guests
Angler Apartments
FromUS $120 per night
7.0 (50 Reviews)
1 Bedroom 2 Guests
Welcoming 1-bedroom apartment in St Thomas.
New
1 Bedroom 2 Guests
Luxurious Beachfront Apartment
FromUS $658 per night
10.0 (2 Reviews)
3 Bedrooms 6 Guests
2 bedroom house near a devolping sub urban town
9.0 (4 Reviews)
2 Bedrooms 4 Guests
Take Five Villa with Private Pool And Spacious Patio
4.9 (18 Reviews)
3 Bedrooms 6 Guests

About St. Thomas Winter Rental on Vacation Cottage

At Vacation Cottage, we showcase a diverse array of accommodations in St. Thomas perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, cottages, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.

Vacation Cottage presents luxury options for travelers seeking to rent a place in St. Thomas. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within St. Thomas and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.

Frequently Asked Questions About St. Thomas Winter Rentals

How much does it cost to rent a place to stay near St. Thomas in the wintertime?

The average cost for winter rentals in St. Thomas is $270 per night. Vacation Cottage has a wide list of great winter places to stay near St. Thomas 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. Thomas that allow pets?

Yes, here are the top cottage/chalet rentals in St. Thomas that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in St. Thomas on Vacation Cottage

Do you have any winter rentals in St. Thomas 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. Thomas to find what works for you.

Are there winter accommodations in St. Thomas that have indoor swimming pools?

As of 2026, the data from Vacation Cottage shows that there are over 22 private swimming pools or indoor pools accommodations near St. Thomas along with other great amenities.

Do any winter holiday rentals in St. Thomas have hot tubs?

About 22 holiday rentals in St. Thomas boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Are there luxury winter rentals in St. Thomas?

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