St. Thomas Winter Rental
House
10.0(70 Reviews)
4 Bedrooms
3 Baths
8 Guests
Private Pool
Oceanfront
Pool
Ocean View
US $579/Night
7 Nights - US $4,052
Apartment
9.9(14 Reviews)
1 Bedroom
1 Bath
2 Guests
495.14 ft²
Skiing
Balcony/Terrace
View
Parking
US $90/Night
7 Nights - US $630
US $293/Night
7 Nights - US $2,054
Apartment
10.0(52 Reviews)
3 Bedrooms
2 Baths
6 Guests
1817 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $711/Night
7 Nights - US $4,979
Apartment
9.6(7 Reviews)
3 Bedrooms
3 Baths
8 Guests
2529.52 ft²
Hot Tub- Balcony/Terrace
- Parking
Air Conditioner
US $203/Night
7 Nights - US $1,421
Villa
10.0(39 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $401/Night
7 Nights - US $2,809
Apartment
8.9(68 Reviews)
6 Bedrooms
4 Baths
6 Guests
748.09 ft²
- Hot Tub
Spa- Pool
- Balcony/Terrace
US $128/Night
7 Nights - US $898
House
10.0(26 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $181/Night
7 Nights - US $1,265
Ski Chalet
7.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
Pet Friendly- Parking
Internet
US $30/Night
7 Nights - US $210
New
Villa
10.0(13 Reviews)
3 Bedrooms
3 Baths
6 Guests
2950 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,215/Night
7 Nights - US $8,502
House
10.0(11 Reviews)
6 Bedrooms
7 Baths
12 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $3,030/Night
7 Nights - US $21,209
New
Villa
10.0(7 Reviews)
4 Bedrooms
1 Bath
8 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,826/Night
7 Nights - US $12,782
Why Choose Rent By Owner for your St. Thomas Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for St. Thomas
How to Book Your St. Thomas 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. Thomas
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
Other Places to Stay in St. Thomas
St. Thomas Parish Church
Bennets
Rock Hall
Bagatelle
Dunscombe
Christie
Durants
Porey Spring
Barbados
Shop Hill
White Hill
Endeavour
Frequently Asked Questions About St. Thomas Winter Rentals
1. What are the top Winter Rentals in St. Thomas?
There are a lot of options in St. Thomas. If you plan on staying in the St. Thomas 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. Thomas:
- New 2-Bedroom Apartment with Swimming Pool
- Affordable Apartment in Holetown St. James
- Apartment in quiet upscale Holetown area near Limegrove Centre and Beach
- Affordable Two Bedroom Two Bathroom Apartment With Private Pool
- #1 in Barbados! Sandy Lane Beach Estate w/50 Foot Pool, Pickleball Court! ★
- Spacious and comfortable Villa with pool in Upmarket Area of Holders, St James.
- Beautiful spacious holiday home private shared pool with neighbour nr Sandy Lane
- BEACH FRONT & SEAVIEW DELUXE PENTHOUSE APARTMENT
- Detached villa, Holetown, private pool/garden near beach shops and restaurants
- Cool top floor 1 bed Apartment with Shared Pool and Beach Club Membership.
2. How many Winter Rentals are available in St. Thomas?
Currently, the total number of properties listed by RBO in 2026 is over 225 in the St. Thomas area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in St. Thomas.
More Rentals You May Like Near St. Thomas
Villa
10.0(6 Reviews)
6 Bedrooms
6 Baths
12 Guests
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $6,152/Night
7 Nights - US $43,061
Apartment
10.0(5 Reviews)
1 Bedroom
1 Bath
2 Guests
205 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $120/Night
7 Nights - US $843
New
Villa
10.0(3 Reviews)
10 Bedrooms
9 Baths
20 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $6,959/Night
7 Nights - US $48,715
Villa
10.0(3 Reviews)
5 Bedrooms
5 Baths
10 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,616/Night
7 Nights - US $11,312
Villa
10.0(2 Reviews)
5 Bedrooms
5 Baths
10 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $4,161/Night
7 Nights - US $29,127
House
10.0(2 Reviews)
4 Bedrooms
5 Baths
6 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $1,672/Night
7 Nights - US $11,705
Villa
10.0(1 Review)
6 Bedrooms
6 Baths
12 Guests
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $6,613/Night
7 Nights - US $46,292
House
10.0(1 Review)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $2,625/Night
7 Nights - US $18,374
Villa
10.0(1 Review)
6 Bedrooms
4 Baths
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $2,488/Night
7 Nights - US $17,419
House
10.0(1 Review)
3 Bedrooms
3 Baths
8 Guests
- Hot Tub
Kitchen- Parking
- Air Conditioner
US $404/Night
7 Nights - US $2,826
House
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $403/Night
7 Nights - US $2,821
Apartment
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $353/Night
7 Nights - US $2,469
