Discover Your Perfect St. Thomas Winter Rental

St. Thomas Winter Rental

Apartment
Designer Penthouse - Amazing Views & Location
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like-icon10.0
Exceptional
(52 Reviews)
3 Bedrooms 2 Baths 6 Guests 1817 ft²
  • Oceanfront
    Oceanfront
  • Parking
    Parking
More amenities
CA $1,005/Night 7 Nights - CA $7,036
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Apartment
Annwin Annex
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like-icon9.9
Exceptional
(14 Reviews)
1 Bedroom 1 Bath 2 Guests 495.14 ft²
  • Parking
    Parking
  • Skiing
    Skiing
More amenities
CA $126/Night 7 Nights - CA $882
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Hotel
Beach View
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like-icon9.6
Exceptional
(437 Reviews)
1 Bath
  • Breakfast
    Breakfast
  • Parking
    Parking
More amenities
CA $411/Night 7 Nights - CA $2,877
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Apartment
Free loaner car…Paradise get away near beach.
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like-icon8.0
Excellent
(2 Reviews)
3 Bedrooms 2 Baths 6 Guests
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
CA $525/Night 7 Nights - CA $3,673
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Ski Chalet
Country Bliss
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like-icon7.0
Very Good
(2 Reviews)
1 Bedroom 1 Bath 2 Guests
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $42/Night 7 Nights - CA $294
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Apartment
Villas & Suites at Beach View
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like-icon10.0
Exceptional
(25 Reviews)
1 Bedroom 1 Bath
  • Kitchen
    Kitchen
  • Air Conditioner
    Air Conditioner
More amenities
CA $605/Night 7 Nights - CA $4,236
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House
SALE - Affordable 2 bed apt 5mins from Holetown beaches car included.
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like-icon7.8
Very Good
(6 Reviews)
2 Bedrooms 1 Bath 4 Guests 950 ft²
  • Oceanfront
    Oceanfront
  • Parking
    Parking
More amenities
CA $158/Night 7 Nights - CA $1,108
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Apartment
Coral Lane Beach Apartments
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like-icon8.4
Excellent
(107 Reviews)
1 Bedroom 1 Bath
  • Oceanfront
    Oceanfront
  • Parking
    Parking
More amenities
CA $191/Night 7 Nights - CA $1,334
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Apartment
A beachfront apartment with a private plunge pool & direct access to the beach
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2 Bedrooms 2 Baths 4 Guests
  • Private Pool
    Private Pool
  • Parking
    Parking
More amenities
CA $1,333/Night 7 Nights - CA $9,333
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Hotel
Angler Apartments
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like-icon7.0
Very Good
(50 Reviews)
1 Bath
  • Oceanfront
    Oceanfront
  • Ocean View
    Ocean View
More amenities
CA $168/Night 7 Nights - CA $1,177
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Apartment
Welcoming 1-bedroom apartment in St Thomas.
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1 Bedroom 2 Baths 2 Guests
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $232/Night 7 Nights - CA $1,625
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New
Apartment
Modern Two-Bedroom Retreat Your Next Getaway Awaits You
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2 Bedrooms 3 Baths 4 Guests
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $225/Night 7 Nights - CA $1,576
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More Top-Rated Winter Rental in St. Thomas Area

Why Choose Rent By Owner for your St. Thomas 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.

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

More Top-Rated Winter Rental in St. Thomas Area
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

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More Places to Stay Near St. Thomas

Frequently Asked Questions About St. Thomas Winter Rentals

1. How many Winter Rentals are available in St. Thomas?

Currently, the total number of properties listed by RBO in 2026 is over 23 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

Apartment
Cozy studio in lovely Saint Thomas with fitness room, AC, WiFi, swimming pool
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1 Bedroom 1 Bath 2 Guests
  • Parking
    Parking
  • Pool
    Pool
More amenities
CA $189/Night 7 Nights - CA $1,322
View Deal
Condo
Luxurious Beachfront Apartment
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like-icon10.0
Exceptional
(2 Reviews)
3 Bedrooms 4 Baths 6 Guests
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $921/Night 7 Nights - CA $6,448
View Deal
Apartment
Stylish villa apt, world famous Bottom Bay 5 min walk,swimming pool.A/C
Map-icon
like-icon9.6
Exceptional
(24 Reviews)
1 Bedroom 1 Bath 2 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
CA $151/Night 7 Nights - CA $1,059
View Deal
House
2 bedroom house near a devolping sub urban town
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like-icon9.0
Exceptional
(4 Reviews)
2 Bedrooms 1 Bath 4 Guests
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $91/Night 7 Nights - CA $637
View Deal
Villa
Three Bedroom Beach Front Townhouse with Private Plunge Pool - Enquire Today
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like-icon5.0
Average
(1 Review)
3 Bedrooms 3 Baths 6 Guests
  • Child Friendly
    Child Friendly
CA $818/Night 7 Nights - CA $5,726
View Deal
Villa
Take Five Villa with Private Pool And Spacious Patio
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like-icon4.9
Average
(18 Reviews)
3 Bedrooms 3 Baths 6 Guests 1200 ft²
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
CA $217/Night 7 Nights - CA $1,520
View Deal
House
Warrens vacation retreat less than12 min our lovely west coast beaches
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4 Bedrooms 4 Baths 8 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
CA $715/Night 7 Nights - CA $5,008
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Villa
Royal Villa 19 Near Ocean - Located in Beautiful Saint James with Private Pool
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3 Bedrooms 3 Baths 6 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
CA $679/Night 7 Nights - CA $4,756
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House
Family house in Spanish style, Overlooking West (platinum) coast of Barbados
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4 Bedrooms 3 Baths 8 Guests
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
CA $626/Night 7 Nights - CA $4,383
View Deal
Condo
Crystal Court Condo - 2 bedroom in gated community
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2 Bedrooms 2 Baths 4 Guests
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
CA $294/Night 7 Nights - CA $2,061
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House
Great Location near Beaches, Restaurants, Stores & Bus Routes in Bridgetown
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2 Bedrooms 1 Bath 3 Guests
  • Kitchen
    Kitchen
  • Air Conditioner
    Air Conditioner
More amenities
CA $126/Night 7 Nights - CA $882
View Deal
More Top-Rated Winter Rental in St. Thomas Area