Caribbean Winter Rental
990 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Pool
- Balcony/Terrace
R6,929/Night
For 7 Nights R48,508
1506.95 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Pool
R6,449/Night
For 7 Nights R45,147
1100 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
R11,708/Night
For 7 Nights R81,956
400 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Ocean View
R1,586/Night
For 7 Nights R11,095
254.02 ft²
14 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R2,366/Night
For 7 Nights R16,561
1350 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Private Pool
- Pool
- Ocean View
R6,958/Night
For 7 Nights R48,704
378.01 ft²
10 Guests
7 Bedrooms
5 Bathrooms
Ocean View
House
- Private Beach
- Oceanfront
- Hot Tub
R2,774/Night
For 7 Nights R19,416
6 Guests
1 Bedroom
1 Bathroom
Pet Friendly
Boat Rental
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
R5,739/Night
For 7 Nights R40,170
861.11 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Villa
- Oceanfront
- Hot Tub
- Spa
R3,965/Night
For 7 Nights R27,754
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Kitchen
- Parking
R2,557/Night
For 7 Nights R17,899
452.08 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Ski Chalet
- Hot Tub
- Ocean View
- Balcony/Terrace
R506/Night
For 7 Nights R3,541
1100 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Pool
- Ocean View
- Balcony/Terrace
R6,419/Night
For 7 Nights R44,935
Why Choose Rent By Owner for your Caribbean 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 Caribbean
How to Book Your Caribbean 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 Caribbean
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
Frequently Asked Questions About Caribbean Winter Rentals
1. What are the top Winter Rentals in Caribbean?
There are a lot of options in Caribbean. If you plan on staying in the Caribbean area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Caribbean:
- Grande Bay: Sugar N' Spice: Studio Condo Great Views & Reviews; Newly Renovated
- Island Time on Sapphire Beach, Beach level walkout, Bldg A, Backup Generator
- 1st Floor POOLSIDE/OCEAN VIEW Protected Cove & Beach-Most 10 Star Reviews on 7MB
- SEA GLASS at Sapphire Beach Unit E-206 - great views of STJ and BVIs!
- Gorgeous Beachfront Condo at the Elysian Beach Resort Pool, Tennis and More
- Grande Bay Luxury 3BR Spectacular Unobstructed View
- Penthouse King Suite! Fully Remodeled and booking with full amenities!
- SERENITY CONDO ON BEAUTIFUL EAGLE BEACH n2 bedroom/2bath - Sleeps 6
- Beach Front Paradise
- Paradise! Private Beachfront Home w/Pool & Beach WiFi! nn
2. How many Winter Rentals are available in Caribbean?
Currently, the total number of properties listed by RBO in 2026 is over 38695 in the Caribbean area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Caribbean.
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- Oceanfront
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- Private Pool
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- Hot Tub
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