Caribbean Winter Rental
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
Oceanfront
Ocean View
Balcony/Terrace
View
R3,521/Night
7 Nights - R24,647
Apartment
10.0(29 Reviews)
2 Bedrooms
2 Baths
6 Guests
1506.95 ft²
- Oceanfront
Hot Tub
Pool- Ocean View
R6,538/Night
7 Nights - R45,771
House
6 Bedrooms
7 Baths
13 Guests
6500 ft²
- Oceanfront
- Hot Tub
Spa- Pool
R33,099/Night
7 Nights - R231,700
Villa
2 Bedrooms
3 Baths
4 Guests
Private Pool- Oceanfront
- Pool
- Ocean View
R31,636/Night
7 Nights - R221,461
House
10.0(21 Reviews)
7 Bedrooms
5 Baths
10 Guests
378.01 ft²
Private Beach- Oceanfront
- Hot Tub
- Pool
R2,812/Night
7 Nights - R19,685
New
Apartment
2 Bedrooms
2 Baths
4 Guests
2000 ft²
- Oceanfront
Fireplace/Heating- Ocean View
- Balcony/Terrace
R14,317/Night
7 Nights - R100,226
Villa
10.0(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
861.11 ft²
- Oceanfront
- Hot Tub
- Spa
- Pool
R4,020/Night
7 Nights - R28,138
New
House
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
R14,107/Night
7 Nights - R98,754
Ski Chalet
10.0(17 Reviews)
1 Bedroom
1 Bath
3 Guests
452.08 ft²
- Hot Tub
- Ocean View
- Balcony/Terrace
- View
R513/Night
7 Nights - R3,590
New
Condo
2 Bedrooms
2 Baths
6 Guests
1324 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R13,970/Night
7 Nights - R97,795
House
10.0(16 Reviews)
3 Bedrooms
2 Baths
9 Guests
96.88 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- View
R1,902/Night
7 Nights - R13,316
House
2 Bedrooms
2 Baths
4 Guests
1152 ft²
- Hot Tub
- Balcony/Terrace
Kitchen
Internet
R11,341/Night
7 Nights - R79,384
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 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
- Luxurious & Spacious Eagle Beach 2 Story Penthouse on 1st class Divi Resort
- Penthouse King Suite! Fully Remodeled and booking with full amenities!
- SERENITY CONDO ON BEAUTIFUL EAGLE BEACH n2 bedroom/2bath - Sleeps 6
- Cozy Cottage Perfect for 2
2. How many Winter Rentals are available in Caribbean?
Currently, the total number of properties listed by RBO in 2026 is over 39387 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.
More Rentals You May Like Near Caribbean
Resort
10.0(15 Reviews)
8 Baths
18 Guests
1078.54 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
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House
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New
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4 Guests
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Cottage
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Villa
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New
Villa
2 Bedrooms
2 Baths
4 Guests
- Internet
Laundry
Bedding/Linens
Wellness Facilities
R5,343/Night
7 Nights - R37,401
Villa
2 Bedrooms
2 Baths
6 Guests
1130 ft²
- Private Pool
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R5,077/Night
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House
2 Bedrooms
3 Baths
8 Guests
1884 ft²
- Hot Tub
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- Balcony/Terrace
R4,626/Night
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Villa
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Pool
- Kitchen
Air Conditioner
R4,486/Night
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House
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
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- Ocean View
- Balcony/Terrace
R4,336/Night
7 Nights - R30,354
