Caribbean Winter Rental
Apartment
10.0(5 Reviews)
2 Bedrooms
3 Baths
6 Guests
Oceanfront
Pool
Ocean View
View
US $202/Night
7 Nights - US $1,417
Apartment
10.0(28 Reviews)
2 Bedrooms
2 Baths
6 Guests
1506.95 ft²
- Oceanfront
Hot Tub- Pool
- Ocean View
US $395/Night
7 Nights - US $2,767
US $34/Night
7 Nights - US $239
Condo
10.0(9 Reviews)
1 Bedroom
1 Bath
4 Guests
990 ft²
- Hot Tub
- Pool
Balcony/Terrace
Kitchen
US $377/Night
7 Nights - US $2,637
House
10.0(22 Reviews)
5 Bedrooms
5 Baths
14 Guests
254.02 ft²
- Oceanfront
Fireplace/Heating- Ocean View
- Balcony/Terrace
US $145/Night
7 Nights - US $1,015
Condo
10.0(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1350 ft²
Private Pool- Pool
- Ocean View
- Balcony/Terrace
US $388/Night
7 Nights - US $2,713
House
10.0(21 Reviews)
7 Bedrooms
5 Baths
10 Guests
378.01 ft²
Private Beach- Oceanfront
- Hot Tub
- Pool
US $170/Night
7 Nights - US $1,190
Apartment
10.0(4 Reviews)
1 Bedroom
1 Bath
4 Guests
400 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $83/Night
7 Nights - US $582
Villa
10.0(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
861.11 ft²
- Oceanfront
- Hot Tub
Spa- Pool
US $243/Night
7 Nights - US $1,701
Villa
10.0(3 Reviews)
1 Bedroom
2 Baths
2 Guests
1170 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $397/Night
7 Nights - US $2,776
Ski Chalet
10.0(17 Reviews)
1 Bedroom
1 Bath
3 Guests
452.08 ft²
- Hot Tub
- Ocean View
- Balcony/Terrace
- View
US $31/Night
7 Nights - US $217
Cabin
10.0(3 Reviews)
1 Bedroom
1 Bath
6 Guests
- Oceanfront
- Pool
- Ocean View
- View
US $277/Night
7 Nights - US $1,941
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
Caribbean Winter Rental Frequently Asked Questions
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
- Penthouse King Suite! Fully Remodeled and booking with full amenities!
- Luxurious & Spacious Eagle Beach 2 Story Penthouse on 1st class Divi Resort
- 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 39099 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
House
10.0(16 Reviews)
3 Bedrooms
2 Baths
9 Guests
96.88 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- View
US $115/Night
7 Nights - US $805
Boat Rental
10.0(3 Reviews)
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
Pet Friendly
Air Conditioner
Internet
US $269/Night
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Apartment
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
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- Balcony/Terrace
US $249/Night
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Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Balcony/Terrace
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Parking- Internet
US $161/Night
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Villa
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $365/Night
7 Nights - US $2,558
Cottage
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $336/Night
7 Nights - US $2,355
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $767/Night
7 Nights - US $5,369
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $557/Night
7 Nights - US $3,897
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $540/Night
7 Nights - US $3,780
New
Condo
10.0(1 Review)
2 Bedrooms
3 Baths
6 Guests
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $527/Night
7 Nights - US $3,686
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Pool
- Ocean View
- View
US $496/Night
7 Nights - US $3,475
New
Condo
10.0(1 Review)
2 Bedrooms
2 Baths
7 Guests
1200 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $495/Night
7 Nights - US $3,462
