Caribbean Winter Rental
Condo
10.0(82 Reviews)
3 Bedrooms
2 Baths
6 Guests
1250 ft²
Private Pool
Oceanfront
Hot Tub
Fireplace/Heating
CA $677/Night
7 Nights - CA $4,739
Apartment
10.0(29 Reviews)
2 Bedrooms
2 Baths
6 Guests
1506.95 ft²
- Oceanfront
- Hot Tub
Pool
Ocean View
CA $560/Night
7 Nights - CA $3,921
CA $48/Night
7 Nights - CA $339
New
House
10.0(47 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Fireplace/Heating
- Ocean View
Balcony/Terrace
View
CA $375/Night
7 Nights - CA $2,626
Villa
10.0(22 Reviews)
2 Bedrooms
1 Bath
4 Guests
861.11 ft²
- Oceanfront
- Hot Tub
Spa- Pool
CA $344/Night
7 Nights - CA $2,411
New
Villa
10.0(44 Reviews)
2 Bedrooms
2 Baths
4 Guests
1670 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
CA $890/Night
7 Nights - CA $6,228
House
10.0(21 Reviews)
7 Bedrooms
5 Baths
10 Guests
378.01 ft²
Private Beach- Oceanfront
- Hot Tub
- Pool
CA $241/Night
7 Nights - CA $1,686
New
Condo
10.0(31 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $520/Night
7 Nights - CA $3,641
Ski Chalet
10.0(17 Reviews)
1 Bedroom
1 Bath
3 Guests
452.08 ft²
- Hot Tub
- Ocean View
- Balcony/Terrace
- View
CA $44/Night
7 Nights - CA $308
Cottage
10.0(26 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
CA $535/Night
7 Nights - CA $3,741
House
10.0(16 Reviews)
3 Bedrooms
2 Baths
9 Guests
96.88 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- View
CA $163/Night
7 Nights - CA $1,141
New
Apartment
10.0(25 Reviews)
1 Bedroom
2 Baths
2 Guests
264 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $111/Night
7 Nights - CA $779
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, great views, Bldg A, Backup Generator.
- 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
- Beach Front Paradise
- On The Beach, Few Steps To The Ocean unit D-204
- Location Location Location II - Simply The Best On The Beach!
2. How many Winter Rentals are available in Caribbean?
Currently, the total number of properties listed by RBO in 2026 is over 38863 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
- Pool
CA $466/Night
7 Nights - CA $3,262
House
10.0(21 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Hot Tub
- Balcony/Terrace
Kitchen
Parking
CA $422/Night
7 Nights - CA $2,958
New
Apartment
10.0(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $564/Night
7 Nights - CA $3,945
New
Apartment
10.0(14 Reviews)
1 Bedroom
1 Bath
3 Guests
550 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
CA $313/Night
7 Nights - CA $2,188
Cottage
10.0(12 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $2,430/Night
7 Nights - CA $17,009
Condo
10.0(6 Reviews)
2 Bedrooms
2 Baths
6 Guests
1067 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
CA $585/Night
7 Nights - CA $4,093
Condo
10.0(4 Reviews)
1 Bedroom
2 Baths
4 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
CA $193/Night
7 Nights - CA $1,349
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
CA $666/Night
7 Nights - CA $4,662
Condo
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
CA $390/Night
7 Nights - CA $2,728
Condo
10.0(1 Review)
1 Bedroom
5 Baths
10 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $1,020/Night
7 Nights - CA $7,142
New
Condo
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
Air Conditioner
CA $553/Night
7 Nights - CA $3,872
New
Condo
10.0(1 Review)
1 Bedroom
2 Baths
2 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
CA $522/Night
7 Nights - CA $3,655
