Caribbean Winter Rental
Condo
10.0(285 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
Oceanfront
Hot Tub
Parking
Pool
AU $632/Night
7 Nights - AU $4,423
Apartment
10.0(29 Reviews)
2 Bedrooms
2 Baths
6 Guests
1506.95 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $634/Night
7 Nights - AU $4,436
AU $49/Night
7 Nights - AU $341
Condo
10.0(274 Reviews)
2 Bedrooms
3 Baths
6 Guests
1500 ft²
- Hot Tub
- Parking
- Pool
Ocean View
AU $647/Night
7 Nights - AU $4,526
Villa
10.0(22 Reviews)
2 Bedrooms
1 Bath
4 Guests
861.11 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $346/Night
7 Nights - AU $2,425
Condo
10.0(274 Reviews)
2 Bedrooms
1 Bath
2 Guests
646 ft²
- Parking
- Pool
- Ocean View
Balcony/Terrace
AU $600/Night
7 Nights - AU $4,202
House
10.0(21 Reviews)
7 Bedrooms
5 Baths
10 Guests
378.01 ft²
Private Beach- Oceanfront
- Hot Tub
Breakfast
AU $242/Night
7 Nights - AU $1,696
Condo
10.0(264 Reviews)
1 Bedroom
1 Bath
2 Guests
900 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $939/Night
7 Nights - AU $6,576
Ski Chalet
10.0(17 Reviews)
1 Bedroom
1 Bath
3 Guests
452.08 ft²
- Hot Tub
- Breakfast
- Parking
- Ocean View
AU $44/Night
7 Nights - AU $309
Condo
10.0(231 Reviews)
1 Bedroom
1 Bath
4 Guests
650 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
AU $551/Night
7 Nights - AU $3,856
House
10.0(16 Reviews)
3 Bedrooms
2 Baths
9 Guests
96.88 ft²
- Hot Tub
- Breakfast
- Parking
- Pool
AU $164/Night
7 Nights - AU $1,147
Condo
10.0(224 Reviews)
2 Bedrooms
2 Baths
5 Guests
1200 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
AU $762/Night
7 Nights - AU $5,335
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.
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:
- Waterfront Vacation Rental - Private & Quiet Location - Fully Air-conditioned
- The Tuscany on Grace Bay
- Stunning And Spacious Beachfront Pool House Near Rio Mar Resort!
- TheBLU — Luxury Beachfront Penthouse at The Grandview, Grace Bay Beach
- Twelve Palms Ocean Front Villa - Reimagined!
- Gorgeous ocean views! Spend your days in pure bliss at a perfect paradise!
- Spectacular Beachfront Condo, Ocean Views of Grace Bay, Suite #123
- Villa Tampico/Beachfront Peninsula/2 Boat Docks/Next to Town
- 4 Bed Luxury Villa , Private Pool, Short Walk To Ritz And Marriott Beach !
- Palm Cay Resort Collection – Signature Sunset Villa Crafted for Resort Living
2. How many Winter Rentals are available in Caribbean?
Currently, the total number of properties listed by RBO in 2026 is over 38112 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
- Parking
- Pool
AU $469/Night
7 Nights - AU $3,281
Condo
10.0(222 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
AU $782/Night
7 Nights - AU $5,472
Condo
10.0(220 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $518/Night
7 Nights - AU $3,622
House
10.0(217 Reviews)
1 Bedroom
1 Bath
4 Guests
1000 ft²
Private Pool- Oceanfront
- Parking
- Pool
AU $708/Night
7 Nights - AU $4,955
Cottage
10.0(207 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $448/Night
7 Nights - AU $3,137
Condo
10.0(205 Reviews)
2 Bedrooms
2 Baths
6 Guests
1182 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
AU $619/Night
7 Nights - AU $4,335
Condo
10.0(204 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
AU $620/Night
7 Nights - AU $4,341
Condo
10.0(196 Reviews)
2 Bedrooms
3 Baths
8 Guests
1500 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
AU $645/Night
7 Nights - AU $4,519
Condo
10.0(190 Reviews)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
AU $649/Night
7 Nights - AU $4,541
Apartment
10.0(188 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $510/Night
7 Nights - AU $3,572
Condo
10.0(174 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
AU $740/Night
7 Nights - AU $5,180
Condo
10.0(169 Reviews)
2 Bedrooms
3 Baths
6 Guests
1998 ft²
- Hot Tub
- Parking
- Pool
Spa
AU $1,393/Night
7 Nights - AU $9,749
