Discover winter rentals Caribbean - We found 35535 exact matches
About Caribbean Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Caribbean perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, rent-by-owner homes, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.
Vacation Cottage presents luxury options for travelers seeking to rent a place in Caribbean. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within Caribbean and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Caribbean Winter Rentals
What are the top rated 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:
- Polkerris Bed & Breakfast
- Grande Bay: Sugar N' Spice: Studio Condo Great Views & Reviews; Newly Renovated
- Island Time on Sapphire Beach, Beach level walkout, Bldg A
- 1st Floor POOLSIDE/OCEAN VIEW Protected Cove & Beach-Most 10 Star Reviews on 7MB
- Palm Heights
- Gray Door Apartments - Adults Only
- 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!
How much does it cost to rent a place to stay near Caribbean in the wintertime?
The average cost for winter rentals in Caribbean is $835 per night. Vacation Cottage has a wide list of great winter places to stay near Caribbean that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Caribbean that allow pets?
Yes, here are the top cottage/chalet rentals in Caribbean that allow you to bring your pet or dog:
- Theatrical retreat set just above Harbour Island's Pink Sand Beach, bold design meets island calm
- TI GARDEN et son jacuzzi privé à Ste Luce
- Oceanfront Sunset Retreat With Heated Pool
- Homerez - Villa in Saint-Louis
See all pet-friendly vacation rentals in Caribbean on Vacation Cottage
Do you have any winter rentals in Caribbean that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Caribbean to find what works for you.
Are there winter accommodations in Caribbean that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 35535 private swimming pools or indoor pools accommodations near Caribbean along with other great amenities.
Do any winter holiday rentals in Caribbean have hot tubs?
About 35535 holiday rentals in Caribbean boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Caribbean?
Yes, there are many luxury places to stay in Caribbean for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Caribbean with all the best amenities for your next trip.
