Discover winter rentals Jamaica - We found 1983 exact matches
About Jamaica Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Jamaica 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 Jamaica. 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 Jamaica and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Jamaica Winter Rentals
What are the top rated Winter Rentals in Jamaica?
There are a lot of options in Jamaica. If you plan on staying in the Jamaica area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Jamaica:
- Beach Front Villa W/Pool, in Gated Community W/Tennis/Gym
- Luxury staffed villa, including staff tips, driver, and beach club
- Beautiful Beachfront Villa in a Gated Community, Private Pool/Bar, Fully Staffed
- Exclusive Oceanfront Villa in Charming Jamaican North Coast Resort Town
- Paradise Plum Villa 5BR - Rose Hall Estates.
- 5 BDR LUX MODERN BEACHFRONT VILLA PRIVATE INFINITY POOL & OCEAN VIEWS STAFF
- Beautiful Luxury Oceanfront Property Montego Bay Property
- Villa Maria montego Bay
- NEW LUXURY VILLA/AMZING OCEAN VIEW/PRIVT KITCHEN/BATHR/LIVING RM/POOL/JACUZZI
- "Sought-After" Luxurious 2100 sq ft Oceanfront Private Residence, in a Resort
How much does it cost to rent a place to stay near Jamaica in the wintertime?
The average cost for winter rentals in Jamaica is $807 per night. Vacation Cottage has a wide list of great winter places to stay near Jamaica that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Jamaica that allow pets?
Yes, here are the top cottage/chalet rentals in Jamaica that allow you to bring your pet or dog:
- Beach Front Villa W/Pool, in Gated Community W/Tennis/Gym
- Lime Tree Farm, Blue Mountains
- Stunning Ocean View
- Luxury staffed villa, including staff tips, driver, and beach club
See all pet-friendly vacation rentals in Jamaica on Vacation Cottage
Do you have any winter rentals in Jamaica that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Jamaica to find what works for you.
Are there winter accommodations in Jamaica that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 1983 private swimming pools or indoor pools accommodations near Jamaica along with other great amenities.
Do any winter holiday rentals in Jamaica have hot tubs?
About 1983 holiday rentals in Jamaica boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Jamaica?
Yes, there are many luxury places to stay in Jamaica for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Jamaica with all the best amenities for your next trip.
