Port of Spain Winter Rentals & Holiday Homes

Discover winter rentals Port of Spain - We found 19 exact matches

About Port of Spain Winter Rental on SunSkiResorts

Planning a winter vacation in Port of Spain? Discover 19 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Port of Spain perfect for your seasonal escape. Our listings include private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments. SunSki's winter vacation homes feature top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Winter accommodations in Port of Spain start at US $152. The most popular properties in Port of Spain include cabins, bungalows, and rental homes. Planning a snowboarding adventure? Explore our snowboard-friendly ski resorts, chalets, and cabins available for short-term or long-term stays. Whether it's a weekend getaway, monthly retreat, or an extended stay, SunSki ensures a memorable winter trip.

To book your winter vacation homes in Port of Spain, visit SunSki's filter option, enter your travel dates, narrow down your preferences, and choose from our extensive list of rentals hassle-free. Explore our interactive map to uncover all accommodations in or around Port of Spain and unlock incredible deals.

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Frequently Asked Questions About Port of Spain Winter Rentals

There are a lot of options in Port of Spain. If you plan on staying in the Port of Spain area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Port of Spain:

The average cost for winter rentals in Port of Spain is $152 per night. SunSki has a wide list of great winter places to stay near Port of Spain that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Port of Spain that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Port of Spain on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Port of Spain to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 19 private swimming pools or indoor pools accommodations near Port of Spain along with other great amenities.

About 19 holiday rentals in Port of Spain boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Port of Spain for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Port of Spain with all the best amenities for your next trip.