1. Trinidad and Tobago
  2. Winter Rental

Trinidad and Tobago Winter Rentals & Holiday Homes

Discover winter rentals Trinidad and Tobago - We found 206 exact matches

About Trinidad and Tobago Winter Rental on SunSkiResorts

Planning a winter vacation in Trinidad and Tobago? Discover 206 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Trinidad and Tobago 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 Trinidad and Tobago start at US $298. The most popular properties in Trinidad and Tobago 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 Trinidad and Tobago, 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 Trinidad and Tobago and unlock incredible deals.

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Frequently Asked Questions About Trinidad and Tobago Winter Rentals

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

The average cost for winter rentals in Trinidad and Tobago is $298 per night. SunSki has a wide list of great winter places to stay near Trinidad and Tobago 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 Trinidad and Tobago that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Trinidad and Tobago on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Trinidad and Tobago to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 206 private swimming pools or indoor pools accommodations near Trinidad and Tobago along with other great amenities.

About 206 holiday rentals in Trinidad and Tobago 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 Trinidad and Tobago for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Trinidad and Tobago with all the best amenities for your next trip.