Tobago Winter Rentals & Holiday Homes

Discover winter rentals Tobago - We found 137 exact matches

About Tobago Winter Rental on SunSkiResorts

Planning a winter vacation in Tobago? Discover 137 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in 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 Tobago start at US $335. The most popular properties in 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 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 Tobago and unlock incredible deals.

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Frequently Asked Questions About Tobago Winter Rentals

The average cost for winter rentals in Tobago is $335 per night. SunSki has a wide list of great winter places to stay near Tobago that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Tobago to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 137 private swimming pools or indoor pools accommodations near Tobago along with other great amenities.

About 137 holiday rentals in 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 Tobago for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Tobago with all the best amenities for your next trip.