- Trinidad and Tobago
- Winter Rental
Trinidad and Tobago Winter Rentals & Holiday Homes
Discover winter rentals Trinidad and Tobago - We found 230 exact matches
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- Pet Friendly
- Air Conditioner
- Parking
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- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Designated Smoking Area
- TV
- Air Conditioner
- Parking
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- Air Conditioner
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- Pool
- Air Conditioner
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- Pet Friendly
Frequently Asked Questions About Trinidad and Tobago Winter Rental
What are the top rated Winter Rentals in Trinidad and Tobago?
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:
- Green Space, Santa Cruz Valley, Trinidad 2
- 2BR 2BTH Apt w patio & garden 3 mins walk to beach boardwalk shops & restaurants
- Vista Stsys.Bamboo View
- Hibiscus - Holiday Home with the Caribbean Sea on its Doorstep!
- Newly Renovated Luxury Waterfront Villa cluster with magnificent ocean views!
- Sugarsands Villa
- Rainbow lodge Caribbean romance, private waterfall & secluded beaches -
- Anayah's Place - 2bed condo Port of Spain- spectacular ocean view, WiFi, AC
- Cozy Trini Apartment, with outdoor patio
- The Hive Boutique Hotel Double Queen Room 103
How much does it cost to rent a place to stay near Trinidad and Tobago in the wintertime?
The average cost for winter rentals in Trinidad and Tobago is $306 per night. Thiscityknows 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.
Are there any winter cottages/chalets in Trinidad and Tobago that allow pets?
Yes, here are the top cottage/chalet rentals in Trinidad and Tobago that allow you to bring your pet or dog:
- Casa Clara - The Perfect Place For A Family/group Of Friends To Gather & Relax
- The Fairway 6BRFamilyVilla 20-24ppl Pool Slide Tub
- The Villas At Stonehaven
- Colonial style Villa in Tobago Plantations Golf, Beach & SPA Resort
See all pet-friendly vacation rentals in Trinidad and Tobago on Thiscityknows
Do you have any winter rentals in Trinidad and Tobago that are suitable for families?
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.
Are there winter accommodations in Trinidad and Tobago that have indoor swimming pools?
As of 2026, the data from Thiscityknows shows that there are over 230 private swimming pools or indoor pools accommodations near Trinidad and Tobago along with other great amenities.
