1. Puerto Rico
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Puerto Rico Winter Rentals & Holiday Homes

Discover winter rentals Puerto Rico - We found 3638 exact matches

About Puerto Rico Winter Rental on SunSkiResorts

Planning a winter vacation in Puerto Rico? Discover 3638 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Puerto Rico 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 Puerto Rico start at US $480. The most popular properties in Puerto Rico 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 Puerto Rico, 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 Puerto Rico and unlock incredible deals.

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Frequently Asked Questions About Puerto Rico Winter Rentals

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

The average cost for winter rentals in Puerto Rico is $480 per night. SunSki has a wide list of great winter places to stay near Puerto Rico 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 Puerto Rico that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Puerto Rico on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Puerto Rico to find what works for you.
As of 2026, the data from SunSkiResorts shows that there are over 3638 private swimming pools or indoor pools accommodations near Puerto Rico along with other great amenities.

About 3638 holiday rentals in Puerto Rico 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 Puerto Rico for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Puerto Rico with all the best amenities for your next trip.