What are the top rated Winter Rentals in Puerto Rico?

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: Residences at Dorado Beach, a Ritz-Carlton Reserve Sunset Paradise Villas - Oceanfront - Rincon - 50 guests - Private Infinity Pool Aguadilla Villa Bonita #1, sleeps 35+, pool, jacuzzi, kids area, volley, basket. Big House with 7 Private Apts, 10 Rooms & 17 beds Modern Beachfront 2BR 2BA Condo, Pool & Gym Steps to Dining Superhost Cabin among Pines: Pool w Heat, Fire Pit and Mini Golf, for couples and families Million Dollar View, Guaranteed! 4br, 3ba Corner Penthouse, Jobos' Beach Isabela Caribbean Penthouse- Front Beach, Roof Pool, 8 max, 2 bed/2 bath, Generator Direct Ocean Views! Private, Large, Home-sized Condo! Newly Renovated! 3BR Oceanfront Community with 3 pools/tennis - Villa de Palma, w/generator

How much does it cost to rent a place to stay near Puerto Rico in the wintertime?

The average cost for winter rentals in Puerto Rico is $477 per night. PerfectforWeddings 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.

Are there any winter cottages/chalets in Puerto Rico that allow pets?

Yes, here are the top cottage/chalet rentals in Puerto Rico that allow you to bring your pet or dog: BEACHFRONT Gated "Beach Bliss" House, Directly On The Beach Courtyard by Marriott Isla Verde Beach Resort Four Seasons Resort and Residence Puerto Rico Spacious Gated "Sea View" House Overlooking the Caribbean See all pet-friendly vacation rentals in Puerto Rico on Perfect for Weddings

Do you have any winter rentals in Puerto Rico that are suitable for families?

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.

Are there winter accommodations in Puerto Rico that have indoor swimming pools?

As of 2026, the data from Perfect for Weddings shows that there are over 3639 private swimming pools or indoor pools accommodations near Puerto Rico along with other great amenities.

Do any winter holiday rentals in Puerto Rico have hot tubs?

About 3639 holiday rentals in Puerto Rico boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include: Puerto Rico Rentals with hot tub

Are there luxury winter rentals in Puerto Rico?

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.