House
10.0(206 Reviews)
3 Bedrooms
8 Guests
Private Pool
Hot Tub
Parking
Pool
US $1,012/Night
7 Nights - US $7,087
Puerto Rico Winter Rentals & Holiday Homes
Discover winter rentals Puerto Rico - We found 3780 exact matches
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Compare Winter Rental in Puerto Rico
10.0
House
10.0(7 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
Balcony/Terrace
View
US $134/Night
7 Nights - US $939
US $229/Night
7 Nights - US $1,606
Apartment
10.0(189 Reviews)
1 Bedroom
3 Guests
- Parking
- Pool
Ocean View- Balcony/Terrace
US $223/Night
7 Nights - US $1,561
House
10.0(6 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- View
US $313/Night
7 Nights - US $2,194
New
House
10.0(177 Reviews)
5 Bedrooms
14 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $798/Night
7 Nights - US $5,587
House
10.0(3 Reviews)
3 Bedrooms
7 Guests
Private Beach
Oceanfront- Hot Tub
Breakfast
US $224/Night
7 Nights - US $1,568
House
10.0(170 Reviews)
3 Bedrooms
7 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $582/Night
7 Nights - US $4,074
Villa
10.0(2 Reviews)
6 Bedrooms
16 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- View
US $922/Night
7 Nights - US $6,454
House
10.0(165 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $696/Night
7 Nights - US $4,874
Villa
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- View
US $430/Night
7 Nights - US $3,008
Condo
10.0(164 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $714/Night
7 Nights - US $4,995
House
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- View
Air Conditioner
US $124/Night
7 Nights - US $865
Villa
10.0(132 Reviews)
5 Bedrooms
11 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $609/Night
7 Nights - US $4,264
House
10.0(132 Reviews)
3 Bedrooms
9 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $553/Night
7 Nights - US $3,874
Villa
10.0(131 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $879/Night
7 Nights - US $6,153
Villa
10.0(126 Reviews)
3 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $467/Night
7 Nights - US $3,271
Villa
10.0(123 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $667/Night
7 Nights - US $4,667
House
10.0(122 Reviews)
6 Bedrooms
12 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $346/Night
7 Nights - US $2,421
Condo
10.0(120 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $250/Night
7 Nights - US $1,749
House
10.0(117 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $591/Night
7 Nights - US $4,140
Villa
10.0(116 Reviews)
3 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,487/Night
7 Nights - US $10,407
House
10.0(111 Reviews)
5 Bedrooms
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $507/Night
7 Nights - US $3,552
Condo
10.0(108 Reviews)
1 Bedroom
2 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
US $255/Night
7 Nights - US $1,784
About Puerto Rico Winter Rental on BedroomVillas
At BedroomVillas, we feature a wide range of listings for accommodations in Puerto Rico that are perfect for your winter trip or seasonal escape. Our listings include hotels, private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that travelers are sure to love. BedroomVillas winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you are escaping the snow or running to it, BedroomVillas helps connect you to the best cabins, bungalows, lodges, and villas, as well as the best places to stay in both sun and ski resorts. BedroomVillas will make your winter getaway an unforgettable experience.
BedroomVillas offers luxury finds for travelers planning on renting a place in Puerto Rico, to enjoy these benefits and to book your winter vacation homes, go to the BedroomVillas filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of incredible winter vacation rentals without hassle. Our interactive map is also available, so you can view destinations spanning the globe or around Puerto Rico and unlock even more amazing deals. Relax with BedroomVillas.
Frequently Asked Questions About Puerto Rico Winter Rentals
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:
- La Casona Blanca Location Location
- Beachfront-Level Private Oasis with Power Backup Generator and A/C for all Areas
- Beaches, Sand, Night Life, Great Food, Great Memories!
- Beautiful,Sandy Beach! 50 steps to the BEACH! Winter dates available book now!
- Location, Location, Location with Pool
- Modern luxury island home
- Oceanfront One Bedroom Condo With Magnificent Beach Views
- Welcome to the Lucky Penny!
- Villa Panorama, Private Home and Pool
- Luxury Villa with Private Pool and Spectacular Ocean Views
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 $506 per night. BedroomVillas 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:
- Stunning And Spacious Beachfront Pool House Near Rio Mar Resort!
- Doa Blanca Cabin Mountain View
- Ache Pa Ti 1
- Beachfront Million View! ~Best Beach! ~ Romantic!~ Marbella Del Caribe West
See all pet-friendly vacation rentals in Puerto Rico on BedroomVillas
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 BedroomVillas shows that there are over 3780 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 3780 holiday rentals in Puerto Rico boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
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.
