- Costa Rica
- Alajuela
- San Jose
- Winter Rental
San Jose Winter Rentals & Holiday Homes
Discover winter rentals San Jose - We found 471 exact matches
When do you want to travel?
- Parking
- Pool
- TV
- Air Conditioner
- Parking
- Child Friendly
- Parking
- Pet Friendly
- Designated Smoking Area
- Parking
- TV
- Security/Safety
- Parking
- Balcony/Terrace
- Accessibility
- Parking
- Pet Friendly
- Balcony/Terrace
- Parking
- Pet Friendly
- Pool
- Parking
- Pet Friendly
- Balcony/Terrace
- Parking
- Pool
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Designated Smoking Area
- Air Conditioner
- Parking
- Pool
- Parking
- Pool
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Parking
- Pool
- Parking
- TV
- Balcony/Terrace
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- TV
- Security/Safety
- Sports/Activities
- Parking
- Pool
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
Frequently Asked Questions About San Jose Winter Rental
What are the top rated Winter Rentals in San Jose?
There are a lot of options in San Jose. If you plan on staying in the San Jose area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in San Jose:
- Gorgeous Villa, Air Conditioning, Pool, Additional Jacuzzi.
- Atenas Mountain Top Villa - Heated Pool- Breathtaking Views. AC in the bedrooms
- Flower gardens pool table 14 x 45 ft outdoor kitch 300+100 Mb fiber opt internet
- Kenai Mountain View
- Paradise Experience Costa Rica
- Peaceful Mountain Experience - Coyote House
- Zen Urbano View of the Irazu Volcano con Jacuzzi and AC
- Peaceful Mountain Experience - Coyote House
- Queen Bed Yogui Studio apartment + Rooftop Hot Tub
- SUITES AND APARTMENTS MERLYN AEROPUERTO # 31, OASIS DE PAZ
How much does it cost to rent a place to stay near San Jose in the wintertime?
The average cost for winter rentals in San Jose is $175 per night. Travelandtribe has a wide list of great winter places to stay near San Jose that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in San Jose that allow pets?
Yes, here are the top cottage/chalet rentals in San Jose that allow you to bring your pet or dog:
- Elegant, fully equipped residence with heated pool and great views
- BEE Suites Curridabat
- Chalets Vistas del Poas
- Bright house Near Paseo Colon
See all pet-friendly vacation rentals in San Jose on Travelandtribe
Do you have any winter rentals in San Jose that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in San Jose to find what works for you.
Are there winter accommodations in San Jose that have indoor swimming pools?
As of 2026, the data from Travelandtribe shows that there are over 471 private swimming pools or indoor pools accommodations near San Jose along with other great amenities.
