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: <a href="/property/gorgeous-villa-air-conditioning-pool-additional-jacuzzi/HA-321149725" class="class="static-page-link"">Gorgeous Villa, Air Conditioning, Pool, Additional Jacuzzi.</a> <a href="/property/casa-vista-del-valle/BC-9057401" class="class="static-page-link"">Casa Vista del Valle</a> <a href="/property/flower-gardens-pool-table-14-x-45-ft-outdoor-kitch-300-100-mb-fiber-opt-internet/HA-321573635" class="class="static-page-link"">Flower gardens pool table 14 x 45 ft outdoor kitch 300+100 Mb fiber opt internet</a> <a href="/property/bee-suites-san-jos%C3%A9-santa-ana/EP-113492946" class="class="static-page-link"">BEE Suites San José - Santa Ana</a> <a href="/property/kenai-mountain-view/BC-13822031" class="class="static-page-link"">Kenai Mountain View</a> <a href="/property/peaceful-mountain-experience-coyote-house/BC-12422604" class="class="static-page-link"">Peaceful Mountain Experience - Coyote House</a> <a href="/property/zen-urbano-view-of-the-irazu-volcano-con-jacuzzi-and-ac/BC-14382841" class="class="static-page-link"">Zen Urbano View of the Irazu Volcano con Jacuzzi and AC</a> <a href="/property/peaceful-mountain-experience-coyote-house/HA-3214089931" class="class="static-page-link"">Peaceful Mountain Experience - Coyote House</a> <a href="/property/original-studio-escalante/BC-14992973" class="class="static-page-link"">Original Studio ESCALANTE</a> <a href="/property/suites-and-apartments-merlyn-aeropuerto-31-oasis-de-paz/HA-6158816749" class="class="static-page-link"">SUITES AND APARTMENTS MERLYN AEROPUERTO # 31, OASIS DE PAZ</a>

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 $168 per night. Beachbaycottages 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 Peaceful Mountain Experience - Coyote House Montehidalgo de Los Alpes Cabin Rental See all <a href="/all/costa-rica/san-jose/san-jose/pet-friendly-rentals" class="class=&#34;static-page-link&#34;">pet-friendly vacation rentals in San Jose</a> on Beachbaycottages

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 Beachbaycottages shows that there are over 462 private swimming pools or indoor pools accommodations near San Jose along with other great amenities.

Winter Rentals in San Jose:【 GREAT PRICES 】

Elegant, fully equipped residence with heated pool and great views

From US $500

10.0 (47 Reviews)

House

Elegant, fully equipped residence with heated pool and great views

Parking
Pool
TV

San Jose Winter Rentals & Holiday Homes

Discover winter rentals San Jose - We found 462 exact matches

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