Guanacaste Winter Rentals & Holiday Homes

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

• Oceanfront Oasis - 9BR Infinity Pool Villa
• Steps away from beautiful Penca Beach
• NEWLY Renovated! Ocean, Beach Casa with 5 Bedrooms, 5 Baths & Private Pool!
• Beautiful Home with Large Private Pool
• Villa in Hacienda Pinilla Near Beach – Private Pool, Golf Cart & Beach Club Access Included
• ONE-OF-A-KIND LUXURY VILLA - Free golf cart!
• FAVORITE HOUSE ON THE BEACH for the last 20 yearsn. steps to the ocean
• Absolutely Stunning Luxury, Ocean Front Villa, Playa Coco/Ocotal -Bahia Pez Vela
• Private Villa - 3BR/3BA w/Pool & Stunning Ocean Views - Gated Community
• Villa Oasis: A luxury villa just steps to beach with private pool, WIFI & A/C

The average cost for winter rentals in Guanacaste is $628 per night. Ownerdirect has a wide list of great winter places to stay near Guanacaste 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 Guanacaste that allow you to bring your pet or dog:

• Palmetto Lodge
• Simply the best, incredible views,pool,delicious food and a friend in the area.
• Amalú Luxury View Cabins
• Canta La Rana

See all pet-friendly vacation rentals in Guanacaste on Ownerdirect

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Guanacaste to find what works for you.

As of 2026, the data from Ownerdirect shows that there are over 2906 private swimming pools or indoor pools accommodations near Guanacaste along with other great amenities.