Santorini Winter Rentals & Holiday Homes

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

• Unique 1868 Winery Canava - Caldera View, Private Pool, Hot tub, Sunbathing deck
• Avista Suites
• Wonderful island Villa, Private pool, Sea views
• Location,Location,Location,PRIVATE POOL, CALDERA VIEWS to infinity; daily maid
• Aleria Villa Santorini - Exclusive facilities and services
• Breathtaking Caldera View, Great Comfort, Romantic And Fully Revamped.
• Sunset View Villa Santorini - 3 Bedroom Villa & Private Jacuzzi
• SWINGING SUNSET villa - Private Swimming pool & Private outdoor heated spa
• Caldera View Private Villa with Private Pool/Heated Jacuzzi/Amazing Sunset
• The Blue Domes Cave Villa with outdoor Hot Tub and Caldera View, Villa

The average cost for winter rentals in Santorini is $900 per night. Cottageromance has a wide list of great winter places to stay near Santorini 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 Santorini that allow you to bring your pet or dog:

• Illusion Villa - Exceptional Private Villa
• Irene's Villa
• Revelis Villa & Canava
• Perfect for Families and Group of Friends. Amazing Caldera View. Private Pool.

See all pet-friendly vacation rentals in Santorini on Cottageromance

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

As of 2026, the data from Cottageromance shows that there are over 1511 private swimming pools or indoor pools accommodations near Santorini along with other great amenities.