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A vineyard with rows of grapevines, rolling hills, and distant buildings.

Search Poggibonsi Villa Rentals from CA $173

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    Check prices for these dates, December 15–16, 2026

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    Our top choices for Poggibonsi villas

    1. Rooster House, Cooking Classes, and Opera

    A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

    2. Villa Montecastello

    A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

    3. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

    A covered balcony with a brick railing, a bench, and a view of lush greenery.

    4. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

    A large estate with a swimming pool, tennis court, and multiple guest rooms.

    5. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

    A long wooden table set for a meal with a view of a hillside town.

    6. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

    A stone building with a swimming pool, wooden deck, and a tall tree.

    7. "A Casa di Franca Villa con piscina"

    A person in a swimming pool with a view of a vineyard and hills.

    8. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

    A villa with a swimming pool, surrounded by lush greenery and vineyards.

    9. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

    A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

    10. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

    A building with a large entrance, potted plants, and a statue in the foreground.

    11. Villa Mami: A Tuscan retreat full of elegance and charm

    A large estate with multiple buildings, a swimming pool, and surrounding olive groves.

    12. Premorae - Tenuta corte dell'Angelo - heated pool and concierge service

    A stone building with a large arched entrance, potted plants, and outdoor seating.

    13. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

    A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

    14. Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

    A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

    15. Villa Liberty in The Centre - No Ztl

    A dining area with a wooden table, white chairs, and a chandelier.

    16. Villa Capanna: A Window onto Tuscany

    A stone building with a tiled roof, surrounded by a well-maintained lawn and trees.

    17. Villa Torre Among the Hills of Siena

    A rustic stone building with a tower, covered walkways, and a grassy courtyard.

    18. VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

    A large, historic building with multiple arches and a prominent tower.

    19. Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

    A rectangular swimming pool with lounge chairs and a pergola, surrounded by a landscaped garden and a mountain backdrop.

    20. VILLA GRAND MEDICI - Eight Bedroom Villa, Sleeps 16

    A rectangular swimming pool with a view of mountains and a clear sky.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Learn more about Poggibonsi

    Medieval towers and historic buildings surround Poggibonsi's charming Piazza Cavour, where locals gather at outdoor cafés serving Tuscan specialties. Climb to Poggio Imperiale fortress for panoramic views, then visit nearby San Gimignano's famous towers or Siena's magnificent Piazza del Campo.

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    A vineyard with rows of grapevines, rolling hills, and distant buildings.

    Frequently Asked Questions

    How much do villas in Poggibonsi cost?

    Villas in Poggibonsi cost between CA $173 and CA $22,273 per night. These getaways offer the privacy of your own space at a price that's gentle to your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

    How many villas are there in Poggibonsi?

    Take your pick of villas in Poggibonsi. No matter if you're taking a trip with the kids or planning a weekend escape with some friends, Expedia can help you find the perfect space for your squad.

    Why book your villa in Poggibonsi with Expedia?

    We think vacation time should be a walk in the park, so if you're in search of villas at a competitive price, Expedia has you covered. Keep the budget under control and pick an all-inclusive stay, or splurge on a luxury villa to spoil your loved ones. Our search filters make it simple to secure a property in Poggibonsi that suits you best.

    How can I find cheap villas in Poggibonsi?

    With Expedia's user-friendly filter tool, locating cheap villas in Poggibonsi is a piece of cake. To find properties that will keep some cash in your pocket, refine your search by amenities, star rating and budget.

    What is there to do near my villa in Poggibonsi?

    Whatever your interests, Poggibonsi has plenty of things to keep you on the move. Fountain of Fate, Church of San Lorenzo and San Lucchese Convent are on most travelers' trip plans. Don't leave without exploring Magione Castle, Poggio Imperiale Fortress and Archeodromo di Poggibonsi either. With Expedia's Poggibonsi hotel deals, you'll be able to discover more fabulous attractions like these with the money you save.