Poggibonsi Villas - Best Villa Poggibonsi 2026

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

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Our top choices for Poggibonsi villas

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

1. Villa Montecastello

Monteriggioni

Alvaro

includes taxes & fees

24 Oct - 25 Oct

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

2. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

includes taxes & fees

20 Oct - 21 Oct

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

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

Certaldo - Firenze

Kelly C.

includes taxes & fees

19 Oct - 20 Oct

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

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

Radda in Chianti

Amber M.

includes taxes & fees

5 Nov - 6 Nov

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

5. "A Casa di Franca Villa con piscina"

Gambassi Terme

"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...

Anonymous traveller

includes taxes & fees

2 Nov - 3 Nov

A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

6. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

Siena

Ron M.

includes taxes & fees

19 Oct - 20 Oct

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

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

Montespertoli

Krista G.

includes taxes & fees

1 Nov - 2 Nov

A two-story building with a stone staircase leading to a wooden door. There is a small outdoor table and a potted plant on the porch.

8. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

includes taxes & fees

19 Oct - 20 Oct

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Top Poggibonsi Hotel Reviews

Villa Lecchi Hotel Wellness

10/10 Excellent

"The view is awesome, the restaurant is very good, the pool is fabulous, the room is perfect, the price is very correct as well"

Tenuta Macericca - Vacation villa with pool

10/10 Excellent

"The villa was lovely. The location was perfect for our plans to visit area sites (Siena, Lucca, Florence, San Gemigniano). There is a market within 15 minutes. The bedrooms were air conditioned and spacious, and each had its own bathroom. Each of us was comfortable. Beds were firm, which was a plus. Kitchen was well-equipped and we did use it, after the long day trips."

One Belvedere Tuscany

10/10 Excellent

"I spent three nights at the villa and couldn’t have been more pleased. The building is new and the rooms are equipped with modern conveniences. They have done very well to keep the look of an old Tuscan Villa while keeping the feel modern inside. The staff were very attentive and helped us with any questions we had. The villa is so small sometimes you feel like you have it all to yourself! The Thank you grounds are stunning in every corner is an opportunity for a photo. The food was excellent, and my wife, being a coeliac still had plenty of options. If you aren’t aware, though, the entire menu is vegetarian. It was all very good for somebody who is a meat, lover! Perhaps my favourite part of the day was breakfast on the terrace in the morning sun beside the restaurant. It was storybook Tuscan beauty. Thank you, 1 Belvedere for our first class experience."

Hotel Villa San Giorgio

10/10 Excellent

"We had an excellent 1 night stay. The hotel is located in beautiful setting among the Tuscany hills with an easy 40 minutes drive south of Florence. IThe property sits an olive orchard directly below to a picture perfect Chianti vineyard. The views of the Tuscan hills at sunset and sunrise were spectacular. The registration process was quick and easy. The receptionist was friendly and helpful. He walked us to our room to make sure we were happy with our accomodations. Our room was spacious, the beds were comfortable and the view of the Tuscan hills through the olive trees was pretty. After a bit of exploring in the August heat, we settled into the hotel bar for a cold beer and light snacks. The nice young lady who served us, Sophia, was so friendly and eager to chat with us about our travel experiences. We had dinner at sunset on the hotel terrace. The food, wine, and service were all excellent, and the price was reasonable. Breakfast on the terrace was also excellent with plenty of fresh, interesting, and tasty choices. It was a memorable 5 star hotel in every way."

Find out more about Poggibonsi

Poggibonsi Villas information

Number of reviews	324
Accommodation	146 Villas
Lowest Price	€135
Highest Price	€13,027

Frequently asked questions

How much do villas in Poggibonsi cost?

Villas in Poggibonsi cost between €135 and €13,027 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 146 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 holiday 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 travellers' 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.

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Treat yourself

Be picky

Check prices for these dates

Our top choices for Poggibonsi villas

1. Villa Montecastello

2. Rooster House, cooking classes and opera

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

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

5. "A Casa di Franca Villa con piscina"

6. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

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

8. Villa Il Signorino

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

10. Luxury Villa in the Florentine hills

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

12. Villa Mami: A Tuscan Retreat of Elegance and Charm

13. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

14. Aureva Tuscany, modern villa with private pool

15. SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

16. Exclusive Estate | Personal Concierge & Heated Pool

17. Villetta Brunelleschi: Privacy and Comfort on Two Levels

18. Villa Sunset, in the heart of Chianti area

19. Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~

Find holiday rentals that suit your style

Top Poggibonsi Hotel Reviews

Villa Lecchi Hotel Wellness

Villa San Lucchese

Tenuta Macericca - Vacation villa with pool

Casale di Villore

Hotel Toscana Ambassador

One Belvedere Tuscany

The timeless elegance with private pool

B&B Poggiobonizio

Hotel Villa San Giorgio

Find out more about Poggibonsi

Poggibonsi Villas information

Frequently asked questions

Search Villas in Poggibonsi

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Poggibonsi villas

1. Villa Montecastello

2. Rooster House, cooking classes and opera

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

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

5. "A Casa di Franca Villa con piscina"

6. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

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

8. Villa Il Signorino

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

10. Luxury Villa in the Florentine hills

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

12. Villa Mami: A Tuscan Retreat of Elegance and Charm

13. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

14. Aureva Tuscany, modern villa with private pool

15. SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

16. Exclusive Estate | Personal Concierge & Heated Pool

17. Villetta Brunelleschi: Privacy and Comfort on Two Levels

18. Villa Sunset, in the heart of Chianti area

19. Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~

Find holiday rentals that suit your style

Top Poggibonsi Hotel Reviews

Villa Lecchi Hotel Wellness

Find out more about Poggibonsi

Poggibonsi Villas information

Frequently asked questions