Best Villas in Poggibonsi 2026

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

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Our top choices for Poggibonsi villas

Villa, Air conditioning, Courtyard View | Exterior

1. Villa Montecastello

Monteriggioni

Alvaro

includes taxes & fees

25 Aug - 26 Aug

2. Rooster House, cooking classes and opera

Toscana

includes taxes & fees

20 Aug - 21 Aug

3. Apartment in villa with pool, A/C, WIFI, TV, terrace, panoramic view, close to San Gimignano

Montaione

Carole G.

includes taxes & fees

21 Aug - 22 Aug

4. Villa "Arnilù" with Private Pool & Wi-Fi

San Gimignano

includes taxes & fees

20 Aug - 21 Aug

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

Certaldo - Firenze

Kelly C.

includes taxes & fees

23 Aug - 24 Aug

6. Villino Tre Pini | Panoramic Private Pool, Nature & Privacy

Toscana

includes taxes & fees

27 Aug - 28 Aug

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

Radda in Chianti

Amber M.

additional charges may apply

17 Sept - 18 Sept

8. "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

24 Aug - 25 Aug

9. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

includes taxes & fees

1 Sept - 2 Sept

10. Luxury Villa in the Florentine hills

Florence

Dawn L.

includes taxes & fees

29 Aug - 30 Aug

11. Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Impruneta

Maria H.

includes taxes & fees

20 Aug - 21 Aug

12. Villetta Leonardo: Independence, Garden & Relaxation in Tuscany

Montaione

includes taxes & fees

28 Aug - 29 Aug

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

Montespertoli

Scott M.

includes taxes & fees

1 Sept - 2 Sept

14. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

Siena

includes taxes & fees

20 Aug - 21 Aug

15. Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi

San Vivaldo

includes taxes & fees

1 Sept - 2 Sept

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

Toscana

includes taxes & fees

9 Sept - 10 Sept

17. My Exclusive Italy - Classic Suite in a Luxury Wine Estate

Rignano sull'Arno

includes taxes & fees

14 Sept - 15 Sept

18. Exclusive Estate | Heated Pool & Personal Concierge

impruneta

Charles S.

includes taxes & fees

13 Sept - 14 Sept

19. My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

Rignano sull'Arno

includes taxes & fees

14 Sept - 15 Sept

20. Villa Marina with private pool, Borgo del Silenzio

Lajatico

"L’hébergement est situé au milieu de champs, superbe vue pour admirer le lever et coucher du soleil! La route en cailloux pour y accéder, dommage. C’est parfait pour les gens qui recherchent le calme! Maison propre. La literie pourrait être améliorée; matelas un peu durs. La piscine parfaite avec les enfants! L’accueil de Ludovica est agréable, très à l’écoute de nos besoins! Nous avons passé une belle semaine de vacances!"

Loic

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Top Poggibonsi Hotel Reviews

B&B Poggiobonizio

10/10 Excellent

"Don't be fooled by outside entrance, it was.very nice inside.was very attentive and helpful. Room had everything and great shower room. Lovely breakfast and kitchen that allowed you to cook should you desire. Great stay Bob"

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."

SPECIAL PRIVE !! Exclusive Villa with Pool near San Gimignano + FREE WIFI

10/10 Excellent

"We enjoyed our stay! Having separate apartments gave each family a little privacy. The large dining space/kitchen and outdoor areas were great for gathering. The AC and pool was needed for this hot, humid temperature. A car is needed to access the villa and surrounding areas. Communication was frequent & easy."

Villa San Lucchese

10/10 Excellent

"Our one-week stay at this villa from the moment we arrived until the day we left, every aspect of our experience was exceptional. The highlight of our stay was the restaurants both breakfast and dinner. Without question, Every meal was outstanding, with incredible flavors, beautifully prepared dishes, and an atmosphere that made every dinner memorable. What truly set this property apart, however, was the people. The service was consistently warm, professional, and attentive. The front desk staff made us feel welcome and to ensure every detail of our stay was perfect. The restaurant team provided impeccable service at every meal, and the owner was gracious, genuinely caring, and clearly passionate about creating an unforgettable guest experience. If you're looking for a place that has world-class dining, and truly exceptional hospitality, this villa is second to none. We left with wonderful memories and can't wait to return. Highly recommended!"

Casale di Villore

10/10 Excellent

"Magnifique hébergement familial et tranquille au cœur de la Toscane. L’appartement était plus grand que sur les photos et la vue sur la région est magnifique. Les espaces extérieurs réservés pour chacun des appartements sont très appréciés et permettent de passer de très beaux moments sur le site. Antonio et Alice sont très sympathiques."

Find out more about Poggibonsi

Poggibonsi Villas information

Number of reviews	280
Accommodation	146 Villas
Lowest Price	£115
Highest Price	£4,540

Frequently asked questions

How much do villas in Poggibonsi cost?

Villas in Poggibonsi cost between £115 and £4,540 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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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. Apartment in villa with pool, A/C, WIFI, TV, terrace, panoramic view, close to San Gimignano

4. Villa "Arnilù" with Private Pool & Wi-Fi

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

6. Villino Tre Pini | Panoramic Private Pool, Nature & Privacy

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

8. "A Casa di Franca Villa con piscina"

9. Villa Il Signorino

10. Luxury Villa in the Florentine hills

11. Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

12. Villetta Leonardo: Independence, Garden & Relaxation in Tuscany

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

14. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

15. Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi

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

17. My Exclusive Italy - Classic Suite in a Luxury Wine Estate

18. Exclusive Estate | Heated Pool & Personal Concierge

19. My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

20. Villa Marina with private pool, Borgo del Silenzio

Find holiday rentals that suit your style

Top Poggibonsi Hotel Reviews

B&B Poggiobonizio

Find out more about Poggibonsi

Poggibonsi Villas information

Frequently asked questions

Explore a world of travel with Expedia