Poggibonsi Villas - Best Villa Poggibonsi 2026

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Poggibonsi villas

Villa, Air conditioning, Courtyard View | Exterior

1. Villa Montecastello

Monteriggioni

Alvaro

includes taxes & fees

3 Sept - 4 Sept

2. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

includes taxes & fees

4 Sept - 5 Sept

3. Private Tuscan Villa Estate w/ Pool & BBQ

Poggibonsi

4. The three owls of san gimignano

San Gimignano

includes taxes & fees

3 Sept - 4 Sept

5. Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence

Oltrarno

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

San Gimignano

includes taxes & fees

3 Sept - 4 Sept

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

Certaldo - Firenze

Kelly C.

includes taxes & fees

3 Sept - 4 Sept

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

Radda in Chianti

Amber M.

includes taxes & fees

17 Sept - 18 Sept

9. Luxury Villa in the Florentine hills

Florence

John G.

includes taxes & fees

3 Sept - 4 Sept

10. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

Gambassi Terme

includes taxes & fees

1 Oct - 2 Oct

11. The San Leonino House

Castellina in Chianti

includes taxes & fees

7 Sept - 8 Sept

12. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

includes taxes & fees

3 Sept - 4 Sept

13. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

Siena

includes taxes & fees

8 Sept - 9 Sept

14. "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

10 Sept - 11 Sept

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

Impruneta

Maria H.

includes taxes & fees

6 Sept - 7 Sept

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

San Vivaldo

includes taxes & fees

3 Sept - 4 Sept

17. AWESHOMEITALY - VILLA SAN MARTINO

La Fornace

includes taxes & fees

4 Sept - 5 Sept

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

Montaione

includes taxes & fees

9 Sept - 10 Sept

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

Montespertoli

Scott M.

includes taxes & fees

4 Sept - 5 Sept

20. Tuscan Sky Villa in San Miniato with Exclusive Private Pool

San Miniato

includes taxes & fees

14 Sept - 15 Sept

View all properties

Find holiday rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Top Poggibonsi Hotel Reviews

Villa Lecchi Hotel Wellness

10/10 Excellent

"Beautiful place, beautiful and amazing people starting with the owners, and then Mateo, Sarah, Georgia and Claudia. We didn’t want to leave they were amazing treat us like family."

Cosy apartment in villa with pool, WIFI, TV, patio and panoramic view, close to San Gimignano

10/10 Excellent

"Hallo, die Gegend war wunderschön, die Unterkunft war authentisch, die Leute sehr nett, hätten wir keinen Pool wäre es nicht auszuhalten gewesen, Die Unterkünfte entsprachen nicht unseren Standard , das Mobiliar war alt bis sehr alt und es war auf den Zimmer nicht auszuhalten, da halfen auch keine Lüfter, es wäre sinnvoll nicht nur im Hauptgebäude sondern in allen Wohnungen Klimaanlagen nachzurüsten , bei Nachttemperaturen von über30 Grad kommt der Körper nicht zur Ruhe........mfg"

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!"

Tenuta Macericca - Vacation villa with pool

10/10 Excellent

"The Villa was very nice, clean all over and well equipped, even better than described. We enjoyed the large kitchen. Nice and very clean pool. The location was nice and quiet, but it was a long drive on very narrow roads and the the last part was an old dusty gravel road. The view from the villa is very nice looking out on Tuscany landscape and wine fields. Whats not to like. The owner was very helpful and can provide private dinning and cooking class. The Antinori winery and headquarter is only 30 min driving from the villa. You should visit the nearby Osteria 1126 and Winery Cinciano only 600 meters from the villa.The Golf course Royal Golf La Bagnia is only 40 min drive from the villa, if you are a golfer you should allow yourselves a round or two."

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	3
Accommodation	146 Villas
Lowest Price	€167
Highest Price	€1,260

Frequently asked questions

How much do villas in Poggibonsi cost?

Villas in Poggibonsi cost between €167 and €1,260 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.

Room 1

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. Private Tuscan Villa Estate w/ Pool & BBQ

4. The three owls of san gimignano

5. Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence

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

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

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

9. Luxury Villa in the Florentine hills

10. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

11. The San Leonino House

12. Villa Il Signorino

13. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

14. "A Casa di Franca Villa con piscina"

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

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

17. AWESHOMEITALY - VILLA SAN MARTINO

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

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

20. Tuscan Sky Villa in San Miniato with Exclusive Private Pool

Find holiday rentals that suit your style

Top Poggibonsi Hotel Reviews

Villa Lecchi Hotel Wellness

B&B Poggiobonizio

Cosy apartment in villa with pool, WIFI, TV, patio and panoramic view, close to San Gimignano

Hotel Villa San Giorgio

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

Hotel Ristorante Alcide

Villa San Lucchese

Tenuta Macericca - Vacation villa with pool

Casale di Villore

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. Private Tuscan Villa Estate w/ Pool & BBQ

4. The three owls of san gimignano

5. Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence

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

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

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

9. Luxury Villa in the Florentine hills

10. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

11. The San Leonino House

12. Villa Il Signorino

13. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

14. "A Casa di Franca Villa con piscina"

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

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

17. AWESHOMEITALY - VILLA SAN MARTINO

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

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

20. Tuscan Sky Villa in San Miniato with Exclusive Private Pool

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