Poggibonsi Villas

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

HK$1,635 total

includes taxes & fees

6 Oct - 7 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

HK$1,157 total

includes taxes & fees

7 Oct - 8 Oct

A stone building with a large glass door, a wooden deck, and a stone wall.

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

San Gimignano

HK$46,899 total

includes taxes & fees

12 Oct - 13 Oct

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

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

Certaldo - Firenze

Kelly C.

HK$5,149 total

includes taxes & fees

6 Oct - 7 Oct

A two-story building with a garden, a gazebo, and a statue.

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

Gambassi Terme

HK$38,087 total

includes taxes & fees

7 Oct - 8 Oct

A brick building with a gravel courtyard, a staircase, and potted plants.

6. GuestHost - Porta Romana Elegant House with Private Parking!

Siena

Kathleen M.

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

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

Radda in Chianti

Amber M.

HK$14,157 total

includes taxes & fees

1 Nov - 2 Nov

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

8. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

Siena

Ron M.

HK$61,946 total

includes taxes & fees

6 Oct - 7 Oct

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

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

Montespertoli

Krista G.

HK$17,161 total

includes taxes & fees

1 Nov - 2 Nov

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

10. "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

HK$16,399 total

includes taxes & fees

19 Oct - 20 Oct

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

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

Montespertoli

HK$53,029 total

includes taxes & fees

14 Oct - 15 Oct

An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

12. Luxury Villa in the Florentine hills

Florence

melissa r.

HK$2,906 total

includes taxes & fees

1 Nov - 2 Nov

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

13. Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco

Montespertoli

"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"

Elise D.

HK$16,658 total

includes taxes & fees

3 Nov - 4 Nov

An outdoor patio with a round table, chairs, a sofa, and a potted plant.

14. Molino In Chianti - Villa with Private Pool

Mercatale Val Di Pesa

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

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

Montespertoli

Scott M.

HK$15,916 total

includes taxes & fees

4 Nov - 5 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.

16. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

HK$3,975 total

includes taxes & fees

6 Oct - 7 Oct

An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

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

Toscana

HK$24,139 total

includes taxes & fees

18 Oct - 19 Oct

A two-story building with a red roof, multiple windows, and a gravel driveway.

18. Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi

Empoli

Vicki C.

HK$14,695 total

includes taxes & fees

8 Oct - 9 Oct

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

19. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

Firenze

HK$115,060 total

includes taxes & fees

6 Oct - 7 Oct

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

20. Exclusive Estate | Personal Concierge & Heated Pool

impruneta

Oli P.

HK$9,822 total

includes taxes & fees

19 Oct - 20 Oct

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Top Poggibonsi Hotel Reviews

Casale di Villore

10/10 Excellent

"Spacious living space with a kitchen and cosy bedroom. Lovely outdoor area to sit in afternoon and a communal swimming pool with great view."

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."

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."

Find out more about Poggibonsi

Poggibonsi Villas information

Number of reviews	337
Accommodation	148 Villas
Lowest Price	HK$1,157
Highest Price	HK$115,060

Frequently asked questions

How much do villas in Poggibonsi cost?

Villas in Poggibonsi cost between HK$1,157 and HK$115,060 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 148 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.

Explore a world of travel with Expedia

Chianti Region Holiday Rentals

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 "Arnilù" with Private Pool & Wi-Fi

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

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

6. GuestHost - Porta Romana Elegant House with Private Parking!

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

8. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

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

10. "A Casa di Franca Villa con piscina"

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

12. Luxury Villa in the Florentine hills

13. Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco

14. Molino In Chianti - Villa with Private Pool

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

16. Villa Il Signorino

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

18. Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi

19. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

20. Exclusive Estate | Personal Concierge & Heated Pool

Find holiday rentals that suit your style

Top Poggibonsi Hotel Reviews

Casale di Villore

Find out more about Poggibonsi

Poggibonsi Villas information

Frequently asked questions

Explore a world of travel with Expedia