Poggibonsi Villas from CA $210

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

CA $268 total

includes taxes & fees

Sep 25 - Sep 26

2. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

CA $210 total

includes taxes & fees

Sep 21 - Sep 22

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

San Gimignano

CA $8,530 total

includes taxes & fees

Sep 21 - Sep 22

4. "Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

Certaldo

CA $8,872 total

includes taxes & fees

Oct 12 - Oct 13

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

Tavarnelle Val di Pesa

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

Certaldo - Firenze

Kelly C.

CA $936 total

includes taxes & fees

Oct 1 - Oct 2

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

Radda in Chianti

Amber M.

CA $1,548 total

includes taxes & fees

Sep 23 - Sep 24

8. Luxury Villa in the Florentine hills

Florence

melissa r.

CA $541 total

includes taxes & fees

Oct 12 - Oct 13

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

Gambassi Terme

CA $5,834 total

includes taxes & fees

Oct 1 - Oct 2

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

Montespertoli

CA $9,645 total

includes taxes & fees

Oct 14 - Oct 15

11. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

CA $725 total

includes taxes & fees

Sep 23 - Sep 24

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

Montespertoli

Scott M.

CA $3,184 total

includes taxes & fees

Sep 30 - Oct 1

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

Impruneta

Maria H.

CA $614 total

includes taxes & fees

Sep 25 - Sep 26

14. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

Siena

CA $11,267 total

includes taxes & fees

Sep 21 - Sep 22

15. Villa Sunset, in the heart of Chianti

Greve in Chianti

elisa b.

16. "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

CA $2,753 total

includes taxes & fees

Sep 21 - Sep 22

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

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.

CA $3,213 total

includes taxes & fees

Sep 21 - Sep 22

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

Montespertoli

Krista G.

CA $3,030 total

includes taxes & fees

Sep 21 - Sep 22

19. Tuscan Sky Villa in San Miniato with Private Pool

San Miniato

CA $1,068 total

includes taxes & fees

Sep 21 - Sep 22

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

Rignano sull'Arno

CA $641 total

includes taxes & fees

Oct 16 - Oct 17

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Top Poggibonsi Hotel Reviews

Casale di Villore

10/10 Excellent

"Our stay in the Cardisco apartment at Casale di Villore was absolutely wonderful. The location is simply stunning, with breathtaking views and the most divine infinity pool, easily one of the highlights of our stay in Tuscany. The apartment was spotlessly clean, and Alice was a fantastic host, welcoming, friendly and always happy to help. We particularly loved having our own designated sun lounger space, which made relaxing by the pool even more enjoyable. The location is also perfect for exploring the Chianti region, with beautiful vineyards and charming towns nearby. We highly recommend visiting La Croce just up the road for some lovely wines. A truly special place to stay, and somewhere we would happily return to."

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!"

Find out more about Poggibonsi

Poggibonsi Villas information

Number of reviews	218
Accommodation	152 Villas
Lowest Price	CA $210
Highest Price	CA $11,267

Frequently asked questions

How much do villas in Poggibonsi cost?

Villas in Poggibonsi cost between CA $210 and CA $11,267 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 152 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.

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Search Poggibonsi Villa Rentals from CA $210

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 Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

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

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

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

8. Luxury Villa in the Florentine hills

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

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

11. Villa Il Signorino

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

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

14. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

15. Villa Sunset, in the heart of Chianti

16. "A Casa di Franca Villa con piscina"

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

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

19. Tuscan Sky Villa in San Miniato with Private Pool

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

Find vacation 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