Gaiole in Chianti Villas - Villas in Gaiole in Chianti NZ$163

A stone castle with battlements overlooking a lush valley with vineyards.

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Our top choices for Gaiole in Chianti villas

1. "Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

Gaiole in Chianti

Bernard K.

includes taxes & fees

26 Aug - 27 Aug

2. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Gaiole in Chianti

"Pros: La casa è sita in una posizione super tranquilla in mezzo al verde e alla natura. Tutto è curato alla perfezione. Nota di merito per il verde e i fiori e per la gentilezza dei proprietari. Cons: La posizione che è un pregio per qualcuno per altri potrebbe non esserlo. In effetti per arrivare al podere ci sono 2 km di strada bianca molto stretta. Una volta arrivati si è però ripagati ampiamente del piccolo disagio!"

Anonymous traveller

includes taxes & fees

27 Aug - 28 Aug

3. Villa Marcolina

Castelnuovo Berardenga

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

Radda in Chianti

Amber M.

includes taxes & fees

1 Sept - 2 Sept

Villa, Air conditioning, Courtyard View | Exterior

5. Villa Montecastello

Monteriggioni

Alvaro

includes taxes & fees

31 Aug - 1 Sept

6. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

includes taxes & fees

12 Sept - 13 Sept

7. Rooster House, cooking classes and opera

Toscana

includes taxes & fees

17 Aug - 18 Aug

8. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

Siena

includes taxes & fees

27 Aug - 28 Aug

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Top Gaiole in Chianti Hotel Reviews

Castello di Tornano Wine Resort

8/10 Good

"We really like this place. Pool was very nice and staff were mostly helpful. Its a pretty good location to visit multiple areas as well. Room air conditioner did an ok job upstairs in bedroom loft but struggled to keep it cool in the sitting area on main level. The view from the tower is awesome but its a climb"

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent

"Our family of 18 stayed at the Villa this July (2026) and could not have been more pleased with everything associated with our stay. Jacopo and Beatrice truly are first class hosts. They helped us book 3 vehicles that were dropped off and picked up directly at the Villa which was a great time saver. They also provided a grocery shopping service so that we had drinks and snacks at the villa when we arrived.The meal service was truly fantastic! We opted for the Welcome dinner and the Florentine BBQ, both of which were great. We visited a lot of places while in Italy but the family dinners at sunset were among our favorites.The Villa was beautiful and spacious. The grandkids really enjoyed the open spaces and the pool. The views from the back deck of the surrounding Tuscan countryside were also very special. We even got to see hot air balloons on a few occasions. The relative close proximity to Firenze was also clutch for day trips on high-speed trains. There is a good reason why this Villa won the VRBO Vacation Rental of the Year. You simply cannot go wrong here. I am very thankful for the memories that will last a lifetime and role this villa and the hosts played in making that happen!"

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend."

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Gaiole in Chianti Villas information

Number of reviews	175
Accommodation	1583 Villas
Lowest Price	NZ$163
Highest Price	NZ$9,526

Frequently asked questions

How much do villas in Gaiole in Chianti cost?

Prices for villas in Gaiole in Chianti range between NZ$163 and NZ$9,526 per night. Whatever your budget, you'll find something that fits the bill with Expedia. 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 Gaiole in Chianti?

Gaiole in Chianti has 1583 villas to select from. Find your perfect stay quickly and easily by checking the "Villa" box under the "Property type" tab in our handy filter tool.

What is there to do near my villa in Gaiole in Chianti?

There are plenty of fantastic things to do in Gaiole in Chianti. Make tracks to leading attractions like Cantalici Winery, Castle of Brolio and Meleto Castle. Badia a Coltibuono, Church of San Sigismondo and PoggioBrandani also appeal to many visitors.

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Activities in Radda in Chianti

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Gaiole in Chianti villas

1. "Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

2. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

3. Villa Marcolina

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

5. Villa Montecastello

6. Villa Il Signorino

7. Rooster House, cooking classes and opera

8. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

9. Villa Torre Among the Hills of Siena

10. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

11. Luxury Villa in the Florentine hills

12. Pool Villa - Breakfast included

13. Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi

14. Villa Capanna: A Window onto Tuscany

15. Artisti del Cavallo Tourism

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

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

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

19. Villa "Il Fornacino" with Pool, Garden & Wi-Fi

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

Find holiday rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Castello di Tornano Wine Resort

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Frequently asked questions

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