Gaiole in Chianti Villas from CA $210

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.

CA $2,206 total

includes taxes & fees

Aug 22 - Aug 23

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

CA $1,879 total

includes taxes & fees

Aug 27 - Aug 28

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

Radda in Chianti

Amber M.

CA $2,323 total

includes taxes & fees

Sep 1 - Sep 2

4. Rooster House, cooking classes and opera

Toscana

CA $210 total

includes taxes & fees

Aug 18 - Aug 19

Villa, Air conditioning, Courtyard View | Exterior

5. Villa Montecastello

Monteriggioni

Alvaro

CA $297 total

includes taxes & fees

Aug 25 - Aug 26

6. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

CA $791 total

includes taxes & fees

Sep 1 - Sep 2

7. Villa Torre Among the Hills of Siena

Vico dʼArbia

CA $3,110 total

includes taxes & fees

Aug 30 - Aug 31

8. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

Siena

CA $7,774 total

includes taxes & fees

Aug 17 - Aug 18

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Top Gaiole in Chianti Hotel Reviews

Villa Olmi Firenze

10/10 Excellent

"We recently spent a week at Villa Olmi and had the most incredible time. The hotel itself is beautiful, a peaceful oasis to escape the busy city. The grounds were kept beautifully and the pool area in particular felt so pristine, plenty of fresh towels, super clean and drinks/food delivered to your sun bed- a total dream! Rooms were great with air con that kept them cool during the recent heatwave. Our room near the pool was the perfect location too, literally steps to our sun beds. The bathrooms could do with updating I feel, but they were fine and kept clean. All staff at the hotel were so lovely, warm and welcoming. The reception team were always helpful with questions we had (for example needing a different adapter for our plugs!). The wait staff were also all very attentive and friendly. The housekeeping team also- working that job during hot weather must be tough but they were so smiley and kind. Food at breakfast was great, such a good selection. The restaurant was also super tasty and a lovely setting to have dinner. One comment would be more of a varied menu, we were there for a week and the menu didn’t change so we did go elsewhere for variety. The shuttle bus was very useful and a great addition to have as it’s too far to walk into Florence. However I think a later shuttle bus to allow staying out for dinner would have been great, also dropping closer to the city centre as the 20 min walk from the bus was hard in the heat. Overall an excellent stay!"

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."

Castello di Leonina Relais

8/10 Good

"The view from the dining area was perfect. The included breakfast was amazing and the complimentary ebike rentals were perfect to get around outside of the hotel to catch more amazing views! The food at dinner was perfect. The only thing that was lacking was the bathroom showers. Ours was leaking. Other than that it was a perfect stay."

Ultimo Mulino Wellness Country Hotel

10/10 Excellent

"Loved this boutique property. Stayed five nights in the newer section, Le Noci, and would love to go back. The staff were all excellent, friendly and helpful. The pool was stunning. The room was large, comfy, and quiet. Breakfast was delicious and eating on the outside terrace was wonderful as the view was incredible. The only downside was the restaurant over at the older section. Would not recommend as the waitress was rude/pushy (made the evening uncomfortable) and the food was just okay. Would recommend going to nearby Radda or Gaiole instead. Highly recommend Il Papavero in Barbischio, a few minutes east of Gaiole. The dinner we had there was the best and a highlight of the trip."

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews	287
Accommodation	1891 Villas
Lowest Price	CA $210
Highest Price	CA $7,774

Frequently asked questions

How much do villas in Gaiole in Chianti cost?

Prices for villas in Gaiole in Chianti range between CA $210 and CA $7,774 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 1891 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.

Why book your villa in Gaiole in Chianti with Expedia?

We think vacation time shouldn't be complicated, so if you're looking for villas at a nice price, Expedia can help. Save those pennies and opt for an all-inclusive stay, or splurge on a luxury villa to spoil your loved ones. Use our convenient search filters to find an escape in Gaiole in Chianti that suits your needs.

How can I find cheap villas in Gaiole in Chianti?

An excellent way to locate cheap villas in Gaiole in Chianti is with Expedia's filter tool. Narrow your search by star rating, amenities and budget to nab unbeatable rates in only a click or two.

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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Search Gaiole in Chianti Villa Rentals from CA $210

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 'La Petrosa' with Private Pool, Private Garden and Balcony

4. Rooster House, cooking classes and opera

5. Villa Montecastello

6. Villa Il Signorino

7. Villa Torre Among the Hills of Siena

8. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

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

10. Luxury Villa in the Florentine hills

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

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

13. Pool Villa - Breakfast included

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

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

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

17. Villa Capanna: A Window onto Tuscany

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

19. Exclusive Estate | Heated Pool & Personal Concierge

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

Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Villa Olmi Firenze

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Frequently asked questions

Explore a world of travel with Expedia