A stone building with a clock tower, steps leading up to it, and people walking around.

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Castellina in Chianti villas

Terrace/patio

1. The San Leonino House

The San Leonino House
Castellina in Chianti
The price is AED 2,865
AED 5,617 total
includes taxes & fees
23 Aug - 24 Aug
The San Leonino House
Exterior

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

Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Gambassi Terme
The price is AED 18,091
AED 18,104 total
includes taxes & fees
21 Aug - 22 Aug
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Exterior

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

Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence
Oltrarno
The price is AED 3,951
AED 4,002 total
includes taxes & fees
9 Aug - 10 Aug
Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence
Property grounds

4. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is AED 466
AED 555 total
includes taxes & fees
7 Aug - 8 Aug
Rooster House, cooking classes and opera
Villa, Air conditioning, Courtyard View | Exterior

5. Villa Montecastello

Villa Montecastello
Monteriggioni
7.0 out of 10, Good, (2 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is AED 701
AED 784 total
includes taxes & fees
14 Aug - 15 Aug
Villa Montecastello
Pool

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

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is AED 4,546
AED 6,583 total
includes taxes & fees
2 Sep - 3 Sep
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Exterior

7. Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is AED 3,119
AED 3,465 total
includes taxes & fees
14 Aug - 15 Aug
Villa Marcolina
Property grounds

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

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Everything about this house is exquisite and very homey. Decors are really tasteful. Outdoors spaces and the views are absolutely beautiful. Kitchen is really well appointed. There is no shortage of dish-wear, silverware and glasses. Location is very central to explore Tuscany. Our host, Lapo is very welcoming and helpful with all recommendations. He is the kind of host that you want to stay in touch and come back to see him. "
United States
Ravin N.
The price is AED 6,977
AED 7,078 total
includes taxes & fees
14 Aug - 15 Aug
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Property grounds

9. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is AED 18,394
AED 20,512 total
includes taxes & fees
11 Aug - 12 Aug
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Exterior

10. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is AED 1,483
AED 2,071 total
includes taxes & fees
2 Sep - 3 Sep
Villa Il Signorino
Exterior

11. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is AED 7,048
AED 7,986 total
includes taxes & fees
12 Aug - 13 Aug
Villa Torre Among the Hills of Siena
Outdoor dining

12. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is AED 6,555
AED 7,493 total
includes taxes & fees
10 Aug - 11 Aug
Villa Capanna: A Window onto Tuscany
Property grounds

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

Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is AED 1,698
AED 4,053 total
includes taxes & fees
27 Aug - 28 Aug
Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Pool

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

"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Certaldo
The price is AED 39,852
AED 41,898 total
includes taxes & fees
14 Aug - 15 Aug
"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Exterior

15. Portion of Villa Il Conventino with Pool and Wi-Fi

Portion of Villa Il Conventino with Pool and Wi-Fi
San Casciano in Val di Pesa
The price is AED 11,158
AED 15,137 total
includes taxes & fees
14 Aug - 15 Aug
Portion of Villa Il Conventino with Pool and Wi-Fi
Exterior

16. Nice apartment in villa with pool, A/C, WIFI, TV, terrace and panoramic view, close to San Gimig...

Nice apartment in villa with pool, A/C, WIFI, TV, terrace and panoramic view, close to San Gimig...
Montaione
10.0 out of 10, Exceptional, (5 reviews)
"We spend a great time, marvellous place and people"
United States
Carole G.
Nice apartment in villa with pool, A/C, WIFI, TV, terrace and panoramic view, close to San Gimig...
Exterior

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is AED 23,246
AED 24,817 total
includes taxes & fees
31 Aug - 1 Sep
Villa "Arnilù" with Private Pool & Wi-Fi
Outdoor dining

18. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (149 reviews)
"Lovely property, nicely appointed, would be happy to stay there again."
United States
David K.
The price is AED 1,059
AED 1,652 total
includes taxes & fees
29 Aug - 30 Aug
Luxury Villa in the Florentine hills
Terrace/patio

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

Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Certaldo - Firenze
2.0 out of 10, (1 review)
"House is very nice and clean , but not equipped for rental, kitchen is poorly equipped, towels are like napkins , no toilet paper, no soap , nothing "
United States
Kelly C.
The price is AED 1,999
AED 2,516 total
includes taxes & fees
16 Aug - 17 Aug
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Outdoor dining

20. Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi

Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
Mercatale Val Di Pesa
The price is AED 5,858
AED 5,875 total
includes taxes & fees
24 Aug - 25 Aug
Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Castellina in Chianti Hotel Reviews

Italiana Hotels Florence

Italiana Hotels Florence

10/10 Excellent
"Room was spacious & clean. Breakfast was good. Staff needs to be more professional. Overall, great stay. The free parking was a plus coz that’s hard to find on big cities."
Clarissa 3-night trip
Posted 2 hours ago
Italiana Hotels Florence

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between AED 555 and AED 41,898 per night. These stays offer the privacy of your own space at a price that doesn't break the bank. 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 Castellina in Chianti?
You can choose from 1851 villas in Castellina in Chianti. No matter if you're traveling with the family or planning a getaway with your buddies, Expedia will help you find the ideal base for your squad.
Why book your villa in Castellina in Chianti with Expedia?
Reserving a villa in Castellina in Chianti is as simple as deciding on your travel dates and picking the option suited to your needs. In search of something affordable or luxurious, or a property that also has a kitchen and laundry? Use Expedia's search filters to narrow your results and find the perfect pad.
How can I find cheap villas in Castellina in Chianti?
The easiest way to compare cheap villas in Castellina in Chianti is with Expedia's convenient filter tool. Narrow your search by amenities, budget and star rating to nab awesome rates in only a few clicks.