A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

Villas in Chianti Region

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Chianti Region villas

Property grounds

Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
$134 nightly
The price is $137
Jul 12 - Jul 13
Total with taxes and fees
Rooster House, cooking classes and opera
Outdoor spa tub

Villa 'Podere Sofia' with Mountain View, Private Terrace and Wi-Fi

Villa 'Podere Sofia' with Mountain View, Private Terrace and Wi-Fi
Gaiole in Chianti
Villa 'Podere Sofia' with Mountain View, Private Terrace and Wi-Fi
Outdoor dining

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

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Impruneta
10.0 out of 10, Exceptional, (3 reviews)
"Super quaint, beatiful, designed, comfortable, not lacking anything house and location. Very informative and accessable host. Listen to the instructions on how to go to Firenze. No need to take your car tyere!"
United States
Maria H.
$431 nightly
The price is $431
Jul 20 - Jul 21
Total with taxes and fees
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Exterior

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
$786 nightly
The price is $874
Aug 10 - Aug 11
Total with taxes and fees
Villa Marcolina
Exterior

Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
$502 nightly
The price is $507
Jul 15 - Jul 16
Total with taxes and fees
Villa Il Signorino
Exterior

My Exclusive Italy - Classic Suite in a Luxury Wine Estate

My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Rignano sull'Arno
$518 nightly
The price is $570
Jul 14 - Jul 15
Total with taxes and fees
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Pool

Podere Le Casette - Five Bedroom Villa, Sleeps 10

Podere Le Casette - Five Bedroom Villa, Sleeps 10
Cassia
10.0 out of 10, Exceptional, (1 review)
"The home was recently renovated immaculately and is an incredible place to enjoy Tuscany as well as Florence. The pictures don’t do it justice. We enjoyed our stay and would recommend to any group of any age. The views will last forever."
United States
Geoff B.
$1,029 nightly
The price is $1,033
Jul 13 - Jul 14
Total with taxes and fees
Podere Le Casette - Five Bedroom Villa, Sleeps 10
Pool

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (2 reviews)
"Upon arrival Guido had everything prepared for us. A bottle of his amazing wine that he makes along with 2 wine glasses we’re waiting on the farmhouse table. The home had 2 very comfortable bedrooms and a bathroom along with a living room and kitchen. Front porch overlooks the stunning Tuscany fields. The swimming pool was refreshing and everything was beyond perfect. This location was everything and more. The hosts were so helpful. I will come back her again..make sure to take time for the...
United States
Marianne H.
$524 nightly
The price is $527
Jul 11 - Jul 12
Total with taxes and fees
Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Exterior

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

My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Rignano sull'Arno
$634 nightly
The price is $698
Jul 14 - Jul 15
Total with taxes and fees
My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Exterior

Villa 'Il Conventino' with Private Pool, Wi-Fi, and Air Conditioning

Villa 'Il Conventino' with Private Pool, Wi-Fi, and Air Conditioning
San Casciano in Val di Pesa
$7,495 nightly
The price is $7,499
Aug 9 - Aug 10
Total with taxes and fees
Villa 'Il Conventino' with Private Pool, Wi-Fi, and Air Conditioning
Exterior

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

My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
Rignano sull'Arno
$873 nightly
The price is $960
Jul 14 - Jul 15
Total with taxes and fees
My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
Pool

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Bucine
$526 nightly
The price is $529
Jul 19 - Jul 20
Total with taxes and fees
Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Exterior

Villa with Concierge service and heated pool

Villa with Concierge service and heated pool
impruneta
10.0 out of 10, Exceptional, (109 reviews)
"The Villa and grounds are absolutely beautiful! Caterina and her family members were the most gracious hosts. They could not do enough to make sure we had a "once in a lifetime" multi-generational family trip and truly made us feel like part of their family during our stay. We loved every second of our time in Tuscany and would highly recommend this amazing property."
United States
Charles S.
$1,861 nightly
The price is $1,866
Aug 9 - Aug 10
Total with taxes and fees
Villa with Concierge service and heated pool
Outdoor dining

Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (2 reviews)
"Pros: Wunderschönes charmantes, rustikales Ferienhaus in der wunderschönen Toskana. Tolle Lage, sehr freundlicher und charmanter Gastgeber. Senore Guidi und seine Ehefrau sind zauberhafte Gastgeber. Sehr hilfsbereit und zuvorkommend! Die Fotos der Unterkunft stimmen zu 100% überein! Toller Poolbereich. Senor Guidi hat zur Wein- und Olivenöl -Verkostung eingeladen und uns auf Anfrage zu einer persönlichen Begehung seiner Oliven-und-Weinberge mitgenommen. Sehr persönliche und menschliche...
Germany
Anonymous traveler
$549 nightly
The price is $552
Jul 18 - Jul 19
Total with taxes and fees
Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
Pool

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.
$2,107 nightly
The price is $2,112
Jul 19 - Jul 20
Total with taxes and fees
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Exterior

Beautiful Tuscan home between Florence & Siena

Beautiful Tuscan home between Florence & Siena
Florence
10.0 out of 10, Exceptional, (8 reviews)
"From the moment we entered to our last day everything was perfect. Group of 15 and we all fit comfortably. "
United States
Debra P.
$2,847 nightly
The price is $2,847
Jul 19 - Jul 20
Total with taxes and fees
Beautiful Tuscan home between Florence & Siena
Exterior

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

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
$2,261 nightly
The price is $2,263
Jul 14 - Jul 15
Total with taxes and fees
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Exterior

Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
$2,014 nightly
The price is $2,019
Jul 11 - Jul 12
Total with taxes and fees
Villa Torre Among the Hills of Siena
Terrace/patio

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.
$716 nightly
The price is $716
Jul 16 - Jul 17
Total with taxes and fees
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Exterior

Romantic stylish villa with private pool & splendid view

Romantic stylish villa with private pool & splendid view
Panzano In Chianti
9.8 out of 10, Exceptional, (24 reviews)
"Beautiful location with spectacular views."
United States
lawrence s.
$1,314 nightly
The price is $1,314
Jul 30 - Jul 31
Total with taxes and fees
Romantic stylish villa with private pool & splendid view
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chianti Region Hotel Reviews

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

10/10 Excellent
"Fantastic stay. Beautiful location. Very pleasant and helpful staff. Excellent!"
Drew 5-night trip
Posted 3 hours ago
Villa I Barronci Resort & Spa

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews
156
Accommodation
568 Villas
Lowest Price
$137
Highest Price
$7,499

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between $137 and $7,499 per night. These escapes 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 Chianti Region?
Chianti Region has 568 villas to choose from. Enter your destination and dates and lock in your perfect trip today.
Why book your villa in Chianti Region with Expedia?
We think arranging a vacation should be a breeze, so if you're looking for villas at a great price, Expedia delivers. Keep costs down and choose an all-inclusive stay, or splurge on a plush villa to spoil the ones you love most. Our handy filters make it easy to find a property in Chianti Region that matches your needs.
How can I find cheap villas in Chianti Region?
With Expedia's user-friendly filter tool, scoring cheap villas in Chianti Region has never been easier. To find stays that won't break the bank, fine-tune your search by star rating, budget and amenities.
What is there to do near my villa in Chianti Region?
Whether you love food, shopping, history or sightseeing, Chianti Region offers something for everyone! The major city of San Gimignano boasts lots of things to do, including Archaeological Museum - Spezieria Santa Fina - Raffaele De Grada Modern and Contemporary Art Gallery, Historical Torture Museum and Ornithological Museum. If you're headed to Radda in Chianti, Castello di Albola, Castello di Radda Winery and Borgo di Vescine - Tenute di Castelvecchi shouldn't be missed.

Explore a world of travel with Expedia