Panoramic view of beautiful rows of colored vineyards nella campagna toscana in the Chianti region near San Casciano in Val di Pesa. Autumn season in October. Italy.

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for San Casciano in Val di Pesa villas

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.
The price is €2,562
includes taxes & fees
15 Jun - 16 Jun
Beautiful Tuscan home between Florence & Siena
Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is €185
includes taxes & fees
16 Jun - 17 Jun
Villa Montecastello
Outdoor dining

Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (147 reviews)
"Beautiful house and views"
United States
Melissa B.
The price is €500
includes taxes & fees
8 Jul - 9 Jul
Luxury Villa in the Florentine hills
Exterior

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is €818
includes taxes & fees
15 Jun - 16 Jun
Villa Marcolina
Exterior

Luxury Tuscan Villa with Private Heated Pool, Concierge service 8 miles Florence

Luxury Tuscan Villa with Private Heated Pool, Concierge service 8 miles Florence
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.
The price is €1,663
includes taxes & fees
15 Jun - 16 Jun
Luxury Tuscan Villa with Private Heated Pool, Concierge service 8 miles Florence
Outdoor dining

Casa dei Renai by Rentbeat

Casa dei Renai by Rentbeat
Signa
The price is €270
includes taxes & fees
5 Jul - 6 Jul
Casa dei Renai by Rentbeat
Exterior

NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!

NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!
Oltrarno
10.0 out of 10, Exceptional, (1 review)
"Struttura a dir poco fantastica. Siamo stati non bene benissimo e sicuramente ci ritorneremo.Approfitto anche per fare un ringraziamento a Serena e Venita per l’immensa disponibilità, professionalità e cordialità ricevuta."
United States
Giuseppe F.
The price is €808
includes taxes & fees
25 Jun - 26 Jun
NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!
Property grounds

Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is €124
includes taxes & fees
16 Jun - 17 Jun
Rooster House, cooking classes and opera
Property grounds

VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34

VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34
Pontassieve
10.0 out of 10, Exceptional, (2 reviews)
"This place is magical!!!!! The host was amazing and so communicative - readily available on the property and was able to answer questions as well as drive us to get food in town and to the train station! Ample space for guests and the property is beautiful. The pool area is great and comes with fun floats / fun activities for near the pool. The ambiance of the outdoor dining area is lovely and the check in/out process was easy. Couldn’t recommend this place more!!!"
United States
Lyndsey S.
The price is €3,568
includes taxes & fees
18 Jun - 19 Jun
VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34
Exterior

Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
10.0 out of 10, Exceptional, (2 reviews)
"Nice place 👌 "
United States
Avi A.
The price is €451
includes taxes & fees
15 Jun - 16 Jun
Villa Il Signorino
Pool

Casa Il Cappero – Villa with Private Pool in the Tuscan Hills

Casa Il Cappero – Villa with Private Pool in the Tuscan Hills
San Rocco
The price is €896
includes taxes & fees
29 Jun - 30 Jun
Casa Il Cappero – Villa with Private Pool in the Tuscan Hills
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.
The price is €402
includes taxes & fees
17 Jun - 18 Jun
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Exterior

My Exclusive Italy - Classic Suite in a Luxury Wine Estate

My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Rignano sull'Arno
The price is €499
includes taxes & fees
16 Jun - 17 Jun
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Exterior

CountryHouse con Piscina Privata 5 min dal centro

CountryHouse con Piscina Privata 5 min dal centro
Careggi Rifredi
9.6 out of 10, Exceptional, (15 reviews)
"The property was outstanding and our family had a blast. It was a nice get away from the crowds in the city to enjoy the animals and greenery of the house on the farm. "
United States
Nancy P.
The price is €480
includes taxes & fees
25 Jun - 26 Jun
CountryHouse con Piscina Privata 5 min dal centro
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
The price is €611
includes taxes & fees
18 Jun - 19 Jun
My Exclusive Italy - Exclusive 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
The price is €484
includes taxes & fees
28 Jun - 29 Jun
Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Exterior

Villino Serena Di Lapigio Florence: Mountain View, Private Garden

Villino Serena Di Lapigio Florence: Mountain View, Private Garden
Saltino
The price is €814
includes taxes & fees
16 Jun - 17 Jun
Villino Serena Di Lapigio Florence: Mountain View, Private Garden
Terrace/patio

Golden Hour - wedding in Florence

Golden Hour - wedding in Florence
Toscana
The price is €3,149
includes taxes & fees
29 Jun - 30 Jun
Golden Hour - wedding in Florence
Exterior

Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi

Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
Empoli
10.0 out of 10, Exceptional, (1 review)
"The villa is divided into 4 apartments and was perfect for our group of eleven. The property was beautiful and it is convenient to the Empoli train station."
United States
Vicki C.
The price is €1,631
includes taxes & fees
17 Jun - 18 Jun
Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
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.
The price is €395
includes taxes & fees
18 Jun - 19 Jun
Villa 'La Tinaia Il Sole Verde' with Shared Pool 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 San Casciano in Val di Pesa Hotel Reviews

The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

10/10 Excellent
"Incredible location, great concept. Staff was fantastic and AC worked perfectly. I will stsy there again!"
Marcela 6-night trip
Posted 3 hours ago
The Social Hub Florence Belfiore

Find out more about San Casciano in Val di Pesa

San Casciano in Val di Pesa Villas information

Number of reviews
290
Accommodation
1498 Villas
Lowest Price
€124
Highest Price
€3,568

Frequently asked questions

How much do villas in San Casciano in Val di Pesa cost?
Rates for villas in San Casciano in Val di Pesa range between €124 and €3,568 per night. Whatever your budget, you can find a place that suits your needs 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 San Casciano in Val di Pesa?
You'll find 1498 villas in San Casciano in Val di Pesa. No matter if you're travelling with the kids or organising a weekend break with your besties, Expedia can help you find the ideal base for your squad.
Why book your villa in San Casciano in Val di Pesa with Expedia?
Reserving a villa in San Casciano in Val di Pesa is as easy as working out your travel dates and choosing a place that checks your boxes. In search of something affordable or luxurious, or a stay that also offers a kitchenette? Use Expedia's search filters to narrow your results and find the ideal fit.
How can I find cheap villas in San Casciano in Val di Pesa?
Expedia is here to help you look for cheap villas in San Casciano in Val di Pesa. Use our filter tool to select amenities, budget and star rating to refine your search and find a fantastic place to stay in a couple of clicks.
What is there to do near my villa in San Casciano in Val di Pesa?
After you've unpacked your things and settled in, get out and explore the incredible things San Casciano in Val di Pesa has to offer. Antinori nel Chianti Classico is a popular attraction to add to your must-do list.