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
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 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 AED 8,426
AED 11,548 total
includes taxes & fees
19 Jul - 20 Jul
Beautiful Tuscan home between Florence & Siena
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
The price is AED 10,173
AED 14,131 total
includes taxes & fees
27 Jun - 28 Jun
Villa 'Il Conventino' with Private Pool, Wi-Fi, and Air Conditioning
Outdoor dining

Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (147 reviews)
"Beautiful property and great experience "
United States
edward p.
The price is AED 1,053
AED 1,660 total
includes taxes & fees
20 Jul - 21 Jul
Luxury Villa in the Florentine hills
Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
10.0 out of 10, Exceptional, (1 review)
"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 677
AED 757 total
includes taxes & fees
24 Jun - 25 Jun
Villa Montecastello
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 AED 2,442
AED 3,179 total
includes taxes & fees
24 Jun - 25 Jun
NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!
Exterior

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is AED 2,999
AED 3,333 total
includes taxes & fees
24 Jun - 25 Jun
Villa Marcolina
Exterior

The three owls of san gimignano

The three owls of san gimignano
San Gimignano
The price is AED 451
AED 536 total
includes taxes & fees
23 Jun - 24 Jun
The three owls of san gimignano
Property grounds

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is AED 19,886
AED 21,993 total
includes taxes & fees
23 Jun - 24 Jun
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Property grounds

Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is AED 417
AED 506 total
includes taxes & fees
24 Jun - 25 Jun
Rooster House, cooking classes and opera
Iron/ironing board, WiFi, bed sheets

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
The price is AED 1,557
AED 1,557 total
includes taxes & fees
30 Jun - 1 Jul
Villa 'Podere Sofia' with Mountain View, Private Terrace and Wi-Fi
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 AED 13,920
AED 16,027 total
includes taxes & fees
23 Jun - 24 Jun
VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34
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 AED 1,911
AED 2,102 total
includes taxes & fees
23 Jun - 24 Jun
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Outdoor dining

Casa dei Renai by Rentbeat

Casa dei Renai by Rentbeat
Signa
The price is AED 235
AED 1,075 total
includes taxes & fees
7 Jul - 8 Jul
Casa dei Renai by Rentbeat
Exterior

Villino Serena Di Lapigio Florence: Mountain View, Private Garden

Villino Serena Di Lapigio Florence: Mountain View, Private Garden
Saltino
The price is AED 1,955
AED 3,429 total
includes taxes & fees
25 Jun - 26 Jun
Villino Serena Di Lapigio Florence: Mountain View, Private Garden
Exterior

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 1,327
AED 1,904 total
includes taxes & fees
23 Jun - 24 Jun
Villa Il Signorino
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 AED 1,409
AED 1,590 total
includes taxes & fees
24 Jun - 25 Jun
Villa 'La Tinaia Il Sole Verde' with Shared Pool 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.
The price is AED 1,261
AED 1,682 total
includes taxes & fees
23 Jun - 24 Jun
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Exterior

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is AED 59,658
AED 59,658 total
includes taxes & fees
6 Jul - 7 Jul
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Exterior

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
Careggi Rifredi
10.0 out of 10, Exceptional, (1 review)
"Staff went over and above for us. Food was wonderful service 5 stars"
United States
robert g.
The price is AED 39,772
AED 39,772 total
includes taxes & fees
26 Jun - 27 Jun
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
Outdoor dining

Villa Cielo Toscano in San Miniato with Private Pool

Villa Cielo Toscano in San Miniato with Private Pool
San Miniato
The price is AED 4,884
AED 6,106 total
includes taxes & fees
23 Jun - 24 Jun
Villa Cielo Toscano in San Miniato with Private Pool
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

Hotel Albani Firenze

Hotel Albani Firenze

10/10 Excellent
"Quaint, elegant place in the heart of the Florence city center. Our room had French doors that overlooked the garden and it was just wonderful. Included breakfast every morning was phenomenal! The staff all went above and beyond there!"
Cassie 3-night trip
Posted 3 hours ago
Hotel Albani Firenze

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 AED 506 and AED 59,658 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 1837 villas in San Casciano in Val di Pesa. No matter if you're traveling with the kids or organizing 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.