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Check prices for these dates

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Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Villas in San Casciano in Val di Pesa

Beautiful Tuscan home between Florence & Siena
Outdoor dining

Beautiful Tuscan home between Florence & Siena

10.0 out of 10, Exceptional, (5)
"Property was just as listed. Clean, large, and a great location for wine tasting, local restaurants, and more. The owners were super helpful in planning some local outings. Highly recommended. "
The price is ￥231,146
￥342,766 total
includes taxes & fees
Aug 24 - Aug 25
Beautiful Tuscan home between Florence & Siena
Villa "Arnilù" with Private Pool & Wi-Fi
Exterior

Villa "Arnilù" with Private Pool & Wi-Fi

The price is ￥756,233
￥820,114 total
includes taxes & fees
Sep 4 - Sep 5
Villa "Arnilù" with Private Pool & Wi-Fi
Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
Dining

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

The price is ￥162,801
￥230,540 total
includes taxes & fees
Sep 2 - Sep 3
Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
Villa 'Country house Sofia Villas' with Private Pool, Wi-Fi and Air Conditioning
Pool

Villa 'Country house Sofia Villas' with Private Pool, Wi-Fi and Air Conditioning

The price is ￥87,808
￥101,102 total
includes taxes & fees
Sep 7 - Sep 8
Villa 'Country house Sofia Villas' with Private Pool, Wi-Fi and Air Conditioning
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Pool

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

The price is ￥1,024,904
￥1,111,030 total
includes taxes & fees
Aug 19 - Aug 20
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Villa Boccaccio
Terrace/patio

Villa Boccaccio

2.0 out of 10, (1)
"Keiner Vor-Ort gewesen. Es war kein Check In möglich trotz Buchungsbestätigung"
The price is ￥25,838
￥29,282 total
includes taxes & fees
Aug 19 - Aug 20
Villa Boccaccio
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Pool

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

10.0 out of 10, Exceptional, (1)
"Pros: Świetna lokalizacja i przyjemne otoczenie domu. Dom położony na wzniesieniu z którego roztaczał się piękny widok. Cons: Osoba opiekująca się domem nie mówiła po angielsku co utrudniało komunikację. Nie byliśmy świadomi że dom podzielony jest na 2 części góra i piwnica w której były dodatkowe 3 pokoje. Uszkodzona pralka która nie dopierała pranych ubrań - brudna woda z zanieczyszczeniami które dodatkowo brudziły ubrania."
The price is ￥245,775
￥355,789 total
includes taxes & fees
Sep 4 - Sep 5
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
"A Casa di Franca Villa con piscina"
Pool

"A Casa di Franca Villa con piscina"

10.0 out of 10, Exceptional, (1)
"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...
The price is ￥139,904
￥203,441 total
includes taxes & fees
Sep 1 - Sep 2
"A Casa di Franca Villa con piscina"
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Pool

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

The price is ￥261,531
￥291,630 total
includes taxes & fees
Aug 25 - Aug 26
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi
TV, fireplace

"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi

10.0 out of 10, Exceptional, (7)
"Country location but easy access to a great local winery/restaurant and the town of Gaiole."
The price is ￥136,123
￥140,257 total
includes taxes & fees
Aug 21 - Aug 22
"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi
Villa 'Vanna - Certaldo' with Garden & Wi-Fi
Exterior detail

Villa 'Vanna - Certaldo' with Garden & Wi-Fi

The price is ￥94,531
￥115,539 total
includes taxes & fees
Sep 1 - Sep 2
Villa 'Vanna - Certaldo' with Garden & Wi-Fi
Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning
Pool

Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning

The price is ￥312,639
￥358,854 total
includes taxes & fees
Sep 14 - Sep 15
Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
Interior

Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.

9.8 out of 10, Exceptional, (21)
"We staid there for a week, great with kids (pool) and good location in the countryside if you have car (30m from Florence, 15m from San Gimignano, 35 from Siena)"
The price is ￥40,479
￥102,145 total
includes taxes & fees
Sep 7 - Sep 8
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (1)
"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!"
The price is ￥311,946
￥312,291 total
includes taxes & fees
Aug 26 - Aug 27
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi
Pool

Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi

9.4 out of 10, Exceptional, (3)
"Beautiful stay in a wonderful Italian villa. "
The price is ￥81,296
￥81,641 total
includes taxes & fees
Sep 3 - Sep 4
Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Pool

Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

The price is ￥40,838
￥41,183 total
includes taxes & fees
Aug 27 - Aug 28
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Outdoor pool

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

10.0 out of 10, Exceptional, (12)
"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"
The price is ￥310,055
￥354,841 total
includes taxes & fees
Sep 9 - Sep 10
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Outdoor pool

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

10.0 out of 10, Exceptional, (38)
"Excellent in every way. Highly recommend"
The price is ￥277,844
￥313,845 total
includes taxes & fees
Aug 25 - Aug 26
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Villa Il Signorino
Interior

Villa Il Signorino

10.0 out of 10, Exceptional, (2)
"Nice place 👌 "
The price is ￥62,011
￥86,643 total
includes taxes & fees
Sep 1 - Sep 2
Villa Il Signorino
Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
Dining

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

10.0 out of 10, Exceptional, (1)
"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."
The price is ￥248,928
￥291,631 total
includes taxes & fees
Sep 17 - Sep 18
Villa 'Martignana' with Private Pool, Private Garden 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

Grand Hotel Baglioni

Grand Hotel Baglioni

10/10 Excellent
"Bed was comfortable, room size is good and small balcony is very good "
Yigang 1-night trip
Posted 17 hours ago
Grand Hotel Baglioni

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 ￥25,838 and ￥25,838 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 2105 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.