Photo by Ashley Robinson

Search Villas in San Casciano in Val di Pesa

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Villas in San Casciano in Val di Pesa and around

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 €2,047
includes taxes & fees
24 Aug - 25 Aug
Beautiful Tuscan home between Florence & Siena
VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34
Terrace/patio

VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34

10.0 out of 10, Exceptional, (1)
"Haben vor Ort geheiratet und es war mehr wie perfekt!"
The price is €4,189
includes taxes & fees
17 Aug - 18 Aug
VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34
Wine Apartments Florence Lawrence
Panoramic Villa, Hill View | Terrace/patio

Wine Apartments Florence Lawrence

The price is €474
includes taxes & fees
17 Aug - 18 Aug
Wine Apartments Florence Lawrence
Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Outdoor pool

Villa Dei Pavoni - Luxury Villa on top of hills in Florence

10.0 out of 10, Exceptional, (1)
"The host was amazing! The property was beautiful. All was seamless! All of our needs were met. Highly recommend! "
The price is €2,094
includes taxes & fees
24 Aug - 25 Aug
Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Casa dei Renai by Rentbeat
Outdoor dining

Casa dei Renai by Rentbeat

The price is €252
includes taxes & fees
17 Aug - 18 Aug
Casa dei Renai by Rentbeat
Villa Cicogna Private Villa, sleeps 2 -10 guests
Pool

Villa Cicogna Private Villa, sleeps 2 -10 guests

10.0 out of 10, Exceptional, (6)
"Our family stayed here for a local wedding and enjoyed the charm of this quiet town and comfortable villa. The hosts were super responsive and welcoming, making sure we had everything we needed for a pleasant stay. Our toddler loved running around and swimming every day in the pool. The location is perfect to drive to nearby cities with parking provided. Would love to visit again!"
The price is €130
includes taxes & fees
20 Aug - 21 Aug
Villa Cicogna Private Villa, sleeps 2 -10 guests
Luxury Villa in the Florentine hills
Fridge, microwave, oven, stovetop

Luxury Villa in the Florentine hills

9.8 out of 10, Exceptional, (141)
"Lovely property, nicely appointed, would be happy to stay there again."
The price is €488
includes taxes & fees
30 Aug - 31 Aug
Luxury Villa in the Florentine 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 €1,813
includes taxes & fees
18 Aug - 19 Aug
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
TV, fireplace

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

10.0 out of 10, Exceptional, (1)
"Staff went over and above for us. Food was wonderful service 5 stars"
The price is €9,520
includes taxes & fees
17 Aug - 18 Aug
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
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)"
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Pool

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

The price is €6,450
includes taxes & fees
17 Aug - 18 Aug
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
Pool

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

10.0 out of 10, Exceptional, (1)
The price is €3,081
includes taxes & fees
15 Sept - 16 Sept
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
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 €1,693
includes taxes & fees
25 Aug - 26 Aug
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and 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

Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Terrace/patio

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

10.0 out of 10, Exceptional, (3)
"Pictures do not do it justice, this house and location is absolutely beautiful. Very comfortable beds, clean house, beauty views, nice fireplace.owner goes above and beyond to make you feel welcome. She had her local wine, cooked us a delishes breakfast, and also brought her olive oil to do tasting. We will definitely be back, i thank you for an amazing experience and a beautiful house."
The price is €404
includes taxes & fees
17 Aug - 18 Aug
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Villa 'Panicale- Toscana' with Private Pool, Private Terrace and Wi-Fi
Outdoor dining

Villa 'Panicale- Toscana' with Private Pool, Private Terrace and Wi-Fi

The price is €3,514
includes taxes & fees
1 Sept - 2 Sept
Villa 'Panicale- Toscana' with Private Pool, Private Terrace and Wi-Fi
Villa Salviati: peaceful stay in a 15th century villa
Outdoor pool

Villa Salviati: peaceful stay in a 15th century villa

Villa Salviati: peaceful stay in a 15th century villa
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 €2,066
includes taxes & fees
4 Sept - 5 Sept
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Pool

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

The price is €239
includes taxes & fees
17 Aug - 18 Aug
Villa Il Frantoio with Shared Pool, Private Terrace & 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top San Casciano in Val di Pesa Hotel Reviews

Bernini Palace

Bernini Palace

10/10 Excellent
"I had a wonderful experience during my stay at this hotel. The service was excellent from start to finish—staff were always attentive, friendly, and ready to help with anything I needed. The hotel itself was spotless, with every detail carefully maintained, which made the stay very comfortable. The combination of cleanliness, professionalism, and genuine hospitality truly made a difference. I highly recommend this hotel and would gladly return."
gilberto 5-night trip
Posted 3 hours ago
Bernini Palace

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 €154 and €1,829 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 2021 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.