Compare San Casciano in Val di Pesa Villa Deals

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Featured Villas in San Casciano in Val di Pesa

Relais Badia a Passignano

Relais Badia a Passignano

Via Martiri di Pratale 12 Barberino Tavarnelle FI
Guests of this villa have access to a seasonal outdoor pool and a garden.
Pool
Kitchen
Authentic Private Tuscan Villa for 12 people in Greve: the Heart of Chianti

Authentic Private Tuscan Villa for 12 people in Greve: the Heart of Chianti

Greve in Chianti (Firenze) Toscana
Guests of this villa enjoy features like a gym, a hot tub, and laundry facilities. Transportation is made easy with limo/town car service. Staff members can help with accommodation requests, and provide concierge services. Other amenities at this family-friendly villa include local meal delivery service, a garden, and barbecue grills.
Pool
Hot Tub
CASA PILAR villa with pool and jacuzzi for exclusive use in chianti.-20% 12_21/5

CASA PILAR villa with pool and jacuzzi for exclusive use in chianti.-20% 12_21/5

Strada In Chianti Città Metropolitana di Firenze
Guests of this villa have access to an outdoor pool, a gym, and a hot tub. Transportation is made easy with limo/town car service. Additional amenities include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
Villa Bartolini Baldelli - Authentic XV century villa with garden and pool

Villa Bartolini Baldelli - Authentic XV century villa with garden and pool

Toscana Città Metropolitana di Firenze
At this villa, guests have access to features like laundry facilities. This smoke-free villa also has a garden.
Pool
Kitchen
Marvelous home just steps from the Chianti and beyond

Marvelous home just steps from the Chianti and beyond

cavriglia Tuscany
Guests staying at this villa have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

San Casciano in Val di Pesa Tuscany
Guests of this villa enjoy features like an outdoor pool, a gym, and a terrace. Staff members can help with accommodation requests, and provide concierge services. Other amenities at this family-friendly villa include laundry facilities, local meal delivery service, and barbecue grills.
Pool
Kitchen
Villa with private pool on 25 acres in the heart of Chianti, close to Siena

Villa with private pool on 25 acres in the heart of Chianti, close to Siena

Pievasciata Tuscany
Guests staying at this villa have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
Exclusive comfort for a small group- Countryside Tuscan Villa near Florence

Exclusive comfort for a small group- Countryside Tuscan Villa near Florence

Bagno a Ripoli, San Bartolomeo A Quarate Tuscany
This villa offers express check-in, express check-out, and laundry facilities. Other amenities at this family-friendly villa include barbecue grills and a garden.
Kitchen
Washer
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

San Gimignano SI, Italy
Guests staying at this villa enjoy an outdoor pool, laundry facilities, and local meal delivery service. Additional amenities include barbecue grills and a garden.
Pool
Kitchen
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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.

Hotel Options in San Casciano in Val di Pesa

    Villa I Barronci Resort & Spa

    Villa I Barronci Resort & Spa

    Via Sorripa 10 San Casciano in Val di Pesa FI
    $141 nightly
    The price is $162 total per night from Oct 4 to Oct 5
    $162 total
    Oct 4 - Oct 5
    Total with taxes and fees
    "Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

    "Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

    San Casciano in Val di Pesa Tuscany
    10/10 Exceptional! (136 reviews)
    Plus Florence - Hostel

    Plus Florence - Hostel

    Via Santa Caterina D'Alessandria, 15 Florence FI
    $136 nightly
    The price is $159 total per night from Sep 13 to Sep 14
    $159 total
    Sep 13 - Sep 14
    Total with taxes and fees

Luxury Villas

Book luxury villas in San Casciano in Val di Pesa
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in San Casciano in Val di Pesa. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in San Casciano in Val di Pesa, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in San Casciano in Val di Pesa
You won’t have a problem finding your own space in San Casciano in Val di Pesa. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore San Casciano in Val di Pesa on your own and use a one-bedroom villa as your home base.

A top-end villa experience in San Casciano in Val di Pesa rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

San Casciano in Val di Pesa Villas essential information

Accommodation
1779 Villas
Lowest Price
$159
Highest Price
$162
Popular accommodation
Relais Badia a Passignano, Authentic Private Tuscan Villa for 12 people in Greve: the Heart of Chianti, CASA PILAR villa with pool and jacuzzi for exclusive use in chianti.-20% 12_21/5, Villa Bartolini Baldelli - Authentic XV century villa with garden and pool, Marvelous home just steps from the Chianti and beyond, "Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C, Villa with private pool on 25 acres in the heart of Chianti, close to Siena, Exclusive comfort for a small group- Countryside Tuscan Villa near Florence, Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano