Entire home

Hillside Villa in the Heart of Chianti

Villa in San Casciano in Val di Pesa with private pool and kitchen

Photo gallery for Hillside Villa in the Heart of Chianti

Pool
Fridge, microwave, oven, dishwasher
Fridge, microwave, oven, dishwasher
Exterior
Property grounds
Nestled in the heart of Tuscany, this charming holiday home offers a serene retreat for families and small groups. Unwind in the private swimming pool, enjoy a barbecue under the stars, or explore Chianti town just a short drive away. With children’s furniture and billiards on site, there’s something for everyone to enjoy.

Reviews

10 out of 10
Exceptional

Entire home

7 bedrooms3 bathroomsSleeps 123165 sq ft

Popular amenities

  • Pool
  • Barbecue grill
  • Parking available
  • Pet friendly
  • Washer
  • Outdoor Space

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About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Hillside Villa in the Heart of Chianti

This villa in San Casciano in Val di Pesa offers a serene Tuscan escape in the heart of the Chianti countryside. Ideal for families or groups, the villa features a private garden with a barbecue area, a refreshing swimming pool (open June to September), and a spacious recreation room with billiards—perfect for relaxed evenings. A high chair and children's beds ensure a family-friendly stay, while pets are welcome to enjoy the open spaces alongside you.

Just 2 km away, local trattorias serve authentic Tuscan flavors like ribollita and Florentine steak—perfect for a leisurely evening meal. Not far, Sant'Andrea in Percussina hosts the famous Albergaccio estate where Niccolò Machiavelli penned The Prince. Today, the estate is a museum and wine bar, and some areas, including the gardens, are pet-friendly.

Outdoor lovers can explore scenic walking trails right from the villa’s doorstep. The Chianti Classico region is dotted with “ring routes” (percorsi ad anello) winding through vineyards, olive groves, and quiet woodlands—great for hiking or walking your leashed dog. Don’t miss the Calcinaia Ring Trail or the panoramic routes leading toward Greve and Montefiridolfi.
Florence, with its Renaissance treasures, lies just 24 km away, while medieval gems like Certaldo, Monteriggioni, and Siena are within easy reach. Whether you're sipping wine under the Tuscan sun or strolling historic towns, this villa offers an idyllic base for unforgettable experiences in central Italy.
Access the house you have to go through 60m of unpaved road
This holiday home is one of the Belvilla Award winners in: 2021,2023,2024

Layout: Ground floor: (Kitchen(fireplace, cooker(4 ring stoves), microwave, dishwasher, fridge-freezer, high chair), bedroom(double bed, children's bed), bedroom(double bed), bedroom(double bed), bedroom(single bed), bathroom(bath tub, 2x washbasin, toilet, bidet, washing machine), recreation room(TV(digital), radio, CD player, billiards), garden(private), garden furniture, BBQ, parking, swimming pool(private, 10 x 3 m., opened from Jun upto and including Sep))

On the 1st floor: (Living room(TV(digital), radio, CD player), Large kitchen(cooker(4 ring stoves), oven, microwave, dishwasher, high chair), bedroom(double bed, children's bed), bedroom(double bed), bedroom(double bed), bathroom(bath tub, washbasin, toilet, bidet, washing machine))

These costs are mandatory and charged on site. They are not included in the rental price.
Bed linen: Present (Beds made on arrival)
Pets: Max. 5; free of charge
Tourist tax: € 2.00 /person/night (Indication)

Optional services that you can arrange on site
Kitchen linen: Present
Heating: € 30.00/night
Wifi: Free

Property amenities

Pool/Spa

  • Private pool

Internet

  • Available in the villa: WiFi

Parking and transportation

  • Car not required
  • Parking on site

Kitchen

  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator

Bedrooms

  • 7 bedrooms

Bathroom

  • 3 bathrooms
  • Bathtub
  • Bidet

Living spaces

  • Fireplace
  • Living room

Entertainment

  • TV

Outdoor areas

  • Barbecue grill
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoking not allowed

Location highlights

  • In a rural location

Things to do

  • Billiards/pool table

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Garden
  • Unit size: 3,165 square feet

Similar properties

Policies

Check-in

Check-in time starts at 5:00 PM
Minimum check-in age: 18

Check-out

Check-out before 12:00 PM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

Events

Events allowed

Smoking

Smoking is not permitted

Property payment types

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards and cash
Parties and events are allowed on site
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Please note that cultural norms and guest policies may differ by country and by property; the policies listed are provided by the property
Property Registration Number IT048038C2WIPA2N6C

We should mention

All guests, including children, must be present at check-in and show their government-issued photo ID card or passport
Cash transactions at this property cannot exceed EUR 5000, due to national regulations; for further details, please contact the property using information in the booking confirmation
A car is not required for transportation to and from this property

Property is also known as

Beautiful Manor House Overlooking Hills Chianti Classico Villa
Beautiful Manor House Overlooking Hills Chianti Classico
Beautiful Manor House Overlooking Hills Chianti Classico Villa
Beautiful Manor House Overlooking Hills Chianti Classico Villa
Beautiful Manor House Overlooking Hills Chianti Classico
IT-50020-231
Peaceful Holiday Home With Pool in Montefiridolfi Italy Villa
Beautiful Manor House Overlooking the Hills of Chianti Classico

About the neighborhood

Map
San Casciano in val di Pesa

What's nearby

  • Antinori nel Chianti Classico - 6 min drive - 4.0 miles
  • Passignano Abbey - 12 min drive - 5.1 miles
  • Verrazzano Castle - 19 min drive - 8.4 miles
  • Ponte Vecchio - 30 min drive - 18.6 miles
  • Uffizi Gallery - 30 min drive - 18.6 miles

Getting around

  • Barberino Val d'Elsa Station - 22 min drive
  • Florence Airport, Peretola (FLR) - 34 min drive

Restaurants

  • ‪Trattoria da Bule - ‬7 min drive
  • ‪La Cantinetta di Rignana - ‬22 min drive
  • ‪Bar Italia - ‬8 min drive
  • ‪Castello Vicchiomaggio - ‬17 min drive
  • ‪Macelleria Francini - ‬6 min drive

Frequently asked questions

Is Hillside Villa in the Heart of Chianti pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Hillside Villa in the Heart of Chianti?

Check-in begins at 5:00 PM.

What time is check-out at Hillside Villa in the Heart of Chianti?

Check-out is at 12:00 PM.

Where is Hillside Villa in the Heart of Chianti located?

Situated in a rural location, this villa is 2.8 mi (4.5 km) from Antinori nel Chianti Classico and 3.1 mi (4.9 km) from Passignano Abbey. Monastary of Sorelle Clarisse and Casa Sola - Chianti Winery are also within 9 mi (15 km).

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