Chianti Hillsides · Olive Groves & Private Cellars

Vineyard & Countryside Luxury Villas in Tuscany

Immerse your group in the rolling landscape of Chianti and Val d'Orcia. Restored stone country estates set amidst private vineyards, olive groves, heated panoramic infinity pools, and in-villa Italian chefs.

24
Verified Villas
4–12
Bedroom Range
24/7
Concierge Service
4.9★
Guest Satisfaction
Vineyard & Hillside Estates

Handpicked Residences

Authentic Tuscan stone estates surrounded by working vineyards and private olive orchards.

Il Cellese - Tuscany

Il Cellese - Tuscany

₹1,066,737/onwards
Chianti Hills, Italy
19 Guests 10 Beds 11 Baths
Air Conditioning Al Fresco Dining Area Alarm System
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Verified by ShavyStays
Casale 1 Bianchi - Tuscany

Casale 1 Bianchi - Tuscany

₹1,800,000/onwards
Toscana Resort Castelfalfi, Montaione, Italy
10 Guests 5 Beds 6 Baths
24/7 Concierge Air Conditioning BBQ Available
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Verified by ShavyStays
Casa Medici - Tuscany

Casa Medici - Tuscany

₹800,000/onwards
Toscana Resort Castelfalfi, Italy
6 Guests 3 Beds 4 Baths
24/7 Concierge Air Conditioning Alcohol Allowed
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Verified by ShavyStays
La Pergola - Tuscany

La Pergola - Tuscany

₹1,200,000/onwards
Toscana Resort Castelfalfi, Montaione, Italy
6 Guests 3 Beds 3 Baths
24/7 Concierge Air Conditioning Alcohol Allowed
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Verified by ShavyStays
Tuscan Terroir

Chianti Vines, Stone Masonry & Farm-to-Table Living

Experiencing the Tuscan countryside from a private villa offers an intimate connection to the land that luxury hotels cannot match. Waking up to morning mist rolling across cypress ridges, walking through working Sangiovese vineyards, and dining on olive oil pressed from trees on your estate define the quintessential Italian holiday.

Each estate features authentic cotto floors, timber-beamed ceilings, private wine cellars for curated tastings, and heated swimming pools positioned to catch golden afternoon sunsets over the hills.

Chianti Vines, Stone Masonry & Farm-to-Table Living Villa Marie Countryside Grounds
Countryside Routes

Drive Times from Florence (FLR) & Pisa (PSA)

Chauffeured Mercedes-Benz transit across iconic cypress roads and regional highways.

Arrange Chauffeur
Destination Corridor
Drive Time
Distance
01
Florence Airport (FLR)Direct highway access into Chianti
35min
38 km
02
Pisa International Airport (PSA)Western Tuscany & Lucca corridor
50min
62 km
03
Siena Historic Piazza del CampoMedieval center & cathedral
30min
32 km
04
San Gimignano Medieval TowersUNESCO World Heritage hillside village
25min
24 km
05
Greve in Chianti Wine SquareFamous butchers, wine shops & weekly markets
15min
14 km
The ShavyStays Standard

Concierge Services Included

Every Tuscan property is audited for verified agricultural heritage, pool heating, and private estate access.

I
🍇

Private Vineyards

Set on active wine estates with private sommelier tastings.

II
🏊

Panoramic Pool

Heated swimming pools overlooking rolling cypress hills.

III
👨‍🍳

In-Villa Italian Chef

Handmade pasta, wood-fired pizza, and Bistecca alla Fiorentina.

IV
🍷

Estate Cellar

Complimentary welcome vintages and private cellar access.

Destination Insights

Curated Villa Guides

Planning intelligence and logistical guides from our on-ground concierge team.

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Before You Book

Frequently Asked Questions

Can we organize private wine tastings and cellar tours on the estate?
Yes. Professional sommeliers can lead private tastings of Chianti Classico, Brunello di Montalcino, and Super Tuscans in your villa's private cellar or on the terrace.
Is heating available for the swimming pool during spring and autumn?
Yes. Many properties feature heated swimming pools, which can be pre-heated to 28°C for stays in May, June, September, and October upon advance notice.
How far are the villas from Florence and historic cultural sites?
Most Chianti and Lucca estates are located between 30 and 45 minutes by car from central Florence, Siena, and San Gimignano.
Can a private chef prepare traditional Tuscan dinners?
Yes. Experienced Tuscan nonnas and Michelin-trained private chefs prepare handmade tagliatelle, ragù, Florentine steak, and tiramisu on site.
Are rental cars necessary for staying in the Tuscan countryside?
Having a rental vehicle or dedicated chauffeured Mercedes van is highly recommended for exploring hilltop villages, markets, and regional trattorias.
Do the villas produce their own olive oil and wine?
Yes, several of our featured estates produce their own cold-pressed extra virgin olive oil and award-winning wines that guests are invited to sample.
What is the air conditioning situation in historic stone villas?
While ancient meter-thick stone walls naturally keep interiors cool, all bedroom suites across our collection are equipped with modern air conditioning.
Are cooking masterclasses available at the villa?
Yes. Private hands-on pasta and pizza-making masterclasses using authentic wood-fired ovens can be scheduled directly at your estate.

Book a Vineyard Estate in Tuscany

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