• olivia
    Tuscany, Castellina In Chianti
     14    7    8
  • Luxury, chic outdoor dining area

    Luxury, chic outdoor dining area

  • outdoor terrace 

    outdoor terrace 

  • main house, living room

    main house, living room

  • main house, living room

    main house, living room

  • main house, kitchen

    main house, kitchen

  • main house, dining room

    main house, dining room

  • main house, foyer

    main house, foyer

  • outdoor views

    outdoor views

  • main house, bedroom 1

    main house, bedroom 1

  • main house, bedroom 2

    main house, bedroom 2

  • main house, bedroom 3

    main house, bedroom 3

  • main house, bedroom 4

    main house, bedroom 4

  • main house, bedroom 5

    main house, bedroom 5

  • main house, bathroom 5 and gym

    main house, bathroom 5 and gym

  • main house, fire pit

    main house, fire pit

  • main house exterior

    main house exterior

  • outdoor pool

    outdoor pool

  • main house, pizza oven

    main house, pizza oven

  • Tuscany, estate views

    Tuscany, estate views

  • granary, living room sitting area

    granary, living room sitting area

  • granary, kitchen

    granary, kitchen

  • granary, dining room and bedroom 6 detail

    granary, dining room and bedroom 6 detail

  • granary, bedroom 6

    granary, bedroom 6

  • granary, bathroom 6

    granary, bathroom 6

  • granary, bathroom 6

    granary, bathroom 6

  • granary, bedroom 7

    granary, bedroom 7

  • granary, bedroom 7

    granary, bedroom 7

  • granary exterior

    granary exterior

  • villa outdoor pool

    villa outdoor pool


Tuscany, Castellina In Chianti
Inland villa
from 27,000 to 30,900 € / week

Doubles 7  Bathrooms 7  Guest bathrooms 1

family friendlywalking distance to villagewalking distance to restaurant

In the heart of the Chianti area, at just 25 minutes from Siena and 50 minutes from Florence, villa Olivia is a luxury retreat offering the best of everything you could wish for a holiday rental in Tuscany.
Dating back to the 17th century, the villa is set in a large estate beyond a narrow road lined with cypress trees. Many details have remained from the ancient structure, such as the old terracotta floors, regal wood beam ceilings and a big 17th-century fireplace.
Restored with passion by the owners in 2017, Olivia has been transformed into a luxurious house consisting of five comfortable bedrooms, most of them with an en suite bathroom and a newly renovated annex featuring two large bedrooms both en suite and a spacious chef kitchen.
The villa is located approximately four kilometres from Castellina in Chianti, one of the most famous parts of the Chianti region, where to go for visiting wine cellars, experience relaxed Italian life by walking through the historic centre, visit local craft shops and taste Tuscan dishes at some typical trattoria. The location of Olivia offers panoramic views over the noble vineyards, silver olive groves and wild oak forests which transport guests into a relaxing and enchanting atmosphere.
The interiors feature a maze-like succession of open and intimate spaces. Each bathroom has been outfitted with Italian Florentine artisanal custom-made brass and bronze furnishings with stunning Tuscan marble and travertine stone. The villa also offers modern amenities such as high-speed Wi-Fi and a flat screen TV. The kitchen is fully equipped with custom-made kitchens fit for cooking lovers and externally a kitchen garden has been created.
In addition to Florence and Siena, there are various cities offering unlimited treasures in the form of art and museums, historic visits, gastronomy and entertainment. Arezzo, San Gimignano, Montalcino, Montepulciano, Cortona, Perugia and the Val D’ Orcia are the most important ones. Besides those, we should not forget the villages and various other historical sites of unforgettable beauty. 

main villa sleeps 10
upper-level floor
entrance into foyer with large 17th-century Tuscan fireplace, 5 steps up to a kitchenette with induction stovetop, stove, dishwasher and fridge, double open style living room with flat-screen TV, 3 steps down to a dining area with table for 6-8 people, and small gym. Staircase down to laundry area with washing machine and dryer.
bedroom 1 double bed (queen size bed, convertible into a twin) with en suite bathroom with shower cabin (plus extra hand held shower).
bedroom 2 double bed (queen size bed, convertible into a twin) with en suite bathroom with shower cabin (plus extra handheld shower).
staircase down leads to lower ground floor; large kitchen with small authentic fireplace.
bedroom 3 double bed (queen size bed, convertible into a twin) with direct access to outdoor. Rock-clad terrace, bathroom with shower cabin (plus extra handheld shower) on upper level next to the gym.
ground floor
fully equipped spacious chef kitchen with double dishwashers, honor bar with an award-winning collection of estate-organic Chianti Classico wines, two large farm-style tables for 16 people, fireplace and direct access to outside pergola-covered terrace with dining table and stone kitchen with grill. Studio with printer and iPad, adjacent to the kitchen.
bedroom 4 double bed (king size bed, not convertible into a twin) with direct access to outdoor area and en suite bathroom with shower cabin (plus extra handheld shower).
bedroom 5 double bed (queen size bed, convertible into a twin) with direct access to outdoor and en suite bathroom with double basin and shower cabin (plus extra handheld shower).

granary sleeps 4
lower ground floor
guest bathroom (disabled-accessible), laundry area with washer and dryer.
ground floor
large fully equipped chef kitchen, large open living room and dining area with table seating up to 10 people, outdoor terrace with pergola-covered outdoor dining area with a large travertine table for up to 14 people.
first floor
bedroom 6 double bed (king size bed, not convertible into a twin) with spacious en suite bathroom with Roman double shower.
bedroom 7 double bed (queen size bed, convertible into a twin) with spacious en suite bathroom with Roman double shower.

large alfresco terrace with table for 12/16 people, outdoor stone kitchen with built in professional BBQ, stone pizza oven, private patio adjacent to lower level bedrooms, wood-burning stone fire pit and sitting area, covered sitting area around the pool, seating area with sofas, covered area for playing ping pong or yoga/Pilates, bocce balls, herb gardens, terrace with pergola adjacent to the granary, fenced-in garden of 1 hectare. 

200 meters of private dirt road leading to the villa. Pets not allowed, smoking only allowed outdoors. Completely fenced in property with automatic double gates, one for the parking area and one for the villa. It is possible to have the pool heated from May to October. External chefs or other service providers are not allowed at the villa.

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+39 075 505 7865

Enquire olivia

what we love about olivia
  • sustainable green home powered by solar energy
  • tastefully decorated
  • multiple outdoor alfresco dining areas
  • sweeping 360-degree views
  • only 30 min. drive to Unesco World Heritage Site Siena

personally selected

finest homes, quality guaranteed

24/7 guest support


  • nearest restaurant in Fonterutoli 2,6km/1,6miles
  • other restaurants and supermarkets 4km/2,5miles in Castellina in Chianti
  • tennis court 13km/8miles
  • horse riding in Siena 21,7km/13,5miles
  • golf course Ugolino Golf Club at Bagno a Ripoli 36,8km/22,8miles
  • nearest highway 20,3km/12,6miles


  • wine fridge wine fridge
  • air conditioning A/C air conditioning A/C
  • fans fans
  • mosquito nets mosquito nets
  • wi-fi internet connection wi-fi internet connection
  • i/Pod docking station i/Pod docking station
  • i/Pad i/Pad
  • satellite TV satellite TV
  • Netflix Netflix
  • stereo system stereo system
  • printer printer
  • telephone telephone
  • Playstation Playstation
  • security system security system
  • safe safe
  • alarm system alarm system
  • fireplace fireplace
  • book collection book collection
  • gym equipment gym equipment
  • fully equipped kitchen fully equipped kitchen
  • ice maker ice maker
  • microwave microwave
  • dishwasher dishwasher
  • washing machine washing machine
  • dryer dryer
  • iron w/ironing board iron w/ironing board
  • toys toys
  • board games board games
  • baby cot baby cot
  • highchair highchair

  • private swimming pool private swimming pool
  • heated pool heated pool
  • gazebo gazebo
  • private patio private patio
  • alfresco dining alfresco dining
  • outdoor furniture outdoor furniture
  • lounge area lounge area
  • outdoor kitchen outdoor kitchen
  • barbecue-BBQ barbecue-BBQ
  • pizza oven pizza oven
  • golf villas golf villas
  • bocce court bocce court
  • tennis table tennis table
  • parking area parking area
  • electric gate electric gate
  • vegetable garden vegetable garden
  • aromatic garden aromatic garden
  • electric car charging station electric car charging station

facilities notes

  • heated swimming pool, salted water (4,5x8,5m, depth 1,30-1,70m / 14,7x27,8ft, depth 4,3-5,6ft)
  • fully air-conditioned
  • built-in stone outdoor kitchen and BBQ
  • Sonos sound system
  • gym equipment: treadmill, cross trainer, weights, exercise gear, exercise bike and yoga mats
  • salon grade hair dryers, toiletries and heated towel warmers in each bathroom
  • solar panels
  • ping-pong table
  • bocce ball

Weekly rates

  • 7 double bedrooms (main villa and guest house)

    From - To EUR USD * GBP **
    Jan 6, 2024 - March 30, 2024On DemandOn DemandOn Demand
    March 30, 2024 - Apr 6, 202430,900.0033,350.0027,500.00
    Apr 6, 2024 - June 1, 202427,000.0029,200.0024,050.00
    June 1, 2024 - Sept 28, 202430,900.0033,350.0027,500.00
    Sept 28, 2024 - Nov 2, 202427,000.0029,200.0024,050.00
    Nov 2, 2024 - Dec 21, 2024On DemandOn DemandOn Demand
    Dec 21, 2024 - Jan 4, 202530,900.0033,350.0027,500.00
    Security deposit

    * For an indication of the weekly price in US Dollars please have a look to this reference rate: 1 EUR = 1.08 USD
    ** For an indication of the weekly price in GBP please have a look to this reference rate: 1 EUR = 0.89 GBP

    concierge service, light daily trash and tidy cleaning (Monday-Saturday, from 10am to 2pm), welcome dinner (including preparation, food, water and one bottle of wine), continental breakfast service (food and beverage not included), change of linen and towels on Saturday,  air conditioning, heating, telephone, full gardening and pool cleaning maintenance, final cleaning.

    not included
    pool heating approx. EUR 150 per day, extra maid service EUR 30 per hour, extra change of linen EUR 50 euro per bedroom, shopping service EUR 90 (plus cost of the groceries), cooking service upon request (rate based on selection), American breakfast upon extra cost, laundry service EUR 30 per hour, ironing service EUR 30 per hour, city tax EUR 3 per day per person only for the first 7 nights (free for children under 14). External chefs or other service providers are not allowed at the villa.

    The price of the extra services, which need to be paid directly to the service providers, can vary according to their availability.
    Inclusions may be subject to changes.


main distances
Siena 21,7km/13,5miles, San Gimignano 36km/22,3miles, Firenze 51km/31,6miles, Montalcino 61,2km/40miles, Arezzo 75,4km/46,7miles, Val d’ Orcia 78km/48,3miles, Montepulciano 84,5km/52,4miles, Cortona 93,4km/58miles, Perugia 129km/80miles. 

airports and trains
airports: Florence Peretola 55,4km/34,3miles, Perugia 137km/85miles, Rome Fiumicino 263km/163miles.
trains: Siena 17km/10,5miles, Poggibonsi 28,5km/17,6miles.

The location indicated on the map is purely indicative.

Guest reviews

Date: July 2018
Name: Caroline&Murray Bye
Country: Canada

"This villa will have you planning how you can move to Tuscany. The decoration is outstanding, beautiful quality fabrics and furniture make the rooms restful and pleasing to the eye. The villa is located in a charming small village but only minutes to a bigger town with a Coop supermarket and excellent butcher. We did daytrips to Siena, Florence and Brolio castle. Liz, the housekeeper kept the house in tip top shape, as well as giving us advice on shops, restaurants and hikes. She came six out of the seven days we stayed at the villa, for three hours each day so the house was immaculate. We used the guest services to arrange a chef to cook dinner for us and also give us a cooking class. Both were wonderful experiences. Everything about our stay exceeded our expectations."

Date: June 2018
Name: Steve Mccarteny
Country: USA

"The coordination and the villa itself exceeded all of our expectations. We were looking for something small in the middle of Tuscany, something quiet as a counterpoint to all the busy city trips we undertook. Our villa was perfect - perfectly located in the middle of a vineyard about 4 km from a small tuscan town that had everything we needed. The staff was there to great us upon arrival and was very helpful getting us settled in. The furniture, pool, and over ambiance of the villa was just as depicted in the pictures. One evening we had chef prepare a local dinner and the food, and service was fabulous - a truly memorable evening and a fantastic week.."