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Casale Cipressi, Castellina in Chianti - Siena

5 bedrooms 3 bathrooms 9 people Private Pool 5 - Superb - Superb 5

This is a great option for multi-generational families or friends who want to be spoilt. The beautifully kept Casale Cipressi impresses from the word go: its cypress-lined drive and a gleaming white stone sculpture announces that you are arriving somewhere special. There’s even a private helipad. A pleasant drive from the small hilltop commune of Castellina in Chianti, this purpose-built bolthole has commanding views across surrounding hills. It is well placed for days out in Siena, San Gimignano and Florence, but the temptation to simply chill out here will be strong.

The property exploits antique and contemporary natural materials – stone, terracotta, wood, rattan – beautifully, inside and out, while offering all the benefits of modern design. Organised on two floors, each with its own facilities, this is an ideal property for a group holiday that also allows individuals downtime. With five well-furnished terraces and loggia, including a delightful courtyard, gently sloping lawns, an outdoor fireplace for cooler evenings, ping-pong table and generous private pool, everyone, older and younger, will find their own favourite spots to colonise.

Ground Floor


Two sofas, four armchairs, coffee table, side table, table and chairs, dresser, fully equipped kitchen, range, two doors to terrace and garden.

Bedroom 1
Double bed (cannot be converted into twins), wardrobe, two benches, door to terrace.

En-suite Bathroom
Jacuzzi with hand-held shower, sink, WC.

Bedroom 2
Twin beds (can be converted to a double), two wardrobes, two bedside tables, antique chest, desk and chair, bookshelves, door to garden.

Sink, WC.

First Floor


Sofa, two armchairs, two pouffes, coffee table, shelving, two antique stools, bench, armoire, table and chairs, fireplace, one door to wraparound terrace, two doors to courtyard

Fully equipped, doors to two terraces.

Bedroom 3
Four-poster double bed (cannot be converted to twins), two wardrobes, chair, bookshelves, door to terrace.

Bedroom 4
Double bed (cannot be converted to twins), wardrobe, chest of drawers, two doors to terrace.

Bedroom 5
Three-quarter bed, bookshelves, wardrobe, sideboard, door to garden.

Bathroom 2
Shower, sink, WC.

Bathroom 3
Shower, sink, WC.

Our Thoughts
As pleasing as the interiors are, this property is designed to allow the views to puncture every room – so, even if you spend a lot of time here, you will be soaking up Chianti. Casale Cipressi’s beautiful furnishings, including on the wraparound loggia, invite a holiday of luxurious indolence. It will be difficult to choose between meals here or in the courtyard – although the latter’s professional barbecue will be a pull for some. Parents can keep an eye on children splashing in the pool from the cool of the loggia. Oh, and don’t forget the sauna, to complete your relaxation.

Five bedrooms. Three bathrooms, one en-suite. If you want the twin beds converted into a double, please specify when booking and note that parties must not exceed nine people, including infants. Two hours of maid service are included three times a week. A private helipad is available for your use. Pets are allowed, for a weekly charge, please discuss with your agent when booking. Firewood is available at an additional cost.
Approach road: 1.7km unpaved road, not suitable for sports cars or small cars that are fully loaded.
The standard time for all arrivals must be between 4pm and 7pm. In the event of a client’s late arrival, they must contact the villa owner on the number provided or check with your To Tuscany villas specialist. If you do not call you will not be able to enter the house.

Immediately next to the house, the pool is set within a stone-flagged surround wide enough for deck chairs. Younger children will not be able to touch the bottom at the shallow end. There is a shower and sauna nearby, and sunloungers on the adjacent lawn. Pool size: 12m x 6m, 1.7m-1.9m deep. Open May to mid-October, weather permitting.


Pet Friendly
Flexible dates
Washing Machine Inhouse
2 CD players
DVD player (Euro)
Fire place (open)
5 furnished terraces
Moka espresso maker
Espresso machine
Filter coffee maker
Fully equipped kitchen
3 covered terraces
Trouser press
1 baby cot
1 highchair
Hairdryer in every bathroom
CD player with speakers also outside in the loggia
Private Chef- extra cost
2 Sat TV
2 working fireplaces
Mid week maid service included
Maid service available for extra charge
Ping-pong table onsite
Pets welcome

Additional information

Arrival/Departure day: Saturday   Click here to request flexible dates

Terms and conditions: please read the booking contract

The Security Deposit is 500 Euro or equivalent in your own currency. This is collected on your arrival and held by the owner for the duration of your stay. Should you or your party cause any damage at the property contact us straight away so that we can help agree a reasonable settlement. Damage does not mean normal usage or wear and tear.

Approach road: Bumpy unpaved road

What time can we arrive? By what time must we vacate the property?
Check in is from 16:00 - 19:00.
Checkout by: 10:00

Are pool towels supplied?
included - provided by local supplier

Is there Internet in the villa?
free WI-FI available

Weekly linen, tea and bathroom towels: included - provided by local supplier

Heating, if used: by consumption

Final clean:included - provided by local supplier

Tourist tax: 1,50 Euro per person, per night for the first 7 nights, some exemptions apply.

Baby cot: 1 available on request, no extra cost

High chair: 1 available on request, no extra cost

Info about children: Due to local area restrictions for visitor numbers, infants must be included in the number count for this property.
Therefore 9 including any infants is the maximum number allowed here.

Optional extra costs: Firewood is available for an extra cost
Pets are allowed however there is a weekly charge of 100 Euros.

Concierge Service
If you would like suggestions and tips regarding different activities you can do during your stay please contact our concierge service at concierge@to-tuscany.com

What is a pre arrival shopping service?
In some villas, it is possible to have a Pre arrival shopping service. The availability of the service is noted in the villa description. To help you through the first day or two of your holiday, owners can do a small shop before your arrival so that you do not have to go immediately to find a supermarket. By contacting your To Tuscany villa specialist in advance and providing them with a shopping list you will find the items in your villa on arrival. Please note that the service cannot be guaranteed with less than 48 hours notice before arrival.​

Villa rates

2018 Prices per villa
Date range
7 night price
23 Jun - 25 Aug 2018
6332 US Dollar
25 Aug - 15 Sep 2018
4712 US Dollar
15 Sep - 10 Nov 2018
3902 US Dollar *
15% discount available between 29 Sep - 13 Oct. Save 586 US Dollar
10 Nov - 15 Dec 2018
3902 US Dollar
15 Dec - 29 Dec 2018
3902 US Dollar
2019 Prices per villa
Date range
7 night price
29 Dec - 05 Jan 2019
3902 US Dollar
05 Jan - 23 Mar 2019
3902 US Dollar
23 Mar - 01 Jun 2019
3902 US Dollar
01 Jun - 22 Jun 2019
4712 US Dollar
22 Jun - 24 Aug 2019
6332 US Dollar
24 Aug - 14 Sep 2019
4712 US Dollar
14 Sep - 09 Nov 2019
3902 US Dollar
09 Nov - 14 Dec 2019
3902 US Dollar
14 Dec - 28 Dec 2019
3902 US Dollar

What's the villa like inside?

Dining Room

Villa location

How far are the airports? Distances and driving time
  • Florence Airport: 57km - 0h 52m
  • Aeroporto Pisa: 116km - 1h 29m
  • Aeroporto Bologna: 140km - 1h 38m
How far are the nearest towns? Distances and driving time
  • Castellina in Chianti: 3km - 0h 10m
  • Radda in Chianti: 14km - 0h 25m
  • Panzano: 15km - 0h 26m
Castellina in Chianti is the nearest town, it is 2.7km away. In this market town there is a wide selection of shops, restaurants and other amenities. We recommend you try the restaurant La Torre.

 More options
Golf Club
Horse riding

Guest reviews: Casale Cipressi <div class='textCenter'>9,5/ 10</div>Score from 4 reviews - Superb (4 Client reviews)

May 2018
Family with older children
Rotterdam, Netherlands Rotterdam, Netherlands
Guest villa score
Would you like to translate?
Gedurende een week verbleven we met 7 volwassenen en een kind van 1 jaar in het prachtige Casale Cipressi. Het heeft aan al onze verwachtingen voldaan!
Een schitterend huis in een ditio omgeving waar genieten vanzelfsprekend is.
Het was er zalig!
Local attractions Sienna, San Gimignano en natuurlijk Florence waren binnen een uur bereikbaar en hadden natuurlijk veel moois te bieden, maar ook de dorpjes vlakbij waren zeer de moeite waard.

Any duration

Duration (weeks)

Any size

Number of Guests

adults (ages 16 +)

children (ages 2 - 15)

infants (ages <2 yr)

7 nights from
3316 to 6332 US Dollar

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