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Chianti has much to offer to those interested in its extraordinary wine; and, to all visitors, it also offers its exceptional food and natural beauty.

Cipresso Vacation Rental

Thanks to its central location, this Tuscan region is a perfect starting point for exploring medieval hilltop villages as well as the historical cities of Florence, Siena and Lucca. Set among 27 hectares of one of Chianti’s many outstanding wine-producing estates is Cipresso, a beautiful 13th century villa located approximately 7 miles from Siena. Now restored, the property offers comfort, peace and privacy. Its stone construction, along with its watchtower, exudes the typical character and charm of Tuscany. The villa’s spacious interiors are ideal for large groups who want to gather or have privacy when needed. What better way is there to end the day than by enjoying a glass of Chianti wine that was produced right here on the premises?

The spacious grassy lawns of the estate are perfect for families with children. The location is ideal for wine-lovers as it is a great starting point for trips to Chianti Classico and its charming villages of Gaiole, Castellina, and the Castle of Brolio, which are within 10 miles from the villa.


Ground Floor

Much attention has been dedicated to the interiors of the villa during the restoration to maintain the original structure.
This care is visible in the wood beamed ceilings, the stone walls, and especially on the ground floor where big arches frame the different areas of the spacious living room. This floor also includes a dining area with a large table that can seat up to 12 guests, a sitting area with comfortable sofas, and a sunk-in reading corner with its inviting leather armchairs. The main dining room, on the west side of this floor, can accommodate up to 20 guests. A spacious, well-appointed fully equipped kitchen and a guest bathroom complete this floor.

First Floor

On the first floor is an air conditioned living room, fireplace, two comfortable sofas and an area dedicated to aperitivo or wine tasting.

Second Floor

On the second floor is a living room featuring a comfortable sitting area with fireplace and TV. There is also a cozy space for relaxing and playing cards among friends.

Third Floor

The third floor is the tower that houses a small art gallery with large windows overlooking the beautiful Chianti landscape.

Outside Features

The villa patio features a large outdoor dining table, perfect for shady relaxing and informal dining, and there is also a BBQ grill and outdoor cooking area to prepare delicious local-food feasts. The private large swimming pool is reachable through a paved path and there are sun beds around the pool to enjoy hours of sunbathing. The pool has a ladder on one side. Manicured gardens surround the property for complete privacy.

Rates Table Key:

  Travel Dates      Bedrooms

 Minimum Stay      Starting Price

Travel Dates
Min. Night Stay
Min. Stay
Now to May 31, 2019 87
$ 1,893  1657 $ 2735 $ 2542  1909 £ 1487
/per night
Jun 1, 2019 to Aug 16, 2019 87
$ 2,565  2245 $ 3706 $ 3444  2587 £ 2015
/per night
Aug 17, 2019 to Oct 11, 2019 87
$ 1,893  1657 $ 2735 $ 2542  1909 £ 1487
/per night
Oct 12, 2019 to Dec 13, 2019 87
$ 979  857 $ 1415 $ 1315  988 £ 769
/per night
Dec 14, 2019 to Jan 3, 2020
Christmas/ New Year's
$ 1,398  1224 $ 2021 $ 1878  1410 £ 1099
/per night

Tourist tax: €1.50 per person/per day for the first 7 days (age 14 and under are exempt) – paid in cash, locally

Heating charges, if used: €60 per day
Telephone calls are additional

Security Deposit: €1,500 pre-collected

Minimum Stay: 1 Week - Saturday to Saturday rentals.

Important! Non-USD rates above based on approximate currency conversion. Please confirm rate and currency with your Villa Specialist at time of booking.

Bedroom Details
  • Bedroom 1 (First Floor): Double bedroom with en-suite bathroom with shower
  • Bedroom 2 (First Floor): Double bedroom with private bathroom with shower
  • Bedroom 3 (First Floor): Triple bedroom with en-suite bathroom with shower
  • Bedrooms 4-6 (First Floor): 2 Double bedrooms and 1 bedroom with bunk beds sharing one bathroom with shower
  • Bedroom 7 (Second Floor): Triple room with a private bathroom with tub/shower
  • Bedroom 8 (Third Floor): Double bedroom with en-suite bathroom with shower
  • All bedrooms have A/C except the children’s bedroom with bunk beds (north exposure); all bathrooms are provided with hair dryers
  • A/C in uppermost floor bedrooms
  • Barbecue
  • Dishwasher
  • Fireplace
  • Laundry room with washing machine and ironing facilities
  • Play Station 3
  • Private covered parking
  • Satellite TV
  • Stereo system
  • Telescope
  • Wi-Fi internet access
Pool Details
  • Large, private swimming pool
Staff and Services
  • Final cleaning
  • Housecleaning (up to 4 hrs) every 2 days, except Sunday
  • Mid-week change of towels (Wed)
  • Weekly gardener and pool maintenance
Staff and Services (at additional cost)
  • Extra housekeeping service
  • Laundry and ironing service
  • Cook services
  • Cost of food and beverages
Location Details
  • Nearest Airport: Florence Peretola 1 h 22 min
  • Nearest serviced town: 10 min
  • Nearest major city: Siena 36 min
Villa Notes
  • Electricity, A/C and water are included
  • Caretakers live in an apartment with separate entrance from the villa (upon request, possibility of full exclusivity - price on request)
  • Check-in: between 4:00 pm - 7:00 pm
  • Check-out: before/by 9:00 am
  • All the above services must be paid locally, prior to departure unless otherwise arranged
Tuscany Villa Notes
  • Important note regarding Chef/ Cook Services: All Chef/Cook services need to be arranged by your Concierge.  Only Villa approved Chef/Cooks can be used.  This also pertains to In-Villa cooking lessons.
  • Due to limited transportation in outlying and rural areas, a rental car is essential for stays at countryside villas in Italy. We are more than happy to arrange a car for you during your stay, please just let us know at time of booking.
  • Please note that Italy villas rent from Saturday to Saturday. Exceptions may be possible on a case by case basis and upon request.
  • The Italian government has implemented a Visitor’s Tax of €1.50 - €5.00 per person, per day and applies to all overnight stays for the first seven days in the destination. This tax is payable to the local property manager.
  • Most villas in Italy require the cost of extra services be paid upon arrival in cash.  Please check with your Villa Specialist or Concierge for details.  

Cipresso Reviews

The villa and the owner and staff exceeded …
Posted by in August 2018

The villa and the owner and staff exceeded all of our expectations. We had a wonderful time, and Pino (the owner) was a most gracious host. We found the villa to be perfect for gatherings of our large group, but also provided many areas for more private gatherings. The pool was large and refreshing. The concierge (Daria) arranged for a breakfast each morning for the group, which was provided by the staff at the villa - a great way to start the day. We also had a dinner cooked for us at the villa one night, which was a lot of fun. A special treat was the two cases of fantastic Chianti Classico made by our host, which we purchased for a very low price. Pino and his son always greeted us with a smile. A fantastic week.

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20% Off »

Book by August 17, 2019 and get 20% off regular villa rates.

Valid for new bookings made now to 8/17/19 for travel now to 8/31/19. 7 Night minimum booking required. Subject to availability and may not be combinable with other offers. Additional restrictions may apply; please call for full details.

Up to $2,000 in Destination Dollars »

We’re committed to transforming already exceptional escapes into something even more extraordinary. That’s why we’re giving you up to $2,000 in Destination Dollars to create the most memorable vacation ever. Add a chef to your villa experience, or enjoy airport fast-track services. The choices are endless – and all yours.

Once your dream villa vacation is booked, your complimentary personal concierge will coordinate and schedule any element of your villa vacation – taking the guesswork out of your getaway like never before.

Here’s how you can earn your Destination Dollars:

Amount Spent Destination Dollar Rewards
$5,000 - $15,000 $150
$15,000 - $25,000 $250
$25,001 - $35,000 $350
$35,001 - $50,000 $500
$50,001 - $75,000 $750
$75,001 - $100,000 $1,000
$100,001 + $2,000

Don't miss out! This offer expires May 25, 2019!

The tiers are based on the base villa cost only. Security deposits, concierge services, TA added booking fees and tax and services are not included in calculating the credit tiers. Offer valid for new bookings made between 5/19/19 – 5/25/19 for travel from 6/1/19 – 8/31/19. Destination Dollars of up to $2,000. Valid for select pre-paid services only. Service offered is subject to availability. No cash value. The value of any unused credit is non-refundable. Credit cannot be applied towards booking value. May not be combinable with other offers. All offers are subject to availability and may not apply to all villas or travel dates. Other restrictions may apply; please call for full details.

Tuscany Travel Guide

Rural Chic

Tuscany is overflowing with natural, architectural, and artistic masterpieces. The birthplace of Italian Renaissance is home to rolling hills, majestic cypress trees, miles of sandy coastline, and beautiful vineyards in addition to the world's finest art center, Florence. Stay in a rustic yet elegant villa enjoying life's greatest pleasures: sprawling countryside, simple, fresh cuisine, and Italy's finest wines.

Each villa rental in this magnificent province is unique to the area in which it resides. A shopper’s delight, Florence is home to charming cobblestone streets, artistic and architectural masterpieces, and some of the world’s biggest fashion icons. Those who rent villas in the 39-square mile Chianti wine region will love sampling the fruits of the region’s spectacular vineyards at the wineries themselves or in the comfort of their villa. Villas in the bigger cities of Pisa and Livorno offer a slightly different experience, allowing vacationers to explore the mystique of the Medici era and visit the Leaning Tower of Pisa. Famous for its butteri, cowboys who managed cattle, Maremma offers visitors the opportunity to go horseback riding or swim in one of the area's beautiful bays. In Siena, one of the region's loveliest medieval cities, visitors can stroll the famous shell-shaped Piazzo del Campo, where horse races are held twice a year. No matter where in Tuscany you choose to stay, your villa vacation is guaranteed to be unforgettable.

Learn more about Tuscany »

Villa information may change without notice and should be confirmed with our villa rental specialists.

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