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.
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.
On the first floor is an air conditioned living room, fireplace, two comfortable sofas and an area dedicated to aperitivo or wine tasting.
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.
The third floor is the tower that houses a small art gallery with large windows overlooking the beautiful Chianti landscape.
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
|Now to May 31, 2019||8||7||
$ 1,893 € 1657 $ 2735 $ 2542 1909 £ 1487
|Jun 1, 2019 to Aug 16, 2019||8||7||
$ 2,565 € 2245 $ 3706 $ 3444 2587 £ 2015
|Aug 17, 2019 to Oct 11, 2019||8||7||
$ 1,893 € 1657 $ 2735 $ 2542 1909 £ 1487
|Oct 12, 2019 to Dec 13, 2019||8||7||
$ 979 € 857 $ 1415 $ 1315 988 £ 769
|Dec 14, 2019 to Jan 3, 2020
Christmas/ New Year's
$ 1,398 € 1224 $ 2021 $ 1878 1410 £ 1099
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 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
- Laundry room with washing machine and ironing facilities
- Play Station 3
- Private covered parking
- Satellite TV
- Stereo system
- Wi-Fi internet access
- 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
- Nearest Airport: Florence Peretola 1 h 22 min
- Nearest serviced town: 10 min
- Nearest major city: Siena 36 min
- 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.
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|
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
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.