Villa Cipresso

Chianti, Tuscany
Children Welcome
Turnover Day is Saturday
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Looking as if it came straight out of a painting or picture postcard for Tuscany, the stunning Villa Cipresso in Chianti, Tuscany can be yours when you visit the region. Built in the 1200s, it has been lovingly restored and offers luxurious accommodation in its nine bedrooms. Only a short distance from the town of Siena, it remains entirely private and peaceful.

The villa has two structures - a main villa and the smaller annex. The entire property is surrounded by nearby vineyards and a rolling landscape of cypresses, fields, and gardens. The property includes a large and private swimming pool surrounded by a stone terrace and partially shaded for hours of relaxation. The vineyards nearby even produce the vintages served at the villa!

The exterior of the villa includes traditional terraces and patios in addition to the pool. There is a large al fresco dining terrace with an outdoor kitchen, and all of the ground floor rooms open to the garden or terrace. Indoors, visitors will be able to enjoy the wooden beams, terra cotta floors, and brick arches that are iconic in Tuscan architecture. With comfortable furnishings, all of the shared living spaces are warm and welcoming.

The main level features a large dining room, several sitting rooms, and a sunken lounge ideal for late night cocktails or leisurely hours of reading. The next floor is where visitors can access the tower, and at its base is an entertainment space with TV and fireplace. There is a full, gourmet kitchen on the main level, and it has a cozy spot for dining.

The annex features a kitchen as well as living and dining spaces, and the upper level has a shared living room too.

Whether for a family event or tour with friends, this villa will provide an unforgettable experience of Tuscany.

Nearest Town/Village: Pianella - 12 mins drive

The Weekly Rate Includes:  Electricity, water and final cleaning.  Daily house cleaning (2hrs) included in high season, except Sunday, rest of the year it is 1 midweek cleaning (4hrs).  Change of towels once per week on Saturday.  WiFi access and weekly gardener and pool maintenence.

Food, beverage and provisioning fee not included.  Heating charges, A/C charges, extra hpusekeeping, laundry and ironing, cook, arrival Welcome dinner and telephone charges are all additional.  Please ask you villa specialist for quotes on these charges.


Bedroom 1: First floor bedroom with a double bed and en-suite bathroom with shower, vanity and WC. 2 guests maximum.

Bedroom 2 & 3: First floor bedrooms with a double bed and shared bathroom with shower, vanity and WC. 2 guests maximum per bedroom.

Bedroom 4: Third floor bedroom with a double bed and private bathroom with shower, vanity and WC. 2 guests maximum.


Bedroom 5 & 6: Ground floor bedrooms with a double bed and en-suite bathroom with shower, vanity and WC. 2 guests maximum per bedroom.

Bedroom 7: First floor bedroom with a double bed and private bathroom with shower, vanity and WC. 2 guests maximum.

Bedroom 8: First floor bedroom with a double bed and shared bathroom with shower, vanity and WC. 2 guests maximum.

Bedroom 9: First floor bedroom with two single beds and shared bathroom with shower, vanity and WC. 2 guests maximum.

A/C is in the uppermost bedrooms only.

Interior Access Bedrooms: 9

  • Air Conditioning - Bedrooms
  • Alfresco Dining Area
  • Bed and Bath Linens
  • Children Welcome
  • Dishwasher
  • Fireplace
  • Heating
  • Interior Bedrooms
  • Outdoor Grill
  • Sound System
  • TV - Satellite
  • Washer
  • WiFi
  • Housekeeper(s)
Housekeeping: Daily maid service except Sundays & holidays
  • Outdoor
  • Private
  • Damage Deposit: 1500 Euro to be collected with the final payment
  • Children Welcome (all ages)
  • No Pets Allowed
  • No Smoking
  • All extra charges to be paid at end of stay in local currency.
  • Rates set in Euros. Prices in other currencies my fluctuate.
  • Turnaround day: Saturday
  • VAT taxes included in rates.
  • Villa orientation
  • Deposit/Payment: 50% deposit. Balance due 90 days prior to arrival.
  • Check In: Check-in window is usually 4pm to 7pm
  • Check Out: check-out is by 10am. Client is advised to CALL the keyholder from the airport to give an ETA and set an appointment for check-in.
Do we share the villa? click to close
No. You will not share the villa with another party. The villa is exclusively yours. If a larger villa offers a lower bedroom rate category, the villa will remain exclusively yours but the unrented bedrooms will be locked off.
For example, a 5 bedroom villa that offers a 3 bedroom rate will be the exclusive use of the guest but two bedrooms and their en-suite bathrooms will be locked off. Capacity is capped at 2 guests per bedroom.
Are we protected from fraud? click to open
Yes. Isle Blue stands behind you throughout your entire vacation. Unlike other companies, each property we offer has been hand picked to ensure that our standards are met. All property managers are vetted and payments are required to be held in escrow. Our primary obligation is to ensure your satisfaction and to have an exceptionally memorable vacation.
Can you explain the reservation process? click to open
Once a reservation request is received, Isle Blue will request a contract from the property manager for your dates of interest. Once the dates are confirmed and contract is received from the property manager, a payment will be required to confirm your reservation.
Once a reservation is confirmed, a concierge will welcome you to the planning stages of your vacation to assist with arrival logistics, rental cars, transfers, and a host of concierge services.
What offerings are included with the concierge service? click to open
Our concierge is a complimentary service to our guests. An exceptional benefit. The concierge will assist with your arrival and departure logistics and offer a host of additional services. Services may vary per destination but typically include the following benefits:
  • Transfers
  • VIP Services
  • Chef Services
  • Spa Services
  • Activity and Excursion booking
  • Rental cars
  • Provisioning
Please do not hesitate with any special requests. Our team is here to ensure you dream vacation becomes a grand reality.
Can we arrange an early check in? click to open
Early check in may be possible but is at the sole discretion of the property manager. Early check in permission may not be granted until 24 hours prior to arrival.
Can we arrange a late check out? click to open
A late check out is rarely granted due to the turnover needs of a villa. A late check out may only be granted 24 hours prior to your departure from the property and only when there is no check in scheduled on the day of your check out. If a late check out is urgently needed please contact us.
Are transfers to the property included? click to open
Select villas may include a one way or roundtrip airport transfer while others may provide an escort or meeting point. Arrival logistics will be handled by your dedicated concierge as well as other concierge needs. The property's transfer policy will be listed under the Policies section.
What to expect upon arrival? click to open
In general, a villa orientation will be provided along with a key turnover. During the orientation, information and instructions for the property will be provided. Emergency contact information will be provided. We are available 7 days a week to assist with any urgent needs.
The arrival procedures due vary from villa to villa, select villas may include welcome provisioning while other properties will provide basic arrival information.
What is the cancellation policy? click to open
Since these vacation homes are one of a kind properties, the cancellation policy is strict. We highly recommend considering trip/travel insurance to protect against any unexpected cancellations or issues that may arise.
For more details, please visit Travel Protection
What happens if the property becomes unavailable after I reserve? click to open
In the unlikely event, the rented property becomes unavailable due to a major issue that may affect a guest's experience or a transfer of ownership, Isle Blue will coordinate with the property manager to find an alternate property of equal or superior standard that is subject to the guest's approval. If an alternate property is not acceptable to the guest, the guest will receive a full refund.
Do you accept credit cards (American Express, Mastercard, or Visa)? click to open
Yes, we accept all major credit cards. American Express, Visa, Mastercard and Discover are accepted. Please note that credit card charges may be subject to additional fees. There are no fees with payment by wire transfer or check.
In late 2018, we expect to accept a greater variety of payment methods and currencies via Stripe.
Is housekeeping included? click to open
Housekeeping tends to be a standard among vacation homes but the frequency may vary greatly depending on the property manager’s standards. Most properties will offer daily housekeeping (except Sunday and holidays) while other villas may only provide a mid-week cleaning. Please refer to the Policies section to learn about the housekeeping frequency of the property.
Are towels and linens provided? click to open
Yes. The property will provide bath and pool towels along with linens. Towels and linens will be refreshed as needed.
Are toiletries and tissues provided? click to open
A property may supply an initial supply of soap, shampoo, toilet paper and paper towels but replenishment of supplies once exhausted may be the responsibility of the guest. Each property varies in their handling of toiletries and paper products.
Is a hair dryer available? click to open
A hair dryer is typically available at the property. Upon arrival, please check the bathrooms or closet. Typically, a hair dryer is included in each bathroom.
Is an iron included? click to open
Typically yes, irons tend to be standard equipment for vacation homes. Please ask the property representative upon orientation for the location of the iron.

Isle Blue provides the most in-depth expertise and insight for vacation home rentals and vacation planning. For further helpful tips, answers and recommendations please visit our extensive Knowledge center that hosts articles and answers on general as well as destination specific topics.

2018 Oct 14 to Dec 15 October 14, 2018 - December 15, 2018 (7 night minimum) 9 $968.41 $6,778.87
2018 Dec 15 to 2019 Jan 5 December 15, 2018 - January 5, 2019 (7 night minimum) 9 $1,383.12 $9,681.84
2018 Oct 14 to Dec 15 October 14, 2018 - December 15, 2018 (7 night minimum)
Bedrooms: 9
Daily: $968.41
Weekly: $6,778.87
2018 Dec 15 to 2019 Jan 5 December 15, 2018 - January 5, 2019 (7 night minimum)
Bedrooms: 9
Daily: $1,383.12
Weekly: $9,681.84

Note: The rates above are subject to 0% Tax/Service Charge.
Payments accepted in US Dollars, Euros, British Pound, Canadian Dollars, Swiss Franc, Fijian Dollars, Thai Baht, Australian Dollars, New Zealand Dollars.
Major credit cards accepted in US Dollars.

STARTING AT $1,028.40/Nt
Please try again or contact us for possible waiver at 1-704-256-8327 or [email protected]
Your Estimate:
(Estimate does not include applicable promotions.)
Date Unavailable Availability calendar may not reflect up to date reservation information.
Availability subject to change.


Due to villa's privacy policy, the nearest town is presented on the map




"Fantastic views, loved the moving TV feature. Loved the bath beside the bed and kitchen design. Fantastic villa. Your services were 5/5."
Amanda W.
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