Gated Estate, Luxury in Prime Chianti. Gorgeous & Classic, Views!

The owner has been emailed.
To book this property, you need to complete your booking through checkout on the VRBO website. We can't protect your payment if we don't know you've booked through us. Learn more


Last updated: 10/19/2016
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:5-30 nights
  • Internet:Yes
  • Pets considered:Yes
  • Wheel chair accessible:N/A

Property description

Please inquire for remaining August and September 2016 availability.
Calendar and summer-season rates are not made public.
See Also VRBO#557879, these properties may be taken together for larger groups.

In the Chianti Countryside: Set atop a private access road, enter a comfortable estate in the prime historic and most central area of Tuscany's Chianti Classico region. ~
Easy access from Rome or Florence make this a perfect choice for your stay in Classic Tuscany. Recently renovated with modern conveniences, this 1500's Stone Farmhouse is situated in the middle of Olive Groves and rolling Chianti Classico Vineyards while still within a short walk from fine restaurants.

A professionally-equipped kitchen and multiple large outdoor living and dining spaces are just two of the premiere features of the estate property. Dreamliner Views overlook beautifully groomed and ancient Sangiovese & Merlot vineyards through to the rolling hills of the Chianti region.

The 'Vineyard Suite': Two bedrooms with en-suite bathroom. Double Bedroom along with Single Bedroom, private entrance, view terraces, bathroom with tub+shower. There is a cozy reading nook / window-seat in the double room.

The 'Garden Suite': Two adjoining bedrooms with large en-suite travertine bathroom. This suite consists of a carved chestnut-wood 17th c. double bedroom, private entrance with view terrace, a French-Empire single-bed sitting room, travertine Bathroom, antique claw-foot iron tub and large walk-in shower room.

The entire property is thoughtfully furnished with fine European antiques and authentic decor. Pressed Italian bed linens and plush towels are provided. Wireless internet throughout.

The main (middle) floor consists of an updated cook's kitchen, dining salon, living room, powder room, our own 'piazza' and rambling view terraces with fireplace and BBQ. A tended kitchen garden full of herbs, greens and seasonable vegetables, with almond, apricot, fig, and berries only an arm's length away for those yearning to be Tuscan chefs.

Exquisite Privacy (see reviews) with private hiking Trails, olive groves, and vineyards surrounding the estate. A private pool features breathtaking views to distant hills of Montalcino. The main dining terrace offers a pergola-covered travertine table with a large BBQ fireplace. All windows are screened, sleeping suites offer individually-controlled air conditioning.

Al fresco dining will accommodate up to 12 guests for your special occasions. Plan a catered and serviced meal on the main terrace for your ultimate Tuscan experience, or select a casual pre-prepared dinner and drinks for your night of arrival to be enjoyed at your own leisurely pace.

The estate is minutes from the village of Castelnuovo Berardenga and is within close walking or biking proximity to gorgeous small villages. Florence is about an hour and twenty minutes, Rome just under three hours.  Siena is twenty minutes away. Reached easily by car are towns such as Montalcino, Arezzo, Greve-in-Chianti, Castellina-in-Chianti, Cortona, Assisi.
White-sand tuscan beaches of the Maremma or fishing villages of the Cinque Terra are 2 to 4 hours away.
Located within short walking distance of the property are four excellent restaurants offering a range of dining opportunities.

Please note that our availability calendar is not publicized.
*See related property VRBO#557879, two charming private homes nearby in similarly private setting with views to Siena. It is possible to take these properties together for a larger group or family desiring separate residences.

Payment may be negotiated in USD or Euro.

"We haven't even been here at the villa for more than 10 hours and I am already in love!!!! This is seriously a piece of heaven on earth. You have managed to make this the best villa that we have ever stayed at and we have traveled the world. You are amazing!!!! This villa is so welcoming and your level of taste is beyond expectations. This is definitely the highlight of our trip to Italy over the past 2 1/2 weeks. The way that you have decorated this villa is beyond words. You have captured Italy beter than an Italian! The decor is PERFECT!!!! I love the art to the bedding to the extra-special touches that you include that are not done without appreciation on our end. Thank you so much for letting us stay here and enjoy your marvelous home.
We ABSOLUTELY willl be back! Like I stated haven't even been here a day yet and we LOVE IT HERE!

Thank you again for sharing your beautiful villa with us".
—Beth B., A Recent Guest

(**See related property VRBO#557879, two charming private homes (4+5) in nearby and similarly private setting, with views to Siena. It is possible to take these properties together for a larger group or family desiring separate residences).

Peace of mind when checking out through VRBO

  • We'll back you with our Book With Confidence GuaranteeTM
  • You'll get comprehensive payment protection when checking out on our website
  • We're always here for you with customer service available 24/7

Read more about our Book with Confidence GuaranteeTM

Property Type

  • Villa
  • 3500 sq. ft.

Accommodation Type

  • Vacation Rental


  • Guests Provide Their Own Meals

Onsite Services

  • Housekeeper Optional


  • Events Allowed
  • Long-Term Renters Welcome
  • Children Welcome
  • Pets Considered

Bedrooms: 5 Bedrooms, Sleeps 6, Beds for 6

Bathrooms: 2 Bathrooms, 1 Half Bathroom

Other Amenities

  • Optional extras: Daily change of linens. Private tours of Siena, Florence or surrounding villages. Home-Cooked Evening Meals and Aperativi Cooking Lessons with Hosted Market Day taught by a local Chef....moreless


  • Books
  • Games
  • Satellite / Cable
  • Television
  • Toys
  • Video Library


  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities


  • Botanical Garden
  • Churches
  • Cinemas
  • Duty Free Shops
  • Festivals
  • Health/Beauty Spa
  • Library
  • Live Theater
  • Marina
  • Museums
  • Playground
  • Recreation Center
  • Restaurants
  • Ruins
  • Synagogues
  • Water Parks
  • Winery Tours

Local Services & Businesses

  • ATM/Bank
  • Babysitter
  • Fitness Center
  • Groceries
  • Hospital
  • Laundromat
  • Massage Therapist
  • Medical Services

Leisure Activities

  • Antiquing
  • Beachcombing
  • Bird Watching
  • Boating
  • Eco Tourism
  • Horseback Riding
  • Horseshoes
  • Outlet Shopping
  • Photography
  • Shopping
  • Sight Seeing
  • Walking
  • Wildlife Viewing

Location Type

  • Downtown
  • Monument View
  • Mountain View:

    Rolling vineyards, olive groves, and adjacent pine forest views....moreless

  • Resort
  • Rural
  • Village

Sports & Adventure Activities

  • Cycling
  • Equestrian Events
  • Golf
  • Golf Privileges Optional
  • Hiking
  • Hot Air Ballooning
  • Hunting
  • Mountain Biking
  • Mountain Climbing
  • Mountaineering
  • Rock Climbing
  • Roller Blading
  • Sailing
  • Swimming


  • Dining
  • Dining Area
  • Seating for 12 people


  • Air Conditioning
  • Fireplace
  • Fitness Room / Equipment
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wood Stove


  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster


  • Balcony
  • Bicycles
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill

Pool / Spa

  • Private Pool

House Cleaning

  • Housekeeper Optional


Write a review 5
from 18 traveler reviews
Rental basis: Per property
Dates Nightly Weekend Night Weekly Monthly * Event
Sep 6 - Nov 30, 2016
5 night min stay

May 1 - Jun 22, 2017
5 night min stay

$6,000 $22,000
Jun 23 - Sep 22, 2017
5 night min stay

$6,200 $22,000
My Standard Rate
30 night min stay

* Approximate Monthly rates, actual rate will depend on the days of the month you stay

Additional information about rental rates


  • Refundable Damage Deposit $300
  • Tax Rate 15%


Payment may be negotiated in USD($) or Euro(€), CreditCard- PayPal, Online or Direct Bank Transfer.

Price includes:

Pressed Italian Bed Linens

Fluffed Bath Towels

Internet Wi-Fi

Basic Pantry & Fridge Items

Gas for Cooking

Firewood for BBQ

A gift of our Chianti Classico House Wine

*Utilities, except winter heating and winter firewood. Winter-season utilities will incur an extra fee dependent on per-day usage of gas for heating and firewood.

Owner's cancellation policy:

Cancelled bookings will not receive a refund.

Don't forget your vacation protection! Get protected now

Adding our Vacation Protection services can make sure your getaway goes smoothly, no matter what. We offer Cancellation Protection and Damage Protection so you can truly relax.

Protect your payments in case you need to cancel.
Travel with peace of mind.
Ensure you're prepared in case of accidental damage.


Last updated: 10/19/2016
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates


5 Miles
Nearest Barpub
Bar Centrale
20 Kilometres
Nearest Train
10 Kilometres
Nearest Motorway

Car: Recommended

Wine-Tasting, Farmer's Markets, Outlet-Shopping, Cooking Classes, Beaches


Owner info

Year Purchased: 2006

About the owner: Michael is design professional based in Los Angeles and Tuscany.

Why the Owner Chose Villa A Sesta SI, Italy:
The estate, dating from about 1550, is situated amidst vineyards and olive groves and offers panoramic 360-degree views. While offering serene privacy, it is possible to walk 10-minutes down the road to a small village, indulging in any one of four of Tuscany's finest and authentic dining establishments.

The Unique Benefits at this Villa:
Privacy, Views, Fine Dining, Family Entertaining. Access to hiking trails, vineyard walks, shaded hammocks amidst olive groves and reclining by the large private pool.

Contact us

Speaks: english, italian

Links to more information:



  • Professionally-Equipped Kitchen

    Professionally-Equipped Kitchen

  • Garden Suite Bath

    Garden Suite Bath

  • Vineyard Suite Single Bedroom

    Vineyard Suite Single Bedroom

  • Powder Room Bath

    Powder Room Bath

  • LaChiusa-in-Chianti


  • Unobstructed Views Amidst Serene Privacy

    Unobstructed Views Amidst Serene Privacy

  • Details Featuring French and Italian Antiques

    Details Featuring French and Italian Antiques

  • Garden Suite Double Bedroom

    Garden Suite Double Bedroom

  • Garden Suite Bath

    Garden Suite Bath

  • Vineyard Suite Double Bedroom

    Vineyard Suite Double Bedroom

  • Tuscan Details

    Tuscan Details

VRBO #412266

This listing was first published here in 2012.

Date last modified - Thursday, October 20, 2016

Partner Offers

Enter dates to see accurate pricing

Minimum stay 5-30 nights
Dates are unavailable
Please enter travel dates
Please enter # of guests
Please stay a bit longer. A stay of nights or more is required for these dates.
This listing requires that rentals start on a .
Request to Book

Booking confirmation within 24 hours

Get an Instant Quote

Pay with confidence
 please wait... When you book through the VRBO website, your booking is backed by our Book with Confidence Guarantee Learn more
  • Reviews
  • Sleeps
  • Bedrooms
  • Bathrooms
  • Property type
Member since: 2012
Speaks: english, italian
Send email
  • Response time Within an hour
  • Response rate 100%
  • Calendar last updated 10/19/2016

+39 3316075049

Add vacation protection services to your booking

Three services to protect your trip:

Protect your payments in case you need to cancel.

Travel with peace of mind.

Ensure you're prepared in case of accidental damage.

Get it now


Share this property via Email

Gated Estate, Luxury in Prime Chianti. Gorgeous & Classic, VIEWS!

Villa A Sesta SI, Italy #412266

5 BR  2.5 BA  Sleeps 6

You must be signed in to share this property by e-mail

Share this property via Email

    Please correct the following errors and resend:
  • Enter one or more valid email addresses separated by commas.
  • Oops! You have exceeded the limit of 10 email addresses.
  • Your message may not contain markup. Please remove the markup and try again.