Villa Anna

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Sleeps: 18 Bedrooms: 9 Bathrooms: 10


Wedding Venue Pool
Wow Factor
Wellness Ideal for Kids
Pets on Request
Hot Tub All Bedrooms En-Suite


Book your 2024 holiday by 29th February and receive a welcome gift, double your Holiday Credit and a Go Beyond charity donation. See full details here

This private Luxury Villa with swimming pool, spa, hot tub and Sauna is the ideal Italian country getaway.

Whether you feel like pottering in the vegetable garden or using the villa's amenities such as the sauna and pool, you will never be at a loose end while staying in this wonderfully authentic property. The villa has such a country feel it will make you feel one with nature the minute you arrive. It is incredibly spacious and a biological farm where the owners produce Wine and Olive Oil.

Hills and vineyards dominate the view and it is only 12km from Montalcino and 30km from Siena so if lounging by the pool gets too much then the beautiful Siena is very easily accessible.

Many services can be provided by the villa upon request such as cooking courses, massages, dinners and breakfast service, horseback riding, animal watching and bike rides.

Oliver Approved

What you should know…

  • Due to the beautiful rural location of this villa, it is recommended to hire a car to be able to visit everything the area has to offer
  • This villa is off the main road, down a small country road

Property Features

Private Pool Wi-Fi/Internet Air-Con Hot Tub BBQ All Bedrooms En-Suite Ground Floor Bed & Bath Satellite TV Table Tennis Pool/Snooker DVD

Main Villa

Ground Floor

- Main entrance with dining room with long table seating 18 and small circle table seating 4  
- Living room with fireplace 
- Suite with king size bed, office and ensuite bathroom with shower
- Kitchen divided in 2 rooms: preparation room and cooking room with double fires and oven 
- Suite with king size bed, living room and ensuite bathroom with bathtub and shower
- Gaming room with pool table
- Spa with hot tub and sauna 
- Bathroom with changing room for the spa 

First Floor 

- Living room with fireplace 
- Study with table 
- Kitchen 
- 5 bedrooms with queen size bed and ensuite bathroom with shower 
- Master bedroom with king size bed and ensuite bathroom with shower and bathtub

Guest House

- Bedroom with queen size bed and ensuite bathroom with shower 
- Living room with sofa 

Outside Grounds

- 3 x covered terraces
- Alfresco dining area with table seating 22
- Garden 
- Swimming pool
- Wood oven pizza
- Sun loungers
- Barbecue
- Vegetable garden
- Bocce court 
- Outside seating area 


- WiFi
- Heating
- Air-conditioning
- TV
- Table tennis
- Pool table
- Sauna


About the surrounding area of Villa Anna
<1hr to Airport Wine Tasting Golf Nearby Fishing
Loading map

Villa Anna is situated in the rolling hills of the Tuscan countryside, on a 300-hectare organic farm. The perfect spot to experience the best vistas of this rural area of Italy, with surrounding vineyards, olive trees and cypress trees. Nearby you will also find plenty of charming villages and towns to enjoy local delicacies, with the closest restaurant and supermarket only 5 km away.

Overlooking the picturesque landscape of the UNESCO world heritage site, Val d’Orcia, this villa is a wonderful base to explore this stunning valley.  If you’re a wine connoisseur, this is the ideal location to try renowned wines such as Brunello di Montalcino. The town of Montalcino itself can be found around 20km away, and a trip to the cellars to learn more about this DOCG (Denominazione di Origine Controllate e Garantita) awarded wine will be sure to delight. Aside from the wine, Montalcino has much to offer. The historical centre with its intact fortress built in 1361 is very impressive, not to mention the wonderful view standing on top of its walls. This town becomes even more alive in July with the jazz and wine festival held within the grounds of the fortress. 

Another nearby town famous for its wine is Montepulciano, 45km away, home to the Vino Nobile. This is one of the most beautiful hilltop towns in Tuscany, full of elegant Renaissance palaces, ancient churches and charming squares. 

Tuscany is full of traditional towns, each with their own unique history and delicious local foods that can be enjoyed in the trattorias, you could visit a new town every day if you wished! However, if you fancy venturing to a city, Siena, only 30km away, is worth a visit, maybe even two; there’s so much to see. Notable sights include the Tower of Mangia, next to the Palazzo Publico, with incredible views over the city and the gorgeous Duomo di Siena. A particularly great time to visit would be in July or August to revel in the festivities held for the Palio horse race, which has been taking place since the 17th century. Siena is overall a must-see and after a long day of visiting beautiful churches and monuments, nothing can beat a pizza enjoyed in the lively atmosphere of the Piazza del Campo.

Read more about Siena

Local Amenities
Nearest Airport Florence

(91-100 Km)

Nearest Train Station Siena

(26-30 Km)

Nearest Village Buonconvento

(5 Km)

Nearest Town/City Siena

(26-30 Km)

Nearest Restaurant Bunconvento

(5 Km)

Nearest Shop Bunconvento

(5 Km)

Nearest Supermarket Bunconvento

(5 Km)

Nearest Beach Talmone

(71-80 Km)

Nearest Golf Bagnaia

(21-25 Km)

Nearest Tennis Bunconvento

(5 Km)


With its rolling fields, historical heritage and a cuisine that’s a delight for all the senses, it’s no wonder Tuscany is one of the most popular regions in Italy for holidaymakers. Yet even with its popularity, you can still kick back in one of our luxury villas in Tuscany and feel peace, tranquillity and the joy of seclusion. 

This is one destination that really does have a little bit of everything for everyone, whether you’re travelling with family, friends or are just looking for a romantic getaway with that special someone.

Download Our Tuscany Travel Guide >>


Best Suited For: All Ages
Ideal for Kids Ideal for Teens

Go on long walks through the rolling Tuscan countryside, enjoy picnics of delicious Italian cheese and meats or hire bikes for a family cycling trip – this area has plenty to keep the children active and enjoying the fresh air and Italian sunshine! It is also perfect for little historians, with endless towns full of ancient castles and churches.

Particularly adventurous children will enjoy the Saltalbero Adventure park which is equipped with 7 acrobatic trails divided by age level and difficulty. The activities include rope bridges, pirate ladders and swinging logs, inducing a real sense of adventure!

For the younger children, there are many playgrounds in Siena as well as the Orto de Pecci park, only a 5 minute walk from the Piazza del Campo. This park is perfect for animal lovers, with a goldfish pond and a fenced area with goats, a donkey and peacocks. Further fun activities in Siena include the natural history museum which has displays about animals as well as rocks and minerals. Another educational museum trip is the Santa Maria della Scala, found opposite the Duomo. This museum contains a small art exhibition catered to children, aiming to educate them about the artistic process. 

Baby and Toddler Equipment

  • Cot(s)
  • High Chair(s)

Kids Activities Close-by

  • <1hr to Airport
  • Fishing

Onsite Facilities

  • Children's videos/DVDs
  • Table Tennis
  • Pool/Snooker
  • DVD

Services Available

  • Chef/Cook Available
  • Maid Service Included
  • Babysitting Available
  • English speaking babysitter available


Oliver's Extras

  • Cooking Classes Available
  • Spa Treatments Available
  • Transfers Available
  • Chef/Cook Available
  • Maid Service Included
  • Babysitting Available
  • On-Site Concierge
  • English speaking babysitter available
  • Meal delivery available

At Oliver’s Travels we pride ourselves on going that little bit further for our guests. From private chefs to babysitters we can help you arrange those little extras that make it a truly memorable holiday. Simply fill in the concierge request form or contact the Oliver’s Concierge Team who will be happy to help. We can typically help you arrange any of the following:

- Maid service/extra cleaning 
- Private chef/cook/catering
- Welcome hamper/pre-stocked fridge
- Local day-trips or tours
- Airport pick-up/drop-off
- Babysitting / childcare services
- Bike hire

Extras included at this property:

- Maid service (5 hours a day, 5 days a week)
- Fresh produce from the garden

Extras available at this property (payable locally):

- Private chef
- Airport transfers
- Wine tastings
- Massage treatments
- Horse back riding
- Hot Air Ballooning 
- Cooking classes

Please note that all extras are subject to availability and must be requested in advance of the holiday (prices on request). Due to some rural/remote locations, not all services will be available at all properties. However, we will always do our best to fulfil your requests!

Oliver's Travels Chef Service: A Gourmet Dining Experience
Make hosting a memorable dinner party at your villa an absolute breeze with our superb Chef Service. Our chefs will take care of everything for you from start to finish so you can just sit back and enjoy the gastronomic experience. They will bring all the necessary ingredients, cook and serve the food and even clean up afterwards. To find out more visit

Event information

With mesmerising views towards Montalcino, Villa Anna is an authentic and romantic venue for a traditional Italian wedding in southern Tuscany, not far from the beautiful towns of Montepulciano and Siena.

With a rustic and relaxed ambience, feast with family and friends beneath the covered terrace or set up a grand marquee within the glorious estate. With some of Tuscany’s finest vineyards close by, plus extra virgin olive oil produced by the owner, this is the ultimate Tuscan experience for your special day.

Wedding Reception

Events are generally for a maximum of 80 guests. A marquee can be hired and there is space for dancing under the covered patio at the front. Tables and chairs can also be set up on the terraces for a sit-down meal.

For a smaller event, a meal can be set up inside the villa for 22 people.

A marquee is the best option in case of poor weather.

There is no time limit on the event but music must stop by 3.00 a.m.

Wedding Ceremony

A symbolic ceremony can take place in the garden or another picturesque spot.

An English speaking celebrant can be provided.

Where to Stay

18 guests can stay in Villa Anna, 12 guests can stay in the owners’ other two properties whilst 60 other guests can stay elsewhere within a 10-minute drive, depending on availability.

Wedding Planning
You should use Villa Anna’s Wedding Planner, you are not able to use your own.


Catering can only be organised via the owners’ exclusive suppliers, you cannot arrange your own. Corkage charges may apply.

Other Information
Events can take place from April to October.

There is a set events fee, a cleaning cost plus the cost of all services/extras (tables, chairs, marquee, catering and all other services)

The owners can arrange everything that you may need. They have exclusive suppliers for catering and the sound and lights system.

Please note that any event rental may be subject to additional charges, venue hire fees and to a higher security deposit, which will be in addition to any published rental rates and fees.

All events are on request only and subject to prior agreement from the owner, who reserves the right to refuse all events without their prior authorisation.

Terms & Conditions

These terms and conditions may be amended from time to time.

Security deposit €1,000 paid in cash to the owner upon arrival and refunded upon departure, subject to full inspection.
Arrival time 4.00 p.m.
Departure time 10.00 a.m.
Energy costs included? Extra €200, payable locally.
End of stay cleaning included? Extra €400, payable locally. However, guests are required to leave the accommodation clean, tidy and in the same condition as on their arrival. Any extra cleaning, laundry, maintenance and/or rubbish disposal required will be charged against the security deposit.
Linen & towels included? Yes.
Smoking Allowed? Outside only.
Minimum stay 7 nights from June to end-September. 5 nights during all other periods.
Changeover day Saturday from June to end-September. Flexible during all other periods.
Tax Italian Visitors Tax payable locally in cash (typically costs €1-€3 per adult per night- please enquire if exact amount is required).

Rental Rates

Prices based on an occupancy of 18 people:

Rental period 5 Nights Weekly
Dec 8th 2023 - Dec 16th 2023 £7,008 £9,811
Dec 16th 2023 - Jan 6th 2024 - £11,783
Jan 6th 2024 - Apr 27th 2024 £5,610 £7,853
Apr 27th 2024 - Jun 1st 2024 £8,417 £11,783
Jun 1st 2024 - Aug 24th 2024 - £13,741
Aug 24th 2024 - Sep 21st 2024 - £12,766
Sep 21st 2024 - Oct 19th 2024 £8,417 £11,783
Oct 19th 2024 - Dec 14th 2024 £7,008 £9,811
Dec 14th 2024 - Jun 10th 2025 - £11,783

Prices based on an occupancy of 18 people:

Rental period 5 Nights Weekly
Dec 8th 2023 - Dec 16th 2023 €7,676 €10,746
Dec 16th 2023 - Jan 6th 2024 - €12,906
Jan 6th 2024 - Apr 27th 2024 €6,144 €8,602
Apr 27th 2024 - Jun 1st 2024 €9,219 €12,906
Jun 1st 2024 - Aug 24th 2024 - €15,050
Aug 24th 2024 - Sep 21st 2024 - €13,982
Sep 21st 2024 - Oct 19th 2024 €9,219 €12,906
Oct 19th 2024 - Dec 14th 2024 €7,676 €10,746
Dec 14th 2024 - Jun 10th 2025 - €12,906

Prices based on an occupancy of 18 people:

Rental period 5 Nights Weekly
Dec 8th 2023 - Dec 16th 2023 $8,287 $11,602
Dec 16th 2023 - Jan 6th 2024 - $13,933
Jan 6th 2024 - Apr 27th 2024 $6,633 $9,286
Apr 27th 2024 - Jun 1st 2024 $9,952 $13,933
Jun 1st 2024 - Aug 24th 2024 - $16,249
Aug 24th 2024 - Sep 21st 2024 - $15,095
Sep 21st 2024 - Oct 19th 2024 $9,952 $13,933
Oct 19th 2024 - Dec 14th 2024 $8,287 $11,602
Dec 14th 2024 - Jun 10th 2025 - $13,933

Please note that these prices/rates are a guide only and may not be correct at the current date. For an accurate quote, please enquire.

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