Villa Gaiole

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Sleeps: 10 - 14 Bedrooms: 7 Bathrooms: 8

Overview

Pool Villa/House
Sustainable Collection
Ideal for Kids Laptop Friendly Workspace All Bedrooms En-Suite Parking Space

Offering panoramic vistas over Chianti’s hills and woodlands, Villa Gaiole is a serene escape in the Tuscan countryside which is also within easy reach of a range amazing towns and cities such as Siena and Florence. Sleeping 14 guests over 7 stunning bedrooms, this historic home is a wonderful choice for those travelling in a larger group but not wishing to compromise on style or comfort. 

Villa Gaiole is over 400 years old and would have started out as a rustic farmhouse in the middle of the olive groves and vineyards which have been tended to for centuries here. The villa is made up of the main building and a smaller annexe and is packed with original features such as the local stone work, exposed beams and open fireplaces. These period details now work in harmony with the more modern touches which have been added over time.

The home sits over two floors and has been renovated extensively throughout, providing every corner of the home with sumptuously decorated rooms and the highest quality furnishings and facilities. From the vast floor to ceiling windows and doors on the garden, light floods in to the living spaces, creating a warm welcome for you and your party.

The ground floor of the home is the social heart of Villa Gaiole; you will find a large living room here with comfy sofas, a feature fireplace and a TV. The dining room is just next door and has incredible views over the valley below. You can also dine in the contemporary kitchen which is fitted with everything you could need for preparing meals and drinks, unless you would prefer to arrange a catering package with the private chef that is. 

In addition to the usual living spaces, this spacious home has plenty more to offer; there is a fully equipped gym, a games room, a wine cellar and an additional sitting room. This means there will always be space for everyone even when travelling in a big group. 

When it is time to turn in for the night, you will have 7 bedrooms to choose from! Each of these are tastefully decorated and boast an en-suite bathroom. One of the bedrooms is fitted with two twin beds which can be converted to a double, while the remaining rooms all have king-sized beds. Two of these bedrooms are set within a separate annexe which would suit a small family who wish for a little privacy from the main party. 

Outside, the property just keeps getting better! As you step in to the garden you will enter an expanse of leafy grounds, vineyards and olive groves which span 2 hectares and offer the most enchanting rural views. The icing on the cake is the gorgeous heated infinity pool, but there are also a wealth of seating areas, covered al-fresco dining spaces and plenty of sun loungers where you can read a good book in the sun. 

Through the concierge team at the house, you are able to arrange plenty of fun extras and activities both at the house and further afield. These include; pizza making classes, truffle hunting walks, guided tours and yoga classes! 

Though the villa enjoys a peaceful, country location, you do not need to worry about being cut off here. The closest villages are just a few kms away, including Gaiole in Chianti which has been voted one of the best places to live in all of Europe. If you would like to visit one of Tuscany’s medieval cities, Siena is a brilliant place to spend the day exploring the historic buildings and visiting some of the area’s finest art galleries and museums, before tucking in to a delicious meal in the Piazza del Duomo. The city is only 28km away, so is well worth the drive.

Oliver Approved

What you should know…

    • The inviting pool is heated for free during cooler months, there is a charge for heating it in the warmer months 
    • Guests can book extra services and experiences when staying here, such as truffle hunting walks, yoga classes, a private chef, catering packages, pizza making and photography courses 
    • As the home is set in Chianti’s rolling farmland, you will need a car in order to explore the nearby villages and towns 
    • You should be aware that two of the bedrooms are located in a separate annexe within the grounds

This home is a part of our Sustainable Collection!

To be part of the collection, homes must meet a minimum of four criteria from our sustainable checklist, or three from the checklist and have a daily carbon footprint of 5kg or lower, based on full occupancy per bedroom. View the full collection here >

This home meets the following criteria from our sustainable checklist:

  • Supports the local community (promotes local businesses)
  • Committed to Renewable and Green Energy
  • Promotes Sustainable Living (Vegetable Patch)

Property Features

Private Pool Child-Safe Pool Heated Pool Wi-Fi/Internet Air-Con Laptop Friendly Workspace BBQ Washing Machine Tumble Dryer Dishwasher Microwave Coffee Machine Hairdryer All Bedrooms En-Suite Ground Floor Bed & Bath TV Bicycles Provided Gym/Fitness Room Wine Cellar Games Room Indoor Games Outdoor Games Table Tennis Table Football Pool/Snooker Heating Parking Space

Villa Interior (800m2 over two floors)

Ground Floor

- Living room with sofas, desk fireplace and TV
- Sitting room with bookshelves and TV
- Dining room with table seating 12
- Fully-fitted kitchen with breakfast bar, oven, hob, fridge freezer, dishwasher, microwave, blender, toaster, kettle and coffee machine 
- Games room with seating area, pool table and football table
- Wine cellar
- Well-equipped gym
- Bedroom with king-sized double bed, seating area an en-suite bathroom with bath, double sink and WC
- 3 x bedroom with king-sized double bed and en-suite bathroom with shower, sink and WC
- Bedroom with two twin beds or a double-sized bed and en-suite bathroom with shower, sink and WC
- Guest WC

Annexe 

- 2 x bedroom with king-sized double bed and en-suite bathroom with shower, sink and WC

Outside Grounds (20,000m2)

- Private heated swimming pool, with safety cover (12m x 6m, 1-3m deep) open approximately start of April- end of October
- Two hectares of private grounds, olive groves and vineyards
- Covered dining pergola
- Al-fresco dining terrace
- Wraparound terrace with outdoor sofas
- Sun loungers and deck chairs 
- Barbecue
- Pizza oven
- Parking

Facilities 

- Wi-Fi
- Air-conditioning
- Underfloor heating
- Home office 
- TVs
- Sound system
- Film projector
- Iron and ironing board 
- Gym equipment 
- Pool table
- Football table
- Board games and toys

Extra Sustainability Gems About the Property

The owners have installed solar panels and a wood pellet burner for hot water, as well as their our own fresh water well (natural and treated) which they encourage guests to use as opposed to buying plastic bottles of water. 

Location

About the surrounding area of Villa Gaiole
Rural Location Walking/Hiking Paths Wine Tasting Cycling Horse Riding Outstanding Landscapes Outdoor Pursuit & Activities Tourist Towns & Villages Historical Sites
Loading map

Villa Gaiole looks out over the verdant green hills of Chianti in Tuscany. On your doorstep here you have access to some of Italy’s most beautiful countryside, scenic walks, medieval villages and family-run vineyards, this is the most amazing place to stay for a holiday, where you can get to know the heart of Italy at your own pace.

This historic villa is a delightful choice for those who love getting out in nature. Just paces from the house, you will find yourself in centuries-old vineyards, olive groves and tranquil walking trails. Without travelling far, you can immerse yourself in the local culture by visiting farms for olive oil sampling or wineries for tours and wine tastings. When you wish to dine out or pick up some groceries, you will have countless idyllic villages and towns to choose from nearby. 

One of the closest villages to the house is Gaiole in Chianti which is 5km away. This lovely village has been named as one of the best places to live in Europe, so you should definitely pay it a visit. The area around the village is beautiful and is filled with historic buildings including a staggering five castles! Some of these are now used as wineries, while others are open to the public for tours. The village is also known for its fantastic cycling routes and its ancient ceramics industry. You can also reach Lecchi in Chianti which is 6km away and is a quaint village with a few shops, cafes and traditional Italian eateries. 

A bigger town with a wider array of restaurants, shops and cafes is Radda in Chianti which is 12km away. The town has a long, rich history and was once the headquarters for a group called the Chianti League which was a military group which protected the area from neighbouring Siena in the 15th century. The labyrinth of medieval streets are a lovely place to stroll around for the afternoon and you can stop off at attractions such as the Palazzo dei Podestà and the Church of San Niccolò. 

If you are interested in art and history, then make sure to spend a day visiting the enchanting city of Siena which is just 28km away from the house. The city is small in size but absolutely packed with incredible galleries, museums and atmospheric town squares. Some of the key sights include the Duomo di Siena and the Palazzo Pubblico which is the town hall. You could easily spend your time here just doing some shopping and enjoying a bit of the local café culture. 

Read more about Chianti & Arezzo

Local Amenities
Nearest Airport Florence or Pisa or Bologna or Perugia

(51-60 km )

Nearest Village Gaiole in Chianti
Nearest Town/City Siena

(28 km )

Nearest Restaurant Lots within 5-7 mins drive
Nearest Bar/Pub In the nearby Radda in Chianti
Nearest Beach 2 hours away

(Over 100 km)

Nearest Golf 1.5 hours away

(71-80 km )

Region

Nestled in the heart of Tuscany, the Chianti and Arezzo region is a captivating destination that effortlessly combines the rustic charm of the Italian countryside with rich historical heritage. This enchanting area is renowned for its rolling vineyards, picturesque landscapes, and quaint villages, making it a haven for travellers seeking an authentic taste of Italy.

Tuscany
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 >>

Kids

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

Villa Gaiole is nestled in 2 hectares of rolling countryside, olive groves and vineyards, meaning there is plenty of space for the children to run around outdoors. The gardens here are an oasis with a private pool for swimming on a sunny day and when the evening falls, why not set up the cinema screen to watch your favourite film together! 

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

  • Booster seat
  • Mattress protector
  • Bath toys
  • Pushchair
  • Plastic crockery
  • Cot(s)
  • High Chair(s)

Kids Activities Close-by

  • Animal farm
  • Cycling
  • Horse Riding
  • Outdoor Pursuit & Activities
  • Tourist Towns & Villages
  • Historical Sites

Onsite Facilities

  • Children's videos/DVDs
  • Children's books
  • Swings
  • Child-Safe Pool
  • Heated Pool
  • Bicycles Provided
  • Games Room
  • Indoor Games
  • Outdoor Games
  • Table Tennis
  • Table Football
  • Pool/Snooker
  • Toys
  • Fenced Grounds

Services Available

  • Breakfast Available
  • Chef/Cook Available
  • Maid Service Available
  • Babysitting Available

Extras

Oliver's Extras

  • Pre-Stocked Fridge Available
  • Cooking Classes Available
  • Yoga Classes Available
  • Spa Treatments Available
  • Wine-Tasting Available
  • Transfers Available
  • Breakfast Available
  • Chef/Cook Available
  • Maid Service Available
  • Babysitting Available
  • On-Site Concierge

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 transfers
- Babysitting/childcare services

Extras included at this property:

- House manager available 24/7
- 3h maid service, 6 days per week
- Drinks and appetisers on arrival
- Concierge service
- Laundry products

Extras available at this property (payable locally):

- Pre-stocked fridge
- Transfers
- Car hire
- Chef
- Cooking/pizza making classes
- Wine tours
- Cultural tours
- Extra cleaning
- Bike hire

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 www.oliverstravels.com/chefs

Terms & Conditions

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

Security deposit €2500 charged to client’s credit card by the owner before arrival and refunded after departure, subject to full inspection.
Arrival time 4.00 p.m.
Departure time 10.00 a.m.
Heating costs included? Yes.
Energy costs included? Yes.
End of stay cleaning included? Included only for one-week stays. 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, with mid-week linen change for one-week stays.
Pets welcome? Pets are not allowed.
Insurance Guests are required to be in possession of a valid insurance policy, which covers them for cancellations, loss of personal belongings, personal liability and any accidental damage caused during their stay.
Smoking Allowed? Outside only.
Pool heating charge? Included in peak months, and at an extra cost for the low season (October to April), payable locally. Please note that like all heated pools, pool heating and water temperature are reliant on weather and outside temperatures.
Pool opening dates? The pool is open approximately April to end-October. Please note that pool opening dates are subject to local weather conditions and pool maintenance requirements and that cooler months may not be suitable for swimming.
Other Ts and Cs Quiet and non-intrusive caretaker/owner lives on-site and will be very happy to help.
Tax Italian Visitors Tax payable locally in cash (typically costs €1-€5 per adult per night- please enquire if exact amount is required).
Minimum stay 7 nights from mid-June to mid-August. 4 nights between January to April and October to December. 5 nights in all other periods.
Changeover day Flexible.

Rental Rates

Prices based on an occupancy of 10 people:

Rental period 4 Nights 5 Nights Weekly
Jun 18th 2024 - Aug 17th 2024 - - £19,475
Aug 17th 2024 - Sep 14th 2024 - - £17,522
Sep 14th 2024 - Oct 26th 2024 - £11,471 £16,058
Oct 26th 2024 - Dec 21st 2024 £8,333 £10,000 £11,666
Dec 21st 2024 - Jan 4th 2025 - £11,471 £16,058
Jan 4th 2025 - Apr 12th 2025 £9,135 £9,135 £12,788
Apr 12th 2025 - May 10th 2025 - £12,415 £17,376
May 10th 2025 - Jun 14th 2025 - - £18,938
Jun 14th 2025 - Aug 16th 2025 - - £20,988
Aug 16th 2025 - Sep 13th 2025 - - £18,938
Sep 13th 2025 - Oct 25th 2025 - £12,412 £17,376
Oct 25th 2025 - Dec 19th 2025 £9,135 £10,962 £12,788
Dec 19th 2025 - Dec 20th 2025 - £12,412 £17,376

Prices based on an occupancy of 14 people:

Rental period 4 Nights 5 Nights Weekly
Jun 18th 2024 - Aug 17th 2024 - - £24,844
Aug 17th 2024 - Sep 14th 2024 - - £22,891
Sep 14th 2024 - Oct 26th 2024 - £14,957 £20,939
Oct 26th 2024 - Dec 21st 2024 £11,471 £13,765 £16,058
Dec 21st 2024 - Jan 4th 2025 - £14,957 £20,939
Jan 4th 2025 - Apr 12th 2025 £12,412 £14,895 £17,376
Apr 12th 2025 - May 10th 2025 - £16,073 £22,501
May 10th 2025 - Jun 14th 2025 - - £24,551
Jun 14th 2025 - Aug 16th 2025 - - £26,601
Aug 16th 2025 - Sep 13th 2025 - - £24,551
Sep 13th 2025 - Oct 25th 2025 - £16,073 £22,501
Oct 25th 2025 - Dec 20th 2025 £12,412 £14,895 £17,376

Prices based on an occupancy of 10 people:

Rental period 4 Nights 5 Nights Weekly
Jun 18th 2024 - Aug 17th 2024 - - €21,447
Aug 17th 2024 - Sep 14th 2024 - - €19,297
Sep 14th 2024 - Oct 26th 2024 - €12,632 €17,684
Oct 26th 2024 - Dec 21st 2024 €9,177 €11,012 €12,847
Dec 21st 2024 - Jan 4th 2025 - €12,632 €17,684
Jan 4th 2025 - Apr 12th 2025 €10,060 €10,060 €14,083
Apr 12th 2025 - May 10th 2025 - €13,672 €19,135
May 10th 2025 - Jun 14th 2025 - - €20,855
Jun 14th 2025 - Aug 16th 2025 - - €23,113
Aug 16th 2025 - Sep 13th 2025 - - €20,855
Sep 13th 2025 - Oct 25th 2025 - €13,669 €19,135
Oct 25th 2025 - Dec 19th 2025 €10,060 €12,072 €14,083
Dec 19th 2025 - Dec 20th 2025 - €13,669 €19,135

Prices based on an occupancy of 14 people:

Rental period 4 Nights 5 Nights Weekly
Jun 18th 2024 - Aug 17th 2024 - - €27,359
Aug 17th 2024 - Sep 14th 2024 - - €25,209
Sep 14th 2024 - Oct 26th 2024 - €16,471 €23,059
Oct 26th 2024 - Dec 21st 2024 €12,632 €15,159 €17,684
Dec 21st 2024 - Jan 4th 2025 - €16,471 €23,059
Jan 4th 2025 - Apr 12th 2025 €13,669 €16,403 €19,135
Apr 12th 2025 - May 10th 2025 - €17,700 €24,779
May 10th 2025 - Jun 14th 2025 - - €27,037
Jun 14th 2025 - Aug 16th 2025 - - €29,294
Aug 16th 2025 - Sep 13th 2025 - - €27,037
Sep 13th 2025 - Oct 25th 2025 - €17,700 €24,779
Oct 25th 2025 - Dec 20th 2025 €13,669 €16,403 €19,135

Prices based on an occupancy of 10 people:

Rental period 4 Nights 5 Nights Weekly
Jun 18th 2024 - Aug 17th 2024 - - $23,025
Aug 17th 2024 - Sep 14th 2024 - - $20,717
Sep 14th 2024 - Oct 26th 2024 - $13,562 $18,986
Oct 26th 2024 - Dec 21st 2024 $9,852 $11,823 $13,792
Dec 21st 2024 - Jan 4th 2025 - $13,562 $18,986
Jan 4th 2025 - Apr 12th 2025 $10,800 $10,800 $15,120
Apr 12th 2025 - May 10th 2025 - $14,679 $20,544
May 10th 2025 - Jun 14th 2025 - - $22,391
Jun 14th 2025 - Aug 16th 2025 - - $24,814
Aug 16th 2025 - Sep 13th 2025 - - $22,391
Sep 13th 2025 - Oct 25th 2025 - $14,675 $20,544
Oct 25th 2025 - Dec 19th 2025 $10,800 $12,961 $15,120
Dec 19th 2025 - Dec 20th 2025 - $14,675 $20,544

Prices based on an occupancy of 14 people:

Rental period 4 Nights 5 Nights Weekly
Jun 18th 2024 - Aug 17th 2024 - - $29,373
Aug 17th 2024 - Sep 14th 2024 - - $27,065
Sep 14th 2024 - Oct 26th 2024 - $17,684 $24,757
Oct 26th 2024 - Dec 21st 2024 $13,562 $16,275 $18,986
Dec 21st 2024 - Jan 4th 2025 - $17,684 $24,757
Jan 4th 2025 - Apr 12th 2025 $14,675 $17,610 $20,544
Apr 12th 2025 - May 10th 2025 - $19,003 $26,603
May 10th 2025 - Jun 14th 2025 - - $29,027
Jun 14th 2025 - Aug 16th 2025 - - $31,451
Aug 16th 2025 - Sep 13th 2025 - - $29,027
Sep 13th 2025 - Oct 25th 2025 - $19,003 $26,603
Oct 25th 2025 - Dec 20th 2025 $14,675 $17,610 $20,544

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.

Reviews

  • We had a wonderful time

    on 23/08/2017

    Villa Gaiole - what a beautiful place. The photographs in the brochure online did not do it justice!We arrived in the early evening to see the moon reflecting on the infinity pool with the hills behind...
    The house is beautifully appointed, the swimming pool is kept at a perfect temperature and the gardens and views are beautiful. We also enjoyed cooking with some of the produce from the vegetable garden.
    The team at Olivers Travels and locally were wonderful. Incredibly responsive, very helpful and very friendly. Also, really fantastic restaurant recommendations.

  • Brilliant stay!

    on 06/10/2016

    Thank you. We had a wonderful week in your beautiful house. Just landed back in London and real life again!

  • The perfect family villa

    on 28/08/2016

    I know that I speak for all my family when I thank you, and all your staff, for making our stay at Villa Gaiole so enjoyable. This was a special occasion for us, as you may already know, as my wife and I were celebrating our golden wedding anniversary.
    Apart from the small inconvenience of the 'leaking shower' everything went very well and Laura was always there to help. We cannot speak too highly of her efficiency and diligence - the cakes were nice too!!
    We all made it home eventually yesterday, nursing our bites (the only blot on an otherwise perfect holiday) after horse fly attacks at the pool. The weather was awful (thunderstorms) from Luton for us travelling up to Worcester and we didn't get home until after 5pm. A long day but Kate and Daniel et al were home in London much before us so they had a much easier journey.

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