Villa Gaiole

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Sleeps: 10 Bedrooms: 5 Bathrooms: 6


Wow Factor
Sustainable Collection
Ideal for Kids All Bedrooms En-Suite Ideal for Parties Stag/Hen Allowed


Book a 2023 villa holiday by 31st January and receive:

  • A welcome hamper on arrival
  • Up to £100 private chef voucher
  • Trees planted to offset 110% of your villa stay

Ts&Cs apply.

Located between Florence and Siena in Chianti, Villa Gaiole's private hilltop position provides 360 degree panoramic views of the breathtaking Tuscan countryside.

Set around an expansive central courtyard with barbeque area, this luxury villa rental provides visitors with three charming terraces for al fresco living, an infinity pool surrounded by a big lawn and two hectares of secluded gardens filled with vines, olives, cypress trees and local herbs. Sightseeing, wine tasting, cycling and more... whatever takies your fancy, it can be provided by Villa Gaiole.

It's also a great place to take the kids. There's plenty of space for relaxing, dining and playing and the infinity-edged private heated pool has a safety cover. Toys and games for all ages are also provided, and the villa has wi-fi throughout.

Oliver Approved

What you should know…

  • The road to the top of hill isn't surfaced so it can get a bit bumpy
  • You'll need a car to go to the shops and explore, but car hire, drivers and taxis are easily arranged (just get in touch!)
  • It's so peaceful you may find yourself not wanting to explore all the local area has to offer!

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 Heated Pool Wi-Fi/Internet Air-Con BBQ All Bedrooms En-Suite Ground Floor Bed & Bath Satellite TV TV Bicycles Provided Gym/Fitness Room Wine Cellar Games Room Indoor Games Outdoor Games Pool/Snooker DVD Heating

Villa Interior

- Two sitting rooms
- Dining room
- Professional kitchen including 2 dishwashers, 2 ovens, wine fridge, gas cooker
- Five double bedrooms with air conditioned and en-suite facilities
- Games room with a full sized pool table, football table and other games
- Gym with treadmill and weights machines
- Laundry room with washer, dryer and iron

Outside Grounds

- Heated infinity pool 12m x 6m, open approximately April to end-October
- Sun bathing area with sun loungers and deck chairs
- Garden with vineyard and olive groves
- Large courtyard for up to 25 people
- Pizza oven and barbeque area
- Dining terrace with seating for up to 12


- Media library
- Laptop pc
- Two DVD players
- Three flat screen televisions, one with cable TV
- Two Ipod docking stations
- Private wine cellar (at extra cost)
- Two high chairs, cots and travel cots
- Children’s books, films & 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. 


About the surrounding area of Villa Gaiole
Rural Location Walking/Hiking Paths Wine Tasting Horse Riding Outstanding Landscapes Outdoor Pursuit & Activities Tourist Towns & Villages Historical Sites
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Located on top of a classically Tuscan hilltop and surrounded by two hectares of secluded and magical gardens, Villa Gaoile is a 400 year old farmhouse converted into an expansive and luxurious family home. Recently restored to the highest standards of design and ecological principles, this luxury villa fuses the height of Italian style and craftsmanship with open plan exposed stone, wooden beams and abundant original features that's complemented by contemporary furniture, luxury design and modern art.

Chianti is located in central Tuscany, only 40km from Florence, 250km from Rome and 15km from Siena. It is located along the river Massellone and was the home of an historically important market for nearby towns and villages. Fantastic cycle routes- home of vintage bike race L'Eroica. Forbes even named Gaiole number one in a list of the most idyllic places to live in Europe!

Nearby places to visit include the Parish Church of Spaltenna, the Castels of Vertine, Brolio and Meleto and the Abbey of Coltibuono, a former monastry now turned into a beautiful wine estate. As you can probably guess from the name, Chianti is surrounded by vineyards, many of which are open to visitors.

Local Amenities
Nearest Airport Florence or Pisa or Bologna or Perugia

(51-60 km )

Nearest Village Gaiole in Chianti

(4 km )

Nearest Town/City Siena

(21-25 km )

Nearest Restaurant Lots within 5-7 mins drive

(3 km)

Nearest Bar/Pub Lots within 5-7 mins drive

(3 km)

Nearest Beach 2 hours away

(Over 100 km)

Nearest Golf 1.5 hours away

(71-80 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

Tuscany is a great place for a family friendly holiday, and this property is perfectly placed to take advantage of what the area has to offer.

In the city of Florence, just over an hour’s drive away, you can take a Segway tour around the winding streets before heading to the Leonardo da Vinci Museum, a great interactive experience which highlights the artist’s various engineering projects. Of course, a trip to an ice cream parlour would top off the day!

Visit Poppi Zoo Park (78km) to see all sorts of animals, including lynx, raccoons, deer and buffalo. There’s also a playground area, restaurant and picnic area.

Particularly adventurous children will enjoy the Saltalbero Adventure park, just 35km away, 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

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

Kids Activities Close-by

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

Onsite Facilities

  • Children's videos/DVDs
  • Children's books
  • Swings
  • Heated Pool
  • Bicycles Provided
  • Games Room
  • Indoor Games
  • Outdoor Games
  • Pool/Snooker
  • DVD
  • Toys
  • Fenced Grounds

Services Available

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


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
- Spa treatments
- Cooking/pizza making classes
- Wine tours
- Cultural tours
- Babysitting
- 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

Terms & Conditions

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

Security deposit €1500 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.
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? Extra cost quoted at time of booking and payable locally. Only available for bookings of minimum 5 days. 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 2022: 7 nights from mid-May to end-September. 4 nights during all other periods. 2023: 7 nights from mid-May to end-September. 5 nights during all other periods
Changeover day Flexible.

Rental Rates

Prices based on an occupancy of 10 people:

Rental period 4 Nights 5 Nights Weekly
Jan 30th 2023 - Apr 1st 2023 £7,173 £8,966 £12,553
Apr 1st 2023 - May 13th 2023 - £11,839 £16,569
May 13th 2023 - Sep 30th 2023 - - £18,578
Sep 30th 2023 - Oct 28th 2023 - £11,836 £16,569
Oct 28th 2023 - Mar 30th 2024 - £9,684 £13,557
Mar 30th 2024 - May 11th 2024 - £11,839 £16,569
May 11th 2024 - Aug 2nd 2024 - - £18,578

Prices based on an occupancy of 10 people:

Rental period 4 Nights 5 Nights Weekly
Jan 30th 2023 - Apr 1st 2023 €7,679 €9,599 €13,438
Apr 1st 2023 - May 13th 2023 - €12,674 €17,738
May 13th 2023 - Sep 30th 2023 - - €19,888
Sep 30th 2023 - Oct 28th 2023 - €12,670 €17,738
Oct 28th 2023 - Mar 30th 2024 - €10,367 €14,513
Mar 30th 2024 - May 11th 2024 - €12,674 €17,738
May 11th 2024 - Aug 2nd 2024 - - €19,888

Prices based on an occupancy of 10 people:

Rental period 4 Nights 5 Nights Weekly
Jan 30th 2023 - Apr 1st 2023 $8,351 $10,439 $14,614
Apr 1st 2023 - May 13th 2023 - $13,784 $19,291
May 13th 2023 - Sep 30th 2023 - - $21,629
Sep 30th 2023 - Oct 28th 2023 - $13,780 $19,291
Oct 28th 2023 - Mar 30th 2024 - $11,274 $15,784
Mar 30th 2024 - May 11th 2024 - $13,784 $19,291
May 11th 2024 - Aug 2nd 2024 - - $21,629

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.


  • We had a wonderful time

    Posted by Rebecca S 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!

    Posted by Kate T. 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

    Posted by Geoffrey S. 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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