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Villa Simone - Luxury Villa with swimming pool

Villa in San Gimignano with private pool and kitchen

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Exterior - Villa Simone - Luxury Villa with swimming pool (San Gimignano)
Fireplace - Villa Simone - Luxury Villa with swimming pool (San Gimignano)
Pool - Villa Simone - Luxury Villa with swimming pool (San Gimignano)
Outdoor dining - Villa Simone - Luxury Villa with swimming pool (San Gimignano)
Dining - Villa Simone - Luxury Villa with swimming pool (San Gimignano)
Perched on a panoramic spot in the Chianti hills, Villa Simone is a beautifully restored 15th-century Tuscan stone villa. With its private pool, tennis court and well-tended garden, this villa offers the perfect blend of relaxation and fun for up to 14 guests.

Reviews

10 out of 10
Exceptional

Entire home

7 bedrooms8 bathroomsSleeps 14450 sq m

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

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About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Villa Simone - Luxury Villa with swimming pool

Villa Simone is a beautiful stone villa rental in Tuscany dating back to the 15th century. It sits on a panoramic spot in the Chianti hills near San Gimignano.
Built around a watchtower, the villa has been restored in 2023 to preserve its original characteristics. It is furnished in Tuscan style, offers all amenities and can accommodate up to 14 people in 7 bedrooms.
Outside, guests can take advantage of a well-tended garden, private pool with deck chairs and umbrellas, an area for dining outside, and a tennis court: it is the perfect place for a fun, relaxing vacation immersed in the Chianti countryside.
The area is renowned all over the world for its food, wine, art and history. The house is a perfect base for exploring the characteristic villages and art cities of the Chianti and Tuscany, such as Certaldo, Volterra, San Gimignano, Colle Val d’Elsa, Florence, Siena, and Castelfiorentino.

At guests’ disposal: 7 bedrooms; large room with billiard table; private, fully-equipped garden; exclusive use of large swimming pool (16 x 8 m); tennis court; gym and welness area with sauna and Jacuzzi; barbecue; parking within the grounds; panoramic view; wi-fi internet.
Access to the property is via an unpaved road in good condition and suitable for all vehicles.
Distances: San Gimignano with shops of all kinds 5 km, Certaldo 15 km, Volterra 25 km, Siena 40 km, Florence approx. 50 km, Pisa (airport) 75 km.

Please carefully check if there are any extra costs to be paid on site!

===== ACCOMMODATION DESCRIPTION =====
450 m2.
Ground floor: entrance, large hall with dining and living area (Smart TV), billiards room, kitchen (oven, freezer, dishwasher, microwaves, toaster, boiler, wine cooler), store-room with washing machine and dryer, double bedroom with ensuite bathroom with shower, toilet, welness area with sauna and Jacuzzi.
1st floor: 4 double bedroms each with ensuite bathroom with shower, 1 double bedroom with ensuite bathroom with shower (without window), twin-bedded room with ensuite bathrom with shower (without window), gym.
Air conditioning is available in all of the rooms.

The following might be to be paid extra: Babycot, Final Cleaning, Heating, Late Arrival, Pets, Refundable Security Deposit by credit card, Tourist tax.

Property amenities

Pool/Spa

  • Hot tub
  • Private pool
  • Sauna

Internet

  • Available in the villa: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Dishwasher
  • Freezer
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • 7 bedrooms

Bathroom

  • 7.5 private bathrooms
  • Bidet
  • Hair dryer
  • Shower

Living spaces

  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • Cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Phone

Location highlights

  • Near a health/beauty spa

Things to do

  • Arcade/game room

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)
  • Fire extinguisher

General

  • Garden
  • Unit size: 4,844 square feet

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  • Outdoor space
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Policies

Check-in

Check-in time starts at 4:00 PM
Late check-in fee: EUR 150
Minimum check-in age - 18

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

Events allowed

Smoking

Smoking is not permitted

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Heating fee: EUR 5 per cubic metre

We have included all charges provided to us by the property.

Optional extras

  • Late check-in fee: EUR 150

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts cash
Parties and events are allowed on site
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number IT052028B5CBRW3PZK
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

We should mention

All guests, including children, must be present at check-in and show their government-issued photo ID card or passport
Cash transactions at this property cannot exceed EUR 5000, due to national regulations; for further details, please contact the property using the information in the booking confirmation

Property is also known as

Vrbo Property Villa
Vrbo Property San Gimignano
Vrbo Property Villa San Gimignano
Villa Simone Holiday Rental in San Gimignano Chianti
1062001

About the area

San Gimignano is home to this villa. Ornithological Museum and Museum San Gimignano 1300 are cultural highlights, and some of the area's activities can be experienced at Sovestro in Poggio Winery and Fattoria San Donato. Ra-Ma snc and The SottoVico Garden are also worth visiting. Visit our San Gimignano travel guide
View more Villas in San Gimignano
Map
San Gimignano, Tuscany

Getting around

  • Barberino Val d'Elsa Station
    23 min drive
  • Peretola Airport (FLR)
    77 min drive

Restaurants

  • Bistrot Magnino
    11 min drive
  • Riccapizza
    11 min drive
  • Gustavo - Bar Enoteca
    11 min drive
  • Ristorante Fuoriluogo
    9 min drive
  • Ristorante La Stella
    11 min drive

Frequently asked questions

Does Villa Simone - Luxury Villa with swimming pool have a pool?

Yes, this property has a pool.

Is Villa Simone - Luxury Villa with swimming pool pet-friendly?

No, pets are not allowed at this property.

How much is parking at Villa Simone - Luxury Villa with swimming pool?

On-site parking is available at the property.

What time is check-in at Villa Simone - Luxury Villa with swimming pool?

Check-in begins at 4:00 PM.

What time is check-out at Villa Simone - Luxury Villa with swimming pool?

Checkout is at 10:00 AM.

Where is Villa Simone - Luxury Villa with swimming pool located?

Situated in San Gimignano, this villa is 3 mi (4.9 km) from Castelvecchio Natural Reserve and within 6 miles (10 km) of Sant'Agostino Church and Rocca of Montestaffoli. Fortress of Montestaffoli and Ornithological Museum are also within 6 miles (10 km).

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Villa Simone - Luxury Villa with swimming pool Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 15 out of 16 reviews
Rating 8 - Good. 1 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 0 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

Reviews

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Wesley S.

Review for stay from 16 October 2023 to 20 October 2023

Very nice and big house with a everything you need. Wonderful furniture en very good rooms and bathrooms. Everything is great. The bedroom next to the upstairs Livingroom has a problem when it is windy. The glass is not kitted and make a big noise.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Dito A.

Review for stay from 07 June 2025 to 14 June 2025

Villa Simone was incredible. It far exceeded our expectations and I would gladly recommend it to anyone staying in the area. Reserving was an easy process and everyone from booking to the concierge, were extremely helpful. Thanks to all for contributing to a vacation of a lifetime!!!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Erika M.

Review for stay from 12 July 2025 to 19 July 2025

Wow! This place is incredible, beyond the description and photos. It’s HUGE, so much space, so comfortable for a large group - each bedroom feels like a master, beautiful pool, kitchen, location. Sunsets under the covered verandah - I could have never left. Easy trip to the supermarket and town of San Gimignano. Emma was super helpful. This villa is truly a dream.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Monica M.

Review for stay from 20 September 2025 to 27 September 2025

Great for a group - nice mix of charming and updated in good location near quaint San Gimignano. We had some confusion about how to work the soaking tub, but they were responsive and willing to help ( I would recommend some clear signage about what the four valves do versus just verbal instructions on check in). We would have liked access to cleaning supplies like a broom, counter spray, cleaning towels. Some of the bathrooms were out of soap when we arrived. We were able to get most of these things at a store. Overall we would recommend and stay again.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Julie B.

Review for stay from 13 September 2025 to 20 September 2025

The Villa was amazing and the pictures matched so expectations were met. Each en-suite bedroom was modern and spacious with well thought out design. There are three different living rooms so people can have their own space if wanted and the grounds are beautiful. Huge pool with plenty of lounging chairs and umbrellas and a very large dining g table inside and outside. The kitchen was equipped with anything needed for cooking, but I would highly recommend the chef you can hire- it’s a husband and wife and their daughter helped two of the nights. They bring everything they need and completely clean up, and they are delightful people. The food was delicious!!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Walter R.

Review for stay from 05 July 2025 to 12 July 2025

My family of twelve — two grandparents, three daughters, three sons-in-law, and four grandchildren — recently spent a week at Villa Simone. Over the years, we’ve stayed in several villas throughout Italy, each with its own charm, but I suspect our time at Villa Simone will always stand out as our favorite. The house is perfectly suited for a group like ours, and the grounds are simply stunning. With panoramic views, a large pool, a tennis court, and a pool table, there was always something for everyone to enjoy. The estate produces excellent wines and olive oils, and Posarelli helped us arrange a truffle hunt that delighted all who participated. The grandchildren were especially enchanted by the little dog who found the truffles — which we later ate! Our time at the villa was effortless and carefree. Emma, the onsite property manager, went above and beyond to ensure we had a truly memorable stay. Five stars are not enough for Villa Simone. We hope to return — and soon.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Christian S.

Review for stay from 12 October 2025 to 17 October 2025

Wir hatten einen wundervollen Aufenthalt! Das Haus verbindet perfekt historischen Charme mit modernem Komfort. Die Lage inmitten der toskanischen Hügel ist traumhaft – mit einem herrlichen Blick über Weinberge und Olivenhaine. Besonders beeindruckt hat uns die liebevolle Restaurierung, die großzügigen Räume und der wunderschöne Poolbereich. Ideal für Familien oder Gruppen, die Ruhe, Stil und italienisches Lebensgefühl suchen. Wir kommen gerne wieder!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Tor H.

Review for stay from 28 September 2025 to 05 October 2025

Fantastisk sted, ryddig, rent og ordentlig og et veldig sjarmerende bygg. Mange fasiliteter på stedet som svømmebasseng, tennis, trimrom, badstu, jacuzzi, biljard osv. Stort og overdekt langbord ute for hyggelig samvær og måltider. Stort kjøkken for felles matlaging og også stor gassgrill rett på utsiden. Soverommene var ganske store og alle med eget bad. Det er 150 meter til Panizzi vingård med prøvesmaking og utsalg. Kort kjøretur til San Gimignano for handling eller sightseeing. Vi var to familier med til sammen fire voksne og åtte voksne ungdommer.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Michael W.

Review for stay from 21 April 2025 to 25 April 2025

Wir waren sehr begeistert von der Unterkunft! Sie war genau wie auf den Bildern dargestellt. Die Zimmer und die Einrichtung waren neu und alles war sehr gepflegt. Der Whirlpool, die Sauna, der Billardtisch, der Fitnessraum und der große TV im Wohnzimmer lassen keine Wünsche mehr übrig. Außerdem hatte jedes Schlafzimmer sein eigenes Badezimmer - ein Luxus der nicht sein muss, aber sehr angenehm ist. Sehr begeistert waren wir auch von dem Tennisplatz mit Flutlichtanlage, auf dem wir bis spät in die Nacht spielen konnten. Der Außenpool ist ebenfalls ein Highlight. Insgesamt ist alles in einem sehr guten und gepflegten Zustand, was auch den erhöhten Preis rechtfertigt. Die Unterkunft hat unsere Erwartungen deutlich übertroffen und wir können sie für größere Gruppen sehr empfehlen.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Giancarlo M.

Review for stay from 12 August 2024 to 18 August 2024

Un’esperienza davvero fantastica. La casa è meravigliosa in ogni suo angolo, la piscina, il campo da tennis e la sala biliardo sono delle ciliegine su di una torta già grandiosa. Lo staff è gentilissimo e super disponibile. Torneremo con molto piacere se ci dovessimo ricapitare.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Giancarlo M.

Review for stay from 12 August 2024 to 18 August 2024

Un’esperienza davvero fantastica. La casa è meravigliosa in ogni suo angolo, la piscina, il campo da tennis e la sala biliardo sono delle ciliegine su di una torta già grandiosa. Lo staff è gentilissimo e super disponibile. Torneremo con molto piacere se ci dovessimo ricapitare.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Raphaela K.

Review for stay from 28 October 2023 to 01 November 2023

Wir waren 3 Familien mit 6 Kindern (8-12 Jahre) und haben 5 schöne Tage in der Villa und Umgebung genossen. Emma war sehr freundlich und jederzeit erreichbar. Die Villa ist genauso schön wie auf den Bildern, alles perfekt sauber, bequeme Betten und jedes Schlafzimmer mit eigenem Bad. Billardtisch und Tennisplatz waren der Hit. Das Schwimmbad war Ende Oktober wie zu erwarten schon sehr kalt, hat uns aber nicht davon abgehalten trotzdem kurz hineinzuspringen. Danke für alles
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Andreas L.

Review for stay from 15 September 2022 to 18 September 2022

Great place with lots of space, pool table and large outdoor pool. Highly recommended.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Elia B.

Review for stay from 24 August 2022 to 28 August 2022

Villa come in foto, abbiamo soggiornato per 4 notti potendo usufruire di tutti i servizi. In 7/8 minuti di macchina si raggiunge San Gimignano, bellissimo borgo. La posizione è strategica, in un ora sei a Firenze verso nord, Siena verso sud e Cecina verso ovest. Grazie per l’ospitalità
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

S L M.

Review for stay from 23 June 2022 to 26 June 2022

We had a wonderful stay at the Villa Simone with an extended family of 10. Our only issue was the lack of air conditioning (temperatures in the high 30s), and a couple of things needing fixing- an absent shower door in one en suite and an absent shower head in another. Loads of space including a snooker table, lovely outside area with tennis court and pool. We would stay there again.
This review was submitted before 2018 and has not been verified.

8/10 Good

Review for stay from 25 August 2007 to 01 September 2007

Fabulous spacious villa close to San Gimignano with pleasing grounds, tennis court and swimming pool, both floodlit. Super bedrooms and modern bathrooms.