Tuscany Villa Chianti Hills – Villa Oliveta

Hotel Description

You know what hit me first when I pulled up to Villa Oliveta? The silence. I mean, you’re still close enough to civilization that you’re not completely cut off, but there’s this incredible quiet that settles over the Chianti hills – just the sound of wind through olive groves and maybe a distant bell from one of the villages below. The villa sits on Via Sette Ponti Ponente, which honestly sounds more intimidating than it is. It’s basically this winding road that locals have been using forever to connect the hillside towns, and once you’re up there, you get why people have been fighting over this particular piece of Tuscany for centuries.

The place itself is exactly what you’d hope for without being too precious about it. Villa Oliveta has that lived-in elegance that’s hard to fake – I’m talking about worn stone steps that actually feel good under your feet, shutters that look like they’ve been painted and repainted by generations of hands, and rooms where the morning light hits just right because someone planned it that way decades ago. The grounds are honestly spectacular, with olive trees that the owner clearly takes seriously (you’ll probably end up buying some of their oil before you leave), and terraced gardens that cascade down the hillside. What I really appreciated was the pool area – it’s positioned so you can watch the sunset over the valley while you’re swimming, and trust me, after a day of bouncing around Tuscan back roads, that’s exactly what you want.

The practical stuff is sorted too, which matters when you’re dealing with these old converted villas. Parking is easy, the WiFi actually works (crucial if you’re trying to upload all those Instagram shots), and the rooms manage to feel authentically rustic without making you feel like you’re roughing it. The hosts clearly know their stuff – they’ll steer you toward the good restaurants in Loro Ciuffenna (skip the touristy place on the main square, honestly) and can arrange tastings at wineries where you’ll actually learn something instead of just getting drunk on mediocre Chianti. Plus, if you’re planning to explore beyond the immediate area, you’re perfectly positioned. San Gimignano’s about an hour away, Florence is doable as a day trip, and there are probably a dozen hill towns within twenty minutes that most people never hear about but are absolutely worth the drive. The whole experience feels like staying with sophisticated friends who happen to have impeccable taste and a really, really good address.

Rooms

• Estimated price from: $212. Superior Villa with 3 × 1 large double bed, 2 × 2 single beds and 2 × 1 sofa bed for Max persons: 2

Reviews

• We had an amazing stay—beautiful place, wonderful experience, and we’d love to come back! – Guillaume from Germany – 31 August 2024 (10/10)

  We spent an unforgettable week at Tuscany Villa Chianti Hills with two families (10 people, including 6 kids), and it was absolutely perfect. The location is breathtaking, with stunning views, a beautiful pool, and well-designed spaces that offer a unique experience from every corner of the property. The villa's layout is brilliant, with cozy spots where you can relax and take in the surroundings from different perspectives. Matteo was an outstanding host—friendly, easygoing, and attentive, which made our stay even more enjoyable. Highly recommended for families or groups looking for a serene Tuscan escape!
  
  What could be improved: The only issue we had was the mosquitoes, which were pretty aggressive. But with some simple precautions like using mosquito lotion and coils, it was easy to handle and didn’t take away from our overall enjoyment.

• Villa is very nice, the place is charming. – Karolina from Czech Republic – 6 May 2023 (10/10)

  Everything was wonderful And the owner Matteo was heplful.

• Hope to come again – Ronen from Israel – 10 October 2022 (10/10)

  Great location. Great host. Spectacular views and property
  
  What could be improved: Would be nice to have a clothes drier.

• Wir hatten eine tolle Woche mit der Familie in der Villa von Matteo. Wir haben es wirklich sehr genossen! – Andreas from Austria – 23 April 2025 (10/10)

  Mehrere Zimmer und Rückzugsorte für größere Gruppen. Voll ausgestattete Küche mit großem Tisch im Esszimmer. Pool und Whirlpool. 3 Duschen mit WC. Sehr ruhige Lage zum Entspannen inmitten von Olivenbäumen. Sehr nette und hilfsbereite Vermieter.

• Exceptional – Vanesa from Czech Republic – 23 October 2024 (10/10)

  Kouzelná vila uprostřed olivovníků.
  
  Především si nás získala komunikace mezi ubytováním. Předání klíčů proběhlo bez problémů. Pan Dr. Grifoni nás doprovodil autem přímo k ubytování, provedl a poradil s plánováním výletů.
  
  Jednu noc byla velká bouřka, kdy elektřina nešla zpět nahodit. Během 10 minut k nám dorazil pan Dr. Grifoni a snažil se problém vyřešit. Moc mu za to děkujeme. Na druhý den ráno dorazil také elektrikář.
  
  Ocenili jsme na ubytování myčku, pračku a druhou kuchyňku. Ubytování je rozdělené na spodní patro, které není propojeno s horními patry. Což ocenili především ti, kteří chtěli mít svůj klid a chodí dříve spát.
  
  Také nebyl problém vzít naše 3 pejsky 🐶
  
  U vily je dostatek prostoru pro parkování. 4 auta se vešla bez problémů.
  
  Také oceňujeme několik teras, kdy každý den můžete snídat na jiném místě.🍴☕️
  
  Doporučuji si koupit olivový olej přímo ze sadů kolem vily 💯

• Exceptional – Dominique from France – 15 September 2024 (10/10)

  Tout le paysage ,la maison, la vue …
  Merci Matteo

• En underbart avkopplande vecka i vacker miljö. – Torbjörn from Sweden – 24 July 2024 (9/10)

  Fantastiskt fin villa med underbar utsikt. Pool, bubbelbad, utematplats, grill, tjocka stenväggar som ger svalka i början av sommaren. Endast ett par km från mysiga byn Loro Ciuffenna. Lätt att ta sig till med endast någon mil från motorvägen. Lugn omgivning.
  
  What could be improved: Baksidan med allt positivt ovan är att man behöver bil för att ta sig runt. Enstaka småskavanker och lite slitage, men det får man vänta sig i ett såpass stort hus på landet.

• Una struttura adeguata per chi ama stare in mezzo alla natura con parenti e amici – Genito from Italy – 28 April 2025 (9/10)

  Verde e tranquillità.
  
  What could be improved: Nulla di veramente importante da segnalare.

• Exceptional – Francesco from Italy – 6 January 2023 (10/10)

  la struttura é ottima per vacanze di gruppo

• Exceptional – Daniele from Italy – 3 November 2024 (10/10)

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