Tuscany Villas by Owner

Tuscany is an incredible land with beautiful landscapes, where striking historical villas dominate the vineyards, olive groves and sunflowers fields. An integral part of the Tuscan story is the Medici family, who have left behind an immense patrimony of elegant summer villas, hunting lodges and country estates, many of which have been restored for guided tours, concerts and events. Impressive, though not as large, are the prestigious homes that many noble families have passed down through generations, carefully renovated to become exclusive vacation accommodations. A select number of the larger villas have been restored into elegant bed and breakfasts, charming apartments, deluxe hotels or luxury resorts that offer the perfect setting for an incredible vacation in Tuscany. Whereas, several of the smaller villas have been transformed into weekly holiday rentals, intended to accommodate a family reunion, a destination wedding, or a special Tuscan vacation.

123 Properties found: List of the Best Villas in Tuscany, Italy

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Villa PiaggiaAdd to
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  • Rooms: 9
  • Sleeps: 17
  • Location: Montaione (Countryside)

Villa Piaggia, located in Montaione near San Gimignano, is an exclusive and elegant villa that can host up to 17 guests. The villa and its swimming pool is surrounded by a large park and vineyards, enjoying a beautiful view over the Tuscan countryside.

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Villa DianellaAdd to
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  • Rooms: 4
  • Sleeps: 8
  • Location: Vinci (Countryside)

Small elegant bed and breakfast near Vinci in a beautiful Medicean villa. The gardens are the perfect setting for weddings and special meetings, with views over the surrounding vineyards and olive groves.

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La Casa in ChiantiAdd to
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  • Apartments: 2
  • Sleeps: 6
  • Location: Gaiole in Chianti (Countryside)
  • Daily price: From € 180 to € 300

This beautiful farmhouse near Gaiole in Chianti features 2 holiday rental villas for families & friends exploring Tuscany. Great views, a Tuscan atmosphere, attentive service & homey comforts for a tranquil vacation.

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Agriturismo ColognoleAdd to
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  • Apartments: 6
  • Rooms: 4
  • Sleeps: 53
  • Location: Pontassieve (Countryside)
  • Daily price: From € 48 to € 680
  • Weekly price: From € 290 to € 3400

Marvellous setting for this rural countryhouse in the heart of Chianti, with easy access to Florence. Clean, tiny and lovely accommodation in rooms, apartments or independent villas.

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Villa VignacceAdd to
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  • Apartments: 3
  • Sleeps: 10
  • Location: Sinalunga (Countryside)
  • Daily price: From € 60 to € 200

Set in the countryside of Siena, between the Crete Senesi and the Val d'Orcia, the villa offers 3 cozy and romantic self-catering apartments and a beautiful outdoor pool. It's a great base to explore central and southern Tuscany and Umbria.

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Villa Rossi MatteiAdd to
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  • Apartments: 7
  • Rooms: 13
  • Sleeps: 32
  • Location: Arezzo (City,Countryside)
  • Weekly price: From € 590

Perfectly organized to accommodate families, large groups & events, this vacation rental Villa is ideally located between the major cities of art in Tuscany. Versatile & comfortable: Seven fully equipped apartments, private pool & common room.

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Villa LysisAdd to
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  • Sleeps: 5
  • Location: Florence (Countryside)
  • Daily price: From € 130 to € 150
  • Weekly price: From € 700 to € 1000

Cosy vacation villa rental on the outskirts of Florence boasts excellent position for holiday travels and lush Tuscan decors with family antiques and a country style motif. The best place to be, close to public transport.

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Villa StolliAdd to
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  • Rooms: 4
  • Sleeps: 10
  • Location: Figline Valdarno (Countryside)
  • Weekly price: From € 1400 to € 3200

Spacious & luminous Villa for 10 persons with a private panoramic pool and luxury decor, is in a prime position between Florence & Chianti. Easy access to Siena, Pisa and relaxing spa services.

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Casa Vacanze i CipressiAdd to
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  • Apartments: 2
  • Sleeps: 9
  • Location: Lucca (Countryside)
  • Daily price: From € 100 to € 280
  • Weekly price: From € 500 to € 2090

Comprised of two independent vacation apartments, I Cipressi can be rented individually or together for a group of up to 9 persons. Close to Lucca, beaches, royal villas, shops & restaurants, this is a great family friendly location.

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I CipressiniAdd to
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  • Rooms: 5
  • Sleeps: 10
  • Location: Pienza (Countryside)
  • Weekly price: From € 2000 to € 3000

This enchantingly simple yet graceful vacation villa rental only minutes from the historic town of Pienza features an ideal holiday accommodation for up to 10 persons. Private pool, WiFi, air conditioning and fabulous views.

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Casa Vacanze SoleadoAdd to
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  • Rooms: 5
  • Sleeps: 10
  • Location: Gambassi Terme (Countryside)
  • Weekly price: From € 1500 to € 3500

This beautifully restored 5 bedroom vacation villa rental features modern comforts, private pool & fabulous panoramic views in the tranquil countryside of Chianti, the area famous for wine & olive oil.

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Villa Il LotoAdd to
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  • Rooms: 6
  • Sleeps: 14
  • Location: Cortona (Countryside)
  • Daily price: From € 280
  • Weekly price: From € 1700

The vacation villa near Cortona is perfect for up to 12 guests who will enjoy the private property during their stay in southern Tuscany. With pool and panoramic views, you can enjoy relaxing at the villa or day trips to nearby Valdorcia, a UNESCO site.

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La CertaldinaAdd to
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  • Apartments: 8
  • Sleeps: 36
  • Location: Certaldo (Countryside)
  • Daily price: From € 55 to € 135

The family & pet-friendly vacation apartments La Certaldina provide the perfect relaxing atmosphere for a holiday in Tuscany. Enjoy the views, the pool, the food & wine while staying close to Certaldo, Florence & Chianti.

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Il CorbezzoloAdd to
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  • Sleeps: 4
  • Location: Gambassi Terme (Countryside)
  • Weekly price: From € 750 to € 980

A one bedroom private villa rental for vacation near San Gimignano and Chianti, promises tranquility, comfort & romantic Tuscan landscapes for your holiday. Perfect base also for a honeymoon.

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Villa La Roveta ApartmentAdd to
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  • Apartments: 1
  • Sleeps: 6
  • Location: Scandicci (Countryside)

Positioned in the Tuscan countryside, only 8 km from Florence, Italy, this vacation rental apartment is the ideal setting for up to 6 persons looking for a luxurious setting that speaks of Tuscany & its tradition.

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Like the nobility

All the Tuscan villas that dot the landscape across Tuscany have ancient origins: many were built during the Middle Ages as fortified summer residences for noble families of the time. Particularly around and near Florence, you’ll be surprised by the large number of beautiful, imposing Medicean villas built during the Italian Renaissance by the powerful Medici family precisely to get away from the city.

Tuscan villas today offer charming accommodations, mixing a taste of the luxury of the past with the comforts of today's modern lifestyle. They are the ideal for spending some time enjoying a very relaxing holiday or hosting a very special event such as a wedding ceremony or banquet, an anniversary or a company meeting. There is a perfect villa in Tuscany for you!


Our Network

  • DiscoverTuscany.com
  • VisitFlorence.com
  • Chianti.com
  • Tuscany Accommodation.com
  • Florence Accommodation.com