Goin2Travel Vacation Homes

Siena, Chianti Vacation Rentals & Villas in Tuscany area


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  • La Tenuta - Sienna, Chianti Vacation RentalLa Tenuta La Tenuta lies half way between Florence and Siena in the very heart of the Chianti area. This is one of the most popular regions between Florence and Siena. Vineyards, olive groves and fields form a paradise-like landscape, which was moulded over centuries by the farmers' patient toil. The surrounding countryside resembles one immense garden.
  • Villa della Torre - Sienna, Chianti Vacation HomeVilla della Torre In the heart of the Chianti region, half-way between Florence and Siena, Villa della Torre is a large, historic estate, perched on a hilltop amidst a lush green countryside. This location is outstanding. The villa was until recently used as the summer retreat for a Florentine family and has now been carefully divided into holiday apartments. Sleeps 2 to 4 people.
  • La Corte - Sienna, Chianti Vacation RentalLa Corte Recently restored traditional Tuscan farmhouse in the CHIANTI CLASSICO with private pool and sweeping views in walking distance to a village with shops and restaurants. A perfect starting point for day trips in the most coveted region of Tuscany. Sleeps 10, 12 or 14 +1.
  • La Primavera - Sienna, Chianti Vacation HomeLa Primavera South of Siena, between Pienza, Montepulciano and Montalcino. La Primavera is a really cozy house - a comfortable spot where guests will immediately feel at home. We have visited it on both sunny and dull days - it remains just as inviting whatever the time of year. We found it to be a lovely place for a family! The owner has renovated her house with great skill, keeping the original patina and many antique features. 2 Bedrooms. Sleeps 4 + 2
  • Villa Fantino - Sienna, Chianti Vacation RentalVilla Fantino The number of striking particularities of Villa Fantino, a romantic 19th century Villa with private pool, are such, that one is uncertain about which to cite first. Is it the spectacular location, only 5 km from Siena, surrounded only by olive groves, cypress trees and a couple of other famous villas in the distance, with breathtaking views onto the skyline of Siena. Sleeps up to 14.
  • Il Sasso - Sienna, Chianti Vacation HomeIl Sasso In the Val d'Orcia, midway between Florence and Rome, 70 km south-east of Siena. Il Sasso is reached on a 2 km private gravel road you will be enchanted by the large shady trees surrounding the farm. Loosely set, spreading oak trees, as well as almond, nut and plumtrees filter the sun, creating an immensely pleasant mixture of light and shade. Sleeps 14.
  • Castle of the 4 Towers - Sienna, Chianti Vacation RentalCastle of the 4 Towers The Castle is situated on a green hill, surrounded by vineyards and olive groves, ii a pleasant place to stay near Siena. As a guest here, you have access to the garden, enjoy a great view, reach the town quickly, and you'll take pleasure in a good night's sleep in a castle. Could you imagine a better place to stay? Sleeps 2 + 2.
  • Santa Emilia - Sienna, Chianti Vacation HomeSanta Emilia 3 km west of Siena. Guest apartment in an antique country house, Santa Emilia, located near Siena, exudes class. Like most of Siena this house was built using traditional red bricks. Recently redecorated and designed and furnished by the owner, it stands as a perfect example of simple elegance. She has done her work magnificently. 2 Br. Sleeps 3+1
  • An Oasis Among Olives - Sienna, Chianti Vacation RentalAn Oasis Among Olives - Podere Olivo used to be the school building for a small, independent 18th century property, near Siena. It served a nearby villa and a few farms belonging to the estate, all of which have now been renovated. Podere Olivo still belongs to a member of this old-established family and has recently been lovingly and carefully restored by the owner, to form a comfortable private home for her own use. It is now available as a holiday home.
  • BETTOLLE VIGNACCE - Sienna, Chianti Vacation HomeBETTOLLE VIGNACCE is an old villa that dates back to the era of the Grand Duke Leopold (XVIII century). The villa is comprised of 3 apartment rentals and can sleep up to 13 guest...
  • villa Casa Serena  - Sienna, Chianti Vacation Rentalvilla Casa Serena Experience an ancient, Tuscan farmhouse, whose first foundation dates all the way back to the XV century. The villa is elegantly furnished in Tuscan countryside style. Sleeps up to 12 guests....
  • Solata - Sienna, Chianti Vacation HomeSolata Villa with pool. An independent residence that is ideal for a single family in a beautifully panoramic position, with views of the Chianti Hills and the Arno Valley. . Sleeps 4 (+2)
  • Siena Italy Villa Rental - Sienna, Chianti Vacation RentalSiena Italy Villa Rental Fattoria and Villa Catignano - set within a lovely Italian garden, the property looks out at the 'English wood' and between the olive groves you glimpse a walk of Cypress trees. These lead to the swimming pool, from which you enjoy lovely views of Siena and its surroundings.
  • Borgo Casa al Vento  - Sienna, Chianti Vacation HomeBorgo Casa al Vento is a charming medieval village in Gaiole in Chianti (Siena), surrounded by one of the lushest Tuscan landscapes. Borgo Casa al Vento features apartment rentals in a beautiful setting. Sleeps from 1 to 20 guests.
  • Pallazo Banfi - Sienna, Chianti Vacation RentalPallazo Banfi recently restored. Located in the centre of a typical village, among the richness of the Tuscan countryside. Lovely place for walking quite rest and for visiting historical sites. 2 bedrooms, sleep 4(+2)
  • Fortilizio di REMOVE - Sienna, Chianti Vacation HomeFortilizio di REMOVE apartment L'Alloro is a 2 bedroom vacation rental. The fort lies on the top of a hill near Rapolano Terme in an area which is well known for it's beneficial hot springs. Accurately restored in accordance with the original characteristics, the rental situated in the green Sienese hills respects the agricultural and rustic style: the furniture and handmade ironbeds make a perfect colorful and antique atmosphere. Sleeps up to 6.
  • Capannetta - Sienna, Chianti Vacation RentalCapannetta The Capannetta is a splendid farm house (18th century) located on the top of a hill at the gateway to the Chianti area. The apartment offers you the unique and rare possibility to enjoy an old, large (170 m2) and luminous house in the Siena area with a 360° open view. Ideal place to enjoy quiet and restful holidays, the Capannetta have also a good position to visit the most beautiful places in Tuscany, like Florence, Lucca, Pisa, Arezzo. The rentals are possible from 2 to 7persons, with different prices according to the number of guests.
  • IL Salice REMOVE - Sienna, Chianti Vacation HomeIL Salice REMOVE nr. Siean. Apartment Il Salice is a 1 bedroom vacation rental. The fort lies on the top of a hill near Rapolano Terme in an area which is well known for it's beneficial hot springs. Accurately restored in accordance with the original characteristics, the rental situated in the green Sienese hills respects the agricultural and rustic style: the furniture and handmade ironbeds make a perfect colorful and antique atmosphere. Sleeps up to 4.
  • Lovely House With Magnificent Terrace and Stunning Views  - Sienna, Chianti Vacation RentalLovely House With Magnificent Terrace and Stunning Views Outstanding location in Historic Centre - Terrazza Pietraviva comfortably accommodates up to 5 people on 130 square metres on two floors, whilst the large living room with its very stylish dining area and the kitchen both with fireplace create an incredible cosy atmosphere. The huge magnificent terrace with its dining area, offers incredibly stunning views and unforgetable romantic evenings...
  • Tuscany II  - Sienna, Chianti Vacation HomeTuscany II - A luxury villa rental in Sienna. 6 Bedrooms.
  • Il Bareto - Sienna, Chianti Vacation RentalIl Bareto Il Bareto stands alone among the rolling hills, 14 km south-west of Siena.in 8 hectares of private land, with many age-old chestnut and oak trees. The house is somewhat out of the way - 200 m from the main road - accessible via a private drive. Its excellent, solitary position guarantees peace, quiet and outstanding panoramic views over the wide Siena countryside. Sleeps 2 to 12.
  • Casa di Vignolo  - Sienna, Chianti Vacation HomeCasa di Vignolo is a 16th century house finely renovated with great care. The house can sleep 6 people. Located in the heart of Tuscany, the village is ideally situation for exploring the wonders of Tuscany. 3 Bedrooms. Sleeps up to 6
  • Capriolo Tuscany 8 BRM Renovated Luxury Villa - Sienna, Chianti Vacation RentalCapriolo Tuscany 8 BRM Renovated Luxury Villa Capriolo 8 bedroom Tuscany Villa - this unique vacation rental is composed of a 17th century Tuscan country house and hay barn (can be rented together or separately and is perfect for small and large groups), newly renovated, restored and decorated... a combination of Old World style and modern luxury! Relax by the the large pool, dine on the outdoor patio, and explore the beautiful Tuscan countryside...
  • Villa la Collina  - Sienna, Chianti Vacation HomeVilla la Collina dates back to 1600. The home has been transformed several times during the centuries. There are wallpaintings and frescues painted by the former owner Countess Zorzi Franchini Stappo in the '20th. The large living-areas are on the ground floor and the bed-rooms on the two upper floors.[
  • Mini Suite Siena - Sienna, Chianti Vacation RentalMini Suite Siena 3 km east of Siena.. A road winds its way up the hill from Vico d'Arbia to the "Castello delle Quattro Torri", the Castle of the Four Towers. A very romantic accomodation for a couple: a small junior suite with bed & breakfast - a pleasant place to stay near Siena. As a guest here, you have access to the garden, enjoy a great view, reach the town quickly, and you'll take pleasure in a good night's sleep in a castle.
  • La Terrazza - Sienna, Chianti Vacation HomeLa Terrazza The 14th-century palace is located in the heart of the quiet old town centre, just a few metres from the renowned Piazza del Campo. The attractive and bright accommodation is on the top floor: a rooftop apartment with a terrace and a panoramic view. The apartment is well laid out with an interior design that is simple and functional creating an ambience of spaciousness and a clear structure. Sleeps up to 4.
  • Podere il Doccio  - Sienna, Chianti Vacation RentalPodere il Doccio Lovingly restored Tuscan farmhouse, fully furnished and equipped with everything necessary for a relaxing and comfortable holiday, located in the heart of the valley of the Arno among Florence, Siena and Arezzo. Sleeps up to 13
  • La Foresteria  - Sienna, Chianti Vacation HomeLa Foresteria The Illuminati family will welcome you on arrival and will accompany you throughout your holiday with hospitality and discretion, showing you the cultural and natural itineraries that can be travelled over, putting every effort into making your 'days in Tuscany' memorable. Sleeps from 1 to 26 guests.
  •  Agriturismo Il Gonzeto - Sienna, Chianti Vacation Rental Agriturismo Il Gonzeto in the immediate vicinity of Montepulciano, in a peaceful and panoramic setting, lies the Agriturismo Il Gonzeto.The carefully restored house has three nice apartments, one of which can also be rented as 3 double bedrooms with private bathrooms. l Gonzeto rises on a hill dominating the fertile Valdichiana and the magic Val d'Orcia, famous for its production of olive oil, wine and wheat.
  • Tuscany Rental - Sienna, Chianti Vacation HomeTuscany Rental This stylish 16th century apartment is ideal for day trips to Florence, Arezzo and Siena.Located in the centre of the historic town of Bucine, the rental offers everything that a true Tuscany fan desires: floors and ceilings in traditional terracott... Sleeps up to 2+2 guests....
  • VILLA IL PALIO    - Sienna, Chianti Vacation RentalVILLA IL PALIO enchants all of her guests - as much by her outstanding location as by her well thought out interior. This villa has both - a private and a completely classy touch. The then master builders chose a great location: the villa is situated on an elevated position on the ridge of a hill directly opposite Siena, which also sits on a hill. You'll have a superb view from here: the skyline of Siena, the cathedral dome and the campanili (bell towers) are within your reach.
Siena and Chianti Italy, Vacation Rentals include villas, homes, farmhouses, and apartments. To view more about a particular Chianti / Siena rental click on its name or on the rentals photo. The homes presented here are privately owned Tuscany vacation rentals rented out by owner or their agents. The Chianti region is nestled between the towns of Siena and Florence. Chianti is a major Italian wine-growing region and is rich in culture, scenery and attractions. It is also known throughout the world for exceptional food. Chianti is a must for a vacation in Italy. Begin your vacation to Chianti today, by booking one of these terrific vacation rentals.