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The best holiday rentals in Siena Area

Check out our pick of great holiday rentals in Siena Area

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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Conveniently located in Siena, Il giardino di Pantaneto Residenza D'Epoca offers a continental breakfast and free WiFi. The property features garden and city views, and is 400 metres from Piazza del Campo. The bed and breakfast has family rooms. Everything regarding this place is amazing. The garden outside with a beautiful view, breakfast, cleanliness, staff. If you find this property, book it right away, you won’t regret!!

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9.4
Superb
2,086 reviews
Price from
US$149
per night

Offering an outdoor pool and a restaurant, Fattoria di Cinciano is located in Poggibonsi, a 10-minute drive from the centre. Free WiFi access is available in all areas.

Each apartment will provide you with a satellite flat-screen TV, air conditioning and a kitchenette with a microwave. Featuring a shower, the private bathroom also comes with a hairdryer and towels. Fattoria di Cinciano is a hidden gem in the Tuscan countryside. Perfectly positioned on a hilltop among olive groves and vineyards, it offers both peaceful seclusion and convenient access to nearby towns and attractions. Our apartment was spacious, comfortable, and well-equipped, making it feel like a home away from home. The estate features beautiful gardens and stunning views of the rolling Tuscan hills. The friendly staff provided excellent recommendations for local restaurants and activities, enhancing our experience of the region. What we appreciated most was the tranquil atmosphere - ideal for unwinding and experiencing the authentic charm of Tuscany. Highly recommended for anyone seeking a relaxing Italian countryside getaway with all the comforts.

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9.3
Superb
1,008 reviews
Price from
US$163
per night

Just 40 metres from Siena’s Piazza del Campo, B&B Il Corso is located on the first floor of a 16th-century building. It offers free Wi-Fi and elegant rooms.

Rooms at the Corso Bed and Breakfast are fitted with exposed beam ceilings and traditional furnishings. Each comes with city views, air conditioning and a private bathroom with free toiletries. Everything was extremely perfect, great location, room super clean and Pietro was the best host I’ve ever met.

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9.3
Superb
1,284 reviews
Price from
US$141
per night

Set 9 km from Siena, this 19th-century country house features a restaurant and outdoor pool. It offers traditional Tuscan rooms with wood-beamed ceilings, surrounded by sunflower fields.

Air-conditioned rooms at Casa Di Campagna In Toscana come with terracotta floors and a memory foam mattress. Each room includes a private bathroom complete with hairdryer and toiletry set. Nice apartment, swimming pool, excellent breakfast, great restaurant, people (staff, Chef, other guests)

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9.3
Superb
1,167 reviews
Price from
US$102
per night

Villa Nottola is a former noble residence in the countryside of Montepulciano, besides the namesake winery. It offers a sun terrace with swimming pool.

The elegant rooms of Villa Nottola feature ceilings with original wooden beams and brick vaults. The walls are painted in soft natural colours matching the Tuscan art furnishings. I liked the staff, they were very friendly and helpful, the look of the place, very beatifuly authentic with a big pool in an olive garden. On top was a very tasty breakfast and very good wines from their own batch. Highly recommend it and will certainly come back when I'll visit the area again!

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9
Superb
2,112 reviews
Price from
US$105
per night

Set in a 15th-century building in the historic centre of Siena, B&B San Francesco is just opposite the Bruco Fountain, a 5-minute walk from Piazza del Campo. All rooms offer city views and free WiFi.

Rooms at San Francesco B&B feature a private bathroom with shower, air conditioning and are typically furnished. Breakfast includes coffee and pastries. Great accommodation. Clean, warm, comfortable, authentic. Quality bathroom supplies are available. Very nice view from the room I stayed in on the 3rd floor. The host Roberto was friendly and gave useful and practical information about the city - thanks for the directions to see the city and check in. Great place if you want to do an evening walk in Siena before your overnight stay - located in the old part of town. If you are driving - free parking can be found within 20 minutes walking distance.

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9.1
Superb
1,847 reviews
Price from
US$142
per night

Borgo Grondaie is a large property built out of an old Tuscan farm, just 2 km from the historical centre of Siena. It offers an outdoor salted-water pool, and room and apartment accommodation of various sizes with free WiFi. Friendly and helpful staff, close to city with country feel.

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9.1
Superb
1,864 reviews
Price from
US$150
per night

Set within 24 km of Piazza del Campo and 29 km of Piazza Matteotti, Agriturismo San Sano offers rooms with air conditioning and a private bathroom in Gaiole in Chianti. This farm stay has a pool with a view, a garden and free private parking. The farm stay features family rooms. The staff, the views, the wine tour with the owner, central to many Tuscany ‘s town

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9.3
Superb
1,236 reviews
Price from
US$93
per night

CastelBigozzi is surrounded by the Tuscan countryside, 12 km from San Gimignano. It offers an outdoor swimming pool with hydromassage, and rustic, air-conditioned rooms. You can book free guided excursions on the Via Francigena path. Everything!!! The views, the peace, sunsets and sunrises…. Delicious food and location.

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9
Superb
1,081 reviews
Price from
US$141
per night

Featuring a garden and views of city, Casa Vacanze la Pineta is a recently renovated apartment set in Montalcino, 42 km from Mount Amiata. With quiet street views, this accommodation features a balcony. The apartment offers rooms with air conditioning, free private parking and free WiFi. Loved our lovely clean apartment. Clean modern and with an amazing view 😍

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9.5
Exceptional
300 reviews
Price from
US$94
per night

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