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Siena City Centre, Siena
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. Great little hotel with very beautiful room with amazing views.
Poggibonsi
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.
Probably one of the best places I have stayed up. 
Rooms, pool, view, the quietness around, everything is perfect. The sunset is fantastic so if you can stay here.
Breakfast fabulous
Siena City Centre, Siena
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.
The disponibillity of the staff (i.e., Pietro) was fantastic: kind, resoursful, and very professional. The location and cleanes were impacapable. If I return to Siena, I will for sure stay here again.
Sovicille
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.
Check-in was extremely quick and easy. The staff were extremely knowledgeable on the area and provided a map with proposed itineraries with QR codes describing them in greater detail. They also recommended some lesser-known local sites worth visiting during our stay. The breakfast was phenomenal, with various pastries, cheeses, cold cuts, fresh fruits, juices, and yogurt. There was more, but overall the freshness and quality were top notch. We had dinner at their restaurant every night, which gave us a wide variety of local tastes. Honestly, we tried 80% of the menu and everything was great! This is a great spot to relax outside the city, but still close enough for day trips anywhere in Tuscany.
Montepulciano
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.
A Dreamy Tuscan Villa Stay – Highlight of Our Italian Road Trip
This villa was the absolute highlight of our Italian road trip. Nestled among cypress-lined pathways, its entrance alone sets the tone for a serene and picturesque escape. Surrounded by its own vineyard and olive orchards, the property offers breathtaking views and a true taste of Tuscany.
The restaurant overlooks the sunset, making every dinner a memorable experience. The rooms are spacious, and the bathrooms are generously sized, adding to the comfort of the stay.
One of our favourite features was the pool set amidst olive trees—a peaceful spot to relax, read, and watch the kids play.
The pool is open from morning to late evening.
I was able to swim quite a few laps as well.
With fewer rooms than large resorts, the atmosphere is calm, clean, and never overcrowded.
The villa produces its own wine and olive oil, and the staff are incredibly polite and courteous. A special mention goes to Giona, who went above and beyond to make our stay special, especially for my husband’s 40th birthday.
The food was outstanding—freshly prepared and full of flavour. The pasta with tomato and aubergine was hands down the best we’ve ever had. For a potato lover like me, the roast potatoes were amazingly seasoned and soooo good.  We tried every dessert on the menu, and each one was exceptional. Their house-baked biscotti was a lovely treat too.
Breakfast was just right—a mix of sweet items, boiled eggs, cereals, cheese, bread, coffee, and juices. It was perfect for making a quick sandwich and starting the day without needing to venture out early. Our kids especially loved the sweet options!
The villa’s location also makes it easy to explore nearby towns like Montepulciano and Siena, which is just about 1 hour and 15 minutes away.
This stay was everything we hoped for and more—peaceful, scenic, and full of warmth. We would return in a heartbeat.
Siena City Centre, Siena
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.
The room and all facilities are top notch! It is well kept, updated, and clean. Breakfast is good and offers variety. The location is a few minutes walk to the center of Siena, making it convenient while also in a quiet neighborhood. The view from my room is spectacular, as it is atop a hill. The bed and pillows are super comfortable! I felt well attended to during my stay.
Siena
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. Very unique stay with a fantastic pool overlooking the old town.
Gaiole in Chianti
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. Peaceful. Comfortable. Drinking wine by the pool was nice and great restaurant less than a block away
Montalcino
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. I liked everything. Very clean, all the facilities in the kitchen, beautiful view.
Montepulciano
Set in Montepulciano within 47 km of Mount Amiata and 5 km of Terme di Montepulciano, Casa del Fauno offers rooms with free WiFi. This guest house is 28 km from Bagni San Filippo. The property offers soundproof units and is located 21 km from Parco dei Mulini. Everything was perfect. Lovely finishing touches, they really do think of everything you need to make a great trip. The greeting from host was top class! The location is great. The most comfortable bed and incredibly clean! Parking was so easy and close to the property.
 
Holiday Rental in Montepulciano
Popular with guests booking holiday rentals in Siena Area
 
Holiday Rental in Siena
Popular with guests booking holiday rentals in Siena Area
 
Holiday Rental in Siena
Popular with guests booking holiday rentals in Siena Area
 
Holiday Rental in Siena
Popular with guests booking holiday rentals in Siena Area
 
Holiday Rental in Siena
Popular with guests booking holiday rentals in Siena Area
 
Holiday Rental in Siena
Popular with guests booking holiday rentals in Siena Area
Many families visiting Siena Area loved staying at B&B La Castellina, La Bellavita B&B and Il Mastio di Spedaletto.
Similarly, Lupaia, L’ Aia del Principe and Dimora delle Muse are also popular among family travellers.
The average price per night for a holiday rental in Siena Area for this weekend is US$231, based on current Booking.com prices.
La Moiana 1756, La casa di Arianna and Agriturismo Il Serraglio have received great reviews from guests in Siena Area regarding the views from these holiday rentals
Guests staying in Siena Area also spoke highly of the views from these holiday rentals: Villa Di Capovento, B&B La Castellina and La Torre.
Couples travelling in Siena Area loved staying at La Torre, Agriturismo Humile and Borgo Argiano.
Similarly, these holiday rentals in Siena Area are highly rated by couples: Villa Sant'Alberto, Poggio Olivo and Casanova di Campriano.
We make it quick and easy to book a holiday rental in Siena Area. Here’s what we offer:
• Free cancellation on most stays
• We Price Match
• 24/7 customer support in 40+ languages
There are 2,634 holiday rentals in Siena Area you can book on Booking.com.
Il giardino di Pantaneto Residenza D'Epoca, Casa Di Campagna In Toscana and Agriturismo San Sano are some popular holiday rentals in Siena Area.
In addition to these holiday rentals, Fattoria di Cinciano, B&B Il Corso and B&B San Francesco are also popular in Siena Area.
Most holiday rentals on Booking.com offer free cancellation.
Beautiful views, very quiet location and comfortable stay. The pool was clean and the small playground on site, as well as the friendly cats kept our 4 year old very entertained. The restaurant at the sister villa was also good. We did self-catering so cannot speak for the breakfasts but the olive oil we bought on site was great!
The location of the villa was perfect. The hosts were really kind and helpful.
Several (small) holiday appartments/houses, offering a lot of privacy though, with nice and authentic decoration, and with airconditioning (a bless with temperatures reaching between 34 and 38°C). Wonderful place to stay, in a huge wild garden on a hill, with a swimming pool, near to the small village of Le Piazze. Very friendly, enthousiastic and helpful hosts, who also provide fresh bread for breakfast.
Big and clean swimming pool, well-equipped house, great spot if you want to visit local towns and villages in Toscania. Each family has their own patio and even grill. Great contact with the owned who will respond to all your questions. My tip is to follow Elisa's directions instead of GPS (beacuse of Google Maps, i ended up on impassable, rocky road)
I loved everything about the villa. It was wonderful. And the hosts - Silvia and her gorgeous mother - were absolutely delightful. I couldn’t fault the beautiful apartment. It’s the best value accommodation I’ve ever booked in all my years of travel. My wife and my daughter feel exactly the same. Can’t wait to come back.
A jewel among the wine yards. Spacious room, great breakfast and friendly staff. The restaurant at the hotel was fantastic. We stayed for 2 nights at the villa and both times dined there. Local wine and home made pasta were to die for.
Claudio very helpful & polite. The hotel is within walking distance of a very nice restaurant. When we are visiting the Montepulciano area again we will stay at hotel Sangallo again. Our holiday home is in Capodimonte Lake Bolsena so we are only at most 2 hours drive away.