Skip to main content

The best holiday rentals in Siena Area

Check out our pick of great holiday rentals in Siena Area

Filter by:


Review score

Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest price first Star rating and price Top reviewed

See the latest prices and deals by choosing your dates.

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. The guesthouse matches the photographs. Clean, well organized and beautiful. The garden is beautiful. The staff were excellent, friendly and efficient. I highly recommend it.

Show more Show less
9.4
Superb
2,053 reviews
Price from
US$91
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. A very cozy place right in the heart of the old town – you couldn’t find a better location. The room was clean and comfortable. It was very convenient to be able to leave our luggage after check-out. An extra bonus – sparkling and still water, as well as coffee, were available 24/7. We also received plenty of useful recommendations for parking, restaurants, and sightseeing. Highly recommended!

Show more Show less
9.2
Superb
1,264 reviews
Price from
US$125
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. Quiet and calm, net and clean. Excellent food and peaceful place, just stay one night but the next time surely more

Show more Show less
9.4
Superb
1,158 reviews
Price from
US$100
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. 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.

Show more Show less
9
Superb
2,105 reviews
Price from
US$121
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. 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.

Show more Show less
9.1
Superb
1,819 reviews
Price from
US$80
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. Perfekt location: close to train station, and located halfway up the hill. It’s tranquil and idyllic, so we could have a nice rest here. The room is tidy and clean, well-decorated. We felt like staying in our own home. The staffs are super friendly and warm-hearted.

Show more Show less
9.1
Superb
1,843 reviews
Price from
US$114
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. It was a lovely village in the vineyards. A great family who looked after us. Nice pool, very peaceful location, very pleasant manners and infomrative hosts.

Show more Show less
9.3
Superb
1,259 reviews

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. Everyone was so friendly. When we arrived, we walked around the area as the room was not ready yet. Beautiful surroundings with several small towns nearby where you can walk up the castles. It is the perfect location to unwind, find rest and be surrounded by an oasis of peace. Whether you want to lay by the pool all day, end your day with an outstanding dinner, or drive through a nearby city for a wine tasting or Italian restaurant - everything is possible.

Show more Show less
9
Superb
1,065 reviews
Price from
US$139
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. House was super nice decorated Everything was very clean The kitchen was fully equipped

Show more Show less
9.5
Exceptional
325 reviews
Price from
US$93
per night

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. Wonderful stay! Great property and host, would stay there again!

Show more Show less
9.5
Exceptional
115 reviews
Price from
US$172
per night

Most booked holiday rentals in Siena Area this month

FAQs about holiday rentals in Siena Area

Holiday Rentals that guests love in Siena Area