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 view out the window was so beautiful! We also loved the breakfast - it had a great selection! Location is also amazing!

Show more Show less
9.4
Superb
2,081 reviews
Price from
US$92
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. Can’t get over this place! Hands down the most beautiful view in all of Tuscany. We truly wished we had stayed longer. The room was clean, spacious, and incredibly comfortable—they truly thought of everything. It had that nostalgic, insanely pure Tuscan charm we dreamed of. We loved the romantic vibe of the pool and gardens, and the restaurant was absolutely amazing. Every little detail was perfect. And the breakfast? Unreal. So delicious—easily the best we had in Italy—and we were so happy it was included. Loved every second of our stay!

Show more Show less
9.3
Superb
1,009 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. Location is in the city centre, relatively clean places

Show more Show less
9.3
Superb
1,278 reviews
Price from
US$126
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. 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.

Show more Show less
9.4
Superb
1,168 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. Very nice area. Very helpful staff and a nice restaurant! Very nice place for a weekend getaway!

Show more Show less
9
Superb
2,111 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. Everything 😀 they had the most comfortable best , a room with the best view (no 5) and wonderful hosts

Show more Show less
9.1
Superb
1,848 reviews
Price from
US$103
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. Clean and big space for couple. Staff are friendly and helpful. Breakfast in room delightful.

Show more Show less
9.1
Superb
1,867 reviews
Price from
US$115
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. Amazing location, everything was picture perfect. Check in/out was smooth, big area to relax. The staff was helpful and gave recommendations. Prior to arrival communication was fast and helpful. I also recommend vinery tour and wine sampling provided by the host.

Show more Show less
9.3
Superb
1,240 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. Great and friendly staff, beautiful location and excellent food. We felt welcome all the time and would love to come back another time.

Show more Show less
9
Superb
1,074 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. Love the balcony with great Tuscany view. We enjoyed having our pre-dinner drinks and breakfast outside.

Show more Show less
9.5
Exceptional
303 reviews
Price from
US$94
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