Top Vacation Homes in Province of Siena in 2026

A historic town with a prominent tower and a rainbow arching over it.

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Top Cities in Province of Siena

A historic square with a prominent tower and statues.

Our top choices for Province of Siena vacation homes

Deluxe Apartment | Premium bedding, down comforters, in-room safe, desk

1. Borgo Argiano

Castelnuovo Berardenga

Blake

2. Villa with large garden in the Chianti hills

Siena

Julie H.

Premium Apartment, 2 Bedrooms, 2 Bathrooms, Annex Building | Lanai

3. Il Palazzetto

Siena

Francois

4. Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!

Sarteano

"The house was very clean and comfortable. The showers are a bit small and the road to the house is a little challenging but overall we enjoyed our stay. The key holders re wonderful people and left us surprises almost daily. It included bottles of wine, pastries and groceries. They stocked the house with bottles of water, laundry detergent, trash bags, basically all our needs. I would highly recommend a stay at this villa."

Michael W.

5. Spacious house between Siena e Firenze with private swimming pool, A/C and Wi-Fi

Radicondoli

MARK P.

6. INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Montepulciano

Michael B.

7. Sweet home, the home of the small village

Colle di Val d'Elsa

Djip d.

8. Beautiful house on Chianti hilltop with exceptional views.

Siena

Darren S.

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Top Province of Siena Hotel Reviews

Hotel Athena

10/10 Excellent

"We had a wonderful stay at Hotel Athena in Siena. The service was exceptional, the staff were warm, welcoming and genuinely helpful throughout our visit. The location was fantastic for exploring Siena, with everything within walking distance, while the hotel itself provided a comfortable and relaxing place to come back to after a day of exploring. We also loved the beautiful views from the terrace which was the perfect spot to unwind with a drink and take in the scenery. Sunset was especially beautiful and I would recommend calling the terrace staff themselves to reserve your seat. They are VERY busy up there so please exercise patience and kindness to the server and bartender as they work so hard to get your orders to you as quickly as possible. Self parking our car was a huge bonus as we rented a vehicle to explore Tuscany. A lovely hotel, a great location and wonderful service. We would happily stay here again when visiting Siena!"

Castello di Velona Resort Thermal SPA & Winery

8/10 Good

"Staying here was a wonderful and truly unique experience. The only reason I’m giving it 4 stars instead of 5 was because of the challenges we had with the air conditioning in our room. That said, the staff really did make an effort to find a workaround for us. While it wasn’t a perfect solution, it definitely helped, and we appreciated how responsive and accommodating they were. The hotel itself is an old castle, and that alone makes staying here such a special experience. The property is beautiful, incredibly charming, and very well maintained. You simply can’t replicate the character, history, and ambiance that come with staying in a property like this. The setting and surroundings are beautiful. It was definitely one of those experiences that felt uniquely Italian and added something special to our trip. My only recommendation would be to visit when the temperatures aren’t quite as hot. Given the age and historic nature of the property, I can appreciate that modernizing certain things like the air conditioning may not be as straightforward as it would be in a newer hotel. During cooler weather, I imagine our experience would have been close to perfect. Overall, we really enjoyed our stay and are glad we had the opportunity to experience such a beautiful and unique property. I would absolutely recommend it, just perhaps not during the hottest part of the summer!"

Precise Tale Poggio Alla Sala

10/10 Excellent

"Incredible stay in a beautiful location. The staff were amazing and the hospitality was top tier. We will most definitely be back. The recommendations given were brilliant and the room was stunning along with the rest of the hotel. We didn’t dine in the restaurant but our breakfast each morning was also wonderful."

Borgo San Felice Resort

10/10 Excellent

"An unforgettable stay in Tuscany!** Our stay at Borgo San Felice was truly incredible from beginning to end. From the moment our private driver picked us up at the train station and brought us through the beautiful Tuscan countryside to the resort, everything felt seamless and special. The property itself is absolutely breathtaking pictures truly don’t do it justice. We enjoyed dinner on the property, a wonderful couples massage, a private wine tour and tasting, and a relaxing pool day. We especially loved the live piano music in the evenings; it added such a romantic and elegant touch to the entire experience. The service was one of the highlights of our stay. A special shout-out to **Herman at the pool**, who was always attentive and completely on point with everything we needed. We also had an amazing experience at **Poggio Rosso**, where **Matia provided top-notch service** and made our Michelin-starred dinner feel even more memorable. Every detail from the beautiful grounds and peaceful atmosphere to the food, wine, spa, and exceptional hospitality—made our time here unforgettable. Borgo San Felice gave us exactly the Tuscany experience we were hoping for and more. We absolutely loved our stay and would return in a heartbeat. Highly recommend! 🇮🇹🍷✨"

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San Giovanni A Cerreto Vacations

Room 1

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Top Cities in Province of Siena

Pienza

Our top choices for Province of Siena vacation homes

1. Borgo Argiano

2. Villa with large garden in the Chianti hills

3. Il Palazzetto

4. Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!

5. Spacious house between Siena e Firenze with private swimming pool, A/C and Wi-Fi

6. INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

7. Sweet home, the home of the small village

8. Beautiful house on Chianti hilltop with exceptional views.

9. The House of Alice, charm and relaxation

10. Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano

11. Villa Mulinello, secluded, panoramic view over Montepulciano valley.

12. Beautiful Tuscan farmhouse with stunning views of Chianti countryside

13. MONTEGONFOLI 4, Apartment for 4 adults with amazing views on San Gimignano

14. Casale di Villore

15. Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

16. Esclusivo per te

17. Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena

18. Tuscan Hilltop Terrace-Poliziano 7

19. Spacious Luxury Apartment: pool, stunning views, 15-min walk from Siena center!

20. GuestHost - Beautiful studio of 25 square meters located on the first floor of a building without elevator (6 steps to access), can comfortably accommodate up to 2 people.The property is located in the historic center (Restricted Traffic Zone), just outs

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Top Province of Siena Hotel Reviews

Hotel Athena

NH Siena

Castello di Velona Resort Thermal SPA & Winery

Grand Hotel Continental Siena – Starhotels Collezione

Fonteverde Thermal Spa Resort Tuscany

Precise Tale Poggio Alla Sala

Borgo San Felice Resort

Fattoria di Vegi

L'Orto delle Terme

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