Top Vacation Homes in Province of Siena in 2026

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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

1. Precise Tale Poggio Alla Sala

Montepulciano

Mark

AED 2,345 total

includes taxes & fees

30 Sep - 1 Oct

2. Poderi Arcangelo

San Gimignano

Lisa

AED 546 total

includes taxes & fees

28 Sep - 29 Sep

3. Castello di Velona Resort Thermal SPA & Winery

Montalcino

Song

AED 3,139 total

includes taxes & fees

27 Sep - 28 Sep

4. Hotel Athena

Siena Historical Center

Jared

AED 1,157 total

includes taxes & fees

30 Sep - 1 Oct

5. Nuovo Etruria Resort

Montepulciano

Jorge

AED 500 total

includes taxes & fees

20 Sep - 21 Sep

6. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Hannah

AED 2,560 total

includes taxes & fees

7 Oct - 8 Oct

7. Borgo Vescine

Radda in Chianti

Gabrielle

AED 3,395 total

includes taxes & fees

10 Oct - 11 Oct

8. Grand Hotel Continental Siena – Starhotels Collezione

Siena City Centre

Lisa

AED 2,565 total

includes taxes & fees

14 Sep - 15 Sep

9. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

Nigel

AED 870 total

includes taxes & fees

5 Oct - 6 Oct

Villa (Agresto) | Living area | LCD TV, pay movies

10. Castiglion del Bosco, A Rosewood Hotel

Montalcino

Talib

AED 9,651 total

includes taxes & fees

8 Oct - 9 Oct

Couples treatment rooms, sauna, hot tub, hot springs, Turkish bath

11. Fonteverde Thermal Spa Resort Tuscany

San Casciano dei Bagni

Susan and Larry

AED 1,701 total

includes taxes & fees

13 Sep - 14 Sep

12. Hotel Casolare Le Terre Rosse

San Gimignano

Stephanie

AED 640 total

includes taxes & fees

11 Oct - 12 Oct

13. Relais Villa Grazianella - UNA Esperienze

Montepulciano

Alisa

AED 1,320 total

includes taxes & fees

11 Oct - 12 Oct

14. Mastrojanni Relais - Small Luxury Hotels of the World

Montalcino

Laura

AED 2,000 total

includes taxes & fees

5 Oct - 6 Oct

15. Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

Rama

AED 1,658 total

includes taxes & fees

5 Oct - 6 Oct

16. Fattoria di Vegi

Castellina in Chianti

Sebastian

AED 1,393 total

includes taxes & fees

29 Sep - 30 Sep

17. La Certosa di Pontignano

Castelnuovo Berardenga

Malena

AED 545 total

includes taxes & fees

10 Oct - 11 Oct

18. Borgo San Felice Resort

Castelnuovo Berardenga

Cynthia

AED 2,837 total

includes taxes & fees

11 Oct - 12 Oct

19. Hotel Chiusarelli

Siena City Centre

sharon

AED 718 total

includes taxes & fees

22 Sep - 23 Sep

20. L'Orto delle Terme

San Quirico d'Orcia

Stimson

AED 696 total

includes taxes & fees

24 Sep - 25 Sep

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Top Province of Siena Hotel Reviews

Hotel Athena

8/10 Good

"Overall okay hotel. It’s meant more to come in during the morning while explore and out all day. Rooms are small and you can hear everything that’s going on in the hallway and in othe rooms (e.g., crying baby at 3am). Reception staff (Simone) was helpful and bartender (Lucas) was super nice. View in the terrace is good and peaceful but can’t be use if too close to dinner time."

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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Top Cities in Province of Siena

Pienza

Our top choices for Province of Siena vacation homes

1. Precise Tale Poggio Alla Sala

2. Poderi Arcangelo

3. Castello di Velona Resort Thermal SPA & Winery

4. Hotel Athena

5. Nuovo Etruria Resort

6. Borgo Scopeto Wine & Country Relais

7. Borgo Vescine

8. Grand Hotel Continental Siena – Starhotels Collezione

9. Villa Scacciapensieri Boutique Hotel

10. Castiglion del Bosco, A Rosewood Hotel

11. Fonteverde Thermal Spa Resort Tuscany

12. Hotel Casolare Le Terre Rosse

13. Relais Villa Grazianella - UNA Esperienze

14. Mastrojanni Relais - Small Luxury Hotels of the World

15. Castello di Spaltenna- Small Luxury Hotels of the World

16. Fattoria di Vegi

17. La Certosa di Pontignano

18. Borgo San Felice Resort

19. Hotel Chiusarelli

20. L'Orto delle Terme

Find vacation rentals that suit your style

Top Province of Siena Hotel Reviews

Hotel Athena

Nuovo Etruria Resort

Castello di Velona Resort Thermal SPA & Winery

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Chiusarelli

Fonteverde Thermal Spa Resort Tuscany

Precise Tale Poggio Alla Sala

Borgo San Felice Resort

Fattoria di Vegi

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