Province of Siena Vacation Rentals from NT$1,980: Search Short-Term Rentals

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

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Our top choices for Province of Siena vacation rentals

A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

1. La Terrazza Sul Campo Rooming House

Siena City Centre

Agnieszka

NT$3,673 total

includes taxes & fees

Nov 2 - Nov 3

A bathroom with a window view of a historic building and a tiled roof.

2. Siena Vip

Siena City Centre

Luis

NT$3,411 total

includes taxes & fees

Nov 2 - Nov 3

An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

3. Guild Living Siena Senior Resort & Residence

Scacciapensieri

Lucy

NT$4,231 total

includes taxes & fees

Nov 1 - Nov 2

A table set with breakfast items on a balcony overlooking a historic town.

4. Residenza d'Epoca Palazzo Borghesi

Siena City Centre

Roman

NT$6,742 total

includes taxes & fees

Nov 3 - Nov 4

An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

5. Palazzo Pacini

Colle di Val d'Elsa

John

NT$4,747 total

includes taxes & fees

Nov 2 - Nov 3

A villa with a swimming pool, outdoor seating, and a tennis court.

6. Villa Curina Resort

Castelnuovo Berardenga

Deanna

NT$4,625 total

includes taxes & fees

Oct 9 - Oct 10

A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

7. PALAZZO DEL PAPA

Siena City Centre

"The setup was more like a guest house/Bed and Breakfast. It was impeccably clean and newly renovated, which made it very cozy and comfortable. Everything needed was provided. The location was half a block from the Piazza del Campo. And last but not least, Hamza was one of the most welcoming and gracious hosts imaginable, directing us to a magical Trattoria, Pappei’s, that felt like you were visiting your own Nonna! Wonderful!!!"

Walter

NT$6,510 total

includes taxes & fees

Nov 3 - Nov 4

A bakery display with pastries and a coffee station.

8. B&B Il Corso

Siena City Centre

Enrique

NT$4,101 total

includes taxes & fees

Nov 1 - Nov 2

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

9. Hotel San Gregorio

Pienza

Nancy

NT$5,236 total

includes taxes & fees

Oct 28 - Oct 29

A wine cellar with stone walls, wine racks, and tables with glasses and candles.

10. Il Battistero Siena - Residenza d'Epoca

Siena City Centre

Kellie

NT$5,953 total

includes taxes & fees

Nov 1 - Nov 2

A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

11. Tuscasì Aparthotel

Sovicille

Sergey

NT$2,655 total

includes taxes & fees

Nov 2 - Nov 3

A table with two wine glasses, a bottle, and a book.

12. Domus il Palio B&B

Ravacciano

Waleska

NT$2,474 total

includes taxes & fees

Oct 20 - Oct 21

A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

13. Riserva di Fizzano Residence

Castellina in Chianti

Janet

NT$6,161 total

includes taxes & fees

Oct 8 - Oct 9

A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

14. Palazzo Saloni

Montalcino

Michael

NT$8,427 total

includes taxes & fees

Nov 2 - Nov 3

A multi-story building with green shutters on windows and balconies.

15. Palazzo Masi

Siena City Centre

Macarena

NT$3,658 total

includes taxes & fees

Oct 27 - Oct 28

An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

16. Bosco della Spina

Murlo

Lizl

NT$3,122 total

includes taxes & fees

Oct 27 - Oct 28

A stone building with a garden in front.

17. Borgo Argenina

Gaiole in Chianti

Tatevik

NT$7,305 total

includes taxes & fees

Oct 5 - Oct 6

A poolside area with two glasses of water, candles, and a stone pathway.

18. Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

"The room snd entire property were spotless clean. Staff wete helpful and friendly. Our room and patio overlooked the d'Orcia valley, gorgeous any time, especially in the morning. The entire grounds, pool, loungers, plants were well maintained. This was our third time at Cassanova and we would come again. A short walk into San Quirico d'Orcia with several good restaurants and a COOP store for drinks and groceries."

Zoltan

NT$6,341 total

includes taxes & fees

Oct 30 - Oct 31

A historic building with arched windows and a prominent entrance.

19. Casa Ciseri

Siena City Centre

Tania

NT$5,738 total

includes taxes & fees

Nov 2 - Nov 3

A room with a bed, a leather sofa, and a window with a view of a building outside.

20. Al Mercato B&B

Siena City Centre

Marie-Christine

NT$2,946 total

includes taxes & fees

Nov 2 - Nov 3

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Top Province of Siena Hotel Reviews

Precise Tale Poggio Alla Sala

10/10 Excellent

"Unbelievable stay at this beautiful property, excellent service and the restaurant was exceptional."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Castiglion del Bosco is truly exquisite, the perfect way to experience Tuscany in luxury while still feeling completely surrounded by nature. The property is impeccable, from the beautiful gardens and grounds to the elegant rooms. Everything feels authentically Italian, refined and incredibly well maintained. The service is exceptional and very personalized. The staff genuinely goes out of their way to make you feel welcome. General Manager Nicola Migheli even greeted us personally upon arrival, which was a lovely touch. We also saw him regularly walking the property with his team, and it was clear how hands-on he is with every detail. One thing to know is that getting in and out requires about 40 minutes on a bumpy dirt road. It wasn’t terrible, but worth mentioning if you plan to explore frequently. That said, this is a hotel you don’t need to leave. It’s a beautiful place to slow down, relax and enjoy Tuscany in a truly special setting. We absolutely loved our stay!"

Fattoria di Vegi

10/10 Excellent

"Booked this as a last minute decision to shorten our time in Milan (and fine a place close to Florence on our way to Montepulciano) We only stayed one night, but wish it had been longer. If you are looking for informal luxury, you will find it at this idyllic Tuscan Estate. They are still expanding their amenities to include a gym, tennis court, and Spa (planned for a 2027 open) what they DO offer is a quiet, thoughtful experience. The room was perfection and the restaurant on the property - delicious. There were a few artists there taking advantage of the atelier, or painting on the property. The estate is located an hour’s drive outside of Florence and is well worth the trip if you are looking for a place to relax. We hope to return with more time to enjoy it."

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Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Province of Siena vacation rentals

1. La Terrazza Sul Campo Rooming House

2. Siena Vip

3. Guild Living Siena Senior Resort & Residence

4. Residenza d'Epoca Palazzo Borghesi

5. Palazzo Pacini

6. Villa Curina Resort

7. PALAZZO DEL PAPA

8. B&B Il Corso

9. Hotel San Gregorio

10. Il Battistero Siena - Residenza d'Epoca

11. Tuscasì Aparthotel

12. Domus il Palio B&B

13. Riserva di Fizzano Residence

14. Palazzo Saloni

15. Palazzo Masi

16. Bosco della Spina

17. Borgo Argenina

18. Casanova - Panoramic Rooms and Suites

19. Casa Ciseri

20. Al Mercato B&B

Find vacation rentals that suit your style

Top Province of Siena Hotel Reviews

Precise Tale Poggio Alla Sala

Castello di Spaltenna- Small Luxury Hotels of the World

Poderi Arcangelo

Nuovo Etruria Resort

Castiglion del Bosco, A Rosewood Hotel

Fattoria di Vegi

Hotel Athena

La Certosa di Pontignano

Hotel Minerva

Find out more about Province of Siena

Vacation Apartments in Province of Siena

Vacation Rentals in Province of Siena

Change your mind

Treat yourself

Be picky

Our top choices for Province of Siena vacation rentals

1. La Terrazza Sul Campo Rooming House

2. Siena Vip

3. Guild Living Siena Senior Resort & Residence

4. Residenza d'Epoca Palazzo Borghesi

5. Palazzo Pacini

6. Villa Curina Resort

7. PALAZZO DEL PAPA

8. B&B Il Corso

9. Hotel San Gregorio

10. Il Battistero Siena - Residenza d'Epoca

11. Tuscasì Aparthotel

12. Domus il Palio B&B

13. Riserva di Fizzano Residence

14. Palazzo Saloni

15. Palazzo Masi

16. Bosco della Spina

17. Borgo Argenina

18. Casanova - Panoramic Rooms and Suites

19. Casa Ciseri

20. Al Mercato B&B

Find vacation rentals that suit your style

Top Province of Siena Hotel Reviews

Precise Tale Poggio Alla Sala

Find out more about Province of Siena

Vacation Apartments in Province of Siena