Province of Siena Holiday Rentals from €55: Search Short-Term Rentals

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 town with tightly packed buildings, a prominent tower, and a church.

Our top choices for Province of Siena holiday 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

includes taxes & fees

29 Oct - 30 Oct

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

2. Siena Vip

Siena City Centre

Luis

includes taxes & fees

1 Nov - 2 Nov

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

3. Guild Living Siena Senior Resort & Residence

Scacciapensieri

Lucy

includes taxes & fees

1 Nov - 2 Nov

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

4. Residenza d'Epoca Palazzo Borghesi

Siena City Centre

Roman

includes taxes & fees

30 Oct - 31 Oct

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

includes taxes & fees

31 Oct - 1 Nov

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

6. Villa Curina Resort

Castelnuovo Berardenga

Deanna

includes taxes & fees

4 Oct - 5 Oct

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

includes taxes & fees

1 Nov - 2 Nov

A bakery display with pastries and a coffee station.

8. B&B Il Corso

Siena City Centre

Enrique

includes taxes & fees

31 Oct - 1 Nov

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

9. Hotel San Gregorio

Pienza

Nancy

includes taxes & fees

28 Oct - 29 Oct

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

includes taxes & fees

1 Nov - 2 Nov

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

includes taxes & fees

31 Oct - 1 Nov

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

12. Domus il Palio B&B

Ravacciano

María

includes taxes & fees

20 Oct - 21 Oct

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

13. Riserva di Fizzano Residence

Castellina in Chianti

Janet

includes taxes & fees

8 Oct - 9 Oct

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

14. Palazzo Saloni

Montalcino

Michael

includes taxes & fees

7 Oct - 8 Oct

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

15. Palazzo Masi

Siena City Centre

Macarena

includes taxes & fees

27 Oct - 28 Oct

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

includes taxes & fees

27 Oct - 28 Oct

A stone building with a garden in front.

17. Borgo Argenina

Gaiole in Chianti

Tatevik

includes taxes & fees

5 Oct - 6 Oct

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

includes taxes & fees

30 Oct - 31 Oct

A historic building with arched windows and a prominent entrance.

19. Casa Ciseri

Siena City Centre

Tania

includes taxes & fees

11 Oct - 12 Oct

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

includes taxes & fees

27 Oct - 28 Oct

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Top Province of Siena Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"From the moment we checked in, This place was a Gem. From the friendly and helpful staff to the beautiful grounds, we were so impressed. Its hard to put into words how wonderful this Hotel is. The food, and drinks were incredible. We also celebrated my wife's birthday at this resort and they did a very special dinner for us to enjoy. Along with Campaign and a personalized Birthday dessert. Special thanks to Noamie (hope i got that right). She was absolutely wonderful. I could go on forever about this Resort. So easy to explore the region while calling this a comfortable landing spot. Can't thank the team enough for a wonderful 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."

Find out more about Province of Siena

Holiday Homes in Province of Siena

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Holiday Rentals in Province of Siena

Change your mind

Treat yourself

Be picky

Top Cities in Province of Siena

Siena

Our top choices for Province of Siena holiday 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 holiday rentals that suit your style

Top Province of Siena Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

Find out more about Province of Siena

Holiday Homes in Province of Siena

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