Province of Siena Vacation Rentals from ₩84,743: 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 bathroom with a window view of a historic building and a tiled roof.

1. Siena Vip

Siena City Centre

Luis

₩167,020 total

includes taxes & fees

Oct 21 - Oct 22

A bakery display with pastries and a coffee station.

2. B&B Il Corso

Siena City Centre

Enrique

₩177,068 total

includes taxes & fees

Oct 30 - Oct 31

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

3. Villa Curina Resort

Castelnuovo Berardenga

Deanna

₩258,018 total

includes taxes & fees

Oct 4 - Oct 5

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

4. Residenza d'Epoca Palazzo Borghesi

Siena City Centre

Roman

₩297,817 total

includes taxes & fees

Oct 30 - Oct 31

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.

5. Tuscasì Aparthotel

Sovicille

Sergey

₩120,088 total

includes taxes & fees

Oct 31 - Nov 1

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

6. 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

₩309,979 total

includes taxes & fees

Oct 31 - Nov 1

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

7. La Terrazza Sul Campo Rooming House

Siena City Centre

Agnieszka

₩203,555 total

includes taxes & fees

Oct 29 - Oct 30

A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

8. Villa di Sotto

Castelnuovo Berardenga

Philippe

₩295,066 total

includes taxes & fees

Oct 1 - Oct 2

An interior courtyard with stone columns, arches, and a mosaic.

9. Meublé Il Riccio

Montepulciano

Christopher

₩246,772 total

includes taxes & fees

Oct 28 - Oct 29

A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

10. B&B Palazzo del Magnifico

Siena City Centre

Khaled

₩242,960 total

includes taxes & fees

Oct 7 - Oct 8

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

11. 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

₩258,208 total

includes taxes & fees

Oct 30 - Oct 31

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

12. Il Battistero Siena - Residenza d'Epoca

Siena City Centre

Kellie

₩206,392 total

includes taxes & fees

Oct 6 - Oct 7

A stone building with a garden in front.

13. Borgo Argenina

Gaiole in Chianti

Tatevik

₩404,213 total

includes taxes & fees

Oct 5 - Oct 6

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

14. Palazzo Pacini

Colle di Val d'Elsa

John

₩203,202 total

includes taxes & fees

Oct 30 - Oct 31

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

15. Palazzo Saloni

Montalcino

Michael

₩514,909 total

includes taxes & fees

Oct 7 - Oct 8

An open wooden door leading to an outdoor patio with a table and chairs.

16. Palazzo al Torrione 2

San Gimignano City Centre

Angela

₩204,573 total

includes taxes & fees

Oct 4 - Oct 5

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

17. Domus il Palio B&B

Ravacciano

María

₩105,924 total

includes taxes & fees

Oct 25 - Oct 26

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

18. Al Mercato B&B

Siena City Centre

Marie-Christine

₩138,650 total

includes taxes & fees

Oct 27 - Oct 28

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

19. Hotel San Gregorio

Pienza

Nancy

₩224,145 total

includes taxes & fees

Oct 28 - Oct 29

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

20. Riserva di Fizzano Residence

Castellina in Chianti

Janet

₩286,594 total

includes taxes & fees

Oct 4 - Oct 5

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Top Province of Siena Hotel Reviews

La Certosa di Pontignano

10/10 Excellent

"good to stay"

Nuovo Etruria Resort

10/10 Excellent

"Todo estuvo perfecto, el hotel muy muy lindo, la piscina extraordinaria, la habitación Muy cómoda, el servicio impecable, pero no funcionó el wifi en la habitación. No nos dieron un early check in ni guardaron las maletas, así que nos tuvimos que ir a Montslcino y ya no pudimos usar la piscina. Pero en general lo recomiendo mucho"

Fattoria di Vegi

10/10 Excellent

"We had a lovely night stay at this villa in September. It is a 900 year-old hunting lodge that has been converted to spacious rooms many with balconies. The views are incredible, the rooms have been renovated with character fixtures, but includes excellent air-conditioning. The view from the pool was out of a storybook. Staff was attentive and very nice to deal with. The grounds have endless opportunities for photos at every turn. Try to explore the grounds a little - including the painters studio with is exquisite. It has only been open four months so there are a few bugs but overall, the stay was excellent. The one area they need to improve however is the food. The selections are pretty limited and the quality was not to the standard of the property. My recommendation is have the breakfast on site and lunch by the pool, but try the surrounding towns for dinner. Castellini in Chianti is a small town 15 minutes away with great choices. One Belvedere and their sister property Locanda are both within 2 kms and have high end dining. Overall I highly recommend this villa for a unique Tuscan experience."

Poderi Arcangelo

8/10 Good

"We enjoyed our stay. The pool, hotel grounds and location were truly amazing. The food was okay but we enjoyed eating off site more. The farmhouse is very quaint and charming. You can hear others in the farmhouse. It was luxurious in many ways and more basic in other ways. But all together a wonderful stay. I would recommend for sure."

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"Amazing views. Relaxing stay! A very romantic hotel, though I was surprised by the number of families there; given its location and amenities, I had assumed it was geared towards couples. That isn't a negative comment, though—it was simply a case of my own mistaken perception."

Find out more about Province of Siena

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Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Province of Siena vacation rentals

1. Siena Vip

2. B&B Il Corso

3. Villa Curina Resort

4. Residenza d'Epoca Palazzo Borghesi

5. Tuscasì Aparthotel

6. PALAZZO DEL PAPA

7. La Terrazza Sul Campo Rooming House

8. Villa di Sotto

9. Meublé Il Riccio

10. B&B Palazzo del Magnifico

11. Casanova - Panoramic Rooms and Suites

12. Il Battistero Siena - Residenza d'Epoca

13. Borgo Argenina

14. Palazzo Pacini

15. Palazzo Saloni

16. Palazzo al Torrione 2

17. Domus il Palio B&B

18. Al Mercato B&B

19. Hotel San Gregorio

20. Riserva di Fizzano Residence

Find vacation rentals that suit your style

Top Province of Siena Hotel Reviews

La Certosa di Pontignano

Nuovo Etruria Resort

Fattoria di Vegi

Poderi Arcangelo

Hotel Minerva

Four Points by Sheraton Siena

Grand Hotel Continental Siena – Starhotels Collezione

Castello di Velona Resort Thermal SPA & Winery

L'Orto delle Terme

Find out more about 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. Siena Vip

2. B&B Il Corso

3. Villa Curina Resort

4. Residenza d'Epoca Palazzo Borghesi

5. Tuscasì Aparthotel

6. PALAZZO DEL PAPA

7. La Terrazza Sul Campo Rooming House

8. Villa di Sotto

9. Meublé Il Riccio

10. B&B Palazzo del Magnifico

11. Casanova - Panoramic Rooms and Suites

12. Il Battistero Siena - Residenza d'Epoca

13. Borgo Argenina

14. Palazzo Pacini

15. Palazzo Saloni

16. Palazzo al Torrione 2

17. Domus il Palio B&B

18. Al Mercato B&B

19. Hotel San Gregorio

20. Riserva di Fizzano Residence

Find vacation rentals that suit your style

Top Province of Siena Hotel Reviews

La Certosa di Pontignano

Find out more about Province of Siena