Province of Siena Vacation Rentals from ￥8,809: 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 vacation rentals

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.

1. Tuscasì Aparthotel

Sovicille

Sergey

￥13,638 total

includes taxes & fees

Sep 30 - Oct 1

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

2. Domus il Palio B&B

Ravacciano

Alissia

￥12,522 total

includes taxes & fees

Oct 1 - Oct 2

A bakery display with pastries and a coffee station.

3. B&B Il Corso

Siena City Centre

Enrique

￥38,001 total

includes taxes & fees

Oct 6 - Oct 7

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

4. Villa Curina Resort

Castelnuovo Berardenga

Mary

￥31,350 total

includes taxes & fees

Sep 27 - Sep 28

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

5. Villa di Sotto

Castelnuovo Berardenga

Philippe

￥27,637 total

includes taxes & fees

Sep 21 - Sep 22

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

6. Siena Vip

Siena City Centre

Luis

￥20,571 total

includes taxes & fees

Sep 7 - Sep 8

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

7. B&B Palazzo del Magnifico

Siena City Centre

Khaled

￥21,100 total

includes taxes & fees

Sep 24 - Sep 25

A patio area with outdoor seating, potted plants, and a view of the landscape.

8. Affitacamere Maria Gabriella

Pienza

Young Rok

￥23,874 total

includes taxes & fees

Oct 4 - Oct 5

A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

9. Villa Fontis Rapolano

Rapolano Terme

Barbara

￥16,093 total

includes taxes & fees

Sep 10 - Sep 11

A building with a sign reading 'Villa Le Camelie' and multiple flags.

10. Villa le Camelie Siena

Petriccio

Mark

￥15,245 total

includes taxes & fees

Oct 1 - Oct 2

A historic building with a tower, a courtyard, and a well-lit entrance.

11. Abbadia Sicille Relais

Trequanda

Robert

￥24,503 total

includes taxes & fees

Oct 6 - Oct 7

A swimming pool with lounge chairs and umbrellas, a brick building in the background, and a clear sky.

12. Podere Vesta

Asciano

Katerine

￥29,388 total

includes taxes & fees

Sep 17 - Sep 18

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

13. Al Mercato B&B

Siena City Centre

Marie-Christine

￥17,496 total

includes taxes & fees

Oct 5 - Oct 6

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

14. Guild Living Siena Senior Resort & Residence

Scacciapensieri

tomaz

￥24,682 total

includes taxes & fees

Oct 6 - Oct 7

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

15. Palazzo Pacini

Colle di Val d'Elsa

John

￥26,980 total

includes taxes & fees

Sep 25 - Sep 26

A stone courtyard with a bench, potted plants, and a building in the background.

16. Casa di Campagna in Toscana

Sovicille

Sally

￥22,595 total

includes taxes & fees

Sep 29 - Sep 30

A modern lobby with white leather sofas, a glass coffee table, and potted plants.

17. ApartHotel Anghel

Siena

jon

￥17,615 total

includes taxes & fees

Sep 9 - Sep 10

An outdoor café with tables and chairs under umbrellas, a stone building with green shutters, and a sign that reads "POSTERIA".

18. B&B Dei Rossi

Siena City Centre

Alana

￥16,244 total

includes taxes & fees

Sep 14 - Sep 15

A traditional stone building with a courtyard, a staircase, and potted plants.

19. Il Pozzo di Sant'Andrea

Siena

Prem

￥18,536 total

includes taxes & fees

Oct 5 - Oct 6

A narrow street with stone buildings, a tower, and an archway.

20. Materia Rooms San Gimignano

San Gimignano City Centre

Bradley

￥21,680 total

includes taxes & fees

Sep 18 - Sep 19

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Top Province of Siena Hotel Reviews

Fonteverde Thermal Spa Resort Tuscany

10/10 Excellent

"Nice clean stay. Staff excellent"

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! 🇮🇹🍷✨"

Nuovo Etruria Resort

10/10 Excellent

"We had a lovely 3 night stay The pool area is just what’s needed to cool off in the afternoon The staff are friendly and helpful, it feels family run and they try to help wherever possible We walked into the old town from the hotel, it’s a steep walk uphill but if you have trouble walking I would recommend a vehicle The surrounding area is stunning Breakfast was good with options of hot and cold The bedroom was very clean, the bed was a little firm for my preference Highly Recommended"

Find out more about Province of Siena

Vacation Apartments in Province of Siena

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Change your mind

Treat yourself

Be picky

Top Cities in Province of Siena

Siena

Our top choices for Province of Siena vacation rentals

1. Tuscasì Aparthotel

2. Domus il Palio B&B

3. B&B Il Corso

4. Villa Curina Resort

5. Villa di Sotto

6. Siena Vip

7. B&B Palazzo del Magnifico

8. Affitacamere Maria Gabriella

9. Villa Fontis Rapolano

10. Villa le Camelie Siena

11. Abbadia Sicille Relais

12. Podere Vesta

13. Al Mercato B&B

14. Guild Living Siena Senior Resort & Residence

15. Palazzo Pacini

16. Casa di Campagna in Toscana

17. ApartHotel Anghel

18. B&B Dei Rossi

19. Il Pozzo di Sant'Andrea

20. Materia Rooms San Gimignano

Find vacation rentals that suit your style

Top Province of Siena Hotel Reviews

Fonteverde Thermal Spa Resort Tuscany

Precise Tale Poggio Alla Sala

Borgo San Felice Resort

Fattoria di Vegi

L'Orto delle Terme

Palazzo Ravizza

Hotel Italia

Nuovo Etruria Resort

Hotel Chiusarelli

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

Top Cities in Province of Siena

Siena

Our top choices for Province of Siena vacation rentals

1. Tuscasì Aparthotel

2. Domus il Palio B&B

3. B&B Il Corso

4. Villa Curina Resort

5. Villa di Sotto

6. Siena Vip

7. B&B Palazzo del Magnifico

8. Affitacamere Maria Gabriella

9. Villa Fontis Rapolano

10. Villa le Camelie Siena

11. Abbadia Sicille Relais

12. Podere Vesta

13. Al Mercato B&B

14. Guild Living Siena Senior Resort & Residence

15. Palazzo Pacini

16. Casa di Campagna in Toscana

17. ApartHotel Anghel

18. B&B Dei Rossi

19. Il Pozzo di Sant'Andrea

20. Materia Rooms San Gimignano

Find vacation rentals that suit your style

Top Province of Siena Hotel Reviews

Fonteverde Thermal Spa Resort Tuscany

Find out more about Province of Siena

Vacation Apartments in Province of Siena