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

Vacation Rentals in Province of Siena

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Dates

November 2026

December 2026

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Top cities in Province of Siena

A historic cathedral with a rainbow, surrounded by traditional buildings.

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Our top choices for Province of Siena vacation rentals

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

1. Residenza d'Epoca Palazzo Borghesi

Siena City Centre

Suelina

₩232,065 total

includes taxes & fees

Nov 10 - Nov 11

A patio with a table and chairs, a view of palm trees, and a stone wall.

2. Palazzo Pacini

Colle di Val d'Elsa

John

₩175,495 total

includes taxes & fees

Dec 7 - Dec 8

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

3. Guild Living Siena Senior Resort & Residence

Scacciapensieri

"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."

Heidi

₩150,325 total

includes taxes & fees

Nov 8 - Nov 9

A bakery display with pastries and a coffee station.

4. B&B Il Corso

Siena City Centre

Heather

₩114,969 total

includes taxes & fees

Dec 3 - Dec 4

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

5. Il Battistero Siena - Residenza d'Epoca

Siena City Centre

Anthony

₩171,714 total

includes taxes & fees

Nov 13 - Nov 14

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

Charles

₩236,797 total

includes taxes & fees

Nov 12 - Nov 13

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

7. Palazzo Saloni

Montalcino

Michael

₩396,498 total

includes taxes & fees

Dec 5 - Dec 6

A historic building with arched windows and a prominent entrance.

8. Casa Ciseri

Siena City Centre

Tania

₩241,106 total

includes taxes & fees

Dec 4 - Dec 5

A crowded restaurant with brick walls and multiple tables and chairs.

9. La Locanda di San Francesco

Montepulciano

Colin

₩231,702 total

includes taxes & fees

Nov 25 - Nov 26

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

10. Siena Vip

Siena City Centre

Jacob

₩154,259 total

includes taxes & fees

Nov 8 - Nov 9

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

₩112,841 total

includes taxes & fees

Nov 20 - Nov 21

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

12. Hotel San Gregorio

Pienza

Michael

₩211,972 total

includes taxes & fees

Nov 8 - Nov 9

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

13. Domus il Palio B&B

Ravacciano

Leo

₩103,739 total

includes taxes & fees

Nov 18 - Nov 19

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

14. B&B Palazzo del Magnifico

Siena City Centre

Khaled

₩150,072 total

includes taxes & fees

Nov 17 - Nov 18

A courtyard with a stone statue, a round table, and chairs.

15. Regis Condo

Siena City Centre

Jessica

₩120,689 total

includes taxes & fees

Nov 29 - Nov 30

A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

16. Idolina Guest House

Montalcino

Jaiden

₩133,554 total

includes taxes & fees

Nov 30 - Dec 1

A covered corridor with brick columns, potted plants, and a view of a lush landscape.

17. Abbadia Sicille Relais

Trequanda

Robert

₩100,813 total

includes taxes & fees

Nov 26 - Nov 27

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

18. Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

Oscar

₩240,208 total

includes taxes & fees

Nov 29 - Nov 30

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

19. Al Mercato B&B

Siena City Centre

Sandra

₩112,189 total

includes taxes & fees

Nov 17 - Nov 18

20. Palazzo Lenzi

Siena City Centre

Chadwick

₩399,327 total

includes taxes & fees

Nov 15 - Nov 16

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Find vacation rentals that suit your style

Top Province of Siena Hotel Reviews

A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.

Castello La Leccia

Castellina in Chianti

10/10 Excellent

Sarah

A stone building with multiple windows and a balcony, surrounded by lush greenery and trees.

Relais Le Macine di Stigliano

Sovicille

10/10 Excellent

Nicholas

A hotel room with a large bed, a vanity with a mirror, and a green archway.

Hotel Certosa Di Maggiano

Siena

10/10 Excellent

Anonymous traveler

A room with two striped armchairs, a small table with chess pieces, and a mirror reflecting a dining area.

La Dimora Dei Monaci

Siena City Centre

10/10 Excellent

we stayed for 4 nights and used Seina as our base for our first visit to Tuscany. The owners were very helpful. They provided maps and information on all the local sights, plus some history of the town. One night we asked them to make dinner reservations and they had to call over 10 places due to a busy night. But they found us a great restaurant for dinner. Another day they provide a detailed schedule for buses to visit one of the towns we were interested in. The B&B is very close to the...

Alan

A person relaxing in a hot tub with a view of a vineyard and mountains in the background.

Villa Le Prata - Residenza del Vescovo

Montalcino

10/10 Excellent

Valentin Y.

A villa with a swimming pool, surrounded by trees and hills.

Castiglion del Bosco, A Rosewood Hotel

Montalcino

10/10 Excellent

KEDARNATH

Palazzo Saloni

Montalcino

10/10 Excellent

My husband and I spent 6 fabulous nights here. From the moment I made the reservation, I felt in good hands with great communication about any question I had. The front desk can assist with wine excursions, spa, cooking class and even are connected with a nice local gym you can attend for a small fee. We rented a car and it is a big bonus that this property has on-site parking included in the rate. The Palazzo is located in a prime location, also easy to get in and out which can be tricky in...

Laura

A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

The Club House

Castelnuovo Berardenga

10/10 Excellent

debbie

An arched entrance with a brick pathway leading to a building, surrounded by lush greenery and purple flowering vines.

Palazzo di Valli

Siena

10/10 Excellent

We stayed 3 nights at Palazzo di Valli in late April 2022. The property is beautiful and located in a quiet residential area just south of the city's center. It sits on a hill overlooking a valley, and has it's own orchard and flower gardens. Instead of waking up to the sound of motorcycles and delivery trucks under your window, we woke up to chirping birds. Hosts Lorenzo and Giancarlo were wonderful, offering us recommendations, and helping arrange reservations and transportation. It's a bit of...

Joan

A large estate with multiple buildings, a well-maintained garden, and a vineyard in the background.

Lupaia

Torrita di Siena

10/10 Excellent

This was the most amazing place to stay! This was our favorite stop on a 30-day trip to Greece, Italy and Switzerland. The surrounding countryside is stunning. Our room had a Turkish Bath - what a fun experience. We were a couple of weeks in to our vacation, and we were ready for some down time. Having a private little garden, overlooking the Tuscan hillside was WONDERFUL. The dinner we had on site was one of the best of our entire trip. Breakfast in the morning was an incredible display...

KC Traveler

A terrace with wicker chairs and a table set for breakfast, overlooking a historic town with terracotta buildings and cypress trees.

Villa del Sole Siena

Siena City Centre

10/10 Excellent

Linna

A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

Agriturismo San Sano

Gaiole in Chianti

10/10 Excellent

Angela

A table set for two with a wine glass, a bowl of nuts, and a glass of water.

Relais degli Angeli

Siena City Centre

10/10 Excellent

Stained here at the end of an eight day trip around Italy. This hotel was head and shoulders above the others I visited, it is a boutique hotel of seven rooms. Our room was a suite. It was bigger than many apartments, with a large living room with daybed, a beautiful master bathroom with jetted tub and separate shower with jets overhead as well as side jets, ample closet storage, fridge, and safe. The rooms here have antique furniture and hand painted ceilings. I loved the breakfast on the...

Susie

A stone wall with a view of rolling hills and mountains.

Castello Banfi - Il Borgo - Relais et Chateaux

Montalcino

10/10 Excellent

Castello Banfi - Il Borgo is either a great place to anchor your restoration or to invigorate your exploration. There's plenty to do on property: a wine tour through the high-tech wine production facility; wine tasting overlooking the Tuscan landscape (you have a substantial selection to choose from); lounging by the pool overlooking the many acres of grape vines, olive and plum trees, and the hills beyond; a visit to their glass museum; an intimate cooking class with one of the top Chefs in...

Greg

A brick building with two arched windows, one with a metal grill and the other with a decorative glass design.

Hotel Palazzetto Rosso

Siena City Centre

10/10 Excellent

A Beautiful and Unique Stay in the Heart of Siena! Our stay at Hotel Palazzetto Rosso was an incredible experience! The atmosphere was absolutely amazing, with stunning medieval architecture that perfectly captures the historic charm of Siena. The hotel beautifully blends its centuries-old character with modern comforts, creating a truly unique and memorable experience. The staff was exceptionally friendly and accommodating, especially when it came to our late arrival. They went above and...

Thomas

A poolside area with lounge chairs, a table with drinks, and a view of hills.

Capanna Suites

Montalcino

10/10 Excellent

This hotel set the bar EXTREMELY high for our 2 week vacation. The staff is truly invested in making sure your stay is superb. This is a relatively new-build hotel for Tuscany, but it’s built to look traditional with modern twists. Our room was very spacious and had a modern shower and changing closet. The bed and pillows were very comfortable. The pool is beautiful and the spa house is great. Currently you have to book the spa access a day ahead due to covid precautions; you get 1 hour to...

Anonymous traveler

A stone building with a pool, lounge chairs, and a garden with flowers.

Podere Brizio

Montalcino

10/10 Excellent

Wonderful, beautiful property! The rooms are immaculate and nicely decorated. Breakfast is bountiful with wonderful homemade tarts, breads, frittatas. Do not miss dining in the restaurant for dinner. We had several dinners among the best of our 3 week trip to Italy. The staff is very professional, friendly and passionate about their job. Thank you Vito and Caterina for going above and beyond expectations and making our stay one I will never forget. We are already planning our return.

Sharon

An outdoor patio with tables and chairs, a pergola structure, and a stone building in the background.

Tenuta CorteDomina

Radda in Chianti

10/10 Excellent

piyanut

A spa area with a stone wall, wooden beams, a large window with a view, and a hot tub.

Mastrojanni Relais - Small Luxury Hotels of the World

Montalcino

10/10 Excellent

Suelina

Find out more about Province of Siena

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Vacation Rentals in Province of Siena

Change your mind

Treat yourself

Be picky

Top cities in Province of Siena

Siena

Check prices for these dates

Our top choices for Province of Siena vacation rentals

1. Residenza d'Epoca Palazzo Borghesi

2. Palazzo Pacini

3. Guild Living Siena Senior Resort & Residence

4. B&B Il Corso

5. Il Battistero Siena - Residenza d'Epoca

6. PALAZZO DEL PAPA

7. Palazzo Saloni

8. Casa Ciseri

9. La Locanda di San Francesco

10. Siena Vip

11. Tuscasì Aparthotel

12. Hotel San Gregorio

13. Domus il Palio B&B

14. B&B Palazzo del Magnifico

15. Regis Condo

16. Idolina Guest House

17. Abbadia Sicille Relais

18. Casanova - Panoramic Rooms and Suites

19. Al Mercato B&B

20. Palazzo Lenzi

Find vacation rentals that suit your style

Top Province of Siena Hotel Reviews

Castello La Leccia

10/10 Excellent

Find out more about Province of Siena