Province of Siena Vacation Rentals from ₩76,389: 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 cathedral with a rainbow, surrounded by traditional buildings.

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Our top choices for Province of Siena vacation rentals

A dining area with tables set for meals, a chandelier, and a view of the outdoors.

1. Palazzo Pacini

Colle di Val d'Elsa

John

₩173,158 total

includes taxes & fees

Dec 3 - Dec 4

A bakery display with pastries and a coffee station.

2. B&B Il Corso

Siena City Centre

Heather

₩112,425 total

includes taxes & fees

Nov 26 - Nov 27

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

3. Il Battistero Siena - Residenza d'Epoca

Siena City Centre

Anthony

₩186,939 total

includes taxes & fees

Nov 22 - Nov 23

A table set with breakfast items, including eggs, pastries, and fruit, overlooking a historic town with a prominent church tower.

4. Residenza d'Epoca Palazzo Borghesi

Siena City Centre

Suelina

₩231,350 total

includes taxes & fees

Nov 20 - Nov 21

A building with a large wooden door and an arched entrance, a sign with a number, and a small window with a view of the interior.

5. Idolina Guest House

Montalcino

Jaiden

₩133,380 total

includes taxes & fees

Dec 9 - Dec 10

A hotel reception area with a green counter, yellow chairs, and a balcony with a view.

6. Tuscasì Aparthotel

Sovicille

Sergey

₩113,618 total

includes taxes & fees

Nov 19 - Nov 20

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

7. Abbadia Sicille Relais

Trequanda

Robert

₩98,582 total

includes taxes & fees

Nov 26 - Nov 27

A rustic stone building with a garden in front, a clear view of the countryside, and a lamp post.

8. Casa di Campagna in Toscana

Sovicille

Sally

₩103,250 total

includes taxes & fees

Nov 16 - Nov 17

A swimming pool with a water feature, surrounded by greenery and a table with chairs.

9. Hotel San Gregorio

Pienza

Michael

₩207,281 total

includes taxes & fees

Nov 16 - Nov 17

A bedroom with a bed, bedside tables, a wardrobe, and a hanging light fixture.

10. Siena Vip

Siena City Centre

John

₩134,800 total

includes taxes & fees

Nov 17 - Nov 18

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

11. PALAZZO DEL PAPA

Siena City Centre

Charles

₩251,390 total

includes taxes & fees

Nov 16 - Nov 17

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

12. Palazzo Masi

Siena City Centre

William

₩138,515 total

includes taxes & fees

Dec 11 - Dec 12

A garden with two chairs under trees, a table, and a view of the landscape.

13. Affitacamere Maria Gabriella

Pienza

Janine und Thomas

₩193,848 total

includes taxes & fees

Nov 16 - Nov 17

A historic building with arched windows and a prominent entrance.

14. Casa Ciseri

Siena City Centre

Kalya

₩237,217 total

includes taxes & fees

Nov 16 - Nov 17

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

15. ApartHotel Anghel

Siena

clifford

₩89,922 total

includes taxes & fees

Dec 1 - Dec 2

A patio with a white table and chairs, a laptop, a basket of fruit, and a glass of juice.

16. RESIDENCE LECCIO

Asciano

Corey

₩109,421 total

includes taxes & fees

Nov 16 - Nov 17

A kitchen area with a marble countertop, a refrigerator, and various food items.

17. B&B Le Scalette di Piazza

Montalcino

Morris

₩178,301 total

includes taxes & fees

Nov 16 - Nov 17

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

Sandra

₩111,252 total

includes taxes & fees

Nov 18 - Nov 19

A garden patio with two metal chairs, a round table, and a picnic setup including a basket, jars, and plates of food.

19. La Coroncina Lodging

Siena

Hassan

₩123,203 total

includes taxes & fees

Nov 16 - Nov 17

20. Residence Arianna

Sovicille

Violeta

₩196,722 total

includes taxes & fees

Nov 16 - Nov 17

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Find vacation rentals that suit your style

Top Province of Siena Hotel Reviews

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 motorcycle parked in front of a brick building with arched doorways and a street lamp.

Torre del Fuggisole

Siena City Centre

10/10 Excellent

Charles

A bedroom with a large bed, a chandelier, a painting, a dining table with chairs, and a view through a window.

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 modern desk with a lamp, a chair, and a book on the desk.

Relais Le Macine di Stigliano

Sovicille

10/10 Excellent

Nicholas

An aerial view of a large estate with a swimming pool, tennis courts, and a vineyard.

The Club House

Castelnuovo Berardenga

10/10 Excellent

debbie

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

Villa Le Prata is absolutely exceptional. A historic villa with truly personalized service that the discerning traveler always seeks. Here, that aspiration is a reality. Centrally placed near Montalcino, you are able to breathe in the Tuscan countryside outside your window. And considering they are located on their own highly regarded Brunello vineyard, what more could you ask for? A Michelin-rated property, you seriously cannot do better if coming to Tuscany. We WILL be back!!!❤️❤️❤️

Scott

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

Castiglion del Bosco, A Rosewood Hotel

Montalcino

10/10 Excellent

KEDARNATH

A view through a window of a town with traditional architecture, cobblestone streets, and a rural landscape.

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 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 dining table with a variety of food and drinks, a vase with flowers, and a view of an outdoor patio with chairs and umbrellas.

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 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 two-story building with a central entrance, green shutters, and a brick staircase leading up to the door.

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 vineyard with rows of grapevines and a large building in the background.

Relais Villa Grazianella - UNA Esperienze

Montepulciano

10/10 Excellent

We were the only guests for 2 nights out of 3, at this lovely B&B on the estate of one of the best wineries in Tuscany. We had sumptuous room with a living room, bedroom and bathroom (nice shower!) all to ourselves. The staff were local women, who made a wonderful breakfast every day and told us of the life in Tuscany. The place was spotless, the food great, and it was so relaxing to come " home" to the vineyards every night, after seeing hordes of people in the towns we explored. One could...

RAP

An aerial view of a hotel with a swimming pool, multiple buildings, and surrounding greenery.

La Posta Hotel & Thermal Spa

San Quirico d'Orcia

10/10 Excellent

Diane

A four-poster bed with a bench, stone flooring, and a stone wall.

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

A stone house with a pool and outdoor seating.

Mastrojanni Relais - Small Luxury Hotels of the World

Montalcino

10/10 Excellent

Suelina

A spacious room with a large sofa, multiple chairs, a desk with a computer, and a television. The room features ornate ceiling and wall decorations.

Palazzo Carletti

Montepulciano

10/10 Excellent

Naomi

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. Palazzo Pacini

2. B&B Il Corso

3. Il Battistero Siena - Residenza d'Epoca

4. Residenza d'Epoca Palazzo Borghesi

5. Idolina Guest House

6. Tuscasì Aparthotel

7. Abbadia Sicille Relais

8. Casa di Campagna in Toscana

9. Hotel San Gregorio

10. Siena Vip

11. PALAZZO DEL PAPA

12. Palazzo Masi

13. Affitacamere Maria Gabriella

14. Casa Ciseri

15. ApartHotel Anghel

16. RESIDENCE LECCIO

17. B&B Le Scalette di Piazza

18. Al Mercato B&B

19. La Coroncina Lodging

20. Residence Arianna

Find vacation rentals that suit your style

Top Province of Siena Hotel Reviews

Hotel Certosa Di Maggiano

10/10 Excellent

Find out more about Province of Siena