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

Vacation Rentals in Province of Siena

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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 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

NT$2,830 total

includes taxes & fees

Nov 20 - Nov 21

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

2. Abbadia Sicille Relais

Trequanda

Robert

NT$2,456 total

includes taxes & fees

Dec 8 - Dec 9

A bakery display with pastries and a coffee station.

3. B&B Il Corso

Siena City Centre

Heather

NT$2,801 total

includes taxes & fees

Nov 15 - Nov 16

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

4. Residenza d'Epoca Palazzo Borghesi

Siena City Centre

Suelina

NT$5,653 total

includes taxes & fees

Nov 26 - Nov 27

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

5. Casa di Campagna in Toscana

Sovicille

Sally

NT$2,572 total

includes taxes & fees

Nov 16 - Nov 17

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

6. Il Battistero Siena - Residenza d'Epoca

Siena City Centre

Anthony

NT$4,527 total

includes taxes & fees

Nov 13 - Nov 14

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

7. ApartHotel Anghel

Siena

clifford

NT$2,412 total

includes taxes & fees

Nov 30 - Dec 1

A building with a sign for 'Residence Leccio' and a café named 'La Rumba Café'.

8. RESIDENCE LECCIO

Asciano

Corey

NT$2,869 total

includes taxes & fees

Nov 16 - Nov 17

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

9. Palazzo Pacini

Colle di Val d'Elsa

John

NT$4,290 total

includes taxes & fees

Dec 11 - Dec 12

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

10. Idolina Guest House

Montalcino

Jaiden

NT$3,654 total

includes taxes & fees

Nov 30 - Dec 1

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

11. Siena Vip

Siena City Centre

John

NT$3,298 total

includes taxes & fees

Nov 12 - Nov 13

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

12. Affitacamere Maria Gabriella

Pienza

Janine und Thomas

NT$4,829 total

includes taxes & fees

Nov 15 - Nov 16

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

Sandra

NT$2,911 total

includes taxes & fees

Nov 18 - Nov 19

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

14. Villa Fontis Rapolano

Rapolano Terme

Barbara

NT$2,922 total

includes taxes & fees

Nov 12 - Nov 13

A terrace with a table set for dining, overlooking a scenic landscape with a castle in the distance.

15. FonteLiving

San Casciano dei Bagni

Dauray

NT$2,849 total

includes taxes & fees

Nov 12 - Nov 13

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

16. PALAZZO DEL PAPA

Siena City Centre

Charles

NT$6,262 total

includes taxes & fees

Nov 12 - Nov 13

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

17. Regis Condo

Siena City Centre

Jessica

NT$3,057 total

includes taxes & fees

Nov 30 - Dec 1

A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

18. TuscanyLettings Studio&Room

Pienza

Lucas

NT$3,318 total

includes taxes & fees

Dec 9 - Dec 10

A view of a traditional European town with stone buildings, a church with a bell tower, and a tiled roof.

19. Birbo Bike Hospitality

Siena City Centre

ralph

NT$2,748 total

includes taxes & fees

Nov 15 - Nov 16

A bedroom with a bed, bedside table, and a window with a view of greenery.

20. La Coroncina Lodging

Siena

Hassan

NT$3,365 total

includes taxes & fees

Nov 23 - Nov 24

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Find vacation rentals that suit your style

Top Province of Siena Hotel Reviews

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

Castiglion del Bosco, A Rosewood Hotel

Montalcino

10/10 Excellent

KEDARNATH

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 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

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

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 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

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 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 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 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 spacious living room with a leather sofa, a wooden coffee table, and a view through large arched windows.

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

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 pool with a tree in the center, surrounded by a deck and a view of hills in the background.

La Posta Hotel & Thermal Spa

San Quirico d'Orcia

10/10 Excellent

Diane

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

Vacation Apartments in Province of Siena

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Look no further and take a look at our great range of rental properties in Province of Siena!

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. Tuscasì Aparthotel

2. Abbadia Sicille Relais

3. B&B Il Corso

4. Residenza d'Epoca Palazzo Borghesi

5. Casa di Campagna in Toscana

6. Il Battistero Siena - Residenza d'Epoca

7. ApartHotel Anghel

8. RESIDENCE LECCIO

9. Palazzo Pacini

10. Idolina Guest House

11. Siena Vip

12. Affitacamere Maria Gabriella

13. Al Mercato B&B

14. Villa Fontis Rapolano

15. FonteLiving

16. PALAZZO DEL PAPA

17. Regis Condo

18. TuscanyLettings Studio&Room

19. Birbo Bike Hospitality

20. La Coroncina Lodging

Find vacation rentals that suit your style

Top Province of Siena Hotel Reviews

Torre del Fuggisole

10/10 Excellent

Find out more about Province of Siena

Vacation Apartments in Province of Siena