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

1. Abbadia Sicille Relais

Trequanda

Robert

NT$2,440 total

includes taxes & fees

Nov 26 - Nov 27

A bakery display with pastries and a coffee station.

2. B&B Il Corso

Siena City Centre

Heather

NT$2,783 total

includes taxes & fees

Nov 30 - Dec 1

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.

3. Tuscasì Aparthotel

Sovicille

Sergey

NT$2,700 total

includes taxes & fees

Nov 20 - Nov 21

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

4. Residenza d'Epoca Palazzo Borghesi

Siena City Centre

Suelina

NT$5,662 total

includes taxes & fees

Nov 21 - Nov 22

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

5. Casa di Campagna in Toscana

Sovicille

Sally

NT$3,099 total

includes taxes & fees

Nov 15 - Nov 16

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

6. RESIDENCE LECCIO

Asciano

Corey

NT$2,841 total

includes taxes & fees

Nov 18 - Nov 19

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

7. Domus il Palio B&B

Ravacciano

Leo

NT$2,502 total

includes taxes & fees

Nov 18 - Nov 19

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

8. Il Battistero Siena - Residenza d'Epoca

Siena City Centre

Anthony

NT$4,189 total

includes taxes & fees

Nov 13 - Nov 14

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

9. ApartHotel Anghel

Siena

clifford

NT$2,063 total

includes taxes & fees

Dec 1 - Dec 2

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

10. FonteLiving

San Casciano dei Bagni

Dauray

NT$3,018 total

includes taxes & fees

Nov 9 - Nov 10

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

11. Idolina Guest House

Montalcino

Jaiden

NT$3,275 total

includes taxes & fees

Nov 13 - Nov 14

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

12. Al Mercato B&B

Siena City Centre

Sandra

NT$2,670 total

includes taxes & fees

Nov 17 - Nov 18

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

13. Affitacamere Maria Gabriella

Pienza

Janine und Thomas

NT$4,798 total

includes taxes & fees

Nov 14 - Nov 15

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

14. 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

NT$3,638 total

includes taxes & fees

Nov 8 - Nov 9

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

NT$4,247 total

includes taxes & fees

Dec 4 - Dec 5

A stone-paved courtyard with a wrought iron gate, a brick building, and a tree.

16. B&B Le Logge Di Sopra

Asciano

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

17. Villa Fontis Rapolano

Rapolano Terme

Barbara

NT$3,461 total

includes taxes & fees

Nov 5 - Nov 6

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

18. La Coroncina Lodging

Siena

Hassan

NT$3,532 total

includes taxes & fees

Dec 2 - Dec 3

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

19. Regis Condo

Siena City Centre

Jessica

NT$2,863 total

includes taxes & fees

Nov 10 - Nov 11

A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

20. Casa Vacanze Le Case

San Gimignano

Andrew

NT$3,309 total

includes taxes & fees

Nov 8 - Nov 9

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

Castiglion del Bosco, A Rosewood Hotel

Montalcino

10/10 Excellent

KEDARNATH

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 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 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 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

Rene

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 hotel room with a bed, a desk, a television, and a window with a view.

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 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

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 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 table set for breakfast with a scenic view of hills and a cloudy sky.

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 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 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

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

Michele

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

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 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

Find out more about Province of Siena

Vacation Apartments in 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. Abbadia Sicille Relais

2. B&B Il Corso

3. Tuscasì Aparthotel

4. Residenza d'Epoca Palazzo Borghesi

5. Casa di Campagna in Toscana

6. RESIDENCE LECCIO

7. Domus il Palio B&B

8. Il Battistero Siena - Residenza d'Epoca

9. ApartHotel Anghel

10. FonteLiving

11. Idolina Guest House

12. Al Mercato B&B

13. Affitacamere Maria Gabriella

14. Guild Living Siena Senior Resort & Residence

15. Palazzo Pacini

16. B&B Le Logge Di Sopra

17. Villa Fontis Rapolano

18. La Coroncina Lodging

19. Regis Condo

20. Casa Vacanze Le Case

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

Vacation Apartments in Province of Siena