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

Vacation Rentals in Province of Siena

Where to?

Dates

November 2026

December 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Top cities in Province of Siena

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

Check prices for these dates

In two weeks

In two months

In three months

In four months

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$2,468 total

includes taxes & fees

Nov 26 - Nov 27

A narrow street with buildings on either side, featuring arched windows and a pedestrian walkway.

2. B&B Il Corso

Siena City Centre

Heather

NT$2,805 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$2,844 total

includes taxes & fees

Nov 13 - Nov 14

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

4. Residenza d'Epoca Palazzo Borghesi

Siena City Centre

Suelina

NT$5,681 total

includes taxes & fees

Nov 10 - Nov 11

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

5. Casa di Campagna in Toscana

Sovicille

Sally

NT$3,135 total

includes taxes & fees

Nov 15 - Nov 16

A white table with a bowl of snacks, two glasses of orange drink, and a small potted plant on a balcony.

6. RESIDENCE LECCIO

Asciano

Corey

NT$2,864 total

includes taxes & fees

Dec 2 - Dec 3

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

7. Domus il Palio B&B

Ravacciano

Leo

NT$2,511 total

includes taxes & fees

Nov 18 - Nov 19

A narrow hallway with a wooden bench, a radiator, and a wooden cabinet.

8. Il Battistero Siena - Residenza d'Epoca

Siena City Centre

Anthony

NT$4,204 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$2,251 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.

10. FonteLiving

San Casciano dei Bagni

Dauray

NT$3,018 total

includes taxes & fees

Nov 19 - Nov 20

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$3,223 total

includes taxes & fees

Nov 13 - Nov 14

A courtyard with a large building featuring arched windows and a tower. There is a parking lot with several cars.

12. Al Mercato B&B

Siena City Centre

Sandra

NT$2,715 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$4,853 total

includes taxes & fees

Nov 8 - Nov 9

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$3,667 total

includes taxes & fees

Nov 8 - Nov 9

A view through a window of a stone staircase leading to a building with arched windows and a tower, overlooking a hilly landscape.

15. Palazzo Pacini

Colle di Val d'Elsa

John

NT$4,335 total

includes taxes & fees

Dec 3 - Dec 4

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

16. B&B Le Logge Di Sopra

Asciano

NT$3,932 total

includes taxes & fees

Nov 24 - Nov 25

A building with a sign reading 'TRATTORIA TRENTO' and a 'BAR' sign. There are outdoor seating areas with tables and chairs.

17. Villa Fontis Rapolano

Rapolano Terme

Barbara

NT$3,125 total

includes taxes & fees

Nov 6 - Nov 7

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

18. La Coroncina Lodging

Siena

Hassan

NT$3,560 total

includes taxes & fees

Dec 2 - Dec 3

A bottle of wine, two glasses, and a decorative tray on a table by a window with a view of buildings.

19. Regis Condo

Siena City Centre

Jessica

NT$2,826 total

includes taxes & fees

Nov 26 - Nov 27

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

20. Casa Vacanze Le Case

San Gimignano

Andrew

NT$3,336 total

includes taxes & fees

Nov 12 - Nov 13

View all properties

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 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 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 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 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 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 courtyard with outdoor seating, a building with multiple windows, and a stone wall.

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 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 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 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 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 pool surrounded by lush greenery and vineyards, with a stone building in the background.

Agriturismo San Sano

Gaiole in Chianti

10/10 Excellent

Angela

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

Search for Vacation rentals in Province of Siena on Expedia.! You can easily find your home rentals, villas, Vacation apartments in Province of Siena using one of the methods below:

View our selection of featured Vacation rentals in Province of Siena
Use the map to find apartments and other Vacation homes in the Province of Siena neighbourhood you prefer
Enter your travel dates to view the best deals on Vacation rentals in Province of Siena while they last

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. 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