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

Search Province of Siena Villa Accommodation

  • 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

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Top Cities in Province of Siena

A historic town with tightly packed buildings, a prominent tower, and a church.
VillasVillas

Siena

Siena

Our top choices for Province of Siena villas

Exterior

1. Villa Costa, Stunning Villa in the heart of Tuscany.

Villa Costa, Stunning Villa in the heart of Tuscany.
Siena
10.0 out of 10, Exceptional, (36 reviews)
"This villa's stunning views and the hospitality of the hostess and all the people of Radicondoli was exceptional. I would book this villa again."
United States
steven a.
Villa Costa, Stunning Villa in the heart of Tuscany.
Exterior

2. Villa with private pool on 25 acres in the heart of Chianti, close to Siena

Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Pievasciata
9.8 out of 10, Exceptional, (80 reviews)
"The house and surroundings are amazing, we had a wonderful stay and the hosts were great and so easy to communicate with."
United States
Jessica K.
Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Terrace/patio

3. PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
chiusi
10.0 out of 10, Exceptional, (60 reviews)
"We had a very nice stay and a well organized pizza night in the villa. Glad to come again:) "
Germany
Florian Maria W.
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Exterior

4. Villa in Montalcino, exclusive for you, stunning view!!!

Villa in Montalcino, exclusive for you, stunning view!!!
Montalcino
10.0 out of 10, Exceptional, (91 reviews)
"Lovely villa in a beautiful location. "
United Kingdom
helen S.
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor dining

5. Hilltop house in the heart of Tuscany with private pool

Hilltop house in the heart of Tuscany with private pool
Montisi
9.8 out of 10, Exceptional, (98 reviews)
"Stunning peaceful location. We found it to be exactly as described on the website. Ideally placed to get around in this part of Tuscany. Tastefully renovated by the owners with its own interesting history. We enjoyed beautiful sunsets and loved chilling with a book and taking in the views. Catherine and Adi were very responsive."
United States
Anonymous traveller
Hilltop house in the heart of Tuscany with private pool
Exterior

6. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (70 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is AU$254
includes taxes & fees
24 Sept - 25 Sept
Il Poggio dell'Eremita
Outdoor dining

7. VILLA SARAH LUXURY SAN GIMIGNANO, 5 EN SUITE ROOMS , SWIMMING POOL, SPA.

VILLA SARAH LUXURY SAN GIMIGNANO, 5 EN SUITE ROOMS , SWIMMING POOL, SPA.
San Gimignano
10.0 out of 10, Exceptional, (48 reviews)
"Thank you Caterina and Carolina for a great stay. Loved our chef Fabio who helped us prepare one meal and cooked another for us. Rooms and view are better than the pictures! "
United States
Robert J.
VILLA SARAH LUXURY SAN GIMIGNANO, 5 EN SUITE ROOMS , SWIMMING POOL, SPA.
Outdoor dining

8. Villa Dipendenza, Historic Holding with wonderful swimming pool

Villa Dipendenza, Historic Holding with wonderful swimming pool
murlo - siena, tuscany
10.0 out of 10, Exceptional, (41 reviews)
"The house, grounds, pool and views were amazing! Eloise was very easy to communicate with. Would definitely recommend. "
United States
Peggy D.
Villa Dipendenza, Historic Holding with wonderful swimming pool
Exterior

9. Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!

Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
San Gusme
9.8 out of 10, Exceptional, (103 reviews)
"Beautiful property with lots of space for a family of 4 adults. Well equipped and the welcome provisions were a delight. The estate and surrounding area couldn’t be more tranquil. We left fully rested and relaxed. "
United Kingdom
Michelle S.
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Terrace/patio

10. Beautifully restored Tuscan villa, with private pool and breathtaking views

Beautifully restored Tuscan villa, with private pool and breathtaking views
Monteroni d'Arbia
10.0 out of 10, Exceptional, (23 reviews)
"A perfect week to celebrate 70th birthday with family "
Brazil
Francisco M.
Beautifully restored Tuscan villa, with private pool and breathtaking views
Pool

11. Villa Sarteano - Villa with private pool

Villa Sarteano - Villa with private pool
Sarteano
9.8 out of 10, Exceptional, (16 reviews)
"Perfect!"
United Kingdom
Johannes W.
Villa Sarteano - Villa with private pool
Outdoor pool

12. panoramica casa con piscina privata

panoramica casa con piscina privata
siena
7.0 out of 10, Good, (10 reviews)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
United Kingdom
Olivier B.
panoramica casa con piscina privata
Villa, Air conditioning, Courtyard View | Exterior

13. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is AU$269
includes taxes & fees
25 Sept - 26 Sept
Villa Montecastello
Exterior

14. Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.

Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Radda in Chianti
10.0 out of 10, Exceptional, (16 reviews)
"One of the best proprties we have ever stayed at. The house and grounds are well appointed and pristine. Samanta and Franco go above and beyond to make your stay memorable. We loved every minute of our visit! We hope to return when the weather is nicer and stay longer so we can enjoy the pool. Don’t miss the wine tour and tasting - it was such a great learning experience and you can taste the love they have for their vineyard in the wines. Simply exceptional in every aspect."
United States
Reed F.
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Property grounds

15. Villa la Quercia By MMega

Villa la Quercia By MMega
Monteriggioni
10.0 out of 10, Exceptional, (2 reviews)
"This villa is a true extension of the essence of Tuscany. It has timeless beauty, modern conveniences, and impressive gardens. It is centrally located within a brief distance to Florence, Seina, San Gimignano, olive and wine farms with tastings, horseback riding and more.The villa is expansive and beautifully appointed with marble, grand chandeliers and exquisite furniture. Outside, the carefully tended gardens wander around the large pool, the hot tub, the wood ovens, and several large patio...
United States
Mark C.
Villa la Quercia By MMega
Exterior

16. Villa Il Caggio - Villa with pool near san Gimignano in Tuscany

Villa Il Caggio - Villa with pool near san Gimignano in Tuscany
San Gimignano
9.2 out of 10, Wonderful, (16 reviews)
"We loved everything about the property, it was better than the pictures, better than we could have imagined, the view was just stunning and we had an amazing time! We barely left the villa as it has everything we needed. Also situated on a vineyard so you can go for wine tasting or buy very nice wine very easily. Emma was an amazing host, was very helpful for whatever we needed."
United Kingdom
Anna-Maria
Villa Il Caggio - Villa with pool near san Gimignano in Tuscany
Property grounds

17. Molino del Ponte, Radda in Chianti, Italy

Molino del Ponte, Radda in Chianti, Italy
Radda in Chianti
9.2 out of 10, Wonderful, (12 reviews)
"We went with our children and grandchildren. We had a great time and Stephano was a great host. We enjoyed trips into Radda and Castellina. The vineyard at Fattoria di Montemaggio is off the beaten track but well worth a visit; La Loggia del Chianti Ristorante in Radda is an absolutely amazing gastronomical experience. For breakfast a coffee and pastry Circolo Bar Italia in Castellina. If you are travelling by EV the chargers locally are reliable and would recommend the Plenitude app."
United States
Andrew L.
Molino del Ponte, Radda in Chianti, Italy
Exterior

18. Relax in the green, in the municipality of Monteriggioni just 7 km from Siena

Relax in the green, in the municipality of Monteriggioni just 7 km from Siena
Monteriggioni
10.0 out of 10, Exceptional, (7 reviews)
"This was the epitome of staying in an authentic Villa, with amazing views of the Tuscany countryside. "
United States
Donna
Relax in the green, in the municipality of Monteriggioni just 7 km from Siena
Exterior

19. Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (1 review)
"The property was easy to find and the hosts were super quick to communicate. Really clear instructions and they showed us around upon arrival . Nothing was too much trouble. The property was well appointed and suited us down to the ground (3 adults and 3 kids) . The pool was great and perfect to amuse the kids. The town is a short drive away and you can get everything you need at the large supermarkets . There’s even a great gelato parlour nearby and a pizza restaurant ."
United Kingdom
alison
Villa Marcolina
Exterior

20. Villa "Le Vallecchie" overlooking Siena and with private swimming pool

Villa "Le Vallecchie" overlooking Siena and with private swimming pool
Siena
9.6 out of 10, Exceptional, (38 reviews)
"Really enjoyed our stay. A great place to relax."
United Kingdom
Michael G.
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Province of Siena Hotel Reviews

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"Lovely historic hotel, certainly captured the essence of the period it was built in. Room was spacious, beds very comfortable and considering the average temp was 35 degrees for the 3 nights we stayed, the air conditioning worked well enough. C The"
Mark 3-night trip
Posted 14 hours ago
Palazzo Ravizza

Find out more about Province of Siena

Vacation Like a Royal in a Province of Siena Villa

Long ago in ancient Rome, villas were made for upper-class members of society to escape the heat of the city in the surrounding hills or the beaches. These luxurious getaways hosted feasts and offered refined tastes to all their visitors. Back then, villas were seen as a mark of wealth and status—something only the elite could achieve. Now thanks to Expedia, you can stay at one for a price you won't believe. You've probably seen shared photos of friends or relatives staying at a fancy villa and wondered, "How in the world did they afford this?" Now you can see these stays aren't out of reach, and are more doable than ever with our team working as your booking agent.

Stay in a Province of Siena Villa for Your Next Vacation

When you are on holiday, the last thing you should worry about is getting separated at a resort, or having to cancel your "fun in the sun" day because the pool is too packed. We can help you get the most out of your visit to Province of Siena without having to hurry to make reservations for lounge chairs or at the nearby bistro. Our charming villas will leave you feeling refreshed, because you will feel like you are actually on a break, rather than a stressful trip. Staying in one of our unique properties is the perfect way for you and your family to enjoy a relaxing getaway. Just think: You can do just about anything you want on a villa property. Isn't that the life?

Book Your Stay in Province of Siena Today

Where you stay in Province of Siena is all based on your personal needs for your holiday. It can be a home away from home...or, if you are craving seclusion, you can choose to stay in a luxury getaway villa. Forget about resorts blaring music at all hours of the night—the party is over when you go to bed. Not familiar with the area? Don't worry; some of our villa rentals have concierge services available if you need someone to help pick the perfect activities and restaurants while you're in Province of Siena. So, when you're ready, Expedia will be here to help you book your perfect villa holiday.

Province of Siena Villas information

Number of reviews
764
Accommodation
1072 Villas
Lowest Price
AU$254
Highest Price
AU$269

Explore a world of travel with Expedia