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Top cities in Province of Siena

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

Siena

Siena

Find holiday rentals that suit your style

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Province of Siena villas

A pool area with lounge chairs and a table, surrounded by a garden with purple flowers and a view of rolling hills.

1. Montalcino: Private villa in the heart of Tuscany, private pool, A/C

Montalcino: Private villa in the heart of Tuscany, private pool, A/C
Montisi
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful house in perfect location with stunning views. Luigi was a very welcoming and helpful host"
United States
Mark G.
Montalcino: Private villa in the heart of Tuscany, private pool, A/C
A hot tub under a pergola with a scenic view of mountains and trees.

2. 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, (61 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
A stone house with a tiled roof, surrounded by a stone fence and potted plants.

3. Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
San Gimignano
10.0 out of 10, Exceptional, (124 reviews)
"Great location. Loved walking to town!"
United States
Todd C.
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
An outdoor seating area with lounge chairs and a table, overlooking a scenic landscape with a pool.

4. Gorgeous view on vineyards, Stone Tuscan private Villa

Gorgeous view on vineyards, Stone Tuscan private Villa
Toscana
10.0 out of 10, Exceptional, (133 reviews)
"We had a very relaxing stay at the Villa. The pool was perfect for us with amazing views. Great location for visiting Siena"
United States
Nicola S.
Gorgeous view on vineyards, Stone Tuscan private Villa
A clear blue pool with a stone edge, surrounded by trees and a clear sky.

5. Podere Il Boschetto - Luxury Estate in Siena

Podere Il Boschetto - Luxury Estate in Siena
Siena
9.8 out of 10, Exceptional, (43 reviews)
"Absolutely Wonderful Place to stay!! Our Hosts were excellent and very nice! Barbara and Michele were very informative and had great suggestions!! Location made you feel like you were in a Fairytale. Clean, spacious and had everything you needed. Just take short walk to town for groceries/restaurants or you can take the bus. The bus stop is right at the gate of your Villa!!"
United States
Nicole M.
Podere Il Boschetto - Luxury Estate in Siena
A stone building with a patio and outdoor seating.

6. 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.
A stone building with a tiled roof, a swimming pool, and a garden with various plants and trees.

7. Villa Simo: exclusive use, private pool, 25 acres in Chianti, close to Siena

Villa Simo: exclusive use, private pool, 25 acres in Chianti, close to Siena
Pievasciata
9.8 out of 10, Exceptional, (81 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 Simo: exclusive use, private pool, 25 acres in Chianti, close to Siena
A villa with a swimming pool, surrounded by lush greenery and rolling hills.

8. Villa Sabrina by PosarelliVillas

Villa Sabrina by PosarelliVillas
San Gimignano
10.0 out of 10, Exceptional, (98 reviews)
"Loved Villa Sabrina, location was brilliant and owners discrete. Probably helped that it was 35 so pool and A/ C a blessingSan G about 15 min drive but a lovely hours walk across hills. Also easily visited Volterra, Siena and Florence. Highlight of trip Antinori Chianti Classico vineyard"
United States
Mark G.
Villa Sabrina by PosarelliVillas
A balcony with a table and chairs, a potted plant, and a view of a green landscape.

9. 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, (100 reviews)
"A hidden gem with a stunning view over the Crete Senesi. Photographs do not do it justice."
United States
André W.
Hilltop house in the heart of Tuscany with private pool
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

10. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (74 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is AU$235
includes taxes & fees
7 Nov - 8 Nov
Il Poggio dell'Eremita
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.
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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.

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