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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Top Cities in Province of Siena

Siena featuring night scenes, landscape views and a city
VillasVillas

Siena

Siena

Our top choices for Province of Siena villas

Exterior

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (59 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is AU$288
includes taxes & fees
9 Feb - 10 Feb
Il Poggio dell'Eremita
Terrace/patio

Villa with private pool, air conditioning near wineries at 3km from village

Villa with private pool, air conditioning near wineries at 3km from village
CHIANCIANO terme
9.4 out of 10, Exceptional, (46 reviews)
"It was amazing!! Great space for 7 adults. Pool area is great. Definitely do a meal with Leonardo. "
United States
Carol W.
Villa with private pool, air conditioning near wineries at 3km from village
Outdoor dining

- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi

- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
San Gimignano
10.0 out of 10, Exceptional, (108 reviews)
"Our stay was absolutely amazing and Barbara is such a kind and attentive host! Barbara makes the most delicious meals we had in Italy."
United States
Olivia B.
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
Exterior

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

Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool

Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (56 reviews)
"We had the trip of a lifetime at this wonderful home. Sherri, the property manager, made sure we had everything we needed upon arrival and organized a truffle hunt and wine tasting with her lovely local connections. She also introduced us to her favorite restaurants nearby (they were amazing) and told us where to shop. And the house itself is stunning- it should be in a movie about Tuscany. Cannot wait to go back!"
United States
jen m.
Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool
Pool

San Gimignano - Panoramic garden and beautiful pool!

San Gimignano - Panoramic garden and beautiful pool!
San Gimignano
9.8 out of 10, Exceptional, (38 reviews)
"We had a group of 7 adult (19-64) family members staying here - property setting is spectacular with great views, gardens, pool , tennis court…. The house is spacious and well equipped - we ate every meal outside and took advantage of having a local chef come and cook for us one night. Very special time for us all / we will be back!"
Canada
Derek A.
San Gimignano - Panoramic garden and beautiful pool!
Outdoor spa tub

Winery Villa in the heart of Nobile Vineyards.

Winery Villa in the heart of Nobile Vineyards.
Toscana, IT
10.0 out of 10, Exceptional, (16 reviews)
"We love our stay. House and property are beautiful."
United States
Cathy F.
Winery Villa in the heart of Nobile Vineyards.
Exterior

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

Villa in Montalcino, exclusive for you, stunning view!!!
Montalcino
10.0 out of 10, Exceptional, (86 reviews)
"The pool area was awesome, very clean and beautiful landscape.Beds were comfortable, house was very clean! Loved the little coffee room.Lots of space to spread out in.Luigi was an excellent host!"
United States
Anne R.
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor dining

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Siena
9.4 out of 10, Exceptional, (67 reviews)
"The villa was clean, spacious and very comfortable. The views were amazing!"
Canada
Aysun P.
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Outdoor pool

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
San Gimignano
10.0 out of 10, Exceptional, (107 reviews)
"Very comfortable and convenient to San Gimignano . Alessandro was very helpful arranging a chef prepared dinner and wine tasting at the Villa...the highlight of our stay!"
United States
Thomas O.
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Interior

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Siena
10.0 out of 10, Exceptional, (108 reviews)
"Villa views were Spectacular, Host was excellent and communicated with us our whole stay. Kitchen and dining were well appointed and the outside dining was perfect for morning and wine and conversation in the evening. "
United States
Sheryl K.
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Exterior

BEAUTIFUL VILLA with private Pool in the heart of Chianti

BEAUTIFUL VILLA with private Pool in the heart of Chianti
castelnuovo berardenga
10.0 out of 10, Exceptional, (27 reviews)
"Great villa great view fantastic hostage "
Germany
Markus B.
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Pool

Private villa in the heart of chianti with view of siena

Private villa in the heart of chianti with view of siena
Fonterutoli
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful villa and stunning location. The host was very responsive and helpful. I would love to return someday. "
United States
Wendy F.
Private villa in the heart of chianti with view of siena
Exterior

Villa Podere Belvedere

Villa Podere Belvedere
Pienza
9.8 out of 10, Exceptional, (14 reviews)
"Thank you for making our trip so enjoyable - great hospitality!"
United States
Moleek D.
Villa Podere Belvedere
Outdoor dining

Villa with private pool and panoramic view in beautiful Val d'Orcia

Villa with private pool and panoramic view in beautiful Val d'Orcia
San Giovanni d'Asso
9.8 out of 10, Exceptional, (11 reviews)
"Beautiful property in a central location of Tuscany. Quiet and isolated."
United States
Stephen S.
Villa with private pool and panoramic view in beautiful Val d'Orcia
Outdoor pool

Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany

Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany
Pienza
9.6 out of 10, Exceptional, (17 reviews)
"The view from the house is spectacular! What a great spot for a group of friends or a large family. Close to vineyards and shopping. We love sitting on the back patio having dinner. The dog and cats were an extra. Lily and her husband were very helpful and we really enjoyed having the meals cooked by the chef while we were there. The last night with the fish was the best!"
United States
julie l.
Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany
Exterior

Stunning Villa: 24 guests, private SwimmingPool

Stunning Villa: 24 guests, private SwimmingPool
Ancaiano
9.8 out of 10, Exceptional, (30 reviews)
"What a Villa!! Four families with a total of 17 people, including kids aged between 12 and 19 stayed at the Villa and there was more than enough space for everyone to be comfortable. The kitchens were well stocked and the outdoor eating area was a great place to have a meal for all of us together. The pool, ping pong, hot tub and bocce provided lots to do when not sight seeing. Most importantly, Fabio was amazing!! Always available to assist or provide advice. And the meal he prepared for all...
Canada
Jonah D.
Stunning Villa: 24 guests, private SwimmingPool
Exterior

9- Villa La Quercia

9- Villa La Quercia
Casole d'Elsa
10.0 out of 10, Exceptional, (6 reviews)
"A beautiful property. We will definitely book this villa again. Thank you Camille!"
United States
Jill C.
9- Villa La Quercia
Exterior

Borgo Belsedere -Perfect for Family-Reunions, Retreats, intimate Weddings & more

Borgo Belsedere -Perfect for Family-Reunions, Retreats, intimate Weddings & more
Trequanda
Borgo Belsedere -Perfect for Family-Reunions, Retreats, intimate Weddings & more
Exterior

'...a delicious farmhouse in the countryside where only the wind blows...'

'...a delicious farmhouse in the countryside where only the wind blows...'
Campiglia d'Orcia
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful stay at the villa - we were a group of 10 adults and 2 children and used the villa as our home base for a week to explore the area (Pienza, Siena, Montalcino, Montelpulciano, etc). There are 4 apartments ranging from 1-3 bedrooms which were fantastic for the families, plus an additional communal kitchen and living room for everyone to gather. It was the perfect setup as it gave everyone the ability to have some privacy as well as for everyone to congregate and eat meals...
United States
Li-Shen L.
'...a delicious farmhouse in the countryside where only the wind blows...'
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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Top Province of Siena Hotel Reviews

Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"Perfect location … great quality/value … nice staff"
Alberto 2-night trip
Posted 3 days ago
Hotel Chiusarelli

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
715
Accommodation
1167 Villas
Lowest Price
AU$288
Highest Price
AU$288

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