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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 July - 5 July
In three months
31 July - 2 Aug
In four months
28 Aug - 30 Aug

Top Cities in Province of Siena

VillasVillas

Siena

Siena

Our top choices for Province of Siena villas

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
Exterior

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (62 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is AU$240
includes taxes & fees
9 May - 10 May
Il Poggio dell'Eremita
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!
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, (5 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

Relax in a private Tuscan Villa with pool and open hill views

Relax in a private Tuscan Villa with pool and open hill views
Montefollonico Torrita di Siena SI
10.0 out of 10, Exceptional, (49 reviews)
"I have rented many villas and this stay was up there among the best. Wonderful villa, everything was clean and worked properly and I can’t emphasize enough how great the location was. When you stay there go to Casa Newton for cocktails, beautiful boutique hotel a six minute drive away. "
United States
Alan H.
Relax in a private Tuscan Villa with pool and open hill views
Property grounds

Villa with unique view of Siena with private pool

Villa with unique view of Siena with private pool
Ascarello
9.8 out of 10, Exceptional, (9 reviews)
"Great place with plenty space for everyone. Fantastic views and short distance to Siena. "
Australia
Regina C.
Villa with unique view of Siena with private pool
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.
Outdoor dining

Exclusive Farmhouse Pool & View of San Gimignano

Exclusive Farmhouse Pool & View of San Gimignano
Toscana
9.0 out of 10, Wonderful, (2 reviews)
"Place was very nice, clean with great views. Beds were comfortable. Communication with owner was not great and some amenities and customer service were average. Emailed owner about WiFi issue, HVAC unit error code and remotes and whether water was potable, no response. Also would’ve have been nice to have toaster/oven/microwave. "
United States
David A.
Exclusive Farmhouse Pool & View of San Gimignano
Outdoor pool, a heated pool

Agricola Neci: Tuscan Rural Luxury with Housekeeping, Infinity Pool and a Lake

Agricola Neci: Tuscan Rural Luxury with Housekeeping, Infinity Pool and a Lake
Bollano
10.0 out of 10, Exceptional, (49 reviews)
"Great place and excellent host."
United States
Cassio F.
Agricola Neci: Tuscan Rural Luxury with Housekeeping, Infinity Pool and a Lake
Outdoor dining

Casanovina, Castellina in Chianti, Siena and Chianti

Casanovina, Castellina in Chianti, Siena and Chianti
Castellina in Chianti
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely loved our stay in this beautiful house in a breathtaking location! "
Sweden
Axel W.
Casanovina, Castellina in Chianti, Siena and Chianti
Exterior

Casale del Conte - Three Bedroom Villa, Sleeps 6

Casale del Conte - Three Bedroom Villa, Sleeps 6
Pienza
9.2 out of 10, Wonderful, (9 reviews)
"Excellent location for those seeking privacy, friendly and helpful owners and a very roomy villa. Car is highly recommended!"
United States
Anonymous traveller
Casale del Conte - Three Bedroom Villa, Sleeps 6
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, (71 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

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
Outdoor dining

FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI

FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Vagliagli
10.0 out of 10, Exceptional, (68 reviews)
"Beautiful home and great host"
United States
Dean B.
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Outdoor dining

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, (46 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.
Exterior

Beautiful Private & Luxurious Tuscan Villa Near Siena/Scenic Views/Crete Senesi

Beautiful Private & Luxurious Tuscan Villa Near Siena/Scenic Views/Crete Senesi
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (86 reviews)
"Very unique and pleasant setting. Everything we hoped it would be. "
United States
John D.
Beautiful Private & Luxurious Tuscan Villa Near Siena/Scenic Views/Crete Senesi
Outdoor pool, a heated pool

WP Relais Villa Vignalunga in Val d'Orcia,luxurious estate with swimming pool

WP Relais Villa Vignalunga in Val d'Orcia,luxurious estate with swimming pool
CASTIGLIONE D'ORCIA (SI)
10.0 out of 10, Exceptional, (50 reviews)
"We loved our stay. The Villa was gorgeous and Gaia was very responsive to any questions we had."
United States
Teresa P.
WP Relais Villa Vignalunga in Val d'Orcia,luxurious estate with swimming pool
Property grounds

Villa Lauretana - Vacation Rental in Torrita di Siena, Tuscany

Villa Lauretana - Vacation Rental in Torrita di Siena, Tuscany
Torrita Di Siena
9.8 out of 10, Exceptional, (37 reviews)
"Property was great, owners were very easy to work with. Renting a house is a bit different than staying in a hotel, you need to think about items you don’t usually consider such as bathroom and kitchen supplies. Propert was exactly as described!"
United States
suzanne j.
Villa Lauretana - Vacation Rental in Torrita di Siena, Tuscany
Terrace/patio

Gorgeous view on vineyards, Stone Tuscan private Villa

Gorgeous view on vineyards, Stone Tuscan private Villa
Toscana
10.0 out of 10, Exceptional, (115 reviews)
"Great location."
United States
Kim B.
Gorgeous view on vineyards, Stone Tuscan private Villa
Exterior

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, (113 reviews)
"We very much enjoyed our stay. Alessandro was very welcoming and had many good suggestions. The views were incredible, both from the home and on the walk to the village. The location was perfect!"
United States
Suzanne H.
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
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

8/10 Good
"Positives: Easy check-in; on-site parking; convenient location just outside the no-traffic zone; good bed; good breakfast; pleasant old-world ambiance. Suggestions: 1. Give guests the ability to turn on air-conditioning even in colder weather in order to circulate air in the room. Without air, the room gets stuffy (and you can't leave the windows open because of the traffic noise). 2. Add a dresser with drawers."
Robert 2-night trip
Posted 1 day 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
809
Accommodation
1157 Villas
Lowest Price
AU$240
Highest Price
AU$240

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