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3 Oct - 5 Oct
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10 Oct - 12 Oct
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24 Oct - 26 Oct
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21 Nov - 23 Nov

Top Cities in Province of Siena

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Siena

Siena

Featured Villas in Province of Siena

Private villa in the heart of chianti with view of siena
Pool

Private villa in the heart of chianti with view of siena

10.0 out of 10, Exceptional, (3)
"Beautiful villa and stunning location. The host was very responsive and helpful. I would love to return someday. "
Private villa in the heart of chianti with view of siena
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Terrace/patio

Villa in Poggiarello-ripa with 3 bedrooms sleeps 5

10.0 out of 10, Exceptional, (110)
"We loved our stay, it was beautiful and relaxing beyond words! Francesca and her team were amazing, providing so many memorable experiences and great support! We will be back! What a wonderful time all around. "
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Property grounds

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

9.4 out of 10, Exceptional, (64)
"If you like a 360-degree view from the top of the hill, this is the place. Amazing views, out in the country with little traffic (more tractors than cars). Very private. We wanted to sit on the patio all day.The house is very comfortable and a good home base for sampling Brunello and visiting the Montalcino vineyards.Camilla was easy to communicate with before and during our stay."
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Outdoor pool

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

10.0 out of 10, Exceptional, (99)
"The location and views were absolutely spectacular! Alessandro was EXTREMELY helpful and accommodating. He helped arrange for chef and wine tasting at the villa and they were memorable. "
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Outdoor pool

Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

10.0 out of 10, Exceptional, (8)
"Fabulous place to stay with a big group of family and friends. Very easy walk to town and the beautiful treasures of Siena."
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Exterior

BEAUTIFUL VILLA with private Pool in the heart of Chianti

10.0 out of 10, Exceptional, (26)
"Great villa great view fantastic hostage "
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Outdoor dining

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

10.0 out of 10, Exceptional, (103)
"Property was fantastic, easily accommodated our group of 9 people. Francesca took very good care of us, arranging wine tours, dinners at the house and a cooking class which we thoroughly enjoyed. I highly recommend this place"
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool
Exterior

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

10.0 out of 10, Exceptional, (55)
"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!"
Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
Property grounds

Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa

10.0 out of 10, Exceptional, (42)
"What an amazing week at Villa Sarah! Every aspect, from the house to the view to the surroundings and to our gracious hosts exceeded our expectations. If there were 10 stars, we would give it 10 stars!"
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
Villa Costa, Stunning Villa in the heart of Tuscany.
Exterior

Villa Costa, Stunning Villa in the heart of Tuscany.

10.0 out of 10, Exceptional, (36)
"You have all the amenities of a large, historic villa - and also the real farmland all around you. Sheep, horses, dogs - beautiful, and not in your personal space (unless you want them to be!). Pasqualina and her son Francesco are perfect hosts. Incredibly responsive, even with a language barrier. If I return to Tuscany I would want to stay here again. Thank you so much."
Villa Costa, Stunning Villa in the heart of Tuscany.
WP Relais Villa Vignalunga in Val d'Orcia,luxurious estate with swimming pool
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (50)
"We loved our stay. The Villa was gorgeous and Gaia was very responsive to any questions we had."
WP Relais Villa Vignalunga in Val d'Orcia,luxurious estate with swimming pool
Villa with private pool, air conditioning near wineries at 3km from village
Outdoor dining

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

9.4 out of 10, Exceptional, (44)
"Guido’s home in Tuscany is great! My family had an awesome time enjoying the pool, the near by wineries and a cooking class at the villa. The house is rustic, charming and in a great location. The beds are a bit old and the showers were a little small but overall the house fit all the needs of my family. The pool was also excellent and the views from the pool area are incredible. Whenever we needed anything it was always answered quickly. Thanks for an awesome stay!"
Villa with private pool, air conditioning near wineries at 3km from village
Winery Villa in the heart of Nobile Vineyards.
Outdoor dining

Winery Villa in the heart of Nobile Vineyards.

10.0 out of 10, Exceptional, (14)
"We had an incredible time staying at this beautiful villa for 5 nights. Very well appointed couldn’t ask for more! Fantastic location quiet and serene located on a vineyard yet only 5 minute drive to lovely town. Christian was a wonderful host even taking the time to give us a tour of the winery. Would stay there again! Highly recommend the property!"
Winery Villa in the heart of Nobile Vineyards.
Luxury Villa Basilio Chianti
Seasonal outdoor pool

Luxury Villa Basilio Chianti

Luxury Villa Basilio Chianti
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor pool

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

10.0 out of 10, Exceptional, (84)
"Lovely villa in a beautiful location. "
Villa in Montalcino, exclusive for you, stunning view!!!
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Exterior

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

10.0 out of 10, Exceptional, (63)
"We had a company retreat at this amazing location. Everyone was in love with the place and the facilities!"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Hilltop house in the heart of Tuscany with private pool
Outdoor dining

Hilltop house in the heart of Tuscany with private pool

9.8 out of 10, Exceptional, (92)
"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."
Hilltop house in the heart of Tuscany with private pool
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (63)
"The property was magical. Every morning coffee overlooking the rolling hills, sitting at the patios or by the pool. The house was full of paintings made by one of the hosts. These added to the beauty!!Gaia was wonderful . So helpful and kind. She went the extra miles. Her husband, a capable chef, cooked an incredible Italian dinner at the Villa. We recommend using him for an Italian dinner.I would recommend this Villa with the highest recommendation. "
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Exterior

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

10.0 out of 10, Exceptional, (56)
"The house was fantastic and had more than enough space for our large family. What was particularly great was the large table where we always ate before we went to the very large swimming pool."
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
Pool

Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany

10.0 out of 10, Exceptional, (80)
"Great place. Great host Driveway….needs work "
Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
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

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"Stayed a very enjoyable three nights. Double room w/ garden view. “garden view” yes but also a stunning view of the Tuscan countryside. Breakfast buffet was bountiful and offered many options. Would stay again in a heartbeat!"
clyde 3-night trip
Posted 3 days ago
Palazzo Ravizza

Find out more about Province of Siena

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
820
Accommodation
1233 Villas
Lowest Price
Highest Price

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