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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Villas in Val d'Orcia and around

Our top choices for Val d'Orcia villas

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

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

9.4 out of 10, Exceptional, (61)
"We wanted to enjoy the Tuscany area and this house checked all the boxes for us. The photos can’t actually capture the true beauty of this place. The host, Camilla was so gracious and kind. Comfortable bed, kitchen well stocked with the dishes we needed. Full size refrigerator was nice too! It’s a little bit of a drive to the property but oh so worth it! "
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
Dining

Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.

9.8 out of 10, Exceptional, (10)
"We stayed together with children and grandchildren and had a great stay. The house and grounds were beautiful and well kept and we had everything needed."
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
Casale Donatelli - Five Bedroom Villa, Sleeps 10
Pool

Casale Donatelli - Five Bedroom Villa, Sleeps 10

10.0 out of 10, Exceptional, (8)
"A well-maintained and comfortable villa - a perfect stay."
Casale Donatelli - Five Bedroom Villa, Sleeps 10
Wonderful private villa with WIFI, private pool, A/C, panoramic view, parking, close to Montalcino
Exterior

Wonderful private villa with WIFI, private pool, A/C, panoramic view, parking, close to Montalcino

9.8 out of 10, Exceptional, (23)
"Wij hebben een supervakantie gehad! Zeer warm ontvangen door de huiseigenaren Luc en Jacqueline. Wat hebben ze er een prachtig huis van gemaakt oud en modern door elkaar heen zeer mooi!!! Zwembad was ook erg lekker en groot! Prachtige omgeving ook!"
Wonderful private villa with WIFI, private pool, A/C, panoramic view, parking, close to Montalcino
Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany
Outdoor pool

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

9.6 out of 10, Exceptional, (17)
"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!"
Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany
Villa Mealli Large Private Pool, WiFi
Exterior

Villa Mealli Large Private Pool, WiFi

9.2 out of 10, Wonderful, (12)
"A wonderful experience from start to finish!"
Villa Mealli Large Private Pool, WiFi
LA PALAZZINA - LA PALAZZINA IN VAL D'ORCIA
An infinity pool

LA PALAZZINA - LA PALAZZINA IN VAL D'ORCIA

LA PALAZZINA - LA PALAZZINA IN VAL D'ORCIA
VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
Pool

VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino

The price is €6,450
includes taxes & fees
5 Sept - 6 Sept
VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
Affittacamere Maria Gabriella, B&B and Holiday Home in Val d'Orcia
Outdoor dining

Affittacamere Maria Gabriella, B&B and Holiday Home in Val d'Orcia

9.8 out of 10, Exceptional, (39)
"Guido and family were the perfect hosts! This property is not only well kept, it's in a beautiful place in the Italian countryside. Highly recommend this property! "
Affittacamere Maria Gabriella, B&B and Holiday Home in Val d'Orcia
'...a delicious farmhouse in the countryside where only the wind blows...'
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (7)
"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...
'...a delicious farmhouse in the countryside where only the wind blows...'
Iperbole country house, between Pienza and Montepulciano
Outdoor pool

Iperbole country house, between Pienza and Montepulciano

10.0 out of 10, Exceptional, (11)
"We had the best time at the Iperbole Country House. The pictures do not even begin to explain the incredible views! Olivia was the an incredible host who helped us with anything we needed!"
Iperbole country house, between Pienza and Montepulciano
WP RELAIS BORGO VIGNALUNGA, 46 HECTARES OF LAND IN THE HEART OF VAL D'ORCIA
Outdoor pool, a heated pool

WP RELAIS BORGO VIGNALUNGA, 46 HECTARES OF LAND IN THE HEART OF VAL D'ORCIA

10.0 out of 10, Exceptional, (36)
"This villa is amazing! The views are spectacular. The home is awesome! The property is beautiful! "
WP RELAIS BORGO VIGNALUNGA, 46 HECTARES OF LAND IN THE HEART OF VAL D'ORCIA
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
Outdoor pool, pool loungers

Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool

10.0 out of 10, Exceptional, (2)
"Beautiful villa in fantastic location . Easy to get to many places and attractions. Well equipped and very comfy beds. Lovely helpful owner. Would love to return."
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
Villa with private pool, hot tub, air conditioning, Wi-fi in Val d'Orcia.
Property grounds

Villa with private pool, hot tub, air conditioning, Wi-fi in Val d'Orcia.

9.0 out of 10, Wonderful, (9)
"Beautiful location and fabulous scenery. Having air conditioning in every room made our stay so comfortable. The pool area is lovely with ample shade. The house is probably more suited to a smaller group as there isn't enough comfortable seating inside or loungers outside for ten adults. There was an issue with the jacuzzi which couldn't be resolved while we were there which was disappointing. Overall we had a wonderful time in this villa."
Villa with private pool, hot tub, air conditioning, Wi-fi in Val d'Orcia.
Villa San Michele - Villa with swimming pool in Orcia Valley, Tuscany
Pool

Villa San Michele - Villa with swimming pool in Orcia Valley, Tuscany

10.0 out of 10, Exceptional, (29)
"Easy to reach, friendly owner and offers everything to make you feel at home."
Villa San Michele - Villa with swimming pool in Orcia Valley, Tuscany
Antico Convento I Cappuccini - Villa & Wedding Venue
Pool

Antico Convento I Cappuccini - Villa & Wedding Venue

10.0 out of 10, Exceptional, (3)
"Very nice Villa, spacious, well kept, in a quiete place in the middle of the forest but close the most beautiful towns in Tuscany. The manager is the kindest person. Huge swimming pool. Ideal for families."
Antico Convento I Cappuccini - Villa & Wedding Venue
Farmhouse 'Villa Agriturismo Il Pratone' with Mountain View, Private Pool and Wi-Fi
Pool

Farmhouse 'Villa Agriturismo Il Pratone' with Mountain View, Private Pool and Wi-Fi

9.6 out of 10, Exceptional, (5)
"Pros: Ein sehr netter Gastgeber, ein tolles Haus mit Charme der Toskana. Wir hatten eine sehr schöne Zeit! Cons: Die Elektrik funktioniert nicht immer tadellos und die Geräte sind z.T. Veraltet oder leicht defekt."
Farmhouse 'Villa Agriturismo Il Pratone' with Mountain View, Private Pool and Wi-Fi
Villa Pernice: An elegant and welcoming two-story villa surrounded by the greenery, with Free WI-FI.
Property grounds

Villa Pernice: An elegant and welcoming two-story villa surrounded by the greenery, with Free WI-FI.

10.0 out of 10, Exceptional, (1)
"Lovely stay for a party of 10. Spacious, peaceful, and quiet. Super easy checkin/checkout process. The entire Summer in Italy team was extremely responsive and helpful in coordinating extras like a private chef dinner. Recommend! Great experience, thank you!"
Villa Pernice: An elegant and welcoming two-story villa surrounded by the greenery, with Free WI-FI.
Large Tuscany Villa rental near Pienza - southern Tuscany
Interior

Large Tuscany Villa rental near Pienza - southern Tuscany

10.0 out of 10, Exceptional, (3)
"This is the quintessential Tuscan farmhouse experience. The location, just outside the beautiful village of Monticchiello, with perfect sunset views of the Val d’Orcia, can’t be beat. The house is large and could have easily accommodated a group much bigger than ours (6 people), but was cozy enough for my two young boys to be comfortable. We didn’t have the chance to use it, but the pool, bread/pizza oven, and wood fire grill all looked great. Check-in and check-out were very easy, and Serena is...
Large Tuscany Villa rental near Pienza - southern Tuscany
Wonderful private villa for 10 people with A/C, WIFI, private pool, TV, patio and parking
Pool

Wonderful private villa for 10 people with A/C, WIFI, private pool, TV, patio and parking

10.0 out of 10, Exceptional, (8)
"Villa Lorian is a lovely villa well positioned in the heart of the Brunello wine region. The villa is well appointed with many antique pieces, plenty of room for privacy among fellow travelers, and great larger areas to assemble comfortably as well. We enjoyed the pool which is very refreshing after a day of sight-seeing. The highlight of Villa Lorian is Mari who helps guests feel welcomed and assists with any needs. Mari is a wonderful cook and makes your experience at Villa Lorian extra...
Wonderful private villa for 10 people with A/C, WIFI, private pool, TV, patio and parking
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 Val d'Orcia Hotel Reviews

SI Montalcino Hotel

SI Montalcino Hotel

10/10 Excellent
"Loved the staff so much!!!!! Amazing people"
Melissa 4-night trip
Posted 3 days ago
SI Montalcino Hotel

Frequently asked questions

How much do villas in Val d'Orcia cost?
Expect to pay between €6,450 and €6,450 per night for villas in Val d'Orcia. Whatever your budget, a perfect getaway is only a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Val d'Orcia?
Take your pick of 137 villas in Val d'Orcia. Whether you're travelling with the little ones or planning a weekend escape with your pals, Expedia will help you find the best space for your crew.
Why book your villa in Val d'Orcia with Expedia?
Booking a villa in Val d'Orcia is as simple as clicking on your travel dates and choosing an option that meets your needs. Want something budget friendly or upmarket, or a stay that also offers free WiFi? Use Expedia's search filters to narrow your results and find your perfect match.