Val d'Orcia Holiday Rentals

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Check prices for these dates

Tonight
13 Dec - 14 Dec
Tomorrow
14 Dec - 15 Dec
Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec

Our top choices for Val d'Orcia holiday rentals

Food and drink
Hotel San Gregorio

Residence in Pienza

Hotel San Gregorio
3.0 star property
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is HK$1,576
HK$1,789 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio
Pool
Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Villa in Siena

Private and cozy retreat in Montalcino with private pool surrounded by vineyards
9.4 out of 10, Exceptional, (67)
"What a lovely place, I will recommend this fabulous home to friends and family and will be returning sometime soon."
United Kingdom
peter H.
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
1 treatment room, massages
Casanova - Panoramic Rooms and Suites

Residence in San Quirico d'Orcia

Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
The price is HK$1,758
HK$1,971 total
includes taxes & fees
26 Dec - 27 Dec
Casanova - Panoramic Rooms and Suites
Property grounds
The House of Alice, charm and relaxation

Holiday Home in Montalcino (SI)

The House of Alice, charm and relaxation
9.8 out of 10, Exceptional, (66)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
The price is HK$1,371
HK$1,855 total
includes taxes & fees
11 Jan - 12 Jan 2026
The House of Alice, charm and relaxation
Dining
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.

Villa in Castiglione d'Orcia

Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
9.8 out of 10, Exceptional, (12)
"This lovely, sprawling farm house in the Val d’Orcia has plenty of space for a large family gathering, with six bedrooms, a gorgeous barbecue and swimming pool. Excellent spot from which to explore hill towns, visit wineries, and eat some excellent Tuscan cuisine. Don’t miss the hot springs at Bagni San Filippo! "
United States
Andrew P.
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
Terrace/patio
Antico Brunello

Villa in Montalcino

Antico Brunello
The price is HK$60,304
HK$66,425 total
includes taxes & fees
14 Dec - 15 Dec
Antico Brunello
View from room
Sarna Residence

Residence in San Quirico d'Orcia

Sarna Residence
9.6 out of 10, Exceptional, (38)
"We enjoyed our stay. The room was very clean. The staff was helpful."
United States
Bokang
The price is HK$814
HK$1,005 total
includes taxes & fees
19 Dec - 20 Dec
Sarna Residence
Outdoor dining
Charming apartment in the historic center with large terrace and beautiful view

Apartment in Montalcino

Charming apartment in the historic center with large terrace and beautiful view
8.0 out of 10, Very good, (1)
"Appartamento vecchio stile ma molto spazioso e con tutto quello che serve, posizione ottima "
Italy
Marco R.
The price is HK$905
HK$1,572 total
includes taxes & fees
19 Dec - 20 Dec
Charming apartment in the historic center with large terrace and beautiful view
Property grounds
VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino

Villa in Montalcino

VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
The price is HK$54,365
HK$58,933 total
includes taxes & fees
14 Dec - 15 Dec
VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
Dining
'...a delicious farmhouse in the countryside where only the wind blows...'

Villa in Campiglia d'Orcia

'...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...
United States
Li-Shen L.
The price is HK$8,680
HK$14,190 total
includes taxes & fees
15 Dec - 16 Dec
'...a delicious farmhouse in the countryside where only the wind blows...'
Exterior
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool

Villa in Pienza

Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
10.0 out of 10, Exceptional, (5)
"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."
United Kingdom
Richard N.
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
Dining
Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany

Villa in Pienza

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!"
United States
julie l.
Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany
Exterior detail
Independent house in the historic center

Holiday Home in CASTIGLIONE D'ORCIA

Independent house in the historic center
9.4 out of 10, Exceptional, (9)
"Stayed here during the Tuscany Trail and was perfect for 4 of us. Centre of town and a great restaurant recommendation too! "
United Kingdom
Graham S.
The price is HK$1,316
HK$1,544 total
includes taxes & fees
14 Dec - 15 Dec
Independent house in the historic center
Outdoor dining
Samsara Apartment elegant apartment in the historical center.

Apartment in Pienza

Samsara Apartment elegant apartment in the historical center.
Samsara Apartment elegant apartment in the historical center.
Property grounds
Splendid farmhouse in Val d'Orcia with private swimming pool and sauna

Holiday Home in Toscana

Splendid farmhouse in Val d'Orcia with private swimming pool and sauna
10.0 out of 10, Exceptional, (11)
"We enjoyed a relaxing time at you house. Close to a lot of nearby activities. "
United States
Michael B.
Splendid farmhouse in Val d'Orcia with private swimming pool and sauna
Terrace/patio
WP Relais Villa Vignalunga in Val d'Orcia,luxurious estate with swimming pool

Villa in CASTIGLIONE D'ORCIA (SI)

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."
United States
Teresa P.
WP Relais Villa Vignalunga in Val d'Orcia,luxurious estate with swimming pool
Exterior
House in Val d'Orcia perfect for relaxation CIN IT052024C2APXZK7PD

Holiday Home in RADICOFANI

House in Val d'Orcia perfect for relaxation CIN IT052024C2APXZK7PD
9.6 out of 10, Exceptional, (49)
"Beautiful home and location. Silvano is excellent host."
United States
David M.
House in Val d'Orcia perfect for relaxation CIN IT052024C2APXZK7PD
Exterior detail
Finestra Dell'Angelo

Apartment in Pienza

Finestra Dell'Angelo
10.0 out of 10, Exceptional, (1)
"Our family of twelve, aged 8 to 80 years, stayed in three separate apartments. Two were in the same building on separate floors, and the third was a 5 minute walk away. All units were located in beautiful downtown Pienza with many dining, shopping and tourist sites within an easy walk for all members of the family. For a family of Midwest Americans staying in the middle of an old city walkable to nearly everything was w amazing. The separate units worked out fine for us as walking the town was...
United States
James M.
Finestra Dell'Angelo
Interior
Villa I Cipressini Tuscany Private luxury pool spa

Holiday Home in Pienza

Villa I Cipressini Tuscany Private luxury pool spa
10.0 out of 10, Exceptional, (57)
"Beautiful villa in a beautiful setting, walkable to Pienza and overall great stay."
United States
leigh t.
Villa I Cipressini Tuscany Private luxury pool spa
An infinity pool
LA PALAZZINA - LA PALAZZINA IN VAL D'ORCIA

Villa in Radicofani

LA PALAZZINA - LA PALAZZINA IN VAL D'ORCIA
10.0 out of 10, Exceptional, (1)
"Ein außergewöhnliches Erlebnis in der Palazzina in Val d’Orcia“Wir hatten die große Freude, eine unvergessliche Woche in der wundervollen La Palazzina in Val d’Orcia zu verbringen – einer authentischen toskanischen Villa aus dem 18. Jahrhundert, umgeben von der üppigen Natur und den sanften Hügeln des Val d’Orcia, eingebettet in einen romantischen Park aus Steineichen und Zypressen.Wir waren eine fröhliche Gruppe von 23 Freunden, Erwachsene und Kinder, und wurden von Nicoletta und ihrem Team vom...
Germany
Ulrich K.
LA PALAZZINA - LA PALAZZINA IN VAL D'ORCIA
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

Villa Le Prata - Residenza del Vescovo

Villa Le Prata - Residenza del Vescovo

10/10 Excellent
"We had a lovely stay here. It's a short drive from town and a beautiful property. We did a wine tasting of the delicious estate wines and a cooking class as well. The room is spacious, comfortable, and well decorated. The staff is really attentive and took great care of us, giving us advice on where to go, helping us get the car to town and make reservations, etc. We used the hot tub which was fantastic. Thanks for a great relaxing stay!"
Marysa 3-night trip
Posted 5 days ago
Villa Le Prata - Residenza del Vescovo

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