
Villa holiday rentals in Montalcino
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Top-rated villa rentals in Montalcino
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Manor House - IlVillinoFarmhouse
Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Cottage in Val d'Orcia Tuscany, Jacuzzi & Hot Tub!
Welcome at Charming Cottage in Tuscan Villa! Immerse in the history of Montepulciano, Pienza, Cortona, Siena, Explore Val d'Orcia, natural hot pools and falls! Fully equipped kitchen, private patio for al fresco dining, magnificent bathroom with large Jacuzzi, and large bedroom with new top quality, Memory foam mattress. Thanks to thick walls, it's very cool in summer! We arrange Winery tours & tasting and cooking class. A/C, Free wifi, comfy sitting and sofas and Hot Tub with great view!

Wine Experience Villa in Montepulciano
🏡 Villa Talosa è immersa nei vigneti della Fattoria della Talosa, storica azienda vitivinicola di Montepulciano produttrice di Vino Nobile. Un luogo autentico, ideale per rilassarsi con la magia della campagna toscana e una vista incantevole da ogni finestra. A soli 1,5 km dal centro storico, raggiungibile anche a piedi, potrete visitare la nostra Cantina Storica del 1500 sotto Piazza Grande: un’esperienza unica tra storia, passione per il vino. Riscaldamento e aria condizionata sono inclusi.

Tuscan charm of villa - countryside
Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Virgi House
Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

Belforti Tower
Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

San Giovanni in Poggio, Villa Meriggio 95 sqm
Detached house, two double bedrooms, two bathrooms with shower, living room with fully equipped kitchen (dishwasher, washing machine, oven, microwave), double sofa bed, private garden with equipped pergola. Satellite TV and free Wi-Fi. Additional services at the property, upon reservation, include Focus brand Jarifa2 6.7 pedal-assisted bicycles and a wellness area with a Forest outdoor Finnish sauna and a heated mini-pool with hydromassage and chromotherapy with panoramic views.

A paradise in Montepulciano...
Villa Il Cubo has a large private park and swimming pool and marvellous views on the Tuscan countryside. It is fully air-conditioned and the decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point at a moderate extra contribution. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY.

Stone farmhouse in Val D'Orcia
19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.

Villa unesco heritage, Jacuzzi & garden. BB Daria
Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant

The Tower
Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.
Popular amenities for villa rentals in Montalcino
Private villa rentals

Tuscan Villa Pienza: stunning views and pure relax

Fattoriafontenovo, country house Perugia Umbria

Podere la Piscina Termale – RestArt

Romantic Villa with private pool - "Il Pollaio"

The Lazy Oak

Villa Blue Melon - private beach

Villa with garden. The Cardinal's Garden.

Country house, private garden, pool by Vacavilla
Luxury villa rentals

Villa Le Murate

Villa in Montepulciano with a Pool

Poggio Novoli 6, Emma Villa

CHARMING TUSCANY VILLA PRIVATE POOL

Riecine Capanna 4

Poggio del Fattore-Villa with pool, hilltop, Chianti

The Villa of the Spendthrift Brigade!

Casa Baiocco Private Villa heated pool and Jacuzzi
Villa rentals with a pool

Tuscany Villa Mammi

Fabulous Farmhouse with Pool & 360 Panoramic View

Casale La Querce-Tuscan Farmhouse with pool & view

Country Charm & Jacuzzi

Montemarcoli

Podere on the Crete Senesi

Villa la Chiusa- con piscina e aria condizionata

Private Villa with semi-Olympic pool and Tennis
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $786 SGD | $997 SGD | $813 SGD | $831 SGD | $944 SGD | $1,145 SGD | $1,209 SGD | $1,081 SGD | $982 SGD | $948 SGD | $1,225 SGD | $1,258 SGD |
| Avg. temp | 8°C | 8°C | 11°C | 13°C | 18°C | 22°C | 25°C | 25°C | 21°C | 17°C | 12°C | 9°C |
Quick stats about villa rentals in Montalcino

Total holiday rentals
Explore 90 holiday rentals in Montalcino

Nightly prices starting at
Montalcino holiday rentals start at $141 SGD per night before taxes and fees

Verified guest reviews
Over 1,280 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Holiday rentals with a pool
80 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
90 of Montalcino holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Montalcino rentals

4.9 Average rating
Montalcino stays are highly rated by guests – averaging 4.9 out of 5!
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- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Del Chianti
- Lake Bolsena
- Cala Violina
- Feniglia
- Cascate del Mulino
- Gulf of Baratti
- Avignonesi Winery Fattoria Le Capezzine
- CavallinoMatto
- Santa Maria della Scala
- Palazzo Pubblico
- Ugolino Golf Club
- Siena Cathedral
- Antinori nel Chianti Classico
- Casa Barthel
- Riserva Naturale Diaccia Botrona
- Abbey of Monte Oliveto Maggiore
- Castello di Verrazzano
- Parco Regionale Della Maremma
- Pozzo di San Patrizio
- Girifalco Fortress
- Cathedral of San Lorenzo
- Rimigliano Natural Park
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