
Villa holiday rentals in Montalcino
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Top-rated villa rentals in Montalcino
Guests agree: these villas are highly rated for location, cleanliness and more.

The Farmhouse Cottage
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!

Poggio del Fattore-Villa with pool, hilltop, Chianti
Poggio del Fattore is situated at the eastern edge of the Chianti region in Valdambra, a green valley that joins the lands of Florence, Siena and Arezzo. The farmstead is on the top of an hill and lies at the end of a long private road through a large olive growing estate; therefore you absolutely need a car. The breathtaking landscapes and the location of the villa offer the privacy needed for a peaceful and relaxing holiday and a perfect departure point from which to explore central Tuscany.

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.

A paradise in Montepulciano...
Villa Il Cubo is a full centralized air conditioned private house with large private swimming pool placed in the best garden spot for incredible views on the countryside around. Decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY!!!!!!

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.

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

Villa Isabella
Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.
Popular amenities for villa rentals in Montalcino
Private villa rentals

Case Bianchi

Podere on the Crete Senesi

The Furnace

Beautiful Country House, near Siena with jacuzzi

L’Apparita del Peruzzi: pool super view save30%7d+

Villa Feronia – Heated Pool & Rooftop Escape

Country house, private garden, pool by Vacavilla

Villa al Pozzo, five bedrooms villa in Tuscany
Luxury villa rentals

Tuscan Villa Pienza: stunning views and pure relax

Stunning Tuscan Villa & Panoramic Infinity Pool

Fabulous Farmhouse with Pool & 360 Panoramic View

Villa Le Murate

Vakantievilla Farmhouse Dolci Hills

Luxury Villa in the very heart of Chianti

The Lazy Oak

Tuscany View - Villa Arianna
Villa rentals with a pool

Tuscany Villa Mammi

Sestuccina

Country Charm & Jacuzzi

Villa privata in Chianti · Piscina e natura

La Vignaccia (Farmhouse) - villa w/private pool

Sasso Canaldo Elegante casale toscano

Montemarcoli

Villa Fortuna with Hot-Tub and pool near Tuscany
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $782 SGD | $991 SGD | $809 SGD | $827 SGD | $939 SGD | $1,139 SGD | $1,203 SGD | $1,075 SGD | $977 SGD | $943 SGD | $1,218 SGD | $1,251 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 $140 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
- Siena Cathedral
- Gulf of Baratti
- Cascate del Mulino
- Avignonesi Winery Fattoria Le Capezzine
- Palazzo Pubblico
- Santa Maria della Scala
- CavallinoMatto
- Ugolino Golf Club
- Casa Barthel
- Saturnia Thermal Park
- Antinori nel Chianti Classico
- Abbey of Monte Oliveto Maggiore
- Riserva Naturale Diaccia Botrona
- Vulci
- Val di Chiana
- Pozzo di San Patrizio
- Abbazia di San Galgano
- Abbey of Sant'Antimo
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