
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

Tuscan Villa for Family & Friends in Montepulciano
Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visit & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

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.

Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

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

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.

Villa La Doccia, Greve in Chianti
Villa La Doccia is located approximately 8 minutes by car from the centre of Greve in Chianti, in the area of Casole, in the heart of the beautiful Chianti countryside. The villa is located in a quiet, peaceful area, on a small farm surrounded by vineyards and olive groves, where guests can enjoy nature and the typical Tuscan landscape. The location is ideal for those who want to relax in the countryside while also being close to the centre of Greve in Chianti.

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

Tuscany View - Villa Arianna
This beautiful villa, which can accommodate up to ten (10) people, will provide an unparalleled Tuscan experience. While positioned perfectly to allow easy access to the most beautiful towns and villages of southern/central Tuscany (such as Arezzo, Florence, Siena, Cortona, Montepulciano) and northern Umbria (such as Perugia, Orvieto, Assisi); you’ll find this villa offers complete privacy as well as a sense of peace and tranquility to all who visit.

Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.
Popular amenities for villa rentals in Montalcino
Private villa rentals

Tuscan retreat surrounded by peace and nature

Stunning Tuscan Villa & Panoramic Infinity Pool

Villa Le Murate

Luxury Villa in the very heart of Chianti

Country Charm & Jacuzzi

Villa with garden. The Cardinal's Garden.

The twigs

Villa la Chiusa – private pool – air conditioning
Luxury villa rentals

Tuscany Villa Mammi

Fabulous Farmhouse with Pool & 360 Panoramic View

Vakantievilla Farmhouse Dolci Hills

Tenuta Virgilio nel Chianti – natural pool – privacy

Romantic Villa with private pool - "Il Pollaio"

The Lazy Oak

Beautiful and cozy country-house, sleeps 11

Historic Villa Getaway with 6BR/9BA, Pool, Views
Villa rentals with a pool

Beautiful villa with swimming pool in Tuscany

Casale La Querce-Tuscan Farmhouse with pool & view

San Giovanni in Poggio, Villa Meriggio 95 sqm

Villa with panoramic pool • Lake Trasimeno

Chianti Villa | Garden & Panoramic Pool

Casa Baiocco Private Villa heated pool and Jacuzzi

Luxurious Villa near village, 10 persons

"La Capanna di Neri" stone farmhouse with swimming pool
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £453 | £574 | £469 | £479 | £544 | £660 | £697 | £623 | £566 | £546 | £706 | £725 |
| 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 80 holiday rentals in Montalcino

Nightly prices starting at
Montalcino holiday rentals start at £74 per night before taxes and fees

Verified guest reviews
Over 1,440 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Holiday rentals with a pool
70 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
80 of Montalcino holiday rentals include wifi access

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

4.8 Average rating
Montalcino stays are highly rated by guests – averaging 4.8 out of 5!
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- Lake Trasimeno
- Lake Bolsena
- Del Chianti
- Cala Violina
- Cascate del Mulino
- Feniglia
- Basilica Di San Miniato A Monte
- Gulf of Baratti
- Avignonesi Winery Fattoria Le Capezzine
- Palazzo Pubblico
- CavallinoMatto
- Santa Maria della Scala
- Ugolino Golf Club
- Castello di Verrazzano
- Antinori nel Chianti Classico
- Siena Cathedral
- Parco Regionale Della Maremma
- Abbey of Monte Oliveto Maggiore
- Casa Barthel
- Cathedral of San Lorenzo
- Saturnia Thermal Park
- La Scarzuola
- Val di Chiana
- Rimigliano Natural Park
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- Things to do Siena
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