
Villa vacation 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.

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

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 95mq
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 the 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.

In a sunny, quiet and rustic area.
The villa is located between Anghiari and Arezzo in a sunny area, absolutely quiet, with a beautiful and panoramic view on the surrounding hills. Through the accurate restoration, the house is well equipped to ensure to just a few guests absolute confidentiality, independent and comfortable stay. Exposed to the south, with independent entrance and direct access to the garden that's exclusively for our guests. Please enjoy yourself.

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.

Villa La Doccia, Greve in Chianti
Villa la Doccia is an 8-minute drive from the center of Greve in Chianti, Località Casole, The Villa in a quiet and quiet area is located inside a small farm surrounded by vineyards and olive groves. ➡️ We want you to know that we're doing everything we can to help and protect our guests by adopting a thorough and strict cleaning approach to this emergency. We disinfect and sanitize all parts of the house.

"Villa Daisy" overlooking Siena
Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Villa Poggio in Mandria in Chianti
Villa Poggio a Mandria is the gateway to the Chianti; it is a good base to reach the most beautiful art cities of Tuscany (Arezzo, Florence, Siena, San Gimignano, Volterra) in about one hour time. On the surrounding hills there are medieval villages, which offer visitors a charming atmosphere of the past and the opportunity to take walks in an unspoiled countryside.
Popular amenities for Montalcino villa rentals
Private villa rentals

Vakantievilla Farmhouse Dolci Hills

Sestuccina

Valluccia 51

Montemarcoli

Villa with garden. The Cardinal's Garden.

Beautiful Country House, near Siena with jacuzzi

Il Casale Di Manuele 12, Emma, Villas

Exclusive villa with pool jacuzzi wifi and green
Luxury villa rentals

Tuscany Villa Mammi

Villa with pool in Chianti Area

Fabulous Farmhouse with Pool & 360 Panoramic View

Magical Family Retreat

Casale La Querce-Tuscan Farmhouse with pool & view

Luxury Villa in the very heart of Chianti

Villa in Montepulciano with a Pool

Villa in Chianti: Swimming Pool and Beach Bar
Villa rentals with a pool

Case Bianchi

Country Charm & Jacuzzi

Romantic Villa with private pool - "Il Pollaio"

Sasso Canaldo: Elegant Tuscan farmhouse

Casa al Fiume - Villa with exclusive pool

Stunning house with pool, privacy and views

Unique Villa in Tuscany

Charming stone house with pool
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$128,036 GYD | G$162,291 GYD | G$132,422 GYD | G$135,347 GYD | G$153,727 GYD | G$186,519 GYD | G$196,963 GYD | G$176,076 GYD | G$159,993 GYD | G$124,277 GYD | G$126,992 GYD | G$130,334 GYD |
| 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 vacation rentals
Explore 100 vacation rentals in Montalcino

Nightly prices starting at
Montalcino vacation rentals start at G$14,621 GYD per night before taxes and fees

Verified guest reviews
Over 1,310 verified reviews to help you choose

Family-friendly vacation rentals
90 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Vacation rentals with a pool
80 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
90 of Montalcino vacation rentals include wi-fi 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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- Lake Trasimeno
- Lake Bolsena
- Feniglia
- Cala Violina
- Gulf of Baratti
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Tenuta Le Velette
- Cala di Forno
- Castiglion del Bosco Winery
- Golf Club Toscana
- Riva del Marchese
- Spiaggia di Marina di Grosseto
- Santa Maria della Scala
- Cavallino Matto
- Palazzo Pubblico
- CavallinoMatto
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Podere La Marronaia, Sosta alle Colonne
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Madonna del Latte
- Podere Il Cocco
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