
House holiday rentals in Montalcino
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Top-rated house rentals in Montalcino
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Casa al Gianni - The Simignano Barn
Converted from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this little slice of paradise!

Montalcino - Casa Gelsomino - garden and relaxation
Immerse yourself in the charm of Montalcino by staying in this enchanting stone vacation home with a private garden, ideal for relaxing moments. Right in the historic center, it offers an authentic and welcoming atmosphere, perfect for exploring the wonders of Tuscany. Take advantage of the central location to visit renowned wineries and enjoy delicious Tuscan cuisine. Discover the wonders of Val d'Orcia, a UNESCO heritage site, and let yourself be captivated by ancient local culture and tradition.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Vineyards Paradise
Amazing country house immersed in the vineyard of Cantina Lapone, viewing Orvieto. Recently restored, over 100 sm, organised on two floors. Ground floor is a single space with a big living room (with fireplace) and a spacious open kitchen. First floor with two bedrooms and two bathrooms: the main bedroom (looking at Orvieto) with a double bed and internal bathroom and a second one with a double bed and a bed sofa. Private garden and parking. Private pool (shared with another 4 guests house).

The Chianti Classico Sunset
Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Casa Dolce Toscana | Panoramic Suite with a View
CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.

Apartment in a detached villa - Val d'Orcia
In a cozy independent villa in Tuscan style apartment recently and finely renovated and located in a land rich in history. A few kilometres from the city of art and on the Via Francigena, the apartment can be a base for nature or food and wine tours. From a beautiful terrace overlooking the view you can enjoy your meals, admire the sunset and observe the majestic and magnificent medieval Rocca From 22/03/18, a municipal tourist tax of €2 per person will be charged. See additional notes

Il Fienile, Luxury Apartment in the Tuscan Hills
‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni
Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

The Chianti window
A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.

Casa delle Giuggiole
Facing the old medieval walls of this ancient city, the location of the house will make you feel relaxed thanks to the peacefulness of the countryside and the vitality of the centre. Bathed in the gorgeous sunlight from sunrise to sunset, Casa delle Giuggiole will give you a sensation of lightness and freedom. Look through any one of the many windows and you can admire both the astonishing landscape of the Val d'Orcia and the typical Tuscan roofs.
Popular amenities for house rentals in Montalcino
House rentals with a pool

S.Ilaria - Private pool Villa with 2 bedrooms

Casa Lucy

Cercis - La Palmierina

Ancient Barn in Chianti with Pool

Private villa/swimming pool in Tuscany

Antico Borgo Ripostena – n. 5 Garage

Country chic house in a village,private pool,wiFi

Luxury Villa with a fantastic view
Weekly house rentals

City Center Palazzo: 4 King BR 6 Bath and Garage

Stunning loft in Montalcino.

Bel Casale with sea view and the mediaeval village

Pienza Center - Stylish Apt, 6 Guests, A/C & WiFi

Domus Antiqua

NEW Panoramic loft with garden in Montalcino

Wine House

Poggiolo
Private house rentals

Hidden gem in Tuscany

Family Forest - Pool in the Crete Senesi

Casa Olivo | Il Fossaccio Farm

Private Cottage with Plunge Pool in Tuscan Estate

Borgo71 - In the Heart of the Val d'Orcia

Dream villa in Chianti with panoramic garden

Casa San Ripa: Relax Oasis with Private Pool

Relaxation and charm in the Chianti hills
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £99 | £108 | £112 | £123 | £125 | £142 | £131 | £135 | £131 | £121 | £120 | £122 |
| 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 house rentals in Montalcino

Total holiday rentals
Explore 160 holiday rentals in Montalcino

Nightly prices starting at
Montalcino holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 3,740 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 80 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
150 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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- 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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