
House holiday rentals in Montepulciano
Find and book unique houses on Airbnb
Top-rated house rentals in Montepulciano
Guests agree: these houses are highly rated for location, cleanliness and more.

Casa al Gianni - The Simignano Barn
Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and 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, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

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.

Montepulciano Historic Center
nice and comfortable apartment in the old town of Montepulciano Placed in the Historical Centre, just a few steps to the most beautiful and oldest wine cellar in Montepulciano (Cantina del Redi dè Ricci) an amazing sixteenth-century structure, great-looking with its huge wine barrels. The apartment is in a perfect position: just a few minutes walk from the main square of the town, Piazza Grande(where, every summer, there are theatre and music events) but at the same time is a quiet district.

Sunset on Chianti Classico
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 Suites & Views
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.

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.

Jenny's Barn
The ancient barn, now finely restored, is located in the heart of the Valdichiana a few steps from the characteristic medieval village of Scrofiano. From the house you can enjoy a breathtaking view of the green Sienese hills where centuries-old olive trees and vineyards alternate from which the prestigious Chianti is obtained. Ideal for 2 people looking for a relaxing stay away from the chaos of the city. On request it is possible to add a baby bed and a cot.

Iole's little house
Typical Tuscan house just renovated while preserving the historical features, such as the wooden beam and brick ceiling. From the window, you can admire a typical view of the town's rooftops and the valley!!! Right in the historic center but very close to parking, it is really in a privileged position!! It has air conditioning, free Wi-Fi, heating, washing machine, kitchen, double bed. Self check-in and parking outside the walls 50 m away, free and paid.

La casa nel Borgo - Superior Tuscany Apartment
La Casa Nel Borgo is located in the small medieval village of Monticchiello, inside the historic center, between the ancient walls, immersed in the classic and enchanting landscapes of Tuscany. Newly renovated, it perfectly blends its historical soul with modern decor, giving the environment personality and charm. The terrace with a view is equipped. NOTE: *Only one room will be available for 2 people, unless explicitly requested.*

PoggiodoroLoft, Tuscan dream e relax
Welcome to Poggiodoro Loft, 16th century stones' villa located in the countryside of Anghiari. Stunning views, charming and furnished interiors providing all type of comforts, the relaxing sauna, the private garden where you can enjoy the open air and lunch under the pergola, BBQ, fantastic in the warm seasons, lounge with brazier a panoramic swimming pool to spend great moments with friends, to be shared with the hamlet guests.

Casa Belmonte
Just renovated elegant house in the historic center of Montepulciano, just 6 minutes from Piazza Grande and 4 minutes from Porta al Prato. Composed on the ground floor by a large open space with kitchenette while on the first floor there are two double bedrooms and two bathrooms. It is equipped with dishwasher, microwave oven, coffee maker, TV and free use of Wi-Fi.
Popular amenities for house rentals in Montepulciano
House rentals with a pool

Hidden gem in Tuscany

Italian Internal

Luxury 4BR Chianti Tuscany Home Pool Ensuite Baths

Il nido del Rondone

Country chic house in a village,private pool,wiFi

Borgo Ripostena – No. 8 Casa Vecchia

Nada Home

Podere San Girolamo
Weekly house rentals

Family Forest - Pool in the Crete Senesi

Lovely home to dream

Casa San Ripa: Relax Oasis with Private Pool

Stunning loft in Montalcino.

Spacious Luxury Stay in Pienza | 3BR 3BA

Domus Antiqua

Poggiolo

Il Bartalino, lost in Tuscany
Private house rentals

Frescoed 18th-C. Farmhouse | Exclusive | Cortona

Luxury Villa with Private Pool

I Fuochi Farmhouse | Casa Susino

Private Cottage with Plunge Pool in Tuscan Estate

City Center Palazzo: 4 King BR 6 Bath and Garage

Casa di Mela

Breathtaking views: Historic House w/Terrace & BBQ

Authentic Tuscany Experience in Our Country House
When is the best time to visit Montepulciano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $165 SGD | $163 SGD | $169 SGD | $171 SGD | $176 SGD | $188 SGD | $175 SGD | $183 SGD | $181 SGD | $163 SGD | $160 SGD | $179 SGD |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
Quick stats about house rentals in Montepulciano

Total holiday rentals
Explore 60 holiday rentals in Montepulciano

Nightly prices starting at
Montepulciano holiday rentals start at $64 SGD per night before taxes and fees

Verified guest reviews
Over 2,560 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Montepulciano holiday rentals include wifi access

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

4.8 Average rating
Montepulciano stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Rentals with a hot tub Montepulciano
- Rentals with breakfast Montepulciano
- Flat rentals Montepulciano
- Rentals with outdoor seating Montepulciano
- Family-friendly rentals Montepulciano
- Rentals with a patio Montepulciano
- Pet-friendly rentals Montepulciano
- Rentals with pools Montepulciano
- Smoking-friendly rentals Montepulciano
- Cottage rentals Montepulciano
- Rentals with a fireplace Montepulciano
- Villa rentals Montepulciano
- Rentals with a washing machine and dryer Montepulciano
- Apartment rentals Montepulciano
- Bed and breakfasts Montepulciano
- House rentals Siena
- House rentals Tuscany
- House rentals Italy
- Lake Trasimeno
- Lake Bolsena
- Del Chianti
- Centro Storico Orvieto
- Basilica of St Francis
- Terme Dei Papi
- La Scarzuola
- Cascate del Mulino
- Siena Cathedral
- Mount Subasio
- Parco Regionale Della Maremma
- Palazzo Pubblico
- Antinori nel Chianti Classico
- Valdichiana Outlet Village
- Ugolino Golf Club
- Casa Vasari
- Eremo Di Camaldoli
- Santa Maria della Scala
- Terme San Filippo
- Mount Amiata
- Saturnia Thermal Park
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore
- Vulci
- Things to do Montepulciano
- Food and drink Montepulciano
- Things to do Siena
- Sightseeing Siena
- Tours Siena
- Sports activities Siena
- Nature and outdoors Siena
- Food and drink Siena
- Art and culture Siena
- Things to do Tuscany
- Food and drink Tuscany
- Tours Tuscany
- Nature and outdoors Tuscany
- Sports activities Tuscany
- Art and culture Tuscany
- Sightseeing Tuscany
- Entertainment Tuscany
- Things to do Italy
- Tours Italy
- Sightseeing Italy
- Food and drink Italy
- Art and culture Italy
- Entertainment Italy
- Sports activities Italy
- Nature and outdoors Italy
- Wellness Italy







