
House vacation rentals in Montepulciano
Find and book unique houses on Airbnb
Quick stats about house rentals in Montepulciano

Total vacation rentals
Explore 60 vacation rentals in Montepulciano

Nightly prices starting at
Montepulciano vacation rentals start at G$10,462 GYD per night before taxes and fees

Verified guest reviews
Over 2,600 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Montepulciano vacation rentals include wi-fi 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!
Top-rated house rentals in Montepulciano
Guests agree: these houses are highly rated for location, cleanliness, and more.

Domus Nannini - Loggia Salimbeni SPA
Apartment of 200 sqm furnished with precious classical furniture and very spacious rooms: 13 windows overlooking the old town, each window offers a unique view of the city. Big and spacious lounge with peerless view on the begin of Banchi di Sopra, Piazza Salimbeni and the headquarter of the Monte dei Paschi, formed by the noble palaces Tantucci, Salimbeni and Spannocchi. Second lounge with library, sofa-bed and the same exclusive view. 2 large bedrooms with city-views and king-size beds. 3 bathrooms one with jacuzzi and one with shower. A long corridor that crosses the apartment, spacious entrance and private terrace on the internal courtyard. Third lounge with sofa-bed and city-view. Dining room with panoramic views of the Duomo of Siena and Basilica of San Domenico which stand out over the medieval roofs of Siena a few meters from us. Fully equipped kitchen with laundry area. It occupies the entire second floor our 1600's palace and offers unique and privileged views of Siena and its architectural wonders. We are on Banchi sopra Sopra, the main course of the historical center of Siena, below the house you will find the best shops in the center with all the brands of high fashion, lots of restaurants; Wineries, Bars and Supermarkets with typical Tuscan products.
ValueFamilyLaundry
4.96 out of 5 average rating, 156 reviews
Casa al Gianni - The Simignano Barn
Converted from an old 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 looking for 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!
ValueLocationCheckout
4.97 out of 5 average rating, 198 reviews
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.
ValueFamilyAmenities
4.96 out of 5 average rating, 142 reviews
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.
LocationValueOutdoor spaces
4.92 out of 5 average rating, 153 reviews
Spacious Luxury Stay in Pienza | 3BR 3BA
Discover an elegant, spacious, and authentic retreat in the heart of Pienza, a Renaissance gem and a UNESCO World Heritage Site. Featuring 3 double bedrooms, 3 bathrooms, a large living area, a fully equipped kitchen, air conditioning, and Wi-Fi, this home is perfect for families or groups of friends who want to experience the most iconic side of Tuscany, with its historic alleyways, unique flavors, and unforgettable views of the Val d’Orcia, all with the comfort of a truly special residence.
FamilyLocationLong stay
4.97 out of 5 average rating, 101 reviews
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.
ValueFamilyWalkability
4.98 out of 5 average rating, 185 reviews
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.
LocationValueAir conditioning
4.99 out of 5 average rating, 232 reviews
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.
LocationValueAccuracy
4.96 out of 5 average rating, 187 reviews
Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.
FamilyLocationGrill
4.98 out of 5 average rating, 145 reviews
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.
ValueLocationBathroom
4.87 out of 5 average rating, 135 reviews
Conca d'Oro villa with private pool, sleeps 4
Just 2 km from the village, cozy typical Tuscan farmhouse, tastefully furnished and equipped. The farmhouse is located in a panoramic position immersed in the peaceful Tuscan countryside. Guests have access to a beautiful infinity pool for their exclusive use, equipped with sun loungers, and a lovely garden with a patio furnished for outdoor dining and enjoying fantastic sunsets. A strategic location for tourists. Free high-speed satellite Wi-Fi
FamilyLocationAccuracy
4.92 out of 5 average rating, 173 reviews
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.*
ValueLocationQuiet
4.95 out of 5 average rating, 223 reviewsPopular amenities for Montepulciano house rentals
House rentals with a pool

Casa Rosmarino Eco-Wellness Country Home
LocationValueOutdoor spaces
4.99 out of 5 average rating, 274 reviews
Cottage surrounded by nature
LocationFamilyComfort
4.99 out of 5 average rating, 111 reviews
PoggiodoroLoft, Tuscan dream e relax
ValueFamilySolo travel
4.87 out of 5 average rating, 167 reviews
Private Chianti Cottage, Garden & Vineyard Views
FamilyLocationCleanliness
4.99 out of 5 average rating, 138 reviews
House Rigomagno Siena
LocationFamilyCleanliness
4.96 out of 5 average rating, 125 reviews
Infinity pool in Chianti 1
ValueLocationCondition
5.0 out of 5 average rating, 143 reviews
Casa Giulia di Sopra Farmhouse
FamilyLocationCondition
4.95 out of 5 average rating, 106 reviews
Borgo Ripostena – n. 9 Frantoio
LocationFamilyIndoor spaces
4.94 out of 5 average rating, 118 reviewsWeekly house rentals

Charming converted Hayloft overlooking the Chianti Hills
LocationFamilyNearby
4.97 out of 5 average rating, 308 reviews
The Chianti window
FamilyLocationCheck-in
4.9 out of 5 average rating, 136 reviews
La Perla del Lago Holiday home on Lake Trasimeno
FamilyValueWifi
4.98 out of 5 average rating, 207 reviews
Amazing Cott. in the heart of Siena
LocationFamilyBreakfast
4.92 out of 5 average rating, 368 reviews
Tuscany House | View Breathtaking
FamilyValuePets
4.97 out of 5 average rating, 112 reviews
Casa del Passerino
ValueFamilyAir conditioning
4.94 out of 5 average rating, 225 reviews
The Chianti Classico Sunset
FamilyLocationOutdoor spaces
4.98 out of 5 average rating, 244 reviews
The Terrace of Victory
ValueFamilyAccess
4.98 out of 5 average rating, 128 reviewsPrivate house rentals

Spacious Tuscan Home – 2 Connected Apts, 4BR/4BA
LocationFamilyParking
5.0 out of 5 average rating, 10 reviews
Private House for 4P – La Capanna Di Azzurra
ValueFamilyCleanliness
4.96 out of 5 average rating, 27 reviews
Lovely home to dream
LocationFamilyDecor
4.99 out of 5 average rating, 84 reviews
Hidden gem in Tuscany
ValueFamilyCheckout
5.0 out of 5 average rating, 56 reviews
Casa di Mela
LocationFamilyAccess
4.97 out of 5 average rating, 38 reviews
Country chic house in a village,private pool,wiFi
ValueFamilyHospitality
5.0 out of 5 average rating, 82 reviews
The Court of the Podestà
LocationFamilyQuiet
4.96 out of 5 average rating, 26 reviews
Il Podere - Rustic charm in Tuscany
LocationFamilyIndoor spaces
5.0 out of 5 average rating, 12 reviewsWhen is the best time to visit Montepulciano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$26,992 GYD | G$26,783 GYD | G$27,619 GYD | G$29,084 GYD | G$30,758 GYD | G$30,549 GYD | G$28,666 GYD | G$29,921 GYD | G$29,712 GYD | G$26,783 GYD | G$26,155 GYD | G$29,293 GYD |
| 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 |
Destinations to explore
- Bed and breakfasts Montepulciano
- Pet-friendly rentals Montepulciano
- Rentals with breakfast Montepulciano
- Villa rentals Montepulciano
- Condo rentals Montepulciano
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- Apartment rentals Montepulciano
- Rentals with pools Montepulciano
- Family-friendly rentals Montepulciano
- Rentals with a hot tub Montepulciano
- House rentals Siena
- House rentals Tuscany
- House rentals Italy
- Lake Trasimeno
- Lake Bolsena
- Parco Regionale Della Maremma
- Del Chianti
- Basilica of St Francis
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino
- Terme Dei Papi
- Eremo Di Camaldoli
- La Scarzuola
- Antinori nel Chianti Classico
- Siena Cathedral
- Avignonesi Winery Fattoria Le Capezzine
- Vulci
- Val di Chiana
- Mount Subasio
- Palazzo Pubblico
- Valdichiana Outlet Village
- Saturnia Thermal Park
- Terme San Filippo
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore
- Piazza del Campo
- Things to do Montepulciano
- Tastings Montepulciano
- Things to do Siena
- Art workshops Siena
- Tastings Siena
- Museums Siena
- Food tours Siena
- Dining Siena
- Cultural tours Siena
- Outdoors Siena
- Landmarks Siena
- Wildlife Siena
- Cooking Siena
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
- Cooking Tuscany
- Wildlife Tuscany
- Landmarks Tuscany
- Workouts Tuscany
- Tastings Tuscany
- Galleries Tuscany
- Outdoors Tuscany
- Food tours Tuscany
- Dining Tuscany
- Museums Tuscany
- Performances Tuscany
- Shopping and fashion Tuscany
- Art workshops Tuscany
- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Food tours Italy
- Cooking Italy
- Flying Italy
- Cultural tours Italy
- Wellness Italy
- Tastings Italy
- Wildlife Italy
- Landmarks Italy
- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Outdoors Italy
- Architecture Italy
- Water sports Italy







