
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$10,457 GYD per night before taxes and fees

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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.

Charming converted Hayloft overlooking the Chianti Hills
Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available
LocationValueCheck-in
4.97 out of 5 average rating, 305 reviews
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.
FamilyLocationView
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!
LocationValueWifi
4.97 out of 5 average rating, 194 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.
FamilyLocationAccuracy
4.96 out of 5 average rating, 138 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.
ValueLocationAccess
4.99 out of 5 average rating, 177 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.
ValueFamilyDecor
4.99 out of 5 average rating, 231 reviews
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.
FamilyLocationParking
4.9 out of 5 average rating, 133 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.
ValueLocationWalkability
4.97 out of 5 average rating, 181 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.
ValueLocationSolo travel
4.86 out of 5 average rating, 130 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
LocationFamilyComfort
4.92 out of 5 average rating, 172 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.*
ValueLocationWifi
4.95 out of 5 average rating, 221 reviews
Cottage surrounded by nature
"IL PODERACCIO" is a typical stone farmhouse located on the hills surrounding Lake Trasimeno, immersed in beautiful Mediterranean vegetation. The building is spread across two floors. The pool and garden frame the whole. The swimming pool is open from May 1st to October 15th. Please note that following the COVID 19 emergency, all the directives required by the legislation have been adopted for cleaning and sanitizing the house.
ValueFamilyLaundry
4.99 out of 5 average rating, 110 reviewsPopular amenities for Montepulciano house rentals
House rentals with a pool

House Rigomagno Siena
LocationFamilyWifi
4.96 out of 5 average rating, 122 reviews
Casa Rosmarino Eco-Wellness Country Home
ValueFamilyCheck-in
4.99 out of 5 average rating, 271 reviews
Private Chianti Cottage, Garden & Vineyard Views
FamilyLocationLaundry
4.99 out of 5 average rating, 136 reviews
PoggiodoroLoft, Tuscan dream e relax
ValueLocationGetting around
4.87 out of 5 average rating, 164 reviews
La Lisa: country house surrounded by fields
ValueFamilyParking
4.94 out of 5 average rating, 135 reviews
Relaxation and charm in the Chianti hills
LocationValueView
4.99 out of 5 average rating, 113 reviews
Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
LocationFamilyView
4.98 out of 5 average rating, 144 reviews
Explore Chianti from a Charming Stone House
LocationFamilyCheckout
4.98 out of 5 average rating, 122 reviewsWeekly house rentals

Montepulciano Historic Center
LocationValueDecor
4.92 out of 5 average rating, 153 reviews
Raffaella's House nel Chianti
FamilyLocationNearby
4.99 out of 5 average rating, 479 reviews
Apartment in a detached villa - Val d'Orcia
ValueLocationLaundry
4.95 out of 5 average rating, 177 reviews
Nada Home
FamilyLocationBeach
4.87 out of 5 average rating, 215 reviews
Rosaspina - Poggio Alla Serra
ValueLocationLayout
4.93 out of 5 average rating, 496 reviews
Da nonna Ornella - nest in Val d'Orcia
LocationFamilySleep quality
4.96 out of 5 average rating, 135 reviews
Tuscany House | View Breathtaking
LocationValueBathroom
4.97 out of 5 average rating, 112 reviews
Stunning Property • Terrazza privata & WiFi 300Mb
LocationValueLayout
4.85 out of 5 average rating, 61 reviewsPrivate house rentals

Casa di Mela
FamilyLocationComfort
4.97 out of 5 average rating, 37 reviews
La finestra - Montepulciano's historic center
FamilyValueLong stay
4.94 out of 5 average rating, 88 reviews
Spacious Luxury Stay in Pienza | 3BR 3BA
FamilyValueLaundry
4.97 out of 5 average rating, 99 reviews
Private House for 4P – La Capanna Di Azzurra
LocationValueParking
4.96 out of 5 average rating, 23 reviews
Cottage in XIIIe villa - pool - vineyard views
LocationHospitalityShared spaces
5.0 out of 5 average rating, 4 reviews
Family Forest - Pool in the Crete Senesi
FamilyValueAmenities
4.91 out of 5 average rating, 85 reviews
Il Podere - Rustic charm in Tuscany
FamilyLocationOutdoor spaces
5.0 out of 5 average rating, 9 reviews
Lovely home to dream
ValueLocationNearby
4.99 out of 5 average rating, 83 reviewsWhen is the best time to visit Montepulciano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$26,980 GYD | G$26,771 GYD | G$27,607 GYD | G$29,071 GYD | G$30,745 GYD | G$30,535 GYD | G$28,653 GYD | G$29,908 GYD | G$29,699 GYD | G$26,771 GYD | G$26,143 GYD | G$29,281 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
- Pet-friendly rentals Montepulciano
- Bed and breakfasts Montepulciano
- Rentals with breakfast Montepulciano
- Villa rentals Montepulciano
- Condo rentals Montepulciano
- Cottage rentals Montepulciano
- 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
- Centro Storico Orvieto
- Cascate del Mulino
- Mount Amiata
- Terme Dei Papi
- Eremo Di Camaldoli
- La Scarzuola
- Avignonesi Winery Fattoria Le Capezzine
- Antinori nel Chianti Classico
- Siena Cathedral
- Vulci
- Val di Chiana
- Palazzo Pubblico
- Mount Subasio
- Valdichiana Outlet Village
- Terme San Filippo
- Saturnia Thermal Park
- Abbey of Monte Oliveto Maggiore
- Abbey of Sant'Antimo
- Rocca Maggiore
- 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
- Tastings Tuscany
- Workouts 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







