Home Vacation Rentals By Owner In Montepulciano, Emilia Romagna

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Exceptional(1)

$2946.24

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Villa

Villa Icario by Fantasia Villas

Montepulciano, Montepulciano, Italy

A hidden gem nestled in the heart of our estate, where the charm of the Tuscan countryside meets the timeless beauty of Montepulciano, just a short walk from the historic town.brbrEvery corner of this high-end retreat radiates elegance and style, offering breathtaking views over vineyards and the enchanting Valdichiana valley. The property features an infinity pool (12×6 m, depth: 1.35m to 1.75m) that gracefully overlooks the vineyards, offering a serene and intimate connection with the surrounding landscape. With three luxurious suites and two charming cottages, a fully equipped kitchen, and refined living spaces, the property is designed to fulfill your every desire. Outside, 3,000 m² of carefully curated gardens, complete with a vegetable garden, blooming roses, and fruit trees, invite you to immerse yourself in the beauty of Tuscan living. The beautiful outdoor patio is the perfect place to enjoy alfresco dining in the serene surroundings of the Tuscan countryside. Covered by a rustic pergola adorned with climbing greenery, the space features a large dining table that comfortably seats 14 people, ideal for hosting meals with family or friends.brbrThe patio is set against the backdrop of the villa’s elegant arched doors, offering a natural flow between the indoor living areas and the lush outdoor space. Whether you’re enjoying a quiet morning coffee, sipping on a glass of wine, or gathering for an evening feast, this dining patio invites you to relax and fully embrace the beauty of Tuscany. The property offers two unique BBQ setups: one with a traditional fireplace for a rustic, wood-fired experience, and the other gas-powered for quick and easy grilling. Imagine gathering with friends and family for an unforgettable BBQ night under the Tuscan sky, with the warmth of the fire or the convenience of the gas grill setting the scene for a perfect evening.
Bed 5

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Bath 6

Bath

Sleep 10

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$240.87

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Apartment

SANGUINETO - DOLCE DORMIRE

Montepulciano, Siena it, Italy

You will find Agriturismo Sanguineto nestled on the gentle slopes of the Tuscan hills, between the Sienese Val di Chiana and the Val d'Orcia. Here the evocative scent of the vineyards of Vino Nobile and Rosso di Montepulciano and centuries-old olive groves will transport you to a beautiful farmhouse that has been perfectly restored with absolute respect for its ancient origins and divided into 9 refined apartments.brAll around the house, at your disposal, a green and well-kept garden at the edge of which you will find a very panoramic solarium equipped with outdoor furniture, a swimming pool with hydromassage (size m. 17 x 9, depth m. 1,40 - open from 01 May to 30 September), which enjoys a splendid view over the countryside and a bowls court, for your moments of relaxation and fun.brbrJust 5 kilometres away you will find the renowned town of Montepulciano, an authentic pearl of the 16th century, a century of which it is still an almost intact expression with its palaces, streets and alleyways, indelible testimony to the splendours of Renaissance architecture and taste.brbrIn the village you will find shops and supermarkets and above all restaurants and trattorias, where you can taste delicious traditional Tuscan dishes, as well as the famous wine cellars, set amidst vineyards, dug into the tuff, built underground with arches, vaults and ancient barrels. We absolutely recommend a visit to the cellars with a tasting of the award-winning local wines, you will not regret it!brbrIf you wish, you can request theme dinners with menus based on typical local dishes, breakfast and also wine tastings. A communal laundry room, mountain-bikes and a children's playground are at your disposal.brA feather in the farmhouse's cap is the modern Wellness Centre with Turkish bath and sauna where you will be able to fully appreciate the serenity and relaxation of your dream holiday.brApartment on two floors connected by an internal staircase. On the ground floor sitting/dining room with kitchenette and double sofa bed. On the first floor there are double bedroom, twin bedroom and bathroom with shower.brbrEQUIPMENT: br• Freezer, microwavebr• Wi-Fi Internet access, Satellite TV, mini bar, communal washing machinebr_________________________________________________________________________________________________________
Bed 2

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Bath 1

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Sleep 6

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Exceptional(5)

$299.05

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Villa

Panoramic villa surrounded by vineyards and olive groves, 5 km from Montepulciano and Torrita di Sie

Montepulciano, SI, Italy

Torrita di Siena and Montepulciano, destinations not to be missed. Podere San Bono is located in a panoramic position overlooking vineyards, olive groves and woods, just a few kilometers from Torrita di Siena and Montepulciano. The two Tuscan towns, destinations of artistic, historical, architectural and gastronomic interest, deserve to be visited with attention. If you love good wine, or if you wish to discover it, you can't miss the appointment with the Nobile di Montepulciano, there are tastings at a good price in the countless ancient cellars of the city.brbrEnclosed swimming pool, and outdoor equipped spaces. Podere San Bono has a large fenced green area equipped with gazebo, garden furniture, barbecue, wood-burning oven. There is plenty of space to spend good family time in the garden and around the swimming pool (size 6x12 m., depth 1,20-1,80 m., completely fenced and safe for children - open from 01st May to 30th September). Your small four-legged friends are also welcome.brbrRustic charm. Podere San Bono has a rustic charm, guests say there is something special about this beautiful property, an atmosphere that remains in the heart. The interior fitting and finishing is of a good standard (washing machine, dishwasher, oven, microwave, toaster, mosquito nets etc.) On request the owner will prepare typical Tuscan dinners for you.brGROUND FLOOR: living-dining room with kitchen corner, open fireplace, double bedroom, twin bedroom, bathroom with shower. brFIRST FLOOR: with entrance through external staircase, composed of kitchen-dining room, two double bedrooms one of which with ensuite bathroom with shower, single bedroom, bathroom with shower. Small panoramic balcony. brbrEQUIPMENT: TV, oven, freezer, microwave, washing machine, dishwasher, fly screens, toaster.
Bed 5

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Bath 3

Bath

Sleep 9

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$299.05

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Villa

Typical Valdichiana farmhouse in red bricks, near the border between Tuscany and Umbria and a few km

Montepulciano, Siena, Italy

In the heart of Valdichiana, a few km from Montepulciano. A lovely brick farmhouse in the countryside, whose ever changing colors mark the passing seasons, a few minutes from Montepulciano. This ancient hill town, which dominates the surrounding valleys of the Val d'Orcia and the Val di Chiana, is full of old buildings many dating from the Renaissance. The holiday house I Cerretini is located just outside the little village of Valiano, reachable also on foot and endowed with bar and little shops for basic food. brbrPanoramic garden, private pool and equipped gazebo. In front of the house a large, panoramic garden where we find a swimming pool (size 6 x 12 m - depth 1,60 m - open from 01st May to 30th September), a gazebo with tables, chairs and barbecue, a small volleyball court, table tennis, swing and 3 covered car spot. The house is simply furnished but equipped with all comfort to guarantee a delightful holiday. Pets are welcome (extra charge could be required).brGROUND FLOOR: Kitchen-dining room with kitchenette, living room with double sofa bed, two double bedrooms, one with an extra single bed, two bathrooms with shower.brFIRST FLOOR: with access via typical external staircase, large and bright living-dining room with kitchenette and fireplace, two double bedrooms, bathroom with shower. From the living room there is access to the very panoramic terrace equipped with table and chairs. EQUIPMENT: dish-washer, washing machine, Satellite TV, oven, freezer, filter coffee maker, espresso coffee maker, toaster, iron and ironing board, mosquito nets, air conditioning , hair dryer in all bathrooms, table tennis, swing, 3 covered car spots.
Bed 4

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Bath 3

Bath

Sleep 10

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Exceptional(1)

$1705.84

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Villa

Villa degli Olivi In Montepulciano, Tuscany

Montepulciano, SI, Italy

Property for exclusive usebrBeautiful stone-built villa rental that has been completely renovated and transformed into a comfortable, exclusive holiday residence, situated near Montepulciano in the beautiful Tuscan countryside. This area of the countryside is, for the most part, made up of the vineyards that produce Vino Nobile di Montepulciano, one of the most famous Italian wines, as well as olive-tree groves and woods. This Montepulciano villa rental measures approximately 450 square meters and is perfect for groups of friends who want to spend their holiday together alternating between dolce far niente (the sweetens of doing nothing) in the swimming pool with outings to the characteristic towns and villages in the area: Pienza, Montepulciano, Bagno Vignoni with its characteristic thermal bath, Etruscan Cortona, Orvieto and many others. The location of the farmhouse, in the outskirts of a small village, allows you to easily use public transport to get around, as well as having all the basic necessities easily available. The villa rental is surrounded by a large lawn with flowering trees, cypress trees and aromatic plants, a pretty equipped pergola for pleasantly eating outdoors as well as shell-shaped swimming pool with infinity edge, massaging water jet area, (approx. 8x6, 1.40 m deep) (15/05-30/09) that is well equipped and with outdoor shower. Comfortable furnishings also with antiques. Available and to be requested when booking (to be paid for on location): baby bed and highchair, maid service, cook, cooking lessons, private transport service, groceries shopping service at arrival, wine tastings. It is possible to add 5 additional sleeps (1 single sofa bed, 1 double sofa bed in the suite, 2 arm-chair beds in the double bedrooms on the first floor) to be requested when booking and to be paid for on location). Wi-Fi internet connection. Central heating and air conditioning in the 4 bedrooms on the 1st floor. brPLEASE NOTE: arrivals must take place between 3.00 pm and 7.00 pm. Departure within 10.00am. Pets are allowed upon payment (100 Euro/week/pet).ACCOMMODATION: Gr. Fl.: large living room (satellite TV), dining room with large brick archway that separates the living room from the well-equipped kitchen (oven, dishwasher, microwave, freezer and small appliances), 1 suite with double bed and bathroom with bath, 1 suite with double bed and bathroom with bath, 1 double bedroom with bathroom with shower. Laundry room (washing machine, sink), WC. 1st fl.: living/reading room with fireplace, 4 double bedrooms all with bathroom with shower. All the double beds are 2.10x2.10 m (superior king size) and 3 double beds can all be separated into single beds. LOCATION: 800 m food shops, tennis and public swimming pool all within a range of 500-1000 m, 4 km Montepulciano, 5 km Chianciano Terme, 15 km the motorway toll booth, 18 km Chiusi and Pienza, 25 km Golf club (9 holes), 60 km Arezzo, 70 km Siena, 120 km Florence, 175 km Romebrbr Tourist tax per person/day 2.50 Eurobr Final cleaning per week 350.00 Eurobr Heating (from November to April) due only if used, per m3 (cubic meter) 4.00 Eurobr Refundable deposit (to be handed over on arrival) per booking. In cash 800.00 Euro
Bed 6

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Bath 6

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Sleep 12

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Exceptional(12)

$136.14

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Apartment

Large shining148sqmt wififiber apartment, view and free parking in Montepulciano

Montepulciano, Provincia di Siena, Italy

-This large second floor apartment ( fully renovated, offers a pleasant, shining, fresh and convenient permanence in the core of Tuscany). (I AM PREMIER HOST WITH MORE THAN 72 5 STARS REVIEWS FOR THE BELOW APARTMENT: https://www.vrbo.com/3877682ha unitId=4251202).br-This larger second floor apartment has two large bed rooms (25sqmt and 15) with beds of 165x195cm(more than queen size for italian standards), a smaller third bedroom with a small double bed (145cmx195cm), two living rooms whose one with a large, new and fully equipped kitchen. The other living room is large and have a large sofa-bed, dining table and large smart monitor (Netflix, Youtube...no RAI). There are 2 independent toilette (One inside the first bedroom) and balconies-terraces with sunny and shining view. Washing and dishes machine are provided. The two balconies-terraces have also place for drying as they enjoy plenty of sunshine. br-The apartment is placed in a central and quiet zone of Montepulciano. brVery accessible and close to the historical part of Montepulciano (100mt.), the apartment is close to 2 large free and safe parking (50mt.) and bus station (100mt.), therefore very easy for luggage transportation (second floor after only 20 steps). Also, it is very close to shopping and food markets, local market (Thursday) bars and restaurants.
Bed 3

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Bath 2

Bath

Sleep 6

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Exceptional(10)

$307.19

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Apartment

Apartment with swimming pool in Tuscany

Montepulciano, Montepulciano, Italy

Set in the rolling hills of the Val d’Orcia, in the peaceful countryside of Montepulciano, this charming farmhouse apartment offers an authentic taste of Tuscany. With its own private entrance on the first floor, the home welcomes you into bright, comfortable spaces designed for pure relaxation. Two inviting bedrooms, a modern bathroom, air conditioning, and mosquito nets ensure restful nights in every season. Step outside and the landscape embraces you. A vast garden surrounded by olive trees and open fields invites quiet moments in the sun, while the beautiful swimming pool and children’s play area create a perfect setting for leisurely afternoons. Comfortable garden furniture lets you linger outdoors from sunrise to sunset.brbrYour stay becomes even more memorable thanks to the experiences offered on-site: tastings of the farm’s own wine and olive oil, discounts at the Chianciano Terme spa, guided tours through Chianti’s vineyards, cooking classes, and more, each one a delightful way to savor the region’s traditions.brbrIdeally positioned, the farmhouse is just a short drive from Tuscany’s most iconic destinations, including Siena, Chianti, and the postcard-perfect towns of the Val d’Orcia. Here, between nature, flavors, and gentle rhythms, you’ll find the perfect place to slow down and immerse yourself in true Tuscan charm.brExpenses related to charging an electric or hybrid car (when possible) are always charged according to use and separately Linen change 1 times per 7 nights includedbrLayout: On the 1st floor: (open kitchen(hob, electric kettle, coffee machine, oven, fridge, dishes and cutlery, Cooking basics), Living/bed room(single folding bed, dining table, seating area), bedroom(double bed), bedroom(double bed or 2 single beds), bathroom(shower, washbasin, toilet, bidet, washing machine, hairdryer, body soap), Internet access, Parking, air conditioning) garden, garden furniture, BBQ, parking, swimming pool(shared with other guests, 12 x 5 m.), play equipmentbrbrThese costs are mandatory and charged on site. They are not included in the rental price.: brPets; Max. 2; free of chargebrTourist tax; € 2,50 (indication)/person/night (maximum 7 nights) from 16 years of agebrbrOptional services that you can arrange on site: brBath towels; PresentbrWifi; FreebrCot + High chair; free (on request)brAirconditioning; IncludedbrHeating; Included
Bed 2

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Bath 1

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Sleep 5

Sleeps

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$3281.36

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Villa

VILLA CORTE ANTICA - Seven Bedroom Villa, Sleeps 15

Montepulciano, Montepulciano, Italy

Located in the heart of the Tuscan countryside between Florence and Rome, just 70 kilometres from Siena, this charming luxury villa, once a 16th-century former convent, is immersed in 65 hectares of hilly landscape embellished with olive groves and gardens.  The villa has 7 suites, each characterised by an individual style and inspired by the rich history of the estate, with rooms containing historic furniture of the family itself, designer touches and custom details created by local artisans.brThe interiors have been tastefully renovated, the Seven Bedrooms, accommodating 15 guests, are equipped with air conditioning, TV and elegant en-suite bathrooms beautifully decorated by travertine marble. The property consists of an elegant and charming villa, an extensive olive grove and an expansive countryside that can be explored on pleasant walks looking for Etruscan remnants. Renovated by the last generation of a Tuscan family, the history of this ancient monastery is linked to the descendants of Popes. This is the perfect place for those wanting to spend a relaxing holiday in the Tuscan countryside, with an outdoor swimming pool, gym, billiard room and an indoor swimming pool with hydromassage. A luxury retreat, a blend of an elegant private villa and a classy hotel.brThe villa is on three levels. The upper level (first floor) has another living room with comfy armchairs and a fireplace. There are two large bedrooms, each with a king bed and an ensuite bathroom on this level. Another large bedroom with an ensuite, shower, and bathtub is also on this level. Lastly, a queen and twin bedded rooms with ensuite are also on this floor. There is also a large bedroom king-size bed with an ensuite bathroom with tub and double sinks and Smart TV.brAs we move onto the second floor (top level), there is a large king-size bed with a walk-in closet and a stunning ensuite bathroom. The final queen bedroom is at ground floor level in the adjacent Guest House. This beautiful room has disabled access and a lovely ensuite bathroom.brSurrounded by oaks and cypress trees is the beautiful private pool where the guests can relax in the comfort of modern outdoor furnishings, sun bake or sip an evening cocktail in absolute poolside relax. In the garden there is a BBQ area where you can spend pleasant evenings, surrounded by magnificent greenery.brPets - not allowedbrSmoking - not allowedbrbrbrplease contact us some days before arrival for your check in details
Bed 7

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Bath 7

Bath

Sleep 15

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$883.51

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Private Vacation Home

Villa Salice-Locanda Cicolina - Tuscan flair in the vineyard with Pool

Montepulciano, Provincia di Siena, Italy

Experience a wonderful vacation amidst vineyards and olive groves...brLocated right where the Etruscans settled thousands of years ago, you will now find Cicolina—a small, privately run wine estate. The origins of the property date back to the 16th century, when it served as a small care facility for the sick.brThe main house was built just over a century ago as a farmhouse and has recently undergone extensive renovations to become a modern vacation home; yet, it has retained its authentic character as a Tuscan country estate...brFrom the terrace and the pool area, the view stretches across the olive groves and vineyards, reaching far into the Valdichiana valley—and on clear days, extending all the way to the Apennine Mountains, where (in spring) glistening snowfields can be seen.brSavor a glass of *Rosso di Montepulciano* from the estate’s own wine cellar in the evening sun, relax by the pool, or take a leisurely stroll through the property’s groves.brThe historic old town of Montepulciano is located approximately 1.5 km away and is easily accessible on foot.brThe upper floor features three spacious, separate bedrooms, each with its own private bathroom and air conditioning. A balcony—accessible from the hallway—offers the perfect spot to enjoy your first cup of coffee in the morning sun or to greet the day with a yoga session.brOn the ground floor, a large open-plan living and dining area—complete with a modern, fully equipped kitchen—invites you to sit back and relax. An adjoining transitional area, featuring additional seating, leads out to the terrace and garden, as well as to two additional bedrooms (measuring 16 m² and 10 m²), which share a bathroom.brA path through the garden leads to the pool area, which boasts a magnificent south-easterly orientation and breathtaking views across the Valdichiana valley.brThe estate also includes a small, separate apartment located in the oldest section of the building (dating back to the 16th century), which is available for rent independently. The on-site restaurant is currently closed to the public but can also be rented separately—by prior arrangement—for private celebrations or similar events. Located in the lower section of the historic building is a small *cantina*—a space you are more than welcome to take a peek at.brThe surrounding region offers countless opportunities for planning excursions. Siena is just 45 minutes away, while Florence is a good hour's drive.brNaturally, however, the historic center of Montepulciano is well worth a visit, beckoning you to indulge in culinary delights amidst its myriad cafés, bars, and restaurants. The surrounding countryside also boasts many wonderful dining options—ranging all the way to the Michelin-starred cuisine of Restaurant Osmosi (approx. 5 km away).brSpend an unforgettable vacation in this Tuscan oasis—whether relaxing by the pool, enjoying a glass of red wine on the terraces, strolling through the vineyards, or embarking on a cultural excursion or two within the region.
Bed 5

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Bath 4

Bath

Sleep 10

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$302.75

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Hotel

B&B Podere Monti - Matrimoniale Andrea Della Robbia

Montepulciano, Siena it, Italy

Podere Monti is located on a hilltop 3 kilometres from the historical centre of Montepulciano and enjoys a magnificent view over the surrounding valley.brbrThe farmhouse overlooks the estate where olive oil and cereals are produced and where there is also a small lake.brbrThe surrounding environment is typical Tuscan, characterized by medieval towns, cypresses, vineyards and gravel roads, the ideal setting for open-air activities but also for tasting premium wines and excellent food.brbrA cook is on hand to prepare delicious breakfasts and dinners at the farmhouse.brbrFurthermore, our cellar offers guests a selection of top wines from Montepulciano.brbrHere you can have lunch under the wisteria, sunbathe in the swimming pool while relaxing under the hydromassage water jet or simply lie on the soft green grass surrounding the farmhouse.brAlberto and Lucrezia will be more than happy to show you as friends this beautiful corner of TuscanybrThis country house is immersed in a beautiful Tuscan landscape of olive groves and surrounded by forest. For your pleasure and enjoyment Podere Monti includes a wonderful swimming pool with hydro-massage, ideal to enhance your stay whilst soaking up the atmosphere of this typical Italian paradise.brPodere Monti is a typical example of a stone country Tuscan farmhouse, beautifully restored with charm and taste. Careful to include all modern comforts without changing the special atmosphere of a private country house.brDouble room with bathroom (30 mq.).brOn one side the rooms overlooks the farm’s garden, while on the other it captures a splendid view of Montepulciano. brThe walls are whitewashed pale blue, giving the room a beautiful atmosphere.brIn the bathroom with shower, the bowl which serves as a wash basin rests on boards which were originally used as a manger in the farm’s barn.brInside the room you will find a extremely cosy king size bed.
Bed 1

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Sleep 2

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