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House vacation rentals in Montepulciano

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Top-rated house rentals in Montepulciano

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Guest favorite
A shaded garden area features a hammock suspended from a tree and a round table with chairs, set against a backdrop of lush greenery and rolling hills. The panoramic view extends under a partly cloudy sky.
Home in Poggio San Marco
4.98 out of 5 average rating, 289 reviews

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

Top guest favorite
A vibrant garden features an array of colorful flowers, with delicate white blooms prominently displayed. In the background, rolling hills are seen under a dramatic sky, creating a serene landscape filled with natural beauty.
Home in Castiglione d'Orcia
4.95 out of 5 average rating, 106 reviews

Da nonna Ornella - nest in Val d'Orcia

Spectacular views and relaxation guaranteed in this romantic studio apartment in the heart of the Val d'Orcia, province of Siena, immersed in the beautiful Tuscany. Ideal for couples. It has a living area, an equipped kitchen, a bathroom, heating, a courtyard, private parking, and a large and panoramic garden with sun loungers and a hammock. Close to iconic destinations: PIENZA, Montepulciano, Montalcino, Bagno Vignoni, Bagni San Filippo, San Quirico d'Orcia, Radicofani, Castiglione d'Orcia, and Monte Amiata. Unforgettable!

Top guest favorite
An outdoor patio area is featured, showcasing a spacious covered space with large, light curtains that gently sway in the breeze. Comfortable seating options consist of bean bags and a dining table, all surrounded by lush greenery and tall cypress trees.
Home in Simignano
4.97 out of 5 average rating, 150 reviews

Casa al Gianni - The Simignano Barn

Transformed from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, large equipped kitchen, large living room and a large private garden with parking, hot tub, patio with sofas, BBQ, fire pit and 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, between relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

Guest favorite
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home in Asciano
4.96 out of 5 average rating, 101 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.

Top guest favorite
A quaint terrace is presented with a small round table and two chairs. Potted flowers add natural color, while a beautiful view of rolling hills and vineyards is visible in the background under a clear blue sky.
Home in Panzano
4.98 out of 5 average rating, 467 reviews

Old Farmhouse near Panzano Castle Abbacìo

The Abbacio apartment is part of an old farmhouse that has been restored respecting the original structure and style. Its location is just on the top of the hill, facing the valley. Surronded by vineyards and olive trees, but also attached to the village. From the house you can easily reach by feet wineries, farms and restaurants. Panzano is halfway between Florence and Siena, easily reached with car. By bus there is a good service from and to Florence, not from and to Siena. A very quiet spot!

Guest favorite
A view of the rolling hills and vineyards is framed by a window. The landscape features lush greenery and a clear blue sky in the distance, offering a serene and tranquil atmosphere.
Home in Montepulciano
4.92 out of 5 average rating, 145 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.

Top guest favorite
A cozy sitting area features a vintage leather sofa with colorful accents, positioned against a light wall adorned with contemporary wall art. Soft bedding is seen at the back, complemented by warm wooden flooring. Natural light filters through a nearby window, enhancing the inviting space.
Home in Montalcino
5 out of 5 average rating, 133 reviews

Montalcino Townhouse with Private Garden & Spa

A luxury apartment that blends traditional elements with all the modern comforts and some contemporary wall art. The apartment is centrally located in the upper part of town, only around the corner from the main square, in the limited traffic area. You can drive close by to download the luggage. The closest free car park is located at less than 10 minutes walk. Please note that to reach the house you need to walk a fairly steep street: it may not be ideal for those with mobility problems.

Top guest favorite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.98 out of 5 average rating, 125 reviews

StageROOM03 - Idyllic Chianti cottage near Siena

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.

Top guest favorite
A spacious living area features a gray sofa adorned with patterned cushions. A rustic wooden table and bookshelves filled with books are visible in the background, illustrating an inviting open layout that connects the living space to the dining area.
Home in Castiglione d'Orcia
4.95 out of 5 average rating, 152 reviews

Apartment in a detached villa - Val d'Orcia

In a detached villa, a cozy Tuscan-style apartment recently and tastefully renovated and located in a land rich in history. A few kilometers 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 panorama you can enjoy your meals, admire the sunset and observe the majestic and magnificent medieval fortress From 03/22/18, municipal tourist tax: €1 per person from 12 years old

Top guest favorite
A view from the window reveals a serene landscape of rolling hills and valleys bathed in soft morning light. The garden below is adorned with colorful flowers and greenery, enhancing the tranquil atmosphere of the Tuscan countryside.
Home in San Quirico d'Orcia
4.99 out of 5 average rating, 218 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.

Top guest favorite
The farmhouse entrance is framed by two potted plants and orange pumpkins. A stone facade features a wooden door with gray shutters, complemented by a tiled roof. Natural surroundings are visible in the background, emphasizing the peaceful rural setting.
Home in Prato
4.98 out of 5 average rating, 139 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.

Top guest favorite
The exterior view captures a rustic stone house bordered by tall trees. A pathway leading to the dwelling is visible, accompanied by lounge chairs set on a grassy area. The tranquil setting reflects the peaceful ambiance of the countryside.
Home in Scrofiano
4.97 out of 5 average rating, 159 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.

Popular amenities for Montepulciano house rentals

Quick stats about house rentals in Montepulciano

  • Total vacation rentals

    Explore 50 vacation rentals in Montepulciano

  • Nightly prices starting at

    Montepulciano vacation rentals start at R868 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 2,460 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 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!

Destinations to explore

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