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Holiday houses in Montisi

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Top-rated holiday rentals in Montisi

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Guest favourite
Apartment in Montisi
4.89 out of 5 average rating, 28 reviews

Frattina1860 Romantic Apartment Free Parking

An oasis of peace between the Crete Senesi and the Val d'Orcia. Ideal for two people who want to relax and explore historic villages, taste wines, and admire the colors and iconic landscapes of Tuscany. Fully equipped kitchen and large open spaces. Surrounded by greenery 12km from Pienza 30 minutes from Montalcino and Montepulciano, 19km from San Quirico, 45 minutes from Siena 20 minutes from the A1 toll booth. Outdoor space and secure parking on private property. Breakfast included. Ideal stop for cyclists and motorcyclists

Guest favourite
A rustic stone farmhouse is nestled in a lush green landscape, surrounded by rolling hills and tall cypress trees. The sun casts a warm glow on the exterior, highlighting the charming architecture. An open courtyard with a small pool can be seen in the foreground.
Farm stay in Campiglia D'orcia
4.92 out of 5 average rating, 625 reviews

Poggio Bicchieri Holiday Farm - Memoria apartment

Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

Top Guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.92 out of 5 average rating, 333 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Top Guest favourite
A shaded pergola adorned with grapevines provides a relaxing spot for outdoor dining. A colorful table features a floral design, surrounded by wrought iron chairs. A private jacuzzi sits nearby, with lush greenery and rolling hills visible in the background.
Cottage in Castelmuzio
5.0 out of 5 average rating, 81 reviews

Panoramic view & outdoor jacuzzi - Pienza

‘L’Orto’ sits on a hill facing the 15th century monastery of Sant’Anna in Camprena, which was featured in the Academy Award-winning film ‘The English Patient’. Relax under a vine-covered pergola or in your private outdoor jacuzzi while enjoying panoramic views of idyllic Tuscan countryside, with its rolling hills and winding paths lined with cypress trees. ‘L’Orto’ is ideally located for a visit to the Val d’Orcia, a UNESCO World Heritage site, Pienza, Montalcino, Montepulciano or Siena.

Guest favourite
Condo in Montisi
4.86 out of 5 average rating, 7 reviews

Apartment in historic residence with pool and view

The "Gerani" apartment, 61 m2, is part of the ancient "Borgo La Grancia". It is located on the first floor and consists of a dining area with kitchenette, a small living room, a double bedroom and a bathroom with shower. It is furnished with Tuscan terracotta floors, beams, and period furniture. It overlooks one of the two historic courtyards, with immediate access to the terraced garden. Our guests can use the garden tables to dine al fresco and enjoy the beautiful view of the valley.

Top Guest favourite
Aerial view of a charming countryside villa surrounded by rolling hills and vineyards. Olive trees are visible lining the roads, which lead to the home nestled within a serene natural landscape. The colors and textures reflect the characteristic beauty of the Tuscan countryside.
Condo in Asciano
4.98 out of 5 average rating, 325 reviews

Celeste – The color of the summer sky in Tuscany

The apartment is located on the 2nd floor and consists of 2 bedrooms (possibility of making single or double beds on request), a bathroom, a living room, and a kitchen equipped for cooking. (Washing machine available from 9 a.m. to 8 p.m. in the laundry room) Free parking and wifi. Convenient location for visiting Tuscany's tourist centers. We are in the countryside, in the heart of the Crete Senesi, a car is recommended to be independent and visit the magnificent Tuscan countryside

Top Guest favourite
A spacious outdoor area features a framed view of rolling green hills in the distance. A swimming pool is visible, surrounded by grass, with a sunshade above a table and chairs. The peaceful landscape showcases the natural beauty of the Tuscan countryside.
Apartment in Castelmuzio
5.0 out of 5 average rating, 54 reviews

Beautiful Sunset Apartment

Welcome to Agriturismo Pascianella, a slice of paradise nestled among the rolling hills of Tuscany, right in the heart of the Val d'Orcia and the Crete Senesi areas. The property is in a panoramic position, perched on a hill overlooking the village of Montisi and the picturesque Castelmuzio easily accessible on foot. Whether you're looking for a retreat with a pool to recharge your energy or a base to explore the villages and flavors of Tuscany, Pascianella is the perfect choice.

Top Guest favourite
Townhouse in Trequanda
5.0 out of 5 average rating, 32 reviews

Romantic Tuscan Holiday House

Recently renovated Casa Etruria features a chic modern home inside its ancient stone walls, with every modern convenience,lots of original charm and the most beautiful sunset view from the bedroom and balcony . Casa Etruria is a 13th century gate house over the Western entrance to Trequanda - Porta al Leccio. Trequanda is medieval borgo located in Val d'Orcia , south of Siena. Val d'Orcia was recognised by UNESCO in 2004 as a World Heritage Site for its outstanding beauty.

Top Guest favourite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci
5.0 out of 5 average rating, 116 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Top Guest favourite
Home in San Giovanni d'Asso
5.0 out of 5 average rating, 81 reviews

Country chic house in a village,private pool,wiFi

La Capanna is a small house hidden at the sight in the very heart of the village of San Giovanni d'Asso in the Community of Montalcino.Private fenced pool (3x6 mt,1mt deep) ,astonishing view from the patio and terrace in front of the house. It can comfortably hold a party of 5 adults plus a child up to 12 . Central heating, fireplace (wood is provided at a little cost)AirCon in the bedrooms, (included in the price from June to mid September) WiFi good for home working

Top Guest favourite
Apartment in Asciano
4.88 out of 5 average rating, 25 reviews

Incredible Views & Pool in the Tuscan Hills

Escape to the heart of Tuscany and enjoy a stay surrounded by rolling hills, timeless beauty, and unforgettable views. The house offers access to a beautiful shared swimming pool and peaceful outdoor areas, perfect for relaxing in the sun or enjoying quiet evenings. Inside, you will find comfort, style, and everything you need for a memorable stay. Ideal for couples, families, or groups of friends looking for an authentic Tuscan experience just a short drive from Siena.

Top Guest favourite
The exterior of the stone house is featured, showcasing rustic charm with green shutters and a welcoming entrance. The garden area includes tables and chairs, surrounded by lush greenery and potted plants, offering a serene outdoor space for relaxation.
Holiday home in Montisi
4.97 out of 5 average rating, 30 reviews

Unique & Historic Getaway: Dreamy Garden

This stylish place to stay is perfect for group or family trips, in a small but precious Tuscan village, Montisi, in the Municipality of Montalcino, famous for wine and for being in the Val d'Orcia park, a UNESCO site. The house has a very quiet roof garden, where you can dine and relax after a day spent among the natural, historical and artistic wonders of the area. Each room of Umberto121 is different from the others, having maintained the characteristics of each.

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