
Holiday rentals in Montisi
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Top-rated holiday rentals in Montisi
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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
4.89 out of 5 average rating, 28 reviews
Apartment in ancient house + pool and terrace
The apartment "Il Glicine" is part of the historic house "Borgo La Grancia", located in a spectacular area of the Tuscan countryside. It is located on the first floor and consists of two bedrooms (one with two single beds and one double), each with its own bathroom, a living room, a kitchen/dining area, and a furnished terrace. It is elegantly furnished with Tuscan terracotta floors, beamed ceilings, and period furniture. It offers beautiful views of the gardens, the pool area, and the valley.
4.95 out of 5 average rating, 19 reviews
Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.
4.95 out of 5 average rating, 146 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
4.93 out of 5 average rating, 334 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.
5.0 out of 5 average rating, 81 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.
5.0 out of 5 average rating, 54 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.
5.0 out of 5 average rating, 32 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.
5.0 out of 5 average rating, 116 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.
4.85 out of 5 average rating, 26 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.
4.97 out of 5 average rating, 30 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, ( metered,on consumption ) WiFi good for home working
5.0 out of 5 average rating, 82 reviews
In Tuscany Rooms
**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.
4.96 out of 5 average rating, 137 reviewsPopular amenities for Montisi holiday rentals
Other great holiday rentals in Montisi

"Lunetta" Private Apartment on Larger Property
4.98 out of 5 average rating, 49 reviews
Tuscan Farmhouse ~ Magic Sunsets ~ 360° view
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Villa "La memoria del tempo" with A/C
4.92 out of 5 average rating, 91 reviews
Elegant farmhouse overlooking Pienza
5.0 out of 5 average rating, 36 reviews
Il Villino
4.95 out of 5 average rating, 59 reviews
Private 16th century farmhouse
5.0 out of 5 average rating, 23 reviews
Il Casone - Castle
4.57 out of 5 average rating, 7 reviews
Casa Oliveto
4.94 out of 5 average rating, 16 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Lake Bolsena
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Cala Violina
- Parco Regionale Della Maremma
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Basilica of St Francis
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Centro Storico Orvieto





