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Vacation rentals in Montisi

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Top-rated vacation rentals in Montisi

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Top guest favorite
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.
Vacation home in Montisi

Unique & Historic Getaway: Dreamy Garden

Questo elegante alloggio è perfetto per viaggi di gruppo o familiari, all'interno di un piccolo, ma prezioso borgo toscano, Montisi, nel Comune di Montalcino, famoso per il vino e per essere nel parco della Val d'Orcia, sito UNESCO. La casa ha un giardino pensile molto tranquillo, dove poter cenare e rilassarsi dopo una giornata passata tra le meraviglie naturali, storiche ed artistiche della zona. Ogni stanza di Umberto121 è differente dall'altra, avendo mantenuto le caratteristiche di ognuna.

4.97 out of 5 average rating, 30 reviews
Guest favorite
Apartment in Asciano

Incredible Views & Pool in the Tuscan Hills

Fuggite nel cuore della Toscana e vivete un soggiorno immersi in dolci colline, una bellezza senza tempo e panorami indimenticabili. La casa offre l'accesso a una splendida piscina in comune e a tranquilli spazi esterni, perfetti per rilassarsi al sole o godersi serate serene. All'interno, troverete comfort, stile, tutto il necessario per un soggiorno memorabile. Ideale per coppie, famiglie o gruppi di amici che desiderano vivere un'autentica esperienza toscana a breve distanza in auto da Siena.

4.85 out of 5 average rating, 26 reviews
Guest favorite
Apartment in Montisi

Frattina1860 Romantic Apartment Free Parking

Oasi di pace tra le Creti Senesi e la Val d'Orcia. Ideale per due persone che desiderano rilassarsi ed esplorare borghi storici, degustare vini ed ammirare colori, paesaggi iconici della Toscana. Cucina attrezzata ed ampi spazzi aperti. Immersa nel verde a 12km da Pienza 30 minuti da Montalcino e Montepulciano, 19km da San Quirico, 45 minuti da Siena 20 minuti dal casello A1. Spazio all'aperto e parcheggio auto sicuro nella proprietà privata. Colazione inclusa. Sosta ideale per ciclisti e moto

4.89 out of 5 average rating, 28 reviews
Guest favorite
A spacious living area features a striped sofa with soft cushions, complemented by a wooden coffee table and a vase of fresh flowers. The warm terracotta flooring and rustic beams enhance the inviting ambiance. Steps lead to additional rooms, visible in the background.
Condo in Montisi

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
Top guest favorite
A stone staircase leads to a second-floor entrance, surrounded by lush greenery and flowering plants. The building is partially illuminated, highlighting the texture of the stone. A small terrace with seating is visible at the top of the stairs.
Farm stay in Montalcino

"Lunetta" Private Apartment on Larger Property

Le Coppiole is an exciting new addition to our properties at the Ville Ferrano. This "agriturismo" is associated with our olive oil and wine activities. The property is situated in the midst of the most tranquil and breathtaking Tuscan countryside. We offer three homes for rent, either individually or together for a large group. The infinite edge pool is located to take advantage of the stunning views and sunsets. The Lunetta apartment is located on the second floor of the Lunette building.

4.98 out of 5 average rating, 49 reviews
Guest favorite
A serene outdoor pool area is surrounded by lush greenery and rustic stone pathways. Lounge chairs are positioned beside the pool, creating a space for relaxation. The picturesque villa can be seen in the background, framed by trees and gentle hillside.
Villa in Castiglione d'Orcia

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
Top guest favorite
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

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
Top guest favorite
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

Appartamento bel Tramonto

Benvenuti all’Agriturismo Pascianella ,un angolo di paradiso incastonato, tra le dolci colline toscane, nel cuore tra la Val d’Orcia e le Crete Senesi. La struttura ,si trova in posizione panoramica, arroccata su una collina che si affaccia sul borgo di Montisi e sul pittoresco Castelmuzio facilmente raggiungibili a piedi. Che tu stia cercando un rifugio con piscina per ricaricare le energie o un punto base per esplorare i borghi e i sapori della Toscana, Pascianella è la scelta perfetta.

5.0 out of 5 average rating, 54 reviews
Top guest favorite
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

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
Top guest favorite
Townhouse in Trequanda

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
Top guest favorite
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

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
Top guest favorite
Home in San Giovanni d'Asso

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, 81 reviews

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