Vacation rentals in Montemassi

Casa al Gianni - Hut

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism property in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds, and the warmth of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a vacation; it’s a return to our roots. This peaceful haven will stay in your soul. We look forward to welcoming you!

Capezzuolo 33

At the foot of the castle of Montemassi, nestled in the medieval walls of the village, a 30 sqm studio apartment, carefully renovated, maintaining the materials of the past. The stone walls, terracotta floor, and fireplace create a cozy and romantic atmosphere. In the outdoor pergola, you can organize relaxing breakfasts and suggestive candlelit dinners. The village is located in the enviable position from which to start for historical and naturalistic itineraries and to reach the beaches of the Maremma

Design loft with private SPA in Tuscany

Welcome to Loft SPA, your personal refuge in the heart of Massa Marittima, an exclusive accommodation equipped with a private indoor swimming pool. This unique property offers an unparalleled stay experience, combining elegance and comfort, the accommodation has been designed with attention to detail and quality, The highlight is the indoor swimming pool with its accessories, an oasis of relaxation. This exclusive accommodation offers a stay experience you will not easily forget.

Casa Sabina

The apartment, which provides your own private entrance, has been recently renovated and furnished with care. It is located at the foot of the ancient Castle of Montemassi in a historic square in the characteristic medieval village. With only pedestrian access allowed in this square, you can be assured to have a tranquil and peaceful stay. A 5 minute walk from the apartment, the Castle of Montemass provides visitors with a cultural activity during their stay.

"DA OSCA" in the heart of Maremma

The "DA OSCA" apartment is located on the first floor (the owners live on the ground floor) of a building located at the foot of the famous Montemassi Castle. The apartment consists of an equipped kitchen, a living room (with sofa, fireplace and dining table), 2 double bedrooms, a bedroom with a double sofa bed, 1 bathroom with shower and tub and 2 balconies. The garden is available to guests for breakfast, lunch, dinner and relaxation (use of barbecue).

Tuscan rural home in Mascagni Farmhouse Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Magical place, medieval and nature!

Montemassi is the Medieval hamlet painted in the famous fresco of 1330 by Simone Martini, entitled “Guidoriccio da Fogliano conquering Montemassi” and preserved in the town hall of Siena. This picturesque village is in the heart of the most stunning area of Tuscan Maremma, in a privileged position, 300 meters height above sea level, only few kilometres far from the sea and from the Tuscan archipelago, which you can see from the house windows.

divo little boutique home

diVO Little Boutique Home is a small house-suite designed and built for quality stays for all those who wish to spend time in total peace and relaxation. Inside, the building elements that tell the centuries-old story of the house are counterbalanced by contemporary amenities and furnishings that blend into a refined functional and material mix declined in versatile spaces ready to be interpreted by guests from time to time.

Green Dome @ The Land Before Time Retreats

Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

Nice apartment with garden and breath-taking view

The house is called 'Il Melo e il Pruno' (" the Apple tree and the Plum"). It is a beautiful flat with terrace and garden and an incredible view of the Grosseto plain and the island of Giglio. Located in the heart of Maremma, 20 minutes by car from the sea. 'Il Melo e il Pruno' is a quiet and naturally rich place, with fruit trees such as apple and plum trees in the garden.

Castel Brunello - 2 doublebed rooms + terrace

Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.

Babe and Madde's house, air-conditioned environment

A nice two-room apartment recently renovated and furnished trying to evoke, through small details, the spirit of the past. Without laughing at the comforts of modernity.