Vacation rentals in Montemassi

4.93 out of 5 average rating, 294 reviews

A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.

Farm stay in Simignano

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!

4.95 out of 5 average rating, 74 reviews

A rustic kitchen area is nestled against a stone wall, featuring a wooden bar table with two round stools. Minimalistic shelves hold kitchen essentials, while light streams through a window, illuminating the space and connecting it with the adjoining sleeping area.

Home in Montemassi

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

4.99 out of 5 average rating, 155 reviews

An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.

Cottage in Geggiano

Villa di Geggiano - Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

4.94 out of 5 average rating, 35 reviews

A kidney-shaped pool is surrounded by a well-maintained patio and lush greenery. Several lounge chairs, each with a white frame, are positioned around the pool. An umbrella provides shade over one seating area, enhancing the inviting outdoor space.

Villa in Montemassi

Private Villa with Swimming Pool and Hot Tub

San Giusto is located in the heart of the Tuscan Maremma. It is an old farmhouse dating back to 1928, completely renovated maintaining the characteristics of the old stone structures. The villa consists of two flats, each about 75 m in size, completely autonomous. San Giusto also offers a large garden equipped with tables, a Jacuzzi and a barbecue with a wood-burning oven. San Giusto offers a large 5m x 10m swimming pool, sunbeds, gazebo and parasols for moments of sunbathing and relaxation.

5.0 out of 5 average rating, 77 reviews

Home in Massa Marittima

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.

A scenic view features a gentle hillside dotted with wildflowers, leading to the ancient Montemassi Castle perched atop. Olive trees are visible in the background, with a sky presenting a soft blend of clouds and blue hues.

4.98 out of 5 average rating, 129 reviews

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.

A scenic view captures a quaint village nestled in the greenery, with terracotta rooftops visible among the landscape. The paved road leads to parked cars, while the distant rolling hills are dotted with trees, creating a serene backdrop.

4.95 out of 5 average rating, 132 reviews

"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).

A freestanding tub is positioned in front of a window framed by rustic stone walls. Light enters from outside, revealing natural greenery and distant architectural elements. The faucet is elegantly designed, adding a modern touch to the serene bathroom setting.

4.97 out of 5 average rating, 87 reviews

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.

4.93 out of 5 average rating, 14 reviews

A bright yellow wall is adorned with a simple artwork of three bottles, leading into a spacious living area. The seating is arranged around a neutral-colored center table, with a mix of modern and rustic design elements visible throughout the space.

Home in Montemassi

Maria's Tower: a Bird's Eye View to the Sea Coast

The house is of stone. The apartment is independent: private entrance, heating and lighting system. Completely restored 90sqm: dining room, 2 double rooms, one with the 40's design and decor and view to the castle, the other one is 35sqm wide, I would say a suite with studio and an incredible view on the plain to sea. 2 bathrooms, one kitchen and a little stone balcony. Laundry room in another floor, out of the apartment

4.95 out of 5 average rating, 190 reviews

Dome in Volterra

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.

A panoramic view of the surrounding landscape is captured, featuring rolling hills and fertile fields under a clear blue sky. Distant mountains are visible, creating a serene backdrop for the charming rooftop of a nearby building, bordered by lush greenery.

4.9 out of 5 average rating, 62 reviews

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.