Vacation rentals in Massa Marittima

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!

Value · Location · Shared spaces

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!

Value · Location · Long stay

Panoramic view 10 minutes from Massa Marittima and the sea

The Casetta Valmora agriturismo is immersed in the Tuscan countryside, overlooking cultivated fields and woods. An infinity pool will be available from June 2026. It is easy to see the typical fauna of the area, pheasants, roe deer and foxes. We are 10 km from the beaches of Follonica and 10 km from the medieval village of Massa Marittima. The apartment was renovated in 2021. It has an open-plan kitchen/living room, a well-equipped kitchen, a double bedroom, a bedroom with 2 beds, and a bathroom with a shower.

Location · Family · Outdoor spaces

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient family-run property from the 1600s located in the beautiful hills of Chianti in Tuscany, with the possibility of arranging a private shuttle and local experiences directly with our family. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with incomparable sunsets.

Family · Location · Air conditioning

Authentic Cave House in the heart of the Village!

The house is in the heart of Massa Marittima, a medieval village which is setting on the top of a hill in the Maremma countryside. This authentic historical small town is short driving distance from many amazing beaches of the Mediterranean coast: Cala Violina, Torre Mozza, the Baratti Etruscan Riviera.. Ideal for a romantic escape but also for those who are looking for a local experience in a relaxed, suggestive, historical context far away from mass tourist routes. PLEASE READ ALL DESCRIPTION!

Value · Location · Quiet

Design apartment in Massa Marittima, "slow city"

A great 65 m2 - 2 bedroom Apartment, entirely renovated in freestone and exposed beams, with design touch. In the upper, medieval part of Massa Marittima, Siena in miniature, with a superb Romanesque cathedral. Central but quiet area. Many restaurants and oeno-gastronomic specialties. Magnificent freshwater lake, Lago dell'Accesa, 10 minutes by car. Sea at 20 minutes. Siena at 1:15 a.m. Massa, "Citta slow", offers many other activities: museums, wine cellars, horse riding, Bike Park, MTB

Value · Location · Indoor spaces

Sunsets wow-relax and slow vacation

casa PàMa is a retreat where every detail has been carefully considered to make you feel at the heart of a unique experience. The day begins with a slow breakfast on the balcony, with birdsong in the background and a view of the Tuscan hills stretching all the way to the sea. In the evening, enjoy unforgettable sunsets while sipping a glass of wine. Here, you can finally slow down, savor every moment in complete harmony. Drive right up to the house without worrying about your luggage.

Location · Checkout · Laundry

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.

Value · Location · Air conditioning

Country cottage C&M surrounded by greenery, love Tuscany

Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.

Family · Location · View

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Value · Location · Indoor spaces

House with private terrace and countryside view

Typical Tuscan house with exposed beams: 4 sleeps, renovated and fully equipped. Large private terrace facing southwest, with views of the Tuscan countryside and evening sunsets! Reach the sea and the beaches of Maremma, just a few kilometers away: Cala Violina, the Sterpaia Park, the Gulf of Baratti, and Lake Accesa! Bike-friendly, with a convenient private storage room on the ground floor for safe bike storage. Easy and free parking throughout the area.

Family · Location · Air conditioning

TerraMadre FIRE

Our apartment on the 1st floor offers a fully equipped kitchen, bathroom with shower and hairdryer, living room with TV and fireplace and 2 bedrooms with double bed. Bed linen and towels are provided. The most beautiful beaches are only 30 minutes away by car. Our pool with the dimensions 14 x 7 equipped with sunbeds and parasols also awaits you. A shaded parking space is reserved for you. For our little guests there is a playground to let off steam.

Location · Family · Amenities