
Holiday houses in Montemassi
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Top-rated holiday rentals in Montemassi
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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

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Pieve di Caminino Historic Farm
Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

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.

Domus Olea BnB
The Domus Olea apartment is part of a Tuscan stone farmhouse that overlooks the Maremma from a prime location. It takes its name from the wonderful restored oil mill, set into the marble base that has been embedded in the floor for over a century. It will be an experience of relaxation and greenery, of sunsets over the sea on the horizon, amidst timeless architecture and a minimalist approach to space. A hot tub to pamper yourself, time for a nice glass of wine, cheers. Have a good trip!

Casa al Gianni - Hut
Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

divo little boutique home
diVO Little Boutique Home, è una piccola casa-suite pensata e realizzata per soggiorni di qualità per tutti coloro che desiderano trascorrere del tempo in totale pace e relax. All'interno, agli elementi costruttivi che raccontano la storia secolare della casa, fanno da contraltare dotazioni ed arredi contemporanei che si fondono in un ricercato mix funzionale e materico declinato in spazi versatili pronti ad essere di volta in volta interpretati dagli ospiti.

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).

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.

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.
Popular amenities for Montemassi holiday rentals
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Apartments Supramonte

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Destinations to explore
- Elba
- Giglio Island
- Parco Regionale Della Maremma
- Cala Violina
- Feniglia
- Spiagge Bianche
- Gulf of Baratti
- Del Chianti
- Spiaggia Di Sansone
- Le Cannelle
- Spiaggia di Marina di Campo
- Spiaggia di Capo Bianco
- Cascate del Mulino
- Spiaggia Di Barbarossa
- Mount Amiata
- Avignonesi Winery Fattoria Le Capezzine
- CavallinoMatto
- Antinori nel Chianti Classico
- Vulci
- Siena Cathedral
- Val di Chiana
- Palazzo Pubblico
- Quercetano
- Terme San Filippo





