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Vacation rentals in Montemassi

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Top-rated vacation rentals in Montemassi

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
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
4.94 out of 5 average rating, 66 reviews

Capezzuolo 33

Ai piedi del castello di Montemassi, incastonato nelle mura medievali del borgo, monolocale di 30 mq, ristrutturato con cura, mantenendo i materiali di un tempo. Le pareti in pietra, il pavimento in cotto, ed il camino creano un'atmosfera accogliente e romantica. Nella pergola esterna potrete organizzare rilassanti colazioni e cene suggestive a lume di candela. Il borgo si trova nell' invidiabile posizione da cui partire per itinerari storici, naturalistici e raggiungere le spiagge della Maremma

Top guest favorite
Apartment in Caminino
4.92 out of 5 average rating, 193 reviews

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.

Guest favorite
Home in Asciano
4.96 out of 5 average rating, 130 reviews

Palazzo Monaci - Piscina nelle crete Senesi

Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

Top guest favorite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Condo in Pienza
5 out of 5 average rating, 145 reviews

Mascagni Farmhouse in Val d'Orcia Pienza

Risali le iconiche colline toscane fino a Mascagni Organic Farm, un'azienda biologica dove ti aspetta la tua nuova casa: un fienile del 1500 finemente ristrutturato immerso tra olivi e campi di grano. Rilassati prendendo una tazza di tè, raccogli rosmarini e lavande nel giardino con vista mozzafiato sulla Val d'Orcia. Riscopri la tua vera natura tra i campi incontaminati e gli olivi: qui le passeggiate e i giri in bici non hanno confini! Pronto a creare ricordi che dureranno tutta la vita?

Top guest favorite
A medieval stone tower stands tall against a clear blue sky, showcasing its historic architecture. The narrow road lined with greenery leads to the entrance, with the texture of the stonework and windows highlighted, inviting guests to explore its unique charm.
Tower in San Quirico d'Orcia
5 out of 5 average rating, 108 reviews

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Top guest favorite
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.
Apartment in Montemassi
4.95 out of 5 average rating, 120 reviews

" DA OSCA " nel cuore della Maremma

L'appartamento " DA OSCA " e' collocato al primo piano ( al piano terra abitano i proprietari) di una palazzina situata ai piedi del celebre Castello di Montemassi. L'appartamento si compone di una cucina attrezzata, un soggiorno ( con divano, caminetto e tavolo da pranzo) , 2 camere matrimoniali, una camera con divano letto matrimoniale, 1 bagno con doccia e vasca e 2 balconi. Il giardino e' a disposizione degli ospiti per colazione, pranzo, cena e relax ( uso di barbecue ).

Top guest favorite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5 out of 5 average rating, 214 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top guest favorite
A spacious terrace is showcased with two comfortable armchairs positioned around a glass table. Potted red flowers adorn the railing, overlooking a panoramic view of the rolling hills of the Tuscan countryside under a partly cloudy sky.
Condo in Montalcino
4.98 out of 5 average rating, 133 reviews

Suite "Note di Paesaggio"

The 80 sqm Suite "Note di paesaggio" is located on the second floor of a historic building where it meets the landscape of the Val d'Orcia. It is divided into several rooms including a furnished double bedroom with air conditioning overlooking the terrace, a living room with a panoramic view, a study with a desk, a marble bathroom with shower, and another double bedroom without air conditioning . You can enjoy a 30sqm terrace and its suggestive view of the countryside.

Top guest favorite
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
4.92 out of 5 average rating, 265 reviews

Casa al Gianni - Capanna

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!

Top guest favorite
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.
Apartment in Montemassi
4.97 out of 5 average rating, 75 reviews

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.

Top guest favorite
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.
Apartment in Montemassi
4.98 out of 5 average rating, 121 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.

Superhost
A spacious bedroom features a double bed dressed in white linens, with a cozy armchair in the corner. Natural light enters through a window, illuminating the stone wall beside wooden beams above. A wooden table displays snacks and additional seating is available.
Condo in Castelnuovo dell’Abate
4.9 out of 5 average rating, 314 reviews

La Casetta di Brunello,very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

Popular amenities for Montemassi vacation rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Grosseto
  5. Montemassi