Vacation rentals in Monticiano

4.96 out of 5 average rating, 159 reviews

Guesthouse in Macciano

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

5 out of 5 average rating, 248 reviews

Aerial view showcases the rustic property nestled among the lush vineyards. Sunlight casts a warm glow over the hills, while a sparkling pool is situated near the residences, surrounded by greenery. The tranquil landscape includes gently rolling hills and rows of grapevines.

Condo in Noce

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica e autentica casa colonica risalente al 1600 situata nelle splendide colline del Chianti in Toscana . L'appartamento è arredato in perfetto stile tradizionale locale dell'antica Toscana : antiche travi in legno, pavimenti in cotto e arredamenti unici. Nel grande cortile esterno troverete a vostra disposizione una grande piscina con terrazza panoramica che si affaccia su una valle con vista mozzafiato su vigneti e oliveti dove godersi tramonti spettacolari.

4.97 out of 5 average rating, 282 reviews

A tranquil plaza is featured, flanked by archways and historical stone buildings. The main church displays a simple yet elegant facade with a bell tower. Dim light filters through the clouds, creating a serene atmosphere in the square.

Condo in Asciano

Verde - I prati in Toscana

Appartamento composto da 1 comoda camera matrimoniale , cucina attrezzata, ampio soggiorno e bagno Tv, BBq, ( mettiamo a disposizione la lavatrice che è nella nostra lavanderia per chi ne fa richiesta ) . Consigliamo l'auto in quanto abitiamo in aperta campagna , sia per essere indipendenti , sia per visitire la magnifica campagna toscana Ti piacerá l'ambiente esterno perché é magico di giorno e di notte Parcheggio e wifi gratis Posizione strategica per visitare la Toscana e l'Umbria.

4.99 out of 5 average rating, 109 reviews

An outdoor terrace is presented with two metal chairs and a glass table, offering sweeping views of the surrounding countryside. Flower boxes adorn the railing, while the expansive sky is filled with scattered clouds, creating a serene backdrop for relaxation.

Condo in Montalcino

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.

4.97 out of 5 average rating, 101 reviews

A wooden table is set for dinner outdoors, featuring bowls of pasta, fresh salads, and a bottle of wine. Two glasses of white wine are placed on the table beside fork and knife settings. The cobblestone pathway is softly illuminated by warm ambient light, suggesting a serene evening atmosphere.

Apartment in Montemassi

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.

Villa in Monteroni d'Arbia

A simple work nook is presented with a white chair and a natural wood desk, positioned near a window. A vase with delicate flowers sits on the desk, with soft light enhancing the serene view of the surrounding landscape.

4.95 out of 5 average rating, 134 reviews

"Villa Daisy" con vista su Siena

Meravigliosa villa con ingresso indipendente all'interno del podere "Caggiolo", riportato alla luce con curata e profonda ristrutturazione che ha mantenuto intatti i lineamenti tipici di un podere toscano. Splendida vista panoramica su Siena. Situato alle Ville di Corsano, a soli 14 km dalla città. Luogo ideale per trascorrere giorni in totale relax e godere delle meraviglie che questa zona offre (Chianti, Val d'Orcia, Crete Senesi..).

Condo in Castelnuovo dell’Abate

A balcony is adorned with blooming flowers and greenery, offering a scenic view of the rolling hills and vineyards. Small outdoor furniture is positioned for relaxation, while the sky features scattered clouds, enhancing the tranquil atmosphere of the surrounding landscape.

4.91 out of 5 average rating, 285 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.

4.89 out of 5 average rating, 191 reviews

A spacious green garden is visible, dotted with trees offering natural shade. A wooden dining table with chairs is positioned under the trees, providing an inviting setting for outdoor meals. The rustic brick building stands in the background, complementing the serene surroundings.

Farm stay in Simignano

Casa al Gianni - Capanna

Ciao, siamo Cristina & Carmelo! Vi invitiamo a vivere un’esperienza autentica nel nostro agriturismo “Casa al Gianni” situato 20 min da Siena. Il nostro marchio è la vita semplice a stretto contatto con la natura e gli animali della nostra fattoria. Immerso tra i boschi e la splendida campagna toscana trascorrerai una vacanza indimenticabile. Questo angolo di paradiso ti rimarrà nel cuore!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Popular amenities for Monticiano vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Monticiano

Apartment in Centro Storico

4.89 out of 5 average rating, 38 reviews

Chic Apartment Macci

Apartment in Centro Storico

A small balcony features a round glass table set for two, accompanied by two wooden chairs. A view of charming green-shuttered buildings and the historic stone wall is visible, creating a serene outdoor space.

4.98 out of 5 average rating, 223 reviews

Art Apartment Luxury Por Santa Maria

4.91 out of 5 average rating, 11 reviews

An aerial view captures the rustic beauty of the Tuscan landscape, showcasing rolling hills of golden fields and vineyards. The agriturismo's main building and pool are nestled within the greenery, surrounded by nature's serenity.

Apartment in Santa Luce

Artemisia Dreamscape with Wooden Hot Tub

Apartment in Castelfranco Piandiscò

4.95 out of 5 average rating, 20 reviews

Casa Lama Apartments, Il Trovatore panoramic view

Home in San Giuliano Terme

4.88 out of 5 average rating, 77 reviews

Pisa / Lucca-Superb Location-Leaning Tower views!

5 out of 5 average rating, 8 reviews

A circular view framed by lush greenery showcases rolling hills under a partly cloudy sky. The vibrant landscape stretches into the distance, highlighting the undulating terrain and distant mountains.

Home in Volterra

Vacanza in agriturismo autentico 10 km dalla citta

4.82 out of 5 average rating, 49 reviews

The exterior of a classic building is showcased, featuring an ornamental balcony with intricate metalwork. The façade displays warm-toned stone walls, complemented by evenly spaced windows adorned with wooden shutters.

Condo in Centro Storico

[Free Garage] 15 Min. walk from Art