Vacation rentals in Petroio

4.96 out of 5 average rating, 164 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.

A panoramic view of a valley unveils rolling hills adorned with clusters of trees and vineyards. Golden autumn foliage frames the foreground, while the distant hills create a tranquil landscape beneath a clear blue sky.

5 out of 5 average rating, 118 reviews

Stuart White Tea Central Panoramic & Garden

Offering ample space, the apartment features two double bedrooms, two full bathrooms, and a living room with a kitchen. The bedroom balconies offer stunning views of the valley and natural light. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. It has also access to a secluded, terraced backyard garden. It provides a comfortable retreat perfect for long term stays. A public parking is available nearby.

4.92 out of 5 average rating, 125 reviews

A private terrace is visible, adorned with vibrant flowers and a small table set for two. A bottle of wine and two glasses are elegantly placed, inviting relaxation with a view of the terracotta rooftops and the distant landscape under a pastel sky.

Condo in Montepulciano

"Dimora Valinda" Montepulciano Piazza Grande +A/C

🏠 Ideal location: within walking distance of stores, restaurants and attractions in the historic center. ❄️ Air conditioning for maximum comfort during hot days. 🛁 Washing machine for extended stays or simply for traveling light. 🌅 Private terrace for relaxing moments outdoors. 🍴 Full kitchen with dishwasher, perfect for those who love to cook even on vacation. 🌐 Ultra-fast 150 Mb/s Wi-Fi, ideal for smart working ☕ Well-stocked coffee station for a perfect start to the day.

Guesthouse in Montefollonico

A wine bottle is being poured into a glass, catching the warm hues of a sunset. The landscape of rolling hills and trees is visible in the background, creating a serene atmosphere enhanced by the vibrant colors of dusk.

4.97 out of 5 average rating, 103 reviews

Casale Santa Barbara - Exclusive Apartment

At a glance: • Location: perfect entry door to the Val d’Orcia between Pienza (8,5 km) and Montepulciano (8,5 km). • Charming warm old stones Tuscan house – completely restored in 2016 • Big apartment (100m2), designed for 2 persons, completely independent, fully furnished, Tuscan style with modern equipment. • Exclusivity: we are living on the 1st floor; the ground floor is yours. You are our only guests. • Spacious private garden (+ 300m2) • Stunning view on the Tuscan hills.

Farm stay in San Giovanni d'Asso

An outdoor space is highlighted with several round tables under large umbrellas. Surrounding greenery adds a natural touch, while potted plants provide color at the base of stone steps leading to the entrance of a rustic building with a brick facade.

4.94 out of 5 average rating, 114 reviews

Flat, Agriturismo "Biofattoria l'Upupa"

The flat is on the first floor of a classic Tuscan farmhouse called ‘Biofattoria l'Upupa’. Magnificent hillside location between the Val d'Orcia and the Crete Senesi. Suitable for families with children. Consisting of kitchen, large living room, bathroom with shower, 1 double bedroom and 1 bedroom with bunk beds. There is a double sofa bed in the living room. The flat is equipped with wifi. Free parking on private property. Complete breakfast kit including homemade cakes.

4.96 out of 5 average rating, 352 reviews

A view of the entrance to a countryside property is presented, featuring a gravel driveway that meanders through lush greenery. Tall cypress trees line the pathway, while olive trees and rolling hills create a serene backdrop under a partly cloudy sky.

Condo in Asciano

Romantic Yellow apartment in Crete Senesi

Apartment consisting of a comfortable double bedroom (it is possible to make 2 single beds on request), an equipped kitchen, a living room, and a bathroom. TV, BBQ, (if needed, we have a washing machine available from 9 a.m. to 8 p.m., which is in our laundry room). A car is recommended as we are in the countryside, so you can be self-sufficient and visit the magnificent Tuscan countryside as well. Free parking and wifi. I look forward to showing you the real Tuscany!

A wooden balcony table is set for tea, featuring delicate china cups accompanied by cookies. A simple vase holds fresh flowers. The stunning countryside view stretches across rolling hills under a clear sky, enhancing the serene atmosphere of the outdoor space.

4.94 out of 5 average rating, 191 reviews

I Tramonti di Eramo, Montepulciano city center.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historical center offers a breathtaking view of the surrounding countryside, giving an authentic and unforgettable experience. You can leave the house and taste the historic atmosphere of Montepulciano. Within walking distance you will have the extraordinary Piazza Grande, high quality restaurants and services of all kinds. Tuscany awaits you to experience unique emotions.

4.99 out of 5 average rating, 271 reviews

An outdoor terrace is visible, furnished with several tables and chairs, providing ample seating. Flower pots with colorful blooms adorn the railing, while a panoramic view of the surrounding hills and greenery stretches into the distance under a clear sky.

Apartment in Sinalunga

Resort Panoramic view - Free parking

Appartamento nuovo , potente Wi-Fi, SMART TV, bagno privato , Aria Condizionata, cucina privata , lavanderia , parcheggio privato gratuito . Sala da tea ad uso gratuito . Vista panoramica mozzafiato . Tra le Crete Senesi e la Val D’Orcia , a 800metri dal centro del paese , con ristoranti , bar e supermercati . Posto strategico per visitare le principali località in Toscana : Montalcino , Pienza , Siena , Arezzo , Rapolano Terme , Montepulciano .

5 out of 5 average rating, 110 reviews

A view through a window showcases rolling hills and green fields under a soft sky. The landscape reveals a peaceful outdoor area, highlighted by a table and chairs nestled amongst the natural scenery, inviting relaxation and contemplation.

Condo in Pienza

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Apartment in Monticchiello

4.97 out of 5 average rating, 152 reviews

Casa Bonari - a paradise for the eyes

Casa Bonari is a single-level independent apartment inside a villa at the foot of Monticchiello. It consists of 3 bedrooms, 2 bathrooms, an equipped kitchen and a living room. The rooms are bright and furnished in Tuscan style, with old restored family furniture combined with contemporary elements. The kitchen is fully equipped and the apartment is surrounded on all sides by a large garden, so that all rooms boast a beautiful view of the countryside.

4.89 out of 5 average rating, 197 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

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Farm stay in Campiglia D'orcia

A rustic stone building is shown, featuring a tiled roof and wooden window shutters. The structure is surrounded by greenery and potted plants, with a clear blue sky above, providing a picturesque view of the landscape beyond.

4.94 out of 5 average rating, 411 reviews

Poggio Bicchieri Holiday Farm - Poesia apartment

Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.

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Popular amenities for Petroio vacation rentals

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Free parking on premises

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Other great vacation rentals in Petroio

Apartment in Monticchiello

A stone pathway leads to an entrance framed by a rustic archway. The doorway features a wooden door with a glass panel, flanked by potted flowers in vibrant hues. Natural stone walls and greenery create a charming setting.

5 out of 5 average rating, 46 reviews

Casa Tórta - comfort room

CharlotteRating, 5 stars5 days ago

Genuinely a secret little heaven, I cant recommend staying here more! Monticchiello is so beautiful and peaceful and their place is just perfect! I can’t wait to hopefully return one day!!

4.99 out of 5 average rating, 67 reviews

The sleeping area features an elegant bed with light linens, complemented by a rich wooden floor. Exposed brick arches and beams create a warm ambiance. A small desk and lamp are present, along with soft lighting that enhances the historical character of the space.

Condo in Montepulciano

a.d. 1237

HeatherRating, 5 stars1 week ago

What an incredible stay!! 10/10. We traveled all over Tuscany for 2 weeks and this stay ranks right up there at the top. From the communication and ease of getting to the apartment to the beautiful old history of the building and town. Just wow! Book it:) We loved the town and her people🫶🏼 The apartment was comfortable in every way. Grazie mille, Heather & Beth

4.98 out of 5 average rating, 46 reviews

Home in Torrita di Siena

Casa Ilda A/C, Wi-Fi Private parking

NicolasRating, 5 stars1 week ago

Great place! Beautiful area and close to the activities we had planned. Very clean and spacious apartment - clear instructions.

4.99 out of 5 average rating, 113 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

"Landscape Notes" Suite

CaliRating, 5 stars2 weeks ago

This was by far the most beautiful view we have ever had at an Airbnb or hotel room. The house was beautiful, but the sunrise from the balcony is something I will remember forever. Vittorio also offered recommendations, and Fulvia was flexible with our check in. The apartment is in the perfect spot to become familiar with town. We want to come back to stay here again. Thank you!

Vacation home in Monticchiello

An arched stone entrance frames a quaint Tuscan street. Vibrant flowers adorn a balcony above cobblestone pathways, while rustic buildings with green shutters and brick facades contribute to the historic charm of Monticchiello. Softly glowing street lamps add to the inviting atmosphere.

4.97 out of 5 average rating, 105 reviews

In Tuscany Rooms

DaphneRating, 5 stars1 week ago

The place was just darling and was really clean and spacious! It was the perfect place in the perfect town. Kasia is a wonderful host!

Vacation home in Monticchiello

5 out of 5 average rating, 20 reviews

Elegant farmhouse overlooking Pienza

CherylRating, 5 stars1 day ago

Apart from the stunning location and beautiful well equipped house, Laura was a delight to deal with. She was responsive and informative. Our guests loved it as much as we did. Thank you Laura.

A round dining table is set on a terrace, surrounded by woven chairs. A colorful yellow vase filled with pink flowers is at the center. The view reveals rolling hills and a clear sky, providing a serene backdrop to outdoor dining.

4.9 out of 5 average rating, 73 reviews

Casa Evelina - Incredible View, Central Location

JodiRating, 5 stars1 week ago

We had a wonderful stay here! Check in was easy. The apartment is huge and of course the view is wonderful. The showers had amazing water pressure and plenty of hot water. As stated in the description there is no AC. We closed the shutters during the day to keep it cooler while we were out and in the evenings it cooled off nicely and had good cross ventilation from the front bedrooms to the back of the apartment. The location is great on the main street with access to many restaurants and shops. Some street noise to be prepared for but certainly manageable.

A panoramic view of the Val di Chiana is framed by a brick archway. Rolling hills and a serene sky displaying soft hues of orange and pink capture the scenic beauty of the landscape, which stretches far into the distance.