Vacation rentals in Montisi

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Top-rated vacation rentals in Montisi

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Superhost

A spacious living area features a white sofa adorned with soft cushions in muted tones. Exposed wooden beams and a stone staircase add rustic charm. Natural light filters through large windows, creating a warm ambiance. A cozy armchair and decorative shelving complete the inviting space.

Home in Anghiari

4.88 out of 5 average rating, 140 reviews

Tuscan dream in the ancient Tobacco's villa, sauna

Welcome to Tobacco Loft, our 16th century stones' villa located in the countryside of Anghiari. The House offers stunning views, charming and furnished interiors providing all type of comforts: a beautiful fireplace that will keep the ambient warm in winter, the relaxing sauna, the private garden where you can enjoy the open air and have lunch under the pergola, BBQ, fantastic in the warm seasons, a panoramic swimming pool to spend great moments with friends, to be shared with the hamlet guests.

Top guest favorite

A cozy sitting area features a vintage leather sofa with colorful accents, positioned against a light wall adorned with contemporary wall art. Soft bedding is seen at the back, complemented by warm wooden flooring. Natural light filters through a nearby window, enhancing the inviting space.

Home in Montalcino

5 out of 5 average rating, 125 reviews

Montalcino Townhouse with Private Garden & Spa

A luxury apartment that blends traditional elements with all the modern comforts and some contemporary wall art. The apartment is centrally located in the upper part of town, only around the corner from the main square, in the limited traffic area. You can drive close by to download the luggage. The closest free car park is located at less than 10 minutes walk. Please note that to reach the house you need to walk a fairly steep street: it may not be ideal for those with mobility problems.

Top guest favorite

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.

Guesthouse in Montefollonico

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.

Top guest favorite

The kitchen area features wooden cabinets and modern appliances, including a gas stove and oven. A round table with a colorful design is surrounded by black wire chairs. Large windows provide natural light and views of the surrounding landscape.

Cottage in Castell'Azzara

4.99 out of 5 average rating, 139 reviews

Your Private Tuscan Retreat

This beautiful sheepherder’s stone cottage is equipped with modern comforts and spa facilities free of charge. The large grounds of forest and meadow span a ridge and provide panoramic views of the valley toward Val d’Orcia to the north, the expansive Maremema to the south, and the ancient volcano of Amiata to the west. This is the perfect getaway for those wanting a private retreat from which to explore the rich wine, food, culture, history, and landscape of southern Tuscany.

Guest favorite

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.

Farm stay in San Giovanni d'Asso

4.94 out of 5 average rating, 115 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.

Top guest favorite

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

4.99 out of 5 average rating, 114 reviews

"Landscape Notes" Suite

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.

Guest favorite

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.

Apartment in Montepulciano

4.94 out of 5 average rating, 196 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.

Guest favorite

A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.

Apartment in Castelnuovo Berardenga

4.93 out of 5 average rating, 161 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Top guest favorite

A view from the entrance features a winding gravel road bordered by tall cypress trees and olive groves. Rolling hills stretch into the distance, creating a gentle and inviting landscape under a partly cloudy sky.

Condo in Asciano

4.97 out of 5 average rating, 290 reviews

Green – The meadows in Tuscany

Apartment consisting of 1 double bedroom, equipped kitchen, large living room, and bathroom TV, BBQ, (we provide the washing machine from 9 a.m. to 8 p.m. in our laundry room to those who request it). We recommend a car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and wifi Convenient location to visit Tuscany and Umbria.

Guest favorite

A charming two-story villa is set amidst a spacious green lawn, surrounded by trees and shrubs. The building features red shutters and a welcoming porch that invites relaxation. Scenic countryside views extend beyond the property, enhancing the tranquil setting.

Apartment in Monticchiello

4.97 out of 5 average rating, 153 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.

Guest favorite

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

4.89 out of 5 average rating, 198 reviews

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!

Top guest favorite

Farm stay in Pisa

4.99 out of 5 average rating, 298 reviews

Tenuta Chiudendone in Tuscany

Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.