Vacation home rentals in Siena

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Top-rated vacation home rentals in Siena

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Top guest favorite

A spacious living room features an archway of exposed brick and stone, with large windows allowing natural light. A comfortable sofa is positioned around a coffee table, while a professional kitchen is visible in the background, complemented by wooden shelves filled with books.

Vacation home in Arezzo

5 out of 5 average rating, 137 reviews

Historic Arched Apartment in the Heart of Arezzo

In the old town centre of Arezzo, next to Casa Vasari, rises up the sixteenth century building, owned in the past by the Ubertini family. A few steps away from all the attractions of the city, the old kitchens of the building have been transformed into an elegant and comfortable guesthouse, rich in charm in every detail. The interior design is well-finished and, making every detail stand out, is finely furnished with traditional carpets and antique pieces. Locanda Bellavita is an apartment for up to 7 people, on the ground floor with an independent entrance. It consists of two master bedrooms, one French bedroom, one restroom with bath and another one with shower, a big living room with a massive fireplace, dining room and professional kitchen. ingresso privato,tutti gli ambienti sono in esclusiva Salvo alcuni giorni della settimana,abito sopra la struttura The apartment is in a building in the old town center of Arezzo next to Casa Vasari. It’s a few steps from all the attractions in the city. a 100mt dalla Chiesa di san Domenico e dal Duomo. Vicinissimo al parcheggio Petri,sotto il Duomo della città. In 5 minuti ovunque a piedi nel centro della città In the middle of the old town centre the guesthouse is a few steps away from every touristic attraction. The apartment is entirely exclusive for you for the period reserved and is provided with every comfort. The kitchen is professionally equipped. The towels and bed linen will be changed every 4 days. To prepare breakfast, there is an area with coffee machine, kettle, toaster and microwave. *The rooms will be naturally chilled thanks to the thick stone walls, so you won’t need any air conditioning.

Top guest favorite

A person interacts with a falcon, demonstrating the connection between humans and raptors. The background features a natural landscape with greenery, and additional animals can be seen grazing in the distance. The setting showcases an engaging outdoor experience in a tranquil environment.

Vacation home in Chianciano Terme

5 out of 5 average rating, 110 reviews

The Eagle and the Olive Tree

At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

Top guest favorite

A bright bedroom features a spacious bed with crisp white linens and a decorative pillow. A vivid landscape painting hangs above, while a window with wooden frames reveals a scenic view of the Tuscan hills, complemented by soft natural light filtering through sheer curtains.

Vacation home in San Gimignano

4.98 out of 5 average rating, 130 reviews

Breathe in Tuscany: 180° view of the hills

Please note that the second bedroom is divided from the hallway by a curtain and not by a door. in Experience your experience in San Gimignano with a splendid view of the Tuscan hills! In the heart of San Gimignano, experience the city with an independent entrance, first floor and breathtaking views of the Tuscan hills. Private parking space available upon request. Entrance, living room, 2 double bedrooms, kitchen, and large bathroom. city tax to add to the price, €2.5 per person per night.

Guest favorite

A rolling landscape is depicted, featuring neatly arranged rows of olive trees and grapevines. In the background, the towers of San Gimignano are visible against a clear blue sky, complementing the serene atmosphere of the agriturismo.

Vacation home in San Gimignano

4.78 out of 5 average rating, 229 reviews

San Gimignano, Montegonfoli SIX

Wonderful apartment in the country side of San Gimignano, at about 3Km and 5min from town center by car, far from noise, but close to all you may need. The apartment is suited for 4 people with 2 bedrooms each one with its en-suite bathroom. Bedrooms have an high privacy, splitted by the living room with kitchen, featured by the huge fireplace where our ancient farmer used to sleep over a FIAT 500 seat. First floor, 20 steps, no elevator. Side view on San Gimignano city and towers on the right

Top guest favorite

An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.

Vacation home in Sovicille

4.97 out of 5 average rating, 146 reviews

Podere La Castellina - No. 1 COTTAGE

Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Top guest favorite

An aerial view captures a charming Tuscan farmhouse nestled within lush green vineyards and rolling hills. The property features a rustic stone exterior and a terracotta roof, complemented by surrounding greenery and a clear blue sky.

Vacation home in Poggibonsi

4.95 out of 5 average rating, 175 reviews

Vittoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

Guest favorite

A spacious living area features exposed wooden beams and a terracotta floor. A sectional sofa, adorned with decorative pillows, faces a wooden coffee table. A dining area with a simple table is visible, along with stairs leading to the upper level and large windows allowing ample natural light.

Vacation home in Porto

4.96 out of 5 average rating, 134 reviews

La Dimora del Lago - Lake views of Tuscany and Umbria

Recently and authentically restored in a small rural hamlet, located halfway between Florence and Rome and Montepulciano and Cortona in the tranquil countryside overlooking tiny Lake Chiusi - less than 2 hours drive by Autostrada or train from Florence or Rome. Forged from a 500-year-old watchtower, an authentic country house among other houses. it also has an excellent internet connection and Netflix. TOURIST TAX TO PAY IN CASH €0,80 per adult, per night of stay for up to 5 nights .

Superhost

A private terrace is seen with a metal table and two chairs, framed by colorful wildflowers. In the background, rolling hills stretch towards the horizon, while lush greenery fills the landscape. A gentle breeze moves through, creating a serene setting.

Vacation home in Casole d'Elsa (SI)

4.89 out of 5 average rating, 236 reviews

Studio in Tuscan farmhouse with pool & views

The studio is nestled in a beautiful Tuscan farmhouse on an olive farm near Casole d'Elsa, an unspoilt hilltop town in central Tuscany. The stone farmhouse has been restored over the years to create 3 totally separate apartments (one of which is my home) each with independent entrance , private terraces and garden space. The farm is surrounded by unspoilt countryside with spectacular views and magnificent sunsets. It is a calm and relaxed place, an idyllic retreat away from the crowds.

Guest favorite

An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.

Vacation home in Monticchiello

4.96 out of 5 average rating, 112 reviews

In Tuscany Rooms

**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

Superhost

A well-equipped kitchen area features modern appliances and ample cabinetry. A dining table set for four is positioned near a large window that opens to scenic views. Light-colored walls and natural stone flooring create a bright and inviting space.

Vacation home in Pianella

4.89 out of 5 average rating, 170 reviews

AM Apartment

The apartment is 10 km from the center of Siena in a very relaxing and quiet place in Chianti where you can enjoy a beautiful view, take long walks on foot and by bike or taste good wine in local companies. The house includes two bedrooms, two bathrooms, a living room with fireplace, sofa and smart TV and a large equipped kitchen. In addition, there are sheets, towels, hairdryer and free wifi

Superhost

A charming rustic farmhouse is set against a dramatic sky, framed by lush green trees. The exterior features warm-toned walls and a tiled roof, while a spacious yard includes seating arrangements for outdoor relaxation, inviting guests to enjoy the serene countryside.

Vacation home in Simignano

4.92 out of 5 average rating, 201 reviews

Casa al Gianni - Quercia

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!