Vacation home rentals in Siena

Find and book unique vacation home rentals on Airbnb

Top-rated vacation home rentals in Siena

Guests agree: these vacation home rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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, 138 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, 131 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.

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 modern kitchen space features a marble countertop with two wooden stools. Large windows showcase a scenic view of Florence's rooftops, including the iconic dome, while natural light fills the room. A fruit bowl and coffee maker are included on the counter.

Vacation home in Centro

4.96 out of 5 average rating, 426 reviews

Breathtaking view from romantic nest in citycenter

Unique and charming attic in the middle of historic center with amazing breathtaking view on the city center. Perfect for a romantic stay in the heart of Florence. Fully windowed on 3/4 walls. Completely renewed with modern design furniture. Powerful A/C, fast wi-fi, fully equipped kitchen. Going downstairs you will immediately be absorbed in the most beautiful area of city center. Attention! Only for young-soul people: 5th FLOOR, NO LIFT, last 2 flights of stairs in a narrow spiral stair.

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 .

Top guest favorite

An aerial view captures the historic castle surrounded by lush green hills and vineyards. The impressive structure features tall towers and ornate architecture, set amid manicured gardens and tree-lined pathways, reflecting the beauty of the Chianti landscape.

Vacation home in Badia a Passignano

5 out of 5 average rating, 113 reviews

Chianti Craft House Badia a Passignano

Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area

Guest favorite

A swimming pool with a wooden deck is framed by lush greenery, providing a backdrop of rolling hills in the distance. An outdoor shower is positioned beside the pool, and the clear water invites relaxation under a partly cloudy sky.

Vacation home in Dimezzano

4.89 out of 5 average rating, 304 reviews

[Authentic StoneHouse] Garden & Viewpool Apartment

Authentic, quiet and cozy entire Stonehouse situated in a medieval small village, with stunning view pool on the top of the garden overlooking hills and vineyards, wide garden, many resting areas, stone-bbq and Pizza oven. Few Km away from Greve in Chianti, about 30 minutes from Florence and Arezzo, 45 minutes from the horse-ride city of Siena. Typical tuscany restaurant and wineries within 5 minutes by car.

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!

Guest favorite

An outdoor area is presented, featuring a stone-paved patio with several potted plants. The entrance to the house is framed by arched doors, which open to a cozy seating arrangement. Views of the surrounding landscape are visible in the background.

Vacation home in Faella

4.93 out of 5 average rating, 123 reviews

Historic apartment Il Prato in Castelfranco

Il Prato is a finely restored historic Tuscan farmhouse on the outskirts of Castelfranco di Sopra, surrounded by olive trees, orchards and woods. It has a beautiful garden with a swimming pool where you can relax and eat. Equidistant from the great cities of art of Siena, Florence and Arezzo.