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Vacation home rentals in Siena

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Top-rated vacation home rentals in Siena

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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, 115 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
An outdoor area features a private jacuzzi under a shaded canopy, surrounded by lush greenery. A dining table with chairs is situated nearby, with a mirrored wall reflecting the tranquil setting. The inviting water's surface reflects the blue sky and trees beyond.
Vacation home in Petrignano del Lago
4.98 out of 5 average rating, 111 reviews

Fontarcella, H&R- mediterranean home with jacuzzi

Situata nelle colline a cavallo tra Montepulciano,Castiglione del Lago e Cortona, Fontarcella si presenta come una villetta indipendente immersa nel verde, che offre jacuzzi e parcheggio privati; Scoprirete un luogo senza tempo, per condividere momenti preziosi. La struttura, arredata in stile mediterraneo, dispone di climatizzazione e wi-fi gratuita. Il giardino, interamente recintato, offre vari comfort. A pochi minuti dalle autostrade, Fontarcella è facilmente raggiungibile dai viaggiatori.

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, 140 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 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, 307 reviews

[Authentic StoneHouse] Garden & Viewpool Apartment

Nestled in a timeless medieval village, this authentic Tuscan stonehouse offers peace, charm and sweeping views across vineyards and hills. The property features a panoramic pool at the top of the garden, multiple terraces for al fresco dining, a stone barbecue and a traditional wood-fired pizza oven. Just a few Km from Greve in Chianti and 30 minutes from Florence or Arezzo, this is the perfect base to explore the heart of Tuscany. Wineries and typical trattorie are within a five-minute drive.

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, 150 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, 182 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
4.95 out of 5 average rating, 442 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.

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Vacation home in Reggello
4.88 out of 5 average rating, 150 reviews

The Florentine Barrels

Bellissima botte abitativa completamente fatta in legno, la botte è una delle più grandi al mondo 3,5 metri di diametro per 8 metri di lunghezza. Dispone di cucina, ampio bagno ,spaziosi armadio e comodo letto. La botte è situata in una tenuta agricola in Toscana nel mezzo di una bellissima oliveta . Massima tranquillità con vista mozzafiato e idromassaggio. Zona molto strategica per visitare le migliori città toscane, come Firenze, Siena e Arezzo . Esperienza fantastica e rilassante.

Guest favorite
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, 211 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!

Top guest favorite
A spacious living area features a light-colored sofa with a decorative throw, complemented by wooden beams overhead. The open kitchen with modern appliances is visible in the background, alongside large windows that provide natural light and a view of the exterior.
Vacation home in Peccioli
4.89 out of 5 average rating, 217 reviews

Michelangelo: entire space in the heart of Tuscany

Come and take a vacation at our beautiful apartment in Peccioli, Tuscany! Enjoy a renovated space, beautifully decorated, with new appliances and furniture, Air conditioner in all spaces, high-speed internet, and all you need to enjoy your time in Italy. Peccioli is a gem in the heart of Tuscany, near all the big cities and touristic attractions.

Guest favorite
The exterior of a two-story terraced apartment features warm, rustic brickwork, a private terrace adorned with potted plants, and a wooden dining table surrounded by seating. Lush greenery and scenic hills are visible in the background under a clear blue sky.
Vacation home in Asciano
4.89 out of 5 average rating, 116 reviews

Charming home Crete Senesi

Less than 15 kilometers from Siena, the terratetto apartment is located in a characteristic Tuscan village on the hill that leads to the suggestive "Site Transitoire". The property is completed by a nice garden overlooking Siena and a comfortable pool.

Guest favorite
A terrace is showcased, featuring a wooden table accompanied by white chairs. The scene includes expansive views of rolling hills and vineyards, framed by tall cypress trees. The sky reveals warm sunset hues, creating a serene atmosphere.
Vacation home in Greve in Chianti
4.92 out of 5 average rating, 114 reviews

Stunning Tuscan apartment for 2

This apartment - tucked away privately and enjoying a stunning view from its terrace - is part of an 'agriturismo' farm which produces organic Chianti Classico. Spacious and light, it has 1 double bedroom, 1 sitting room, 1 bathroom and a kitchen.

Popular amenities for Siena vacation home rentals

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