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Holiday Homes in Siena

Find and book unique holiday homes on Airbnb

Top-rated Holiday Homes in Siena

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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Top Guest favourite
Holiday home in Petrignano del Lago
4.98 out of 5 average rating, 115 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 favourite
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.
Holiday 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.

Top Guest favourite
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.
Holiday home in Chianciano Terme
5 out of 5 average rating, 115 reviews

L'Aquila e L'Ulivo

All'Aquila e l'Ulivo, un antico casale ristrutturato del 1200, troverai non solo tutti i confort necessari per uno splendido soggiorno, ma vivrai anche l'emozione di sentirti libero e immerso nella natura incontaminata della Val D'Orcia. Qui avrai la possibilita' di passeggiare con i due falchi Ayga e Sayen e interagire con le aquile, e perchè non sorseggiare un eccellente aperitivo a bordo piscina. Ti aspettiamo nel nostro mondo, fatto di animali, relax, natura e anche un pizzico di Magia.

Guest favourite
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.
Holiday home in Centro
4.95 out of 5 average rating, 443 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 favourite
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.
Holiday home in Porto
4.96 out of 5 average rating, 135 reviews

La Dimora del Lago - Lake views 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 .

Guest favourite
A bright double bedroom is presented with a spacious bed featuring crisp white linens. Natural light floods the room through an open window, framing a view of the surrounding valley. Wooden beams add character to the ceiling, and bedside tables with lamps are positioned beside the bed.
Holiday home in Montepulciano
4.92 out of 5 average rating, 192 reviews

Stuart Jasmine central, panoramic top location

This abode boasts 1 double and 1 single bedroom, a spacious living room with a fully equipped kitchen, and 1 bathroom with shower. Every window frames a breathtaking view, filling the space with natural light. High-speed Wi-Fi ensures comfort for both work and leisure. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. Here, you can unwind and relax, study and learn, discover and explore, or create and dream.

Guest favourite
Holiday home in Reggello
4.88 out of 5 average rating, 151 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 favourite
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.
Holiday home in Sovicille
4.97 out of 5 average rating, 150 reviews

Podere La Castellina - N°1 COTTAGE

Cottage indipendente in pietre e mattoni all'interno del "Podere la Castellina" (ex convento 13° secolo), nel magnifico parco naturale della Montagnola Senese. Il cottage può ospitare comodamente 5 persone e comprende: - ampio soggiorno con tv e camino - cucina abitabile con forno - camera matrimoniale - camera con tre letti singoli - bagno con doccia A disposizione degli ospiti piscina panoramica, solarium e terrazza con vista mozzafiato, dotata di forno a legna e barbecue.

Superhost
Holiday home in Impruneta
4.84 out of 5 average rating, 289 reviews

Lovely farmhouse Tuscany

Tuscan farmhouse of 140 square meters with two bedrooms up to four people, very large living room with fireplace with terracotta floors and typical ceilings, kitchen equipped for cooking with fridge and microwave, external courtyard in ancient stone with table and chairs and private garden with olive trees. Customers are requested to come by car. If you want the heating is paid and according to consumption and can only be switched on from the period established by the region.

Top Guest favourite
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.
Holiday home in Monticchiello
4.97 out of 5 average rating, 119 reviews

In Toscana Camere

**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.

Guest favourite
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.
Holiday home in Simignano
4.92 out of 5 average rating, 213 reviews

Casa al Gianni - Quercia

Ciao, siamo Cristina & Carmelo! Vi invitiamo a vivere un’esperienza autentica nel nostro agriturismo “Casa al Gianni” situato 20 min da Siena. Il nostro marchio è la vita semplice a stretto contatto con la natura e gli animali della nostra fattoria. Immerso tra i boschi e la splendida campagna toscana trascorrerai una vacanza indimenticabile. Questo angolo di paradiso ti rimarrà nel cuore!

Guest favourite
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.
Holiday 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 holiday homes

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