
Holiday Homes in Siena
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Top-rated Holiday Homes in Siena
Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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.

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.

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.

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.

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.

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.

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.

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

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.

The Cricket's Cage <Anna Maria> (A-04)
The apartment, located in the historic center, is located in a private internal courtyard overlooking the Duomo. You can use tables and chairs outside to relax and enjoy a unique view. In the bedroom and in the living room there are large wooden windows that make the apartment very bright; the parquet floors and the colors of the walls create a welcoming and relaxing atmosphere.

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!

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.
Popular amenities for Siena holiday homes
Family-Friendly holiday homes

Fede and Romy's Nest

"Lisa" apartment with fireplace

Living Siena - "Chiantigiana" Apartment

Tuja

Apartment in historic Villa in Siena_"FORIPORTA"

Apartment in Farmhouse with swimming pool Tuscany 2

La Civetta Deliziosa, a studio apartment in the center

TOSCANELLA STUDIO TOPAZIO
Holiday home rentals with a patio

Tuscany Breath - Panoramic Pool & Tennis Court

Canapino - Rifugium

Unique & Historic Getaway: Dreamy Garden

★ Romantic apartment & stunning view of Tuscany ★

City Centre Patio - 10 mins to Duomo

Cenerentola chianti 1 apartment - near Panzano

Elegant farmhouse overlooking Pienza

Tuscany Country House, Central Chianti, Pano Views
Holiday home rentals with a washing machine and dryer

Elegant farmhouse surrounded by nature, Terra

Tuscan Suite Amiata in Villa Q Dimorae Adults Only

Melarancio Residence

Tuscany country Village near Siena

Podere Vittoria Apartment: Heart of Chianti

Two floors of BLUE in the center of Florence

Cosy house with private pool

Tower House of the 1000
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- Santa Maria Novella
- Piazzale Michelangelo
- Lake Trasimeno
- Duomo di Firenze
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Cala Violina
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- Kite Beach Fiumara
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- The Boboli Gardens
- Spiagge bianche
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Mugello Circuit
- Spiaggia Marina di Cecina
- Palazzo Vecchio
- Things to do Siena
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- Things to do Italy
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