
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.

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.

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 .

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.

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.

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.

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.

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!

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
Family-Friendly holiday homes

Fede and Romy's Nest

Experience rustic off-grid life in the wilderness

"Lisa" apartment with fireplace

White lily with a view of Siena

Podere Vittoria Apartment: Heart of Chianti

Apartment in historic Villa in Siena_"FORIPORTA"

AM Apartment

Michelangelo: entire space in the heart of Tuscany
Holiday home rentals with a patio

Tuscany Breath - Panoramic Pool & Tennis Court

Canapino - Rifugium

Podere di Montecchio - Guardiana

[History & Design] Garden & Viewpool Apartment

City Centre Patio - 10 mins to Duomo

Tuja

Elegant farmhouse overlooking Pienza

Flat, terrace, pool,Spa resort,restaurant, A/C, G1
Holiday home rentals with a washing machine and dryer

Elegant farmhouse surrounded by nature, Terra

Tuscan Suite Amiata in Villa Q Dimorae Adults Only

Unique & Historic Getaway: Dreamy Garden

Melarancio Residence

[Colline Firenze] Borgo Le Palaie

Tuscany country Village near Siena

Florence Elegant Suite

Cenerentola chianti 1 apartment - near Panzano
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- Santa Maria Novella
- Mercato Centrale
- Piazzale Michelangelo
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Basilica of Santa Maria Novella
- Spiagge Bianche
- Ponte Vecchio
- Cala Violina
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Gulf of Baratti
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- Boboli's Garden
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapel
- Palazzo Vecchio
- Stadio Artemio Franchi
- Spiaggia Marina di Cecina
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