
Holiday rentals in Siena
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Top-rated holiday rentals in Siena
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Casa al Gianni - The Simignano Barn
Converted from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this little slice of paradise!

Castelvecchio number 12 Siena, long stay top rent.
Discounted rates 👉🏻from 30% to 60% off. Perfect for master's and PhD students, business travellers or those who want to experience Siena for longer. Oldest historic apartment in Siena, in the quiet and exclusive alley of Castelvecchio, equipped with a unique garden terrace. Two large bedrooms, living room and kitchen, two bathrooms, bookcase. The house is furnished with high-quality furniture and equipped with everything you need for a longer stay. The special element consists of a terrace overlooking the garden.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Luxurious Medieval Tower & Private Concierge
It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Villa di Geggiano - Perellino Suite
The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Mascagni Farmhouse in Val d'Orcia, Pienza
Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Palazzo del Taja - in the center with whirlpool
Brand new apartment just renovated, located inside the historic Palazzo del Taja in the heart of Siena's historic center, a few meters from Piazza del Campo and the city's main attractions. Subjected to a renovation attentive to details, the apartment is elegant, bright, welcoming and quiet. Complete with every comfort, including a beautiful bathroom with a whirlpool tub, to offer an unforgettable stay to our customers.

"Red Rose" apartment with view of Siena.
Caggiolo is a completely renovated farm consisting of several apartments, each with an independent entrance and private garden, with a panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Terrace with a view of Siena
A fianco della Basilica di San Domenico, a pochissimi passi dal Duomo e da Piazza del Campo, in questo splendido ed elegante attico potrete godere della splendida vista e della comoditĂ di raggiungere a piedi in pochi minuti tutti i maggiori punti di interesse della cittĂ .

Palazzo Bichi Ruspoli-Historical Home-Very Central
Historical Home Palazzo Bichi Ruspoli is situated on the elegant main street, in the heart of Siena. Located in a beautiful and ancient medieval building, the house is on the third floor with elevator and has a stunning view on the city.

Secret Garden Siena
A beautiful house located inside the city walls of Siena. The house develops on two floors has three bedrooms and two toilets. The real strong point of this location is the private garden. Walking distance to all the main attractions.

Stilnuovo apartment in the heart of Siena
Elegant and bright apartment located in the heart of Siena. The street is full of restaurants, cafes and shops. The apartment is in a historic building and can comfortably accommodate four people. Very close to bus and train station.
Popular amenities for Siena holiday rentals
Other great holiday rentals in Siena

AnticaVista, Luxury Apartment with Tower Views

Tufi Frames: 3 suite, free parking, view, downtown

Siena Centre Luxury Design TownHouse -Parking Near

Rossella’s House overlooking the Mangia tower

Relax a few steps from the Campo

"Dragoncello Senese" Apartment

BV Apartment Siena

La Casa Nell'Onda, living Siena and its history.
Destinations to explore
- Rentals with an accessible-height bed Siena
- Tiny house rentals Siena
- Family-friendly rentals Siena
- Flat rentals Siena
- Townhouse rentals Siena
- Rentals with a balcony Siena
- Castle rentals Siena
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- Rentals with a sauna Siena
- Rentals with a firepit Siena
- Rentals with lake access Siena
- Fitness-friendly rentals Siena
- Holiday home rentals Siena
- Pet-friendly rentals Siena
- Waterfront rentals Siena
- Bed and breakfasts Siena
- Rentals with an EV charger Siena
- Villa rentals Siena
- Serviced apartment rentals Siena
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- Smoking-friendly rentals Siena
- Cottage rentals Siena
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- Rentals with pools Siena
- Rentals with beach access Siena
- Rentals with a hot tub Siena
- Tent rentals Siena
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- Rentals with a patio Siena
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- Farm stay rentals Siena
- Hotel rooms Siena
- Barn rentals Siena
- Guest house rentals Siena
- Boutique hotels Siena
- Rentals with a fireplace Siena
- Nature eco lodge rentals Siena
- Rentals with outdoor seating Siena
- Luxury rentals Siena
- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Mercato Centrale
- Parco Regionale Della Maremma
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Stazione Santa Maria Novella
- Del Chianti
- Piazza della Repubblica
- Piazzale Michelangelo
- Parco delle Cascine
- Pitti Palace
- Piazza della Signoria
- Boboli's Garden
- Palazzo Vecchio
- Cascate del Mulino
- Basilica of Santa Croce
- Things to do Siena
- Sightseeing Siena
- Tours Siena
- Art and culture Siena
- Sports activities Siena
- Food and drink Siena
- Nature and outdoors Siena
- Things to do Tuscany
- Sightseeing Tuscany
- Tours Tuscany
- Sports activities Tuscany
- Entertainment Tuscany
- Wellness Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Food and drink Tuscany
- Things to do Italy
- Food and drink Italy
- Art and culture Italy
- Entertainment Italy
- Tours Italy
- Wellness Italy
- Sightseeing Italy
- Sports activities Italy
- Nature and outdoors Italy





