
Cottage vacation rentals in Siena
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Top-rated cottage rentals in Siena
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Monteriggioni Castello, holiday house in Tuscany
Our accommodation is a historic building that dates back to the construction of the castle. It has been recently restored and furnished with attention to every detail. It is very welcoming and has all the most modern amenities. Tourists who decide to be our guests will have the advantage of living in the medieval environment of the castle, taking advantage of all the conveniences. They will feel pampered and have the opportunity to return home having lived a unique and unforgettable experience.
4.95 out of 5 average rating, 298 reviews
Villa di Geggiano - Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.
4.99 out of 5 average rating, 155 reviews
Stone House with Exclusive Pool Codilungo in Chianti
Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.
4.98 out of 5 average rating, 218 reviews
EcoLodge – modern design in a peaceful panoramic location
The modern, ecological and comfortable EcoLodge is quiet and secluded, surrounded by olive groves, chestnut and fruit trees, vines and meadows. In front of you are the hills of the Val d'Orcia; behind you is Monte Amiata. Three worlds meet here: Val d'Orcia, Monte Amiata, and Maremma. The Vielfältigkeit is an ideal base for culture, wine, hiking, mountain biking, hot springs and the sea – and at the same time a place to enjoy Tuscan country life away from the crowds of tourists.
4.94 out of 5 average rating, 111 reviews
Your Tuscan oak tree house, enchanting Val d'Orcia
The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.
5.0 out of 5 average rating, 116 reviews
Country cottage C&M surrounded by greenery, love Tuscany
Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.
4.94 out of 5 average rating, 204 reviews
Tuscan Barn Apartment for 6 with panoramic pool
Panoramic Tuscan apartment converted from an old barn, with direct access to the garden and a shared panoramic swimming pool overlooking the Senese hills. Ideal for families or small groups of friends looking to enjoy for an authentic rural experience, privacy and relax. The apartment features three double bedrooms each with private bathroom, air-conditioning and WI-FI. A perfect place to enjoy nature, silence and unforgettable Tuscan sunsets.
4.89 out of 5 average rating, 100 reviews
Lovely apartment with garden and views near Siena
At just 18km from Siena, the apartment is part of a traditional Tuscan farmhouse, Santa Barbara, tucked away in the scenic rolling hills of Tuscany. The uniquely positioned grounds dominate the valley, allowing for stunning views with the most enchanting sunsets, or sunrises for those early birds! The apartment allows for a relaxing and recharging break, as well as being in the perfect location to go out and explore.
4.9 out of 5 average rating, 162 reviews
Casa Roberta: a beautiful view of the Crete!
Beautifully renovated stone house, located on the hill of Vescovado di Murlo. It is on the edge of the historic center in a quiet area where you can only hear the sound of nature. Two floors with a small garden with a beautiful view. It can accommodate four guests. The house is not suitable for disabled people (presence of stairs, unsuitable doorways). Cars must be parked outside, in the many parking lots of the Borgo.
4.83 out of 5 average rating, 161 reviews
Countryside Cottage With View - Le Papere apt
The cottage is part of a charming traditional Tuscan farmhouse, built in stone and situated in one of the most beautiful areas of Tuscany. A lovely garden surrounds the house and has magnificent views of the medieval town with its famous towers. Warm and cozy atmosphere that makes you feel instantly at home. For those who wish to live the experience of the Tuscan countryside as it is lived by the locals.
4.88 out of 5 average rating, 139 reviews
Countryside, 10 min from Siena
Apartment and large fenced garden for exclusive use. It's a must for countryside, peace and relaxation, close to major places of cultural interest, trekking, biking trails. In a hilly area characterized by beautiful oak and holm oak forests, it enjoys a quiet location and a beautiful view of Siena, which is only 7 km away. (2 km are dirt road).
4.84 out of 5 average rating, 289 reviews
Open-space rural house in San Galgano
The stylishly restored open space house has a large garden with an orchard and a vine arbor with barbecue and a spectacular view of the valley. Located in a village in the Municipality of Chiusdino near the Abbey of San Galgano.
4.93 out of 5 average rating, 174 reviewsPopular amenities for Siena cottage rentals
Cottage rentals with a hot tub

From Simone, podere santi Lucia and Pietro
4.94 out of 5 average rating, 243 reviews
Panoramic view & outdoor jacuzzi - Pienza
5.0 out of 5 average rating, 81 reviews
Romantic House in Tuscany with jacuzzi
4.96 out of 5 average rating, 85 reviews
"Rosso Poggiolo" farmhouse with swimming pool.
4.75 out of 5 average rating, 145 reviews
Cottage in the countryside with private jacuzzi and swimming pool
4.88 out of 5 average rating, 81 reviews
Capanna at S. Carlo in Buonconvento
4.95 out of 5 average rating, 39 reviews
Podere Coreno / Authentic Tuscan Peace & Relaxation
5.0 out of 5 average rating, 7 reviews
Farmhouse with Private Saltwater Pool • Montepulciano
4.55 out of 5 average rating, 22 reviewsPet-friendly cottage rentals
Cottage Leccio - Masseto In Chianti
4.95 out of 5 average rating, 105 reviews
Piccolo Cottage San Gimignano
4.95 out of 5 average rating, 174 reviews
La Dolce Vita Romantic Sea-view Cottage. Tuscany
4.96 out of 5 average rating, 130 reviews
La Casa del Frantoiano - Pari -
4.94 out of 5 average rating, 179 reviews
Typical Tuscan Cottage with swimming pool and park
4.95 out of 5 average rating, 42 reviews
House in Sogna
4.71 out of 5 average rating, 34 reviews
Private Country House with swimming pool -Chianti
4.95 out of 5 average rating, 57 reviews
Stunning cottage on the Tuscan hills
4.85 out of 5 average rating, 98 reviewsPrivate cottage rentals

Cottage "Girasole" in Tuscany
4.85 out of 5 average rating, 140 reviews
Charming cottage in Tuscany
4.94 out of 5 average rating, 141 reviews
Podere Grignano, beautiful Tuscany.
4.94 out of 5 average rating, 108 reviews
Peaceful modern eco house in the Tuscan hills
4.88 out of 5 average rating, 161 reviews
CASA MARIA
5.0 out of 5 average rating, 20 reviews
Crete Senesi - Asciano Cavoni Hut
5.0 out of 5 average rating, 58 reviews
Old Chianti chapel-style cottage
4.83 out of 5 average rating, 133 reviews
Stone cottage + private garden near San Gimignano
4.9 out of 5 average rating, 21 reviewsDestinations to explore
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- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Cala Violina
- Parco Regionale Della Maremma
- Mercato Centrale
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Parco delle Cascine
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Cascate del Mulino
- Things to do Siena
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- Things to do Tuscany
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- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Food tours Italy
- Cooking Italy
- Flying Italy
- Cultural tours Italy
- Wellness Italy
- Tastings Italy
- Wildlife Italy
- Landmarks Italy
- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Outdoors Italy
- Architecture Italy
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