
Cottage vacation rentals in Siena
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Top-rated cottage rentals in Siena
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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.

Stone House with Exclusive Pool Codilungo in Chianti
Spend a holiday in the heart of the Tuscan countryside in this cozy stone house with terracotta floors and beamed ceilings in solid oak, furnished with paintings of author , equipped with all comforts. Enjoy yourself by swimming in the large infinity pool (18m X 9m, open from May 1st to October 15th for guests of Stone house use only) or relax in an armchair under the loggia, tasting a glass of Chianti wine in front of the rolling hills of vineyards, olive groves, woods and medieval villages.

Cottage Cappero - Masseto In Chianti
MASSETO IN CHIANTI è un villaggio privato dove potrete rilassarvi nel vostro giardino privato e in piscina, fare sport, o utilizzare come base per visitare città rinascimentali: Firenze, Siena, San Gimignano, Arezzo, Volterra. Offriamo altri tre cottage con accesso indipendente e giardinetto privato: Quinto (2 letti), Vittoria (4 letti), Leccio (6 letti). La piscina è condivisa dai 4 cottage, ciascuno dispone di un gazebo privato, con distanze garantite e sanificazione a norma Covid-19.

Monteriggioni Castello, holiday house in Tuscany
Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

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.

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.

EcoLodge – modern design in a peaceful panoramic location
The EcoLodge, modern, ecological, comfortable, is in the middle of nature in a peaceful, fertile cultural landscape on Monte Amiata in the quiet southern Tuscany. It belongs to an old farmhouse with plenty of space, beautiful views, many old fruit, chestnut, olive trees and our vineyard. It's an ideal location. From here you can explore world-famous sights, do a lot and enjoy the tranquility of Tuscan country life away from the hordes of tourists.

Il Fienile, Cottage in the country with Jacuzzi
Surrounded by wineyards, close to Florence, a charming accomodation in a cozy cottage with heated jacuzzi at your exclusive use. Perfect starting point to discover Florence and Siena. Kitchen, wide living room, bathroom, two double bedroom (one with an extra single bed). In the living room a sofa bed for other 2 people. Tasteful furniture, Air Conditioning, barbecue, private parking. Partnership for: bike rental, private chef, private driver

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.

Lovely apartment with garden and views near Siena
At just 18km from Siena, the apartment is part of a traditional Tuscan farmhouse 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.

Lovely countryhouse on Chiant hills
Lovely view on the valley, sweet relax in the smelling garden under a very old tree tasting a good wine and then to visit Firenze, Pisa, Siena only 30 km far from here and medieval castles,little churchs ,winery,across the beautiful Chianti road.....

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.
Popular amenities for Siena cottage rentals
Cottage rentals with a hot tub

Romantic House in Tuscany with jacuzzi

From Simone, podere santi Lucia and Pietro

Cottage in the countryside with private jacuzzi and swimming pool

"Rosso Poggiolo" farmhouse with swimming pool.

NEW Leccino home pool&Jacuzzi a Fontanaro Property

Tuscany Villa Girasole

Hut at S. Carlo in Buonconvento

Detached Cottage with Private Spa
Pet-friendly cottage rentals

Stunning cottage on the Tuscan hills

Tuscan countryside vacation home with pool

Cottage in the south of Tuscany

Casa degli ulivi, live Chianti with swimming pool

Villetta Belvedere

Private pool nature Hideway

Tuscan Barn Apartment for 6 with panoramic pool

La Casa del Frantoiano - Pari -
Private cottage rentals

Castagnatello Country House – Walnut Cottage

Il Fienile, characteristic stone cottage for 2

Crete Senesi - Asciano Cavoni Hut

Angalia Guesthouse

Stone cottage in beautiful Umbrian countryside

Typical Tuscan cottage

Chianti Loft (AC & Pool)

Casale Poggiolo Basso - The place of silence
Quick stats about cottage rentals in Siena

Nightly prices starting at
Siena vacation rentals start at G$37,653 GYD per night before taxes and fees

Verified guest reviews
Over 90 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Siena rentals

4.9 Average rating
Siena stays are highly rated by guests—averaging 4.9 out of 5!
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- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Lake Trasimeno
- Marina di Cecina
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Cala Violina
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Del Chianti
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazzale Michelangelo
- Pitti Palace
- Mugello Circuit
- Parco delle Cascine
- Palazzo Vecchio
- Spiagge Bianche
- Boboli's Garden
- Gulf of Baratti
- Avignonesi Winery Fattoria Le Capezzine
- Piazza della Signoria
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