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Holiday houses in Bolgione

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Top-rated holiday rentals in Bolgione

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.98 out of 5 average rating, 174 reviews

Casa al Gianni - The Simignano Barn

Transformed from a historic barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living area, and 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 looking for 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 outdoor dinners. A memorable getaway awaits you in this little slice of paradise!

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 130 reviews

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.

Top Guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 151 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.

Top Guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 221 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Guest favourite
An entrance is framed by natural stone walls, showcasing wooden shutters on either side of the door. A small outdoor terrace is furnished with a table and chairs, adorned with vibrant flowers in pots, inviting a serene outdoor experience.
Apartment in Siena
4.94 out of 5 average rating, 125 reviews

Escape to Tuscany: Stunning Chianti Views Await

As you have come across this advert, it means that curiosity is part of you. The same will bring you to appreciate this little jewel in the middle of the Chianti countryside, just 6 km away from the city centre of Siena. Recently renovated you will be amazed by peace, relaxation and cosiness. If you are looking for a small and comfortable place in the tranquillity of Siena’s countryside, far away from city stresses, then this cosy flat will be ideal for your next holiday retreat.

Top Guest favourite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.98 out of 5 average rating, 130 reviews

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Guest favourite
Apartment in Ponte a Bozzone
4.92 out of 5 average rating, 36 reviews

The touch in Chianti

Welcome! Il tocco nel Chianti is a cozy apartment just 7 km from Siena, in a very convenient location to visit all of Tuscany. The lovely apartment has two bedrooms, one with a small en-suite bathroom, a living room with a kitchen, a bathroom, and two terraces with breathtaking views of the Chianti hills. The house is on the second floor without an elevator and is only 300 meters from the bus stop and two pizzerias, Siena can be reached in 10 minutes by car.

Guest favourite
An outdoor dining area is featured under a wooden pergola, with a long table surrounded by chairs. Colorful potted flowers add vibrancy to the scene. A stone patio is visible under a lush green lawn, with trees and foliage creating a shaded backdrop.
Condo in Siena
4.93 out of 5 average rating, 80 reviews

Casa Piccola

“Casa Piccola” is a lovely home for your vacation in Tuscany. A small romantic retreat for two, ready to welcome you and let you taste the tranquility of the Tuscan countryside, just 3 km from Siena. Ideal starting point to visit all the nearby destinations, such as the Chianti Classico area, Val d 'Orcia, San Gimignano, Rapolano Terme (famous spas) and nearby Florence, "Casa Piccola" will give you a unique and unforgettable experience.

Guest favourite
Villa in Siena
4.89 out of 5 average rating, 300 reviews

Villa Capanna, Private Pool, Breathtaking Views

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

Top Guest favourite
A charming country loft is enveloped in lush green vines, with steps leading from a grassy area to the entrance. Sun loungers are situated on the lawn, providing a serene space for relaxation. This rustic exterior is framed by trees and open skies.
Loft in Siena
4.95 out of 5 average rating, 251 reviews

Siena Country Loft Hideway

Country loft, ideal gateway for a couple looking to experience the flavour of Tuscan countryside 2 bathrooms, one with shower and one with bath tub with unique windows view Fully equipped kitchen Eclectic style with antique accents Endless rolling hills view, modern amenities in typical country side setting Concierge service upon request Wifi Internet connection Only 7km far from Siena town

Guest favourite
A wide arched window frames a panoramic view of the historic cityscape at dusk. Illuminated buildings, including two prominent towers and a cathedral, are visible amidst the gently rolling rooftops. A wrought iron railing adds a touch of elegance to the architectural detail.
Apartment in Siena
4.89 out of 5 average rating, 181 reviews

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 comodità di raggiungere a piedi in pochi minuti tutti i maggiori punti di interesse della città.

Top Guest favourite
A warm living area is presented, featuring a comfortable sofa adorned with soft pillows and a round dining table. The space is illuminated by wall sconces, while an arched entryway leads to another room. Large windows allow natural light to fill the area.
Farm stay in Gaiole in Chianti
4.96 out of 5 average rating, 105 reviews

La Pieve - the house next to the church

To the right of the Argenina church, after which it is named, it has the persuasive look of its 2 small arches facing west. Perhaps it was once the parish priest's house, or the one where cooking was done in the large wood-burning oven, who knows?

Popular amenities for Bolgione holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Bolgione