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Vacation rentals in Colombaiolo

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Top-rated vacation rentals in Colombaiolo

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Top guest favorite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.93 out of 5 average rating, 281 reviews

Casa al Gianni - Hut

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism property in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds, and the warmth of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a vacation; it’s a return to our roots. This peaceful haven will stay in your soul. We look forward to welcoming you!

Top guest favorite
Home in Siena
4.97 out of 5 average rating, 195 reviews

Podere Piazza house with panoramic view

Podere Piazza is an estate, has its origin in the 15th century. The vacation home was built at the beginning of the 17th century. Podere Piazza was the residence of Alessandro Cervini degli Spannocchi, who was appointed Archbishop of Siena on May 29, 1747. He was a Nobile di Montepulciano and Patrizier of Siena. The buildings of Podere Piazza still bear his coat of arms today. This also explains our little church, at the road junction, in front of it to the right to the pine avenue and to the left into the driveway.

Guest favorite
An outdoor swimming pool surrounded by olive trees is depicted. Sun loungers and umbrellas provide shaded seating areas. The water is clear, reflecting the sky, while a ladder leads into the pool. A vibrant orange life preserver is mounted on the nearby fence.
Farm stay in Colombaiolo
4.92 out of 5 average rating, 48 reviews

Colombaiolo Farmhouse, Marta apartment

The apartment is inside the Colombaiolo farm, in the municipality of Siena. There are 4 apartments used as a farmhouse, a swimming pool. The Marta apartment is 75 sqm, on two floors. On the ground floor, there is a living room-kitchen with a half bathroom; on the first floor, a double bedroom, single/double bedroom, and a bathroom with shower. Private outdoor space, equipped with tables and chairs, shared barbecue with other apartments, swimming pool (open from May 20 to October 6), private parking.

Top guest favorite
Home in Siena
5.0 out of 5 average rating, 18 reviews

Private House for 4P – La Capanna Di Azzurra

Ideal for families, couples or friends looking for an elegant and welcoming home, this house is designed for those who want to experience the Tuscan countryside without sacrificing the comfort of the city. Imagine a breakfast looking at the profile of Siena, days between art, wine and nature, and the return at sunset, when the light warms the stone and the silence restores the authentic rhythm of these places. A practical, charming and scenic retreat, perfect for visiting Siena and its surroundings!

Guest favorite
Home in Asciano
4.96 out of 5 average rating, 134 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 favorite
Townhouse in Scandicci
4.88 out of 5 average rating, 336 reviews

Florence Sunset Hills • Giogoli

Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Top guest favorite
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, 153 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.

Guest favorite
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, 129 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 favorite
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, 132 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 favorite
A charming stone villa stands surrounded by green grass and trees, featuring ivy-covered walls. The exterior is complemented by a pathway made of light-colored stones leading to seating arrangements. Clear blue skies are visible above, enhancing the tranquil outdoor setting.
Villa in Siena
5.0 out of 5 average rating, 23 reviews

The Villa of the Spendthrift Brigade!

Beautiful villa with swimming pool, five minutes from the historic center of Siena, located in the most beautiful area of the city as well as in the circuit of the famous "Strade Bianche" cycling race. A series of outdoor spaces, an indoor pool with a whirlpool, a large park with centuries-old oaks and a private olive grove, and the extreme proximity to the center of Siena, complete this splendid setting located literally in the heart of the Sienese hills!

Top guest favorite
Home in Siena
4.98 out of 5 average rating, 121 reviews

Relay moderno a Siena

This elegant accommodation, just 5 km from the center of Siena, is close to the city and Chianti. Suitable for couples who love relaxation, families and sportsmen (perfect starting point for Chianti tours). The accommodation includes two double bedrooms and a study room with sofa bed, two bathrooms with shower and a half bathroom. Large and free parking, garden with solarium space, grass soccer field, guarded and covered shelter for bicycles.

Guest favorite
A warm dining area features a large wooden table surrounded by wooden chairs. A centerpiece of colorful flowers and fruit is placed on the table. Natural light enters through a window with simple curtains, highlighting the wooden beams and tiled flooring.
Farm stay in Siena
4.87 out of 5 average rating, 52 reviews

"Annarosa" Apartment on Chianti hills

The apartment has three comfortable bedrooms (one double, one with two single beds and one with a single bed), a large kitchen (with dishwasher, washing machine, oven and microwave) two new bathrooms with shower. The apartment is completed by a large living room with a sofa and TV, a dining room whose large windows illuminate the interior and offer an incredible view of the garden.

Popular amenities for Colombaiolo vacation rentals