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Holiday houses in Staggia

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Top-rated holiday rentals in Staggia

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Top Guest favourite
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, 282 reviews

Casa al Gianni - Hut

Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship 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 with you in your heart. We look forward to welcoming you!

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Guest favourite
Apartment in Staggia
4.96 out of 5 average rating, 24 reviews

Cozy Apt near Siena, Chianti WiFi A/C Free Parking

Beautiful, newly renovated apartment in the heart of Tuscany, in Staggia, with new furnishings and all the essential amenities. Ideal for couples looking for a cozy, modern, and functional option. Convenient location: just minutes from Siena and San Gimignano, and in the heart of the Chianti area. Also convenient for visiting the Val d'Orcia (Montalcino, Pienza, and Montepulciano) and reaching Florence in about 45 minutes. Free parking is just a short walk from the apartment (about a 3-minute walk).

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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, 154 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.

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Top Guest favourite
A panoramic terrace is visible, featuring a small table set with a light purple tablecloth and dark chairs. The surrounding stone wall offers views of the landscape at sunset, highlighting rolling hills and distant towers.
Tower in San Gimignano
4.95 out of 5 average rating, 129 reviews

Medieval Tower experience with Panoramic Rooftop

If you are looking for a unique experience in the heart of San Gimignano, this is the place for you. With its 42 mt of height, Torre Salvucci Maggiore is one of the medieval town's famous towers and today the only one turned into a vertically-spread accommodation divided into 11 floors for a total of 143 steps. A magical setting unlike any other. The tower can hosts couples or small groups of up to 3 people. At the top, the panoramic terrace awaits for you with an axtraordinary 360° city view.

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Top Guest favourite
An infinity pool reflects a clear blue sky, offering expansive views of rolling hills and lush valleys. A sun umbrella provides shade beside the pool, while a charming rustic structure is positioned nearby, surrounded by trees and Mediterranean flora.
Barn in Castellina in Chianti
5.0 out of 5 average rating, 97 reviews

Cipressini 1 - Swimming pool and stunning view

Ancient stone barn adjacent to the main farmhouse dating back to the 17. century, located in the heart of the Chianti Classico on the side of a slope with breathtaking views over the Val d'Elsa. Luxuriously renovated and furnished, equipped with every comfort, it is located in such a way as to guarantee absolute privacy. On the GF: Kitchen, large living room with fireplace and double sofa bed. On the LGF: Bedroom with double bed, built-in wardrobes, desk, bathroom with shower, utility room

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Top Guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5.0 out of 5 average rating, 344 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.

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Top Guest favourite
The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 212 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.

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Top Guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5.0 out of 5 average rating, 227 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

ValueLocationLong stay

Guest favourite
Apartment in Staggia
4.89 out of 5 average rating, 66 reviews

The Optimist's House

Small, fully renovated studio apartment located in the heart of Tuscany, near the Via Francigena: 15 km from Siena, 40 km from Florence, 10 km from San Gimignano and 5 km from Monteriggioni. We are on the 1st floor of a historic building. In our apartment you will find every comfort. A complete kitchen: induction cooktop, microwave oven, toaster, coffee machine, kettle, dishes, washing machine. Bed linen and towels, hairdryer, shampoo are provided. Free public parking nearby.

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Top Guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 102 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

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Top Guest favourite
A spacious living area is adorned with intricate frescoes and elegant decor, featuring a comfortable cream-colored sofa and a wooden coffee table. Light filters through large windows, illuminating the room’s artistic details. In the background, a cozy sleeping area with a canopy bed is visible.
Condo in Florence
5.0 out of 5 average rating, 155 reviews

[SAN LORENZO-DUOMO] Prestigious Historic Residence

Make your stay a unique experience and give yourself an emotion that will last for life. Located in the heart of Florence, this magnificent historic residence is the ideal solution for those looking for an exclusive and prestigious location to combine with a central position, perfect for easily visiting the main sites of interest, reachable in less than 10 minutes on foot. The apartment enjoys exclusive views of the Medici Chapels, offering a unique view.

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Top Guest favourite
Condo in Colle di Val d'Elsa
5.0 out of 5 average rating, 23 reviews

Florence & Siena • Terrace • Private Parking • A/C

Imagine waking up to sunlight filling the apartment and enjoying breakfast overlooking the Tuscan hills. Bright top-floor apartment with elevator, panoramic terrace and 180° open views, between Florence and Siena, in a quiet private area with no through traffic. Perfect for families, with parking, air conditioning, fast Wi-Fi, fully equipped kitchen and all the comforts to explore Tuscany’s villages, wineries, art cities and iconic landscapes.

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Popular amenities for Staggia holiday rentals