
Places to stay near Val di Chiana
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Top-rated holiday rentals near Val di Chiana
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Casa al Gianni - Hut
Hi, we’re Cristina and Carmelo! We look forward to welcoming you to ‘Casa al Gianni’, our farm stay 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 companionship of our animals. It’s an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a holiday; it’s a return to our roots. This haven of peace will stay with you in your heart. We look forward to welcoming you!
4.93 out of 5 average rating, 294 reviews
Poggio Bicchieri Holiday Farm - Memoria apartment
Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!
4.92 out of 5 average rating, 626 reviews
Tuscan charm of villa - countryside - Villa Senaia
In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas
4.9 out of 5 average rating, 241 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.
4.96 out of 5 average rating, 142 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.
4.97 out of 5 average rating, 251 reviews
Casa Dolce Toscana | Panoramic Suite with View
CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.
4.98 out of 5 average rating, 185 reviews
Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.
4.95 out of 5 average rating, 146 reviews
Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking
4.93 out of 5 average rating, 335 reviews
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.
4.99 out of 5 average rating, 116 reviews
Tuscan farmhouse stay with restaurant and pool
Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.
4.94 out of 5 average rating, 108 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
Fontarcella, H&R- mediterranean home with jacuzzi
Located in the hills between Montepulciano, Castiglione del Lago, and Cortona, Fontarcella is a detached villa surrounded by greenery, offering a private jacuzzi and parking. You'll discover a timeless place to share precious moments. The property, furnished in Mediterranean style, features air conditioning and free Wi-Fi. The fully fenced garden offers a variety of amenities. Just minutes from the highways, Fontarcella is easily accessible for travelers.
4.98 out of 5 average rating, 168 reviewsPopular amenities for holiday rentals near Val di Chiana
Condo rentals with Wi-Fi

The walnut tree view, Montepulciano
5.0 out of 5 average rating, 137 reviews
Chicca: Cortona's historic centre
4.98 out of 5 average rating, 224 reviews
Podere Vergianoni nestled in Chianti with a pool
5.0 out of 5 average rating, 352 reviews
Romantic Yellow apartment in Crete Senesi
4.97 out of 5 average rating, 440 reviews
La Casetta di Brunello, very panoramic with terrace
4.9 out of 5 average rating, 324 reviews
Amazing Apartment near Piazza Grande w/ Terrace
4.92 out of 5 average rating, 189 reviews
Chianti, elegant barn among vineyards and pool
4.95 out of 5 average rating, 181 reviews
Residence In cerca d'Autore
4.97 out of 5 average rating, 345 reviewsFamily-friendly house rentals

La Lisa: country house surrounded by fields
4.94 out of 5 average rating, 135 reviews
Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni
4.99 out of 5 average rating, 232 reviews
House Rigomagno Siena
4.96 out of 5 average rating, 125 reviews
Tuscany House | View Breathtaking
4.97 out of 5 average rating, 112 reviews
Casa Rosmarino Eco-Wellness Country Home
4.99 out of 5 average rating, 274 reviews
Casa del Passerino
4.94 out of 5 average rating, 225 reviews
Jenny's Barn
4.96 out of 5 average rating, 187 reviews
La Perla del Lago Holiday home on Lake Trasimeno
4.98 out of 5 average rating, 207 reviewsApartment rentals with air conditioning

Beautiful medieval village!!!
4.99 out of 5 average rating, 474 reviews
I Tramonti di Eramo, central Montepulciano.
4.91 out of 5 average rating, 310 reviews
Piazza Grande Boutique Apartment
5.0 out of 5 average rating, 155 reviews
Luxury frescoed apartment in the historical center
4.97 out of 5 average rating, 116 reviews
Dimora dell'Erbe - Rooftop Apartment
5.0 out of 5 average rating, 124 reviews
Cortona Shabby Chic House - independent & balcony-
4.96 out of 5 average rating, 423 reviews
Romantic Tower's dating 1200
4.97 out of 5 average rating, 414 reviews
Castel Brunello - 2 doublebed rooms + terrace
4.99 out of 5 average rating, 118 reviewsOther great holiday rentals near Val di Chiana

Old hayloft on the Chianti hills
4.99 out of 5 average rating, 481 reviews
Villa di Geggiano – Guesthouse
4.99 out of 5 average rating, 155 reviews
Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
4.98 out of 5 average rating, 145 reviews
Farmhouse Fattoria La Parita
4.99 out of 5 average rating, 531 reviews
Stone farmhouse in Val D'Orcia
4.98 out of 5 average rating, 160 reviewsLa Piazzetta - Cozy open space in the historic center of Montepulciano
5.0 out of 5 average rating, 514 reviews
In Tuscany Rooms
4.96 out of 5 average rating, 137 reviews
Unique view 3 bdr villa with pool & A/C in Pienza
4.95 out of 5 average rating, 104 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Lake Bolsena
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Basilica of St Francis
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino





