
Holiday home rentals in Montalcino
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Top-rated holiday home rentals in Montalcino
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Casa al Gianni - Oak
Hi, we're Cristina and Carmelo! We look forward to welcoming you to โCasa al Gianni,โ 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!
4.93 out of 5 average rating, 244 reviews
The Eagle and the Olive Tree
At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.
5.0 out of 5 average rating, 127 reviews
Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.
4.97 out of 5 average rating, 160 reviews
Vittoria Chianti Vacations ๐๐ท
Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.
4.94 out of 5 average rating, 205 reviews
Stuart Jasmine central, panoramic top location
This abode boasts 1 double and 1 single bedroom, a spacious living room with a fully equipped kitchen, and 1 bathroom with shower. Every window frames a breathtaking view, filling the space with natural light. High-speed Wi-Fi ensures comfort for both work and leisure. Its proximity to all town amenities ensures convenience, while a delightful cafรฉ downstairs provides a delectable gourmet breakfast. Here, you can unwind and relax, study and learn, discover and explore, or create and dream.
4.92 out of 5 average rating, 206 reviews
Chianti Craft House Badia a Passignano
Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area
5.0 out of 5 average rating, 121 reviews
Casa Isla, near Orvieto, amazing views + pool
Located between the villages Viceno and Benano with incredible views of Orvieto and surrounded by olive trees. Casa Isla is a refurbished 70sqm 2 bedroom cottage next to the main house, completely self-contained with its own private garden and BBQ area. There is a double bedroom and a second with twin-beds, both with air-con. The lounge/kitchen comes with fridge, gas hob, oven, and dishwasher, a sofa bed, and a smart TV for movie nights. Relax in our salt-water/mineral pool.
4.99 out of 5 average rating, 124 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, 166 reviews
In Tuscany Rooms
**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.
4.96 out of 5 average rating, 137 reviews
La Loggia. House with pool and stunning view
LA LOGGIA House, renovated in 2015, is a large independent apartment, ideal to be rented by those who love nature, tranquility and peace of these uncontaminated places immersed in nature. The apartment is characterized by a huge window overlooking the valley where you can enjoy one of the most spectacular views in the region. The view that can be admired from LA LOGGIA spans more than 60 km on the Chianti and the Crete Senesi.
4.99 out of 5 average rating, 102 reviews
Villa Madonna of the Rose
Villa a few steps from the historic center but facing the countryside and the famous 16th century Madonna della Rosa church, there is a private parking for guests inside the property, the structure is surrounded by a garden and in front of an olive grove. there is a gazebo in the garden surrounded by Tiglio trees, a solarium on the top floor. The villa has all the comforts and large outdoor green spaces.
4.92 out of 5 average rating, 103 reviews
AM Apartment
The apartment is 10 km from the center of Siena in a very relaxing and quiet place in Chianti where you can enjoy a beautiful view, take long walks on foot and by bike or taste good wine in local companies. The house includes two bedrooms, two bathrooms, a living room with fireplace, sofa and smart TV and a large equipped kitchen. In addition, there are sheets, towels, hairdryer and free wifi
4.89 out of 5 average rating, 200 reviewsPopular amenities for holiday home rentals in Montalcino
Family-friendly holiday home rentals

The Loggia of San Giovenale
4.96 out of 5 average rating, 294 reviews
Experience rustic off-grid life in the wilderness
4.97 out of 5 average rating, 157 reviews
Montalcino Vacation Home Idolina Guest House
4.96 out of 5 average rating, 28 reviews
Glicine Apartment
5.0 out of 5 average rating, 21 reviews
Elegant farmhouse overlooking Pienza
5.0 out of 5 average rating, 36 reviews
Tuja
5.0 out of 5 average rating, 35 reviews
VACATION HOME I DUE CIPRESSI "Rosa Canina Apartment"
4.96 out of 5 average rating, 93 reviews
Unique & Historic Getaway: Dreamy Garden
4.97 out of 5 average rating, 30 reviewsHoliday home rentals with a patio

Il Toscano - New with terrace in downtown Greve
4.93 out of 5 average rating, 104 reviews
Pian'D'olmo, an ancient farmhouse in the heart of Tuscany
4.9 out of 5 average rating, 30 reviews
Flat, terrace, pool, Spa resort,restaurant, A/C,S1
5.0 out of 5 average rating, 4 reviews
Tuscan House with Private Jacuzzi in Chianti
4.95 out of 5 average rating, 92 reviews
the oasis of the foxes
5.0 out of 5 average rating, 96 reviews
The Piccola Villa of Borgo Argenina
4.97 out of 5 average rating, 38 reviews
Tuscany Country House, Central Chianti, Pano Views
4.98 out of 5 average rating, 46 reviews
Villa Amici Apartment
5.0 out of 5 average rating, 14 reviewsHoliday home rentals with a washing machine and dryer

Linearis apt B (4+2) Toscana
4.89 out of 5 average rating, 155 reviews
Chianti Panorama | House with 3 En-Suite Bathrooms
4.95 out of 5 average rating, 146 reviews
Summer in Tuscany MAE
4.87 out of 5 average rating, 98 reviews
My cozy home in Chianti
4.98 out of 5 average rating, 94 reviews
Chiantissima Tuscany
5.0 out of 5 average rating, 5 reviews
Vicolo delle Rose Apartment
5.0 out of 5 average rating, 11 reviews
โ Romantic apartment & stunning view of Tuscany โ
4.86 out of 5 average rating, 21 reviews
Granducato contemporary design and private pool
4.96 out of 5 average rating, 57 reviewsDestinations to explore
- Flat rentalsย Montalcino
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- Lake Trasimeno
- Lake Bolsena
- Cala Violina
- Parco Regionale Della Maremma
- Feniglia
- Gulf of Baratti
- Del Chianti
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino
- La Scarzuola
- Antinori nel Chianti Classico
- Avignonesi Winery Fattoria Le Capezzine
- Siena Cathedral
- CavallinoMatto
- Vulci
- Val di Chiana
- Palazzo Pubblico
- Basilica Di San Miniato A Monte
- Saturnia Thermal Park
- Valdichiana Outlet Village
- Rimigliano Natural Park
- Riserva Naturale Diaccia Botrona
- Terme San Filippo
- Things to doย Montalcino
- Things to doย Siena
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- Things to doย Tuscany
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- Cultural toursย Tuscany
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- Things to doย Italy
- Workoutsย Italy
- Shopping and fashionย Italy
- Cookingย Italy
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- Wellnessย Italy
- Tastingsย Italy
- Wildlifeย Italy
- Museumsย Italy
- Performancesย Italy
- Art workshopsย Italy
- Diningย Italy
- Galleriesย Italy
- Outdoorsย Italy
- Architectureย Italy
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- Landmarksย Italy







