
Holiday Homes in Montalcino
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Top-rated Holiday Homes in Montalcino
Guests agree: These holiday homes are highly rated for location, cleanliness and more.

Casa al Gianni - Oak
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!
FamilyLocationShared spaces
4.93 out of 5 average rating, 245 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.
FamilyLocationAccuracy
5.0 out of 5 average rating, 129 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.
LocationValueBathroom
4.97 out of 5 average rating, 161 reviews
Vittoria Chianti Vacations 🍇🍷
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.
LocationValueHospitality
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 café downstairs provides a delectable gourmet breakfast. Here, you can unwind and relax, study and learn, discover and explore, or create and dream.
ValueLocationCheckout
4.92 out of 5 average rating, 207 reviews
Cottage "Casa Luisa "with private pool
The house is independent and consists of 2 apartments. The house is located about 500 meters from the medieval village of S. Giovanni D'Asso. The apartment is very comfortable and bright and surrounded by a private garden with gazebo, barbecue. The swimming pool is private. In the village you can taste excellent dishes in the "La locanda del castello" restaurant and "Osteria delle Crete". The location allows you to quickly reach the most beautiful places in the Val d'Orcia , Crete Senesi.
LocationValueIndoor spaces
4.84 out of 5 average rating, 100 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
FamilyLocationCleanliness
5.0 out of 5 average rating, 123 reviews
Breathe in Tuscany: 180° view of the hills
Please note that the second bedroom is divided from the hallway by a curtain and not by a door. Experience San Gimignano with a splendid view of the Tuscan hills! In the heart of San Gimignano, experience the city with a separate entrance, second floor and breathtaking views of the Tuscan hills. Private parking is available upon request. Entrance, living room, 2 double bedrooms, kitchen and large bathroom. city tax to be added to the price, €2.50 per person per night.
ValueFamilyCheck-in
4.98 out of 5 average rating, 165 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.
LocationFamilyPets
4.98 out of 5 average rating, 168 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.
ValueFamilyPets
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.
LocationFamilyDecor
4.99 out of 5 average rating, 103 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.
ValueLocationTV
4.92 out of 5 average rating, 104 reviewsPopular amenities for Montalcino holiday homes
Family-Friendly holiday homes

Fienile Santa Teresa
ValueLocationView
4.98 out of 5 average rating, 174 reviews
The Loggia of San Giovenale
FamilyValueAir conditioning
4.96 out of 5 average rating, 295 reviews
Linearis apt B (4+2) Toscana
LocationFamilyLaundry
4.89 out of 5 average rating, 160 reviews
Casa Isla, near Orvieto, amazing views + pool
FamilyLocationPets
4.99 out of 5 average rating, 126 reviews
Stunning Tuscan apartment for 2
LocationFamilyCondition
4.9 out of 5 average rating, 130 reviews
Montalcino Vacation Home Idolina Guest House
FamilyValueDecor
4.97 out of 5 average rating, 29 reviews
Elegant farmhouse overlooking Pienza
FamilyLocationWalkability
5.0 out of 5 average rating, 36 reviews
Glicine Apartment
LocationHospitalityAir conditioning
5.0 out of 5 average rating, 21 reviewsHoliday home rentals with a patio

Il Toscano - New with terrace in downtown Greve
LocationValueEV charging
4.93 out of 5 average rating, 106 reviews
Pian'D'olmo, an ancient farmhouse in the heart of Tuscany
LocationValueDecor
4.9 out of 5 average rating, 31 reviews
Flat, terrace, pool, Spa resort,restaurant, A/C,S1
LocationAmenitiesView
5.0 out of 5 average rating, 5 reviews
the oasis of the foxes
LocationValueIndoor spaces
5.0 out of 5 average rating, 97 reviews
Tuscany Breath - Panoramic Pool & Tennis Court
LocationDecorAccuracy
5.0 out of 5 average rating, 10 reviews
Tuscan House with Private Jacuzzi in Chianti
FamilyLocationWi-Fi
4.95 out of 5 average rating, 97 reviews
Tuscany Country House, Central Chianti, Pano Views
LocationValueIndoor spaces
4.98 out of 5 average rating, 46 reviews
The Piccola Villa of Borgo Argenina
LocationFamilyCheck-in
4.97 out of 5 average rating, 38 reviewsHoliday home rentals with a washing machine and dryer

Chianti Panorama | House with 3 En-Suite Bathrooms
FamilyValueGetting around
4.95 out of 5 average rating, 146 reviews
Apartment in historic Villa in Siena_"LE CONTRADE"
ValueLocationParking
4.96 out of 5 average rating, 91 reviews
My cozy home in Chianti
LocationFamilyParking
4.98 out of 5 average rating, 99 reviews
Casale Le Fonti
LocationFamilyCondition
5.0 out of 5 average rating, 6 reviews
Chiantissima Tuscany
LocationCleanlinessSleep quality
5.0 out of 5 average rating, 8 reviews
Granducato contemporary design and private pool
FamilyLocationAccuracy
4.97 out of 5 average rating, 58 reviews
Vicolo delle Rose Apartment
FamilyLocationAir conditioning
5.0 out of 5 average rating, 11 reviews
Summer in Tuscany MAE
FamilyLocationAccess
4.87 out of 5 average rating, 99 reviewsDestinations to explore
- Apartment rentals 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
- Siena Cathedral
- CavallinoMatto
- Avignonesi Winery Fattoria Le Capezzine
- Vulci
- Val di Chiana
- Basilica Di San Miniato A Monte
- Palazzo Pubblico
- Valdichiana Outlet Village
- Saturnia Thermal Park
- Rimigliano Natural Park
- Riserva Naturale Diaccia Botrona
- Terme San Filippo
- Things to do Montalcino
- Things to do Siena
- Art workshops Siena
- Tastings Siena
- Museums Siena
- Food tours Siena
- Dining Siena
- Cultural tours Siena
- Outdoors Siena
- Landmarks Siena
- Wildlife Siena
- Cooking Siena
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
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- Food tours Tuscany
- Dining Tuscany
- Museums Tuscany
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- Shopping and fashion Tuscany
- Art workshops Tuscany
- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Food tours Italy
- Cooking Italy
- Flying Italy
- Cultural tours Italy
- Wellness Italy
- Tastings Italy
- Wildlife Italy
- Landmarks Italy
- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Outdoors Italy
- Architecture Italy
- Water sports Italy







