
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!
FamilyValueDecor
4.93 out of 5 average rating, 246 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.
FamilyLocationSleep quality
5.0 out of 5 average rating, 129 reviews
Podere La Castellina - No. 4 FICO
Stone and brick apartment inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of the Montagnola Senese. The apartment located on the first floor can comfortably accommodate 4 people (2+2 children) and includes: - large living room with TV, sofa and 2 single beds - kitchen with oven - master bedroom - bathroom with shower Panoramic pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue are available to guests.
LocationValueBathroom
4.96 out of 5 average rating, 110 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.
LocationValueAccuracy
4.92 out of 5 average rating, 207 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
ValueFamilyParking
5.0 out of 5 average rating, 123 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.
LocationFamilyKitchen
4.98 out of 5 average rating, 168 reviews
Barrel Suite Tuscany • Hot Tub • Vineyard View
Sleep inside a wine barrel in Tuscany — one of the largest in the world (3.5 m × 8 m) — nestled in an olive grove in Reggello, with panoramic views over the hills and vineyard. Private bathroom, kitchenette, veranda, private courtyard and exclusive hot tub: everything for a total escape from the world. 40 min from Florence, with Siena, Arezzo, The Mall Luxury Outlet and Vallombrosa all within easy reach. Free private parking included.
LocationFamilyAccess
4.88 out of 5 average rating, 229 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.
ValueLocationPets
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.
FamilyLocationCheckout
4.99 out of 5 average rating, 104 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.
LocationFamilyView
4.92 out of 5 average rating, 104 reviews
Pienzalettings
Relax in this peaceful place in the small village. Our PienzaLettings vacation home is an explosion of uniqueness and beauty, with a timeless charm. Equipped with every comfort, it is ready to welcome you and ready to make you experience a relaxing and exciting adventure in a timeless place. Not included: €1 tourist tax per person per night, excluding children under 15 years of age
LocationValueNearby
4.92 out of 5 average rating, 115 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property
LocationFamilyCleanliness
4.91 out of 5 average rating, 100 reviewsPopular amenities for Montalcino holiday homes
Family-Friendly holiday homes

The Loggia of San Giovenale
FamilyValueGetting around
4.96 out of 5 average rating, 296 reviews
Charming farmhouse with garden, views & pool
LocationFamilyNearby
4.92 out of 5 average rating, 233 reviews
Cottage "Casa Luisa "with private pool
LocationValueCondition
4.84 out of 5 average rating, 100 reviews
Vittoria Chianti Vacations 🍇🍷
ValueLocationLaundry
4.94 out of 5 average rating, 205 reviews
[Traditional Cozy House] Garden & Viewpool Apt
FamilyLocationNearby
4.91 out of 5 average rating, 117 reviews
Linearis apt B (4+2) Toscana
FamilyLocationNearby
4.89 out of 5 average rating, 160 reviews
Montalcino Vacation Home Idolina Guest House
ValueFamilyCheck-in
4.97 out of 5 average rating, 29 reviews
Glicine Apartment
LocationGetting aroundAccuracy
5.0 out of 5 average rating, 21 reviewsHoliday home rentals with a patio

Casa Isla, near Orvieto, amazing views + pool
ValueLocationDecor
4.99 out of 5 average rating, 126 reviews
Il Toscano - New with terrace in downtown Greve
LocationFamilyCheckout
4.93 out of 5 average rating, 107 reviews
Pian'D'olmo, an ancient farmhouse in the heart of Tuscany
ValueFamilyParking
4.9 out of 5 average rating, 31 reviews
the oasis of the foxes
LocationFamilyIndoor spaces
5.0 out of 5 average rating, 97 reviews
Tuscany Breath - Panoramic Pool & Tennis Court
LocationHospitalityAir conditioning
5.0 out of 5 average rating, 10 reviews
Flat, terrace, pool, Spa resort,restaurant, A/C,S1
LocationGetting aroundPool
5.0 out of 5 average rating, 5 reviews
The Piccola Villa of Borgo Argenina
FamilyLocationIndoor spaces
4.97 out of 5 average rating, 38 reviews
Tuscan House with Private Jacuzzi in Chianti
FamilyLocationHot tub
4.95 out of 5 average rating, 97 reviewsHoliday home rentals with a washing machine and dryer

Chianti Panorama | House with 3 En-Suite Bathrooms
FamilyValueNearby
4.95 out of 5 average rating, 147 reviews
Apartment in historic Villa in Siena_"LE CONTRADE"
ValueLocationWi-Fi
4.96 out of 5 average rating, 91 reviews
Chiantissima Tuscany
LocationOutdoor spacesAir conditioning
5.0 out of 5 average rating, 8 reviews
My cozy home in Chianti
LocationValueLong stay
4.98 out of 5 average rating, 99 reviews
Casale Le Fonti
LocationFamilyOutdoor spaces
5.0 out of 5 average rating, 6 reviews
Vicolo delle Rose Apartment
LocationFamilySleep quality
5.0 out of 5 average rating, 11 reviews
Granducato contemporary design and private pool
FamilyLocationPets
4.97 out of 5 average rating, 58 reviews
Tuscany country Village near Siena
LocationValueBathroom
4.88 out of 5 average rating, 25 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
- Tastings Siena
- Museums Siena
- Food tours Siena
- Cultural tours Siena
- Art workshops Siena
- Outdoors Siena
- Dining Siena
- Landmarks Siena
- Wildlife Siena
- Cooking Siena
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
- Cooking Tuscany
- Wildlife Tuscany
- Landmarks Tuscany
- Tastings Tuscany
- Galleries Tuscany
- Outdoors Tuscany
- Museums Tuscany
- Workouts Tuscany
- Art workshops Tuscany
- Food tours Tuscany
- Shopping and fashion Tuscany
- Dining Tuscany
- Performances Tuscany
- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Cooking Italy
- Cultural tours Italy
- Flying Italy
- Tastings Italy
- Wildlife Italy
- Food tours Italy
- Museums Italy
- Performances Italy
- Wellness Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Landmarks Italy
- Architecture Italy
- Outdoors Italy
- Water sports Italy







