
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.

Podere La Castellina - N°4 FICO
Appartamento in pietre e mattoni all'interno del "Podere la Castellina" (ex convento 13° secolo), nel magnifico parco naturale della Montagnola Senese. L'appartamento situato al primo piano può ospitare comodamente 4 persone (2+2 bambini) e comprende: - ampio soggiorno con tv, divano e 2 letti singoli - cucina abitabile con forno - camera matrimoniale - bagno con doccia A disposizione degli ospiti piscina panoramica, solarium e terrazza con vista mozzafiato, dotata di forno a legna e barbecue.
4.96 out of 5 average rating, 110 reviews
L'Aquila e L'Ulivo
All'Aquila e l'Ulivo, un antico casale ristrutturato del 1200, troverai non solo tutti i confort necessari per uno splendido soggiorno, ma vivrai anche l'emozione di sentirti libero e immerso nella natura incontaminata della Val D'Orcia. Qui avrai la possibilita' di passeggiare con i due falchi Ayga e Sayen e interagire con le aquile, e perchè non sorseggiare un eccellente aperitivo a bordo piscina. Ti aspettiamo nel nostro mondo, fatto di animali, relax, natura e anche un pizzico di Magia.
5.0 out of 5 average rating, 129 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.
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
5.0 out of 5 average rating, 123 reviews
Casa al Gianni - Quercia
Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!
4.93 out of 5 average rating, 246 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 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.
4.88 out of 5 average rating, 228 reviews
In Toscana Camere
**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, 104 reviews
Villa Madonna della Rosa
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, 104 reviews
Pienzalettings
Rilassati in questo spazio tranquillo nel piccolo borgo. La nostra casa vacanze PienzaLettings è un'esplosione di unicità e bellezza, dotata di un fascino senza tempo. Dotato di ogni comfort, è pronto ad accogliervi e pronto a farvi vivere un'avventura rilassante ed emozionante in un luogo senza tempo. Non sono inclusi 1€ di tassa di soggiorno per persona a notte, esclusi minori di 15 anni
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
4.91 out of 5 average rating, 100 reviewsPopular amenities for Montalcino holiday homes
Family-Friendly holiday homes

La Loggetta di San Giovenale
4.96 out of 5 average rating, 296 reviews
Charming farmhouse with garden, views & pool
4.92 out of 5 average rating, 233 reviews
Cottage "Casa Luisa "with private pool
4.84 out of 5 average rating, 100 reviews
Vittoria Chianti Vacations 🍇🍷
4.94 out of 5 average rating, 205 reviews
[Traditional Cozy House] Garden & Viewpool Apt
4.91 out of 5 average rating, 117 reviews
Linearis apt B (4+2) Toscana
4.89 out of 5 average rating, 160 reviews
Casa Vacanze Montalcino Idolina Guest House
4.97 out of 5 average rating, 29 reviews
Appartamento Glicine
5.0 out of 5 average rating, 21 reviewsHoliday home rentals with a patio

Casa Isla, near Orvieto, amazing views + pool
4.99 out of 5 average rating, 126 reviews
Il toscano - Nuovo con terrazza in centro a Greve
4.93 out of 5 average rating, 106 reviews
Pian'D'olmo, antico casale nel cuore della Toscana
4.9 out of 5 average rating, 31 reviews
l'oasi delle volpi
5.0 out of 5 average rating, 97 reviews
Tuscany Breath - Panoramic Pool & Tennis Court
5.0 out of 5 average rating, 10 reviews
Flat, terrace, pool, Spa resort,restaurant, A/C,S1
5.0 out of 5 average rating, 5 reviews
The Piccola Villa of Borgo Argenina
4.97 out of 5 average rating, 38 reviews
Tuscan House with Private Jacuzzi in Chianti
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
4.95 out of 5 average rating, 147 reviews
Apartment in historic Villa in Siena_"LE CONTRADE"
4.96 out of 5 average rating, 91 reviews
Chiantissima Tuscany
5.0 out of 5 average rating, 8 reviews
My cozy home in Chianti
4.98 out of 5 average rating, 99 reviews
Casale Le Fonti
5.0 out of 5 average rating, 6 reviews
Appartamento vicolo delle Rose
5.0 out of 5 average rating, 11 reviews
Granducato design contemporaneo e piscina privata
4.97 out of 5 average rating, 58 reviews
Tuscany country Village near Siena
4.88 out of 5 average rating, 25 reviewsDestinations to explore
- Apartment rentals Montalcino
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- Holiday home rentals Siena
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- Holiday home rentals Italy
- 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







