
Villa vacation rentals in Monticiano
Find and book unique villas on Airbnb
Quick stats about villa rentals in Monticiano

Total vacation rentals
Explore 10 vacation rentals in Monticiano

Nightly prices starting at
Monticiano vacation rentals start at G$48,116 GYD per night before taxes and fees

Verified guest reviews
Over 80 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Vacation rentals with a pool
10 properties feature pools

Wi-Fi availability
10 of Monticiano vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Monticiano rentals

4.8 Average rating
Monticiano stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated villa rentals in Monticiano
Guests agree: these villas are highly rated for location, cleanliness, and more.

Manor House - IlVillinoFarmhouse
Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area
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Wine Experience Villa in Montepulciano
🏡 Villa Talosa is immersed in the vineyards of the Fattoria della Talosa, a historic winery in Montepulciano that produces Vino Nobile. An authentic place, ideal for relaxing with the magic of the Tuscan countryside and an enchanting view from every window. Just 1.5 km from the historic center, which can also be reached on foot, you can visit our Historic Winery from the 1500s under Piazza Grande: a unique experience between history and passion for wine. Heating and air conditioning are included.
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Charming Tuscan Villa with View forFamily&Friends
The house is a typical podere of the late 1800, stone walls, chestnut beams, and hand-made tiles have all been kept; what has changed is the comfort behind them. The Host Fulvia lives in the ground-floor apt. and she's on hand throughout your stay without ever intruding — a rhythm that guests consistently single out. Total accommodation is 8 guests across 2 bdr and 2 bathrooms. Visit Montepulciano, Pienza, Bagni Vignoni and iconic Unesco sites in Val d'Orcia within short and easy driving away
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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.
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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
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Villa dei 2 Ulivi (Abbadia Isola)
FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)
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Torre dei Belforti
Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.
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Villa Tonacato - Charming Villa with private pool
An old rural farmhouse, located in the Tuscan hills overlooking the surrounding countryside. Isolated and ideal for those who want to relax but close to the main Italian tourist cities. Each room is equipped with air conditioners with windfree technology, in the living room there is an 82" ULTRA HD TV with SKY and international channels. The pool is equipped with Philips Hue lighting to create the right atmosphere at all times and a Bose Soundtouch bluetooth sound system
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Stone farmhouse in Val D'Orcia
19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.
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Villa unesco heritage, Jacuzzi & garden. BB Daria
Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant
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Farmhouse in Chianti
Beautiful portion of a farmhouse immersed in Chianti with a beautiful swimming pool, surrounded by vineyards and olive trees, perfectly furnished with a large garden and parking spaces. It is located 20 minutes from Florence, 40 from Siena and 50 from Pisa, in a few minutes you can reach Certaldo (birthplace of Boccaccio) and Vinci (birthplace of Leonardo Da Vinci). The house is halfway between Montespertoli and San Casciano (7km).
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Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.
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Popular amenities for Monticiano villa rentals
Private villa rentals

Villa L'Olivo w/Private pool (Close San Gimignano)
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Independent country house with private pool
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Panoramic villa in Crete Senesi, overlooking Siena.
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Casa di Leo Romantic House
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Villa Casale "Il Diaccio" with views of the Maremma
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Beautiful tuscan country house
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Capanna di Elfo - Capanna Di Elfo
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The Villa of the Spendthrift Brigade!
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Luxury villa rentals

La Vignaccia (Farmhouse) - villa w/private pool
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A paradise in Montepulciano...
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Luxury Villa in the very heart of Chianti
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Podere la Pompa
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Villa with garden. The Cardinal's Garden.
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Podere on the Crete Senesi
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Villa il Laghetto with Infinity Pool in Tuscany
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Sestuccia
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Villa rentals with a pool

Stone villa with a pool
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Podere San Carlo
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Luxury Villa on Chianti Wine Estate
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Villa Montanina - relax in esclusiva in Toscana
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Private Villa with semi-Olympic pool and Tennis
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Poggio Fra gli Ulivi
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Gli sterpi
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Podere il Trebbio
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Destinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Cala Violina
- Stazione Santa Maria Novella
- Parco Regionale Della Maremma
- Mercato Centrale
- Spiagge Bianche
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Spiaggia di Capo Bianco
- Boboli's Garden
- Mount Amiata





