
House vacation rentals in Monticiano
Find and book unique houses on Airbnb
Quick stats about house rentals in Monticiano

Total vacation rentals
Explore 20 vacation rentals in Monticiano

Nightly prices starting at
Monticiano vacation rentals start at G$10,452 GYD per night before taxes and fees

Verified guest reviews
Over 320 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

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 house rentals in Monticiano
Guests agree: these houses are highly rated for location, cleanliness, and more.

Casa al Gianni - The Simignano Barn
Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!
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Relaxation and charm in the Chianti hills
Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.
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Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.
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Casa Dolce Toscana | Panoramic Suite with a View
CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.
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House Rigomagno Siena
Apartment with beamed ceilings and terracotta floors, this apartment is set in a 19th-century farmhouse located in the hills of Siena in Rigomagno Toscana. From the solarium next to the swimming pool in the middle of the olive trees, you can admire the panorama of the Sienese hills and the medieval village of Rigomagno ... all this characterizes the ideal holiday for couples or families who want to relax. Solarium, garden, terrace, swimming pool are exclusively for guests of the apartment.
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Podere Scorno country house with swimming pool
Small and cozy country house ideal for couples, on a hill in the Sienese countryside. Tuscan-style stone building with a centuries-old history. The property was bought and renovated in the late '90s. With a large garden with pool, orchard, olive grove, vineyard and vegetable garden, for lovers of greenery. The swimming pool is open from mid-May until the end of September. We don't accept pets. We inform our guests that as private hosts we are not authorized to provide breakfast.
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Il Fienile, Luxury Apartment in the Tuscan Hills
‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.
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Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.
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The Chianti window
A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.
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Nada Home
In my home, you can experience the most authentic side of Tuscany, surrounded by peace, warmth and family traditions. Set among olive groves and vineyards in the heart of Chianti, you’ll have a private garden with a small whirlpool pool, cool and refreshing in summer and heated in winter. On request, you can join a cooking class featuring Nonna Graziella’s family recipes or share a special dinner with us in a warm, intimate atmosphere.
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"La Lambarda" tower Suite
In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.
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Siena Countryside Colle Ciupi
Countryside Villa apartment. Located in the nearby of Siena (Colle Ciupi, 10 kms away) Ground floor: Kitchen, living room with fireplace, bathroom with shower. First Floor: 3 Double Bedrooms and 2 bathrooms, outdoor with courtyard and huge garden
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Popular amenities for Monticiano house rentals
House rentals with a pool

Conca d'Oro villa with private pool, sleeps 4
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Cercis - La Palmierina
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Infinity pool in Chianti 1
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LECCIONE RESIDENCE
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SuiteLouise.pool, Hot Tub,homeGym & private Garden
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Country House in the Crete Senesi
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Infinity view
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Explore Chianti from a Charming Stone House
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Weekly house rentals

Raffaella's House nel Chianti
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The Chianti Classico Sunset
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Domus Nannini - Loggia Salimbeni SPA
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Charming converted Hayloft overlooking the Chianti Hills
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"La Casa di Maria Luce"® with panoramic terrace
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Alma Vignoni - Vignoni Val d'Orcia - Bagno Vignoni
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Podere Piazza house with panoramic view
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Love in Chianti
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Private house rentals

CASA DI ZIO Comfort, nature and relax
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Charming rural house in Iesa
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130 sqm farmhouse in nature with 2 bathrooms, 20 minutes from Siena
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La Capanna: country house with magnificent view
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Beautiful farmhouse in the Chianti panoramic garden
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Design loft with private SPA in Tuscany
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Authentic Tuscany Experience in our Country House
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Apartment in the village of Castello di Tocchi
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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
- Parco Regionale Della Maremma
- Cala Violina
- Stazione Santa Maria Novella
- Mercato Centrale
- Spiagge Bianche
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Parco delle Cascine
- Piazza della Repubblica
- Del Chianti
- Piazzale Michelangelo
- Piazza della Signoria
- Palazzo Vecchio
- Pitti Palace
- Boboli's Garden
- Spiaggia di Capo Bianco
- Cascate del Mulino





