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

Total holiday rentals
Explore 20 holiday rentals in Monticiano

Nightly prices starting at
Monticiano holiday rentals start at $85 NZD per night before taxes and fees

Verified guest reviews
Over 320 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Wi-Fi availability
10 of Monticiano holiday 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
Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and 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 seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!

Apartment in a detached villa - Val d'Orcia
In a detached villa, a cozy Tuscan-style apartment, recently and tastefully renovated, located in an area rich in history. Located just a few kilometers from cities of art and on the Via Francigena, the apartment can serve as a base for nature trails or food and wine tours. From a lovely terrace overlooking the panorama, you can enjoy your meals, admire the sunset, and gaze at the majestic and magnificent medieval fortress. .As of March 22, 2018, a municipal tourist tax of €2 per person applies. See additional notes.

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.

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.

Casa Dolce Toscana | Panoramic Suites & Views
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.

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 pool is open from mid-May to the end of September. We don't accept pets. We would like to inform our guests that, as private hosts, we are not authorized to provide breakfast.

The Chianti Classico Sunset
If you are looking for an idyllic location in the heart of the Chianti Classico region, surrounded by the vineyards and olive groves of the beautiful Tuscan hills, on the estate of a historic 16th-century villa, then come to our barn!! It has a commanding position with an amazing view, where you can enjoy breathtaking sunsets. The complete privacy of the house, the cozy garden, and the large loggia allow you to enjoy your stay in total tranquility. Our reviews are your best guarantee.

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.

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.

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.

"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.

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
Popular amenities for Monticiano house rentals
House rentals with a pool

Infinity pool in Chianti 1

Private Chianti Cottage, Garden & Vineyard Views

Cercis - La Palmierina

Ancient Barn in Chianti with Pool

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Explore Chianti from a Charming Stone House

Casa Giulia di Sopra Farmhouse

Country House in the Crete Senesi
Weekly house rentals

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni

130 sqm farmhouse in a natural setting with 2 bathrooms, 20 minutes from Siena

Casa Al Poggio in Chianti Shire

Raffaella's House in Chianti

CASA DI ZIO Comfort, nature and relax

"La Casa di Maria Luce"® with panoramic terrace

Podere Piazza house with panoramic view

Charming converted Hayloft overlooking the Chianti Hills
Private house rentals

Design loft with private SPA in Tuscany

Private Cottage with Plunge Pool in Tuscan Estate

beautiful farmhouse in the Chianti region with panoramic garden

Country chic house in a village,private pool,wiFi

Breathtaking Views in Our Chianti Country House

Domus Antiqua

Poggiolo

Tosco Suite "Solis"
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





