
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 $70 AUD 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.

Domus Nannini - Loggia Salimbeni SPA
Apartment of 200 sqm furnished with precious classical furniture and very spacious rooms: 13 windows overlooking the old town, each window offers a unique view of the city. Big and spacious lounge with peerless view on the begin of Banchi di Sopra, Piazza Salimbeni and the headquarter of the Monte dei Paschi, formed by the noble palaces Tantucci, Salimbeni and Spannocchi. Second lounge with library, sofa-bed and the same exclusive view. 2 large bedrooms with city-views and king-size beds. 3 bathrooms one with jacuzzi and one with shower. A long corridor that crosses the apartment, spacious entrance and private terrace on the internal courtyard. Third lounge with sofa-bed and city-view. Dining room with panoramic views of the Duomo of Siena and Basilica of San Domenico which stand out over the medieval roofs of Siena a few meters from us. Fully equipped kitchen with laundry area. It occupies the entire second floor our 1600's palace and offers unique and privileged views of Siena and its architectural wonders. We are on Banchi sopra Sopra, the main course of the historical center of Siena, below the house you will find the best shops in the center with all the brands of high fashion, lots of restaurants; Wineries, Bars and Supermarkets with typical Tuscan products.
ValueFamilyDecor
4.96 out of 5 average rating, 156 reviews
Casa al Gianni - The Simignano Barn
Transformed from a historic barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living area, 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 looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this little slice of paradise!
ValueLocationBarbecue
4.97 out of 5 average rating, 194 reviews
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.
FamilyValueSleep quality
4.99 out of 5 average rating, 113 reviews
Podere Piazza house with panoramic view
Podere Piazza is an estate, has its origin in the 15th century. The vacation home was built at the beginning of the 17th century. Podere Piazza was the residence of Alessandro Cervini degli Spannocchi, who was appointed Archbishop of Siena on May 29, 1747. He was a Nobile di Montepulciano and Patrizier of Siena. The buildings of Podere Piazza still bear his coat of arms today. This also explains our little church, at the road junction, in front of it to the right to the pine avenue and to the left into the driveway.
FamilyLocationCheck-in
4.97 out of 5 average rating, 195 reviews
LECCIONE RESIDENCE
Characteristic country house with exposed wooden beams, 2 double bedrooms, 1 bedroom with bunk bed and a double sofa bed in the living room. The 2 bathrooms with shower. Large and well-equipped kitchen. Dishwasher, wood-burning and electric oven, espresso machine. Large garden with barbecue, swimming pool and a hot tub. Expenses to be paid on-site based on consumption: wood €8 per box, LPG €6 per cubic meter, electricity €0.36 per kW. Wood will be provided for a barbecue and a hot bath in the hot tub for free.
FamilyValueCondition
4.93 out of 5 average rating, 143 reviews
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.
FamilyLocationOutdoor spaces
4.96 out of 5 average rating, 138 reviews
Casa Dolce Toscana | Panoramic Suite with 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.
FamilyLocationBathroom
4.99 out of 5 average rating, 178 reviews
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.
FamilyLocationBathroom
4.9 out of 5 average rating, 133 reviews
Nada Home
3 comfortable, fully air-conditioned double bedrooms, each with its own private bathroom, in the heart of Chianti, ideally located between Florence, Siena and San Gimignano. A welcoming, well-kept home in the peaceful Tuscan countryside. Fully equipped kitchen with dishwasher, oven and bar area, plus a laundry room with washing machine and dryer. Private garden for your exclusive use with a private hydromassage pool, heated in winter upon request 🌷
LocationValueWi-Fi
4.87 out of 5 average rating, 215 reviews
Cercis - La Palmierina
The apartment is part of a completely fenced estate of 60 hectares of unspoiled nature: more than 1000 olive trees, countless cypresses and fragrant forests create an idyllic environment for those seeking tranquility and silence. The Palmierina estate is near Castelfalfi (a true jewel of medieval architecture) and close to Florence (50 Km), Siena (50 Km), and Pisa (50 Km). There are two golf courses nearby.
LocationFamilyIndoor spaces
4.96 out of 5 average rating, 144 reviews
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
ValueFamilySleep quality
4.9 out of 5 average rating, 217 reviews
Borgo Ripostena – No. 8 Casa Vecchia
Charming cottage in the heart of Tuscany on a peaceful property surrounded by 5 hectares of private gardens and forest. The apartment has stunning views over San Gimignano and the Chianti Hills. One of the two bedrooms has air conditioning.
ValueFamilyShared spaces
4.95 out of 5 average rating, 200 reviewsPopular amenities for Monticiano house rentals
House rentals with a pool

Private Chianti Cottage, Garden & Vineyard Views
FamilyLocationWalkability
4.99 out of 5 average rating, 136 reviews
House Rigomagno Siena
FamilyLocationHospitality
4.96 out of 5 average rating, 122 reviews
Explore Chianti from a Charming Stone House
LocationFamilyHospitality
4.98 out of 5 average rating, 122 reviews
Conca d'Oro villa with private pool, sleeps 4
FamilyLocationNearby
4.92 out of 5 average rating, 172 reviews
Podere Scorno country house with swimming pool
LocationCheckoutShared spaces
4.93 out of 5 average rating, 143 reviews
Villa Lolù with private heated swimming-pool
ValueFamilyPets
4.97 out of 5 average rating, 159 reviews
Infinity pool in Chianti 1
ValueFamilySleep quality
5.0 out of 5 average rating, 141 reviews
Country Rentals - La Canonica
LocationFamilyCleanliness
4.86 out of 5 average rating, 101 reviewsWeekly house rentals

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni
LocationValueQuiet
4.99 out of 5 average rating, 231 reviews
Charming rural house in Iesa
ValueFamilyQuiet
4.96 out of 5 average rating, 89 reviews
CASA DI ZIO Comfort, nature and relax
ValueLocationParking
4.95 out of 5 average rating, 43 reviews
Apartment in the village of Castello di Tocchi
LocationHikingGetting around
4.97 out of 5 average rating, 66 reviews
Private House for 4P – La Capanna Di Azzurra
ValueLocationIndoor spaces
4.96 out of 5 average rating, 23 reviews
130 sqm farmhouse in the heart of nature with 2 bathrooms, 20 minutes from Siena
FamilyLocationCheck-in
4.87 out of 5 average rating, 60 reviews
La Capanna: country house with magnificent view
LocationFamilyKitchen
4.92 out of 5 average rating, 83 reviews
Wp Relais Etruscan House
FamilyLocationView
4.89 out of 5 average rating, 55 reviewsPrivate house rentals

Poggiolo
LocationValueGetting around
5.0 out of 5 average rating, 32 reviews
Wine House
FamilyLocationCheck-in
4.97 out of 5 average rating, 70 reviews
Sosta Eroica • Panoramic View & Quiet Pool Retreat
LocationFamilyCondition
5.0 out of 5 average rating, 34 reviews
Domus Antiqua
FamilyLocationParking
4.95 out of 5 average rating, 40 reviews
Family Forest - Pool in the Crete Senesi
FamilyValueWalkability
4.91 out of 5 average rating, 85 reviews
Tosco Suite "Solis"
LocationHospitalityCleanliness
4.97 out of 5 average rating, 72 reviews
Malamerenda's House in Siena
FamilyLocationGetting around
4.91 out of 5 average rating, 56 reviews
Stunning loft in Montalcino.
LocationFamilyHospitality
5.0 out of 5 average rating, 19 reviewsDestinations 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





