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Vacation Rentals in Monticchiello

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August 2026

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Find the right vacation rental for you in Monticchiello

The best vacation rentals in Monticchiello

Check out our selection of great vacation rentals in Monticchiello

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L'Olmo

Monticchiello

Offering a heated outdoor pool, L'Olmo is located in Pienza, in the heart of Val d 'Orcia. Free WiFi access is available. The suites here offer air conditioning and parquet floors.

C
Claudia
From
Puerto Rico
Beautiful sights, rooms are spacious, thoughtfully decorated. Excellent service, attention to detail, even the pool was heated.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 168 reviews
Price from
$507.96
1 night, 2 adults

Agriturismo Riposati

Monticchiello

Providing garden views, Agriturismo Riposati in Monticchiello offers accommodations and a garden. This country house provides free private parking, private check-in and check-out, and free Wifi.

J
Jongsuek
From
United Kingdom
Hosts were very kind and it has splendid sight seeing from the facility. Delicious food and cozy accomodation. Thank you so mcuh!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 270 reviews
Price from
$125.94
1 night, 2 adults

Agriturismo Barbi

Monticchiello

Overlooking Val d'Orcia and 5 mi from the town of Pienza in southern Tuscany, Azienda Agricola Barbi offers 2 stone farmhouses that still maintain its original features.

R
Rodrigo
From
Brazil
We loved absolutely everything! The panoramic view of the valley is perfect, you can see Pienza in the distance and at night you can see the city lit up. It is close to the main activities, everything in the house is of excellent quality and everything is even more beautiful than in the photos! It is a place to be in this life! We have already recommended it and will return with our friends!
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 263 reviews
Price from
$173.17
1 night, 2 adults

B&B Daria - Deb'S Monticchiello

Monticchiello

Featuring a restaurant and garden with sun terrace, B&B Daria - Deb'S Monticchiello is located in the village of Monticchiello.

A
Ashwin
From
United Kingdom
Beautiful location and the owner was extremely responsive and communicative
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 14 reviews
Price from
$820.71
1 night, 2 adults

Terre di Nano

Monticchiello

29 miles from Mount Amiata in Monticchiello, Terre di Nano offers accommodations with access to an open-air bath. This farm stay features free private parking and a shared kitchen.

V
Vanessa
From
Canada
Incredible! We absolutely loved our stay here. The property is beautiful, the food is wonderful and location is lovely!
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 19 reviews
Price from
$409.31
1 night, 2 adults

b&b BORGO CAPITANO COLLECTION Albergo diffuso, Village Experience - Centro Storico

San Quirico dʼOrcia (Near Monticchiello)

B&b BORGO CAPITANO COLLECTION Albergo diffuso, Village Experience - Centro Storico features air-conditioned rooms in San Quirico dʼOrcia.

D
Diego
From
Mexico
Andrea was amazing and very kind and helpful.
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 1,089 reviews
Price from
$226.69
1 night, 2 adults

Casa del Fauno

Montepulciano (Near Monticchiello)

Casa del Fauno offers accommodations in Montepulciano, 13 miles from Bagno Vignoni and 17 miles from Bagni San Filippo.

A
Andrea
From
Costa Rica
Excellent location! Beautifully decorated! Very clean and cozy!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 143 reviews
Price from
$192.37
1 night, 2 adults

Il Colombaiolo

Castelmuzio (Near Monticchiello)

Il Colombaiolo enjoys a location in Castelmuzio, 13 miles from Bagno Vignoni and 21 miles from Bagni San Filippo. This farm stay features a garden.

O
Oleg
From
Israel
The location, owner and everything around was excellent
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 171 reviews
Price from
$69.79
1 night, 2 adults

L’ Aia del Principe

Montepulciano (Near Monticchiello)

30 miles from Mount Amiata in Montepulciano, L’ Aia del Principe features accommodations with access to a hot tub.

C
Cheryl
From
United States
Beautiful villa located a few minutes by car outside of the town center. Nicoletta provided such exceptional hospitality. The room was very comfortable with jacuzzi and sensory shower. Could not have asked for a better stay. Thank you!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 299 reviews
Price from
$225.14
1 night, 2 adults

MontepulcianoLettings

Montepulciano (Near Monticchiello)

MontepulcianoLettings provides air-conditioned rooms in Montepulciano.

L
Linda Lisette
From
Canada
It was very clean and close to restaurants and bars.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 391 reviews
Price from
$97.29
1 night, 2 adults
All vacation rentals in Monticchiello

Most booked vacation rentals in Monticchiello and surrounding area in the past month

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Popular with guests booking vacation rentals in Monticchiello

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 263 reviews

Popular with guests booking vacation rentals in Monticchiello

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 270 reviews

Popular with guests booking vacation rentals in Monticchiello

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 168 reviews

Popular with guests booking vacation rentals in Monticchiello

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 99 reviews

Popular with guests booking vacation rentals in Monticchiello

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 208 reviews

Popular with guests booking vacation rentals in Monticchiello

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 116 reviews

Popular with guests booking vacation rentals in Monticchiello

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 88 reviews

Popular with guests booking vacation rentals in Monticchiello

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 64 reviews

Popular with guests booking vacation rentals in Monticchiello

Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 129 reviews

Popular with guests booking vacation rentals in Monticchiello

Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 90 reviews

Vacation Rentals with swimming pools in Monticchiello and nearby

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Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 439 reviews

Poggio ai Gelsi provides a solarium and air-conditioned accommodations in Pienza, 28 miles from Mount Amiata. This property offers a pool with a view and free private parking.

Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 605 reviews

Featuring a free outdoor pool and a farm producing its own olive oil, Agriturismo Marinello has accommodations with a patio and wrought-iron beds.

Incanto b&b

Pienza
Swimming pool
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 433 reviews

Incanto b&b offers accommodations in Pienza, 28 miles from Mount Amiata and 10 miles from Bagno Vignoni. With inner courtyard views, this accommodation provides a swimming pool.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 719 reviews

Offering a sun terrace with panoramic view over the surrounding hills, Agriturismo Il Casalino is set in a 19th-century farmhouse with olive trees and vineyards in Pienza.

Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 355 reviews

The Grapevine by MANVI provides air-conditioned rooms in Montepulciano. Both free Wifi and parking on-site are available at the bed and breakfast free of charge.

Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 127 reviews

Offering pool views, Agriturismo Zampugna in Montefollonico offers accommodations, pool with a view, a garden, and barbecue facilities.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 236 reviews

In Tuscan countryside, Tenuta Santagnese farm offers self-catering apartments surrounded by extensive gardens with barbecue facilities and an outdoor pool. Parking is free.

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 52 reviews

Featuring a garden, Podere Le Crete features accommodations in Montepulciano. This property offers access to a terrace, free private parking, and free Wifi. The pool features a fence and garden views.

Highly rated vacation rentals in Monticchiello and nearby

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Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 70 reviews

Finestra Dell'Angelo enjoys a location in Pienza, 28 miles from Mount Amiata and 10 miles from Bagno Vignoni. Featuring city and quiet street views, this apartment also includes free Wifi.

ROSSELLINO®

Pienza
8.0+ review score
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 378 reviews

Housed in a historic building, the recently renovated ROSSELLINO® provides accommodations with a terrace and free Wifi. The air-conditioned accommodations are 28 miles from Mount Amiata.

Beccofino

Pienza
8.0+ review score
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 495 reviews

Beccofino enjoys a location in Pienza, 28 miles from Mount Amiata and 10 miles from Bagno Vignoni. Both free Wifi and private parking are available at the guest house free of charge.

Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 187 reviews

Appartamenti Il Leone offers accommodations in Pienza, 28 miles from Mount Amiata and 10 miles from Bagno Vignoni. There's a private entrance at the apartment for the convenience of those who stay.

Casa Beccofino

Pienza
8.0+ review score
Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 214 reviews

Casa Beccofino offers accommodations in Pienza, 16 miles from Bagni San Filippo. With free private parking, the property is 28 miles from Mount Amiata and 10 miles from Bagno Vignoni.

Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 532 reviews

Affittacamere Dal Falco enjoys a location in Pienza, 9.5 miles from Bagno Vignoni and 16 miles from Bagni San Filippo.

Montorio

Montepulciano
8.0+ review score
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 145 reviews

Montorio in Montepulciano provides accommodations with a garden and barbecue facilities. There's a private entrance at the vacation home for the convenience of those who stay.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 51 reviews

Providing a garden, Appartamento Panoramico provides accommodations in Montepulciano. This property offers access to a balcony, free private parking, and free Wifi.

Enjoy breakfast in Monticchiello and nearby

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L'apparita Camere

Pienza
Breakfast options
Scored out of 10, guest rating 7.1
Good - What previous guests thought, 250 reviews

L'apparita Camere features accommodations in Pienza. The property is around 28 miles from Mount Amiata, 10 miles from Bagno Vignoni, and 16 miles from Bagni San Filippo. Guests can enjoy city views.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 68 reviews

Contucci Residenze d'Epoca offers accommodations in Montepulciano, 29 miles from Mount Amiata and 13 miles from Bagno Vignoni.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 237 reviews

Palazzo del Mercante offers accommodations in Montepulciano, 29 miles from Mount Amiata and 13 miles from Bagno Vignoni.

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 595 reviews

Residenza Fabroni offers accommodations in Montepulciano, 13 miles from Bagno Vignoni and 18 miles from Bagni San Filippo.

Il Corso

Montepulciano
Breakfast options
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 256 reviews

Il Corso features air-conditioned rooms in Montepulciano. Among the facilities at this property are free shuttle service and an elevator, along with free Wifi throughout the property.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 401 reviews

Delcorto Suites is offering accommodations in Montepulciano. This 4-star hotel offers free WiFi. The property is non-smoking throughout and is located 30 miles from Mount Amiata.

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 245 reviews

B&B L'Agnolo Di Caroti Cinzia offers accommodations in Montepulciano, 30 miles from Mount Amiata and 13 miles from Bagno Vignoni.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 390 reviews

Housed in a historic building, Palazzo Mosela Alla Porta offers accommodations with a bar and free Wifi in Montepulciano, 30 miles from Mount Amiata.

These vacation rentals in Monticchiello and nearby have options with free cancellation

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Scored out of 10, guest rating 7.8
Good - What previous guests thought, 366 reviews

Set in a historic 16th-century building in central Montepulciano, Palazzo Bellarmino is 164 feet from the town’s main square. It offers spacious apartments with free Wi-Fi.

Residenza San Donato

Montepulciano
Free cancellation options available
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 220 reviews

Featuring a shared lounge, Residenza San Donato provides accommodations in Montepulciano.

Palazzo Danesi

Montepulciano
Free cancellation options available
Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 145 reviews

Palazzo Danesi offers accommodations in Montepulciano, 12 miles from Bagno Vignoni and 17 miles from Bagni San Filippo.

Palazzo Tombesi Trecci

Montepulciano
Free cancellation options available
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 320 reviews

Palazzo Tombesi Trecci offers accommodations in Montepulciano, 12 miles from Bagno Vignoni and 17 miles from Bagni San Filippo.

Meublé il Riccio

Montepulciano
Free cancellation options available
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 424 reviews

Meublé il Riccio is a recently renovated bed and breakfast in Montepulciano where guests can make the most of its garden and bar.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 143 reviews

Appartamento centro storico La Pulcianella con vista is located in Montepulciano, just 13 miles from Bagno Vignoni and 17 miles from Bagni San Filippo.

Casa del Fauno

Montepulciano
Free cancellation options available
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 143 reviews

Casa del Fauno offers accommodations in Montepulciano, 13 miles from Bagno Vignoni and 17 miles from Bagni San Filippo.

Camere Bellavista

Montepulciano
Free cancellation options available
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 312 reviews

Camere Bellavista provides air-conditioned rooms in Montepulciano. Among the facilities at this property are luggage storage space and an ATM, along with free Wifi throughout the property.

FAQ about vacation rentals in Monticchiello

Vacation Rentals That Guests Love in Monticchiello

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Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 208 reviews
The village was so beautiful and scenic..the home run by francesco was amazing. Francesco was attentive, and nothing was too much trouble. It's a very small village and everyone is friendly. A few restaurants, a couple of regional shops and a small grocery shop down the hill. It's definitely a place to relax and use has a pit stop, for visiting other places.
Guest review byChristina
Family with young children
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 168 reviews
L’Olmo had everything! The location was fantastic for exploring the villages and towns of Tuscany. The room was perfect and the bed, wow, could sleep in that forever! Staff were fantastic and really made you feel welcomed and nothing was ever too much trouble. The gardens and pool were magical. The breakfast was delicious.
Guest review byMatt
Young couple
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 29 reviews
1. Very nice location in a quiet, small village with restaurants just mere steps away 2. Beautiful, cosy cottage furnished with lots of care, it was very comfortable 3. Supplies were provided for cooking 4. Kasia was very helpful arranging wine tasting and truffle hunting activities for us
Guest review byLandy
Family with young children
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 129 reviews
Amazing location in the quiet village of Monticchiello. Beautiful studio on the second floor with a splendid view over the valley. Wonderful double bed and very nice and functional bathroom. Amazing help of our host Sarah with anything you need.
Guest review byKatrien
Young couple
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 208 reviews
Everything. Nicest stay in Italy. Francesco was the perfect host. The breakfast was fresh and almost healthy. Francesco cooked eggs, crepes and pies. The Village is between Pienza and Montepulciano, so you have a good spot.
Guest review byDavid
Family with young children
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 88 reviews
Proactive and responsive hosts. Well-equipped kitchen that includes condiments and coffee. We had a memorable stay. 'Villa Poliflora' gives log cabin vibes... lots of books, comfortable furniture, beautiful Tuscan views within walking distance, the scent of lavender and the forest. Futura is very knowledgeable about activities to do in the area and gave a few recommendations. Thank you Futura, for hosting us.
Guest review byMira
Young couple
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 15 reviews
Everything! Monticchiello is the most beautiful village of Tuscany and this apartment is a dream come true. The views, the garden, the antique furniture, old wooden doors and huge kitchen fireplace all add to the charm of this beautiful place. And our host, Luigi, is so kind...he greeted us with a plate of bread, cheese, salami and olive oil that he makes himself. We loved everything about our stay here and hope to return again.💗
Guest review byJanis M H
Travelers with friends
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 90 reviews
The property was located in a walled village, in an 11th Century building. Felt very quintessential Toscana, with modern amenities.
Guest review byAmy
Family with young children
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 168 reviews
Simply beautiful property, quiet and within an hour radius of many medieval towns, villages and wineries.
Guest review byChristopher
Young couple
Avg. price/night: $138.53
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 270 reviews
Everything about this stay was wonderful. Adeline is the perfect host. Montichellio is a lovely little village, close enough to a few of the other larger towns. The property offers great views in every direction. We would come back here for sure!
Guest review byLouis
Young couple