Villas in Monticchiello

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Monticchiello villas

Exterior
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

Villa in Montalcino

$7,500 nightly
The price is $7,500
Dec 13 - Dec 14
Total with taxes and fees
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Pool
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Villa in Siena

$6,957 nightly
The price is $6,957
Dec 17 - Dec 18
Total with taxes and fees
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Exterior
Artisti del Cavallo Tourism

Villa in Foiano della Chiana

8.4 out of 10, Very Good, (24)
"Good house for one night. "
Germany
Heiner
$81 nightly
The price is $92
Dec 16 - Dec 17
Total with taxes and fees
Artisti del Cavallo Tourism
Exterior
Il Poggio dell'Eremita

Villa in Sinalunga

10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
$162 nightly
The price is $165
Dec 13 - Dec 14
Total with taxes and fees
Il Poggio dell'Eremita
Terrace/patio
Antico Brunello

Villa in Montalcino

$7,674 nightly
The price is $8,453
Dec 15 - Dec 16
Total with taxes and fees
Antico Brunello
Terrace/patio
Godiluva, wine villa

Villa in Toscana

$3,598 nightly
The price is $3,602
Dec 22 - Dec 23
Total with taxes and fees
Godiluva, wine villa
Exterior
'...a delicious farmhouse in the countryside where only the wind blows...'

Villa in Campiglia d'Orcia

10.0 out of 10, Exceptional, (7)
"We had a wonderful stay at the villa - we were a group of 10 adults and 2 children and used the villa as our home base for a week to explore the area (Pienza, Siena, Montalcino, Montelpulciano, etc). There are 4 apartments ranging from 1-3 bedrooms which were fantastic for the families, plus an additional communal kitchen and living room for everyone to gather. It was the perfect setup as it gave everyone the ability to have some privacy as well as for everyone to congregate and eat meals...
United States
Li-Shen L.
$1,801 nightly
The price is $1,806
Dec 13 - Dec 14
Total with taxes and fees
'...a delicious farmhouse in the countryside where only the wind blows...'
Exterior
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

Villa in Cortona

$403 nightly
The price is $409
Dec 17 - Dec 18
Total with taxes and fees
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
Exterior
Red Heart - relax with those you love in Tuscany.

Villa in Trequanda

$1,063 nightly
The price is $1,066
Dec 13 - Dec 14
Total with taxes and fees
Red Heart - relax with those you love in Tuscany.
Outdoor dining
Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Villa in Rapolano Terme

9.0 out of 10, Wonderful, (4)
"Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host."
Netherlands
Toon M.
$851 nightly
The price is $855
Dec 17 - Dec 18
Total with taxes and fees
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Exterior
VILLA LEOPOLDINA - Nine Bedroom Villa, Sleeps 18

Villa in Cortona

10.0 out of 10, Exceptional, (1)
"The villa was simply awesome and perfect for our family holiday."
United Kingdom
Caroline H.
$831 nightly
The price is $831
Jan 7 - Jan 8, 2026
Total with taxes and fees
VILLA LEOPOLDINA - Nine Bedroom Villa, Sleeps 18
A heated pool
POGGIO AL SOLE - Five Bedroom Villa, Sleeps 10

Villa in Siena

8.0 out of 10, Very Good, (1)
"Villa magnifique dans un environnement superbe. Les chambres sont d'un grand confort. S'agissant d'une maison récemment rénovée, quelques réglages sont à réaliser pour atteindre la perfection : nombre de fauteuils bain de soleil insuffisant, améliorer la protection solaire sur la terrasse extérieure et le nombre de fauteuils ; petites difficultés liées à l'usage du lave linge mais très vite réglées. Globalement c'est un très agréable séjour dans une magnifique demeure, rénovée avec goût et...
France
Pierre V.
$2,427 nightly
The price is $2,427
Jan 3 - Jan 4, 2026
Total with taxes and fees
POGGIO AL SOLE - Five Bedroom Villa, Sleeps 10
Exterior
Wonderful villa with private pool near Arezzo

Villa in Foiano della Chiana

$1,841 nightly
The price is $1,843
Dec 12 - Dec 13
Total with taxes and fees
Wonderful villa with private pool near Arezzo
Exterior
Villa 'Loft' with Shared Pool, Wi-Fi and Air Conditioning

Villa in Cortona

$574 nightly
The price is $580
Dec 17 - Dec 18
Total with taxes and fees
Villa 'Loft' with Shared Pool, Wi-Fi and Air Conditioning
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Monticchiello Hotel Reviews

Abbadia Sicille Relais

Abbadia Sicille Relais

10/10 Excellent
"Room was beyond expectations. Helpful staff and overall great experience. "
Robert 1-night trip
Posted 3 days ago
Abbadia Sicille Relais

Find out more about Monticchiello

Monticchiello Villas information

Number of reviews
85
Accommodation
1064 Villas
Lowest Price
$92
Highest Price
$8,453

Frequently asked questions

How much do villas in Monticchiello cost?
You'll pay between $92 and $8,453 per night for villas in Monticchiello. Whatever your budget, an epic getaway is only a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Monticchiello?
You'll find 1064 villas in Monticchiello. Whether you're traveling with the little ones or getting away with your buddies, Expedia can help you find the ideal base for your crew.
Why book your villa in Monticchiello with Expedia?
We think arranging a vacation shouldn't be difficult, so if you're in search of villas at an affordable price, Expedia can help. Keep the budget under control and go for an all-inclusive stay, or splurge on a deluxe villa to spoil your loved ones. Use our convenient search filters to find a property in Monticchiello that suits your needs.
How can I find cheap villas in Monticchiello?
Expedia can help you search for cheap villas in Monticchiello. Simply use our convenient filter tool to select amenities, star rating and budget to refine your search and find a great place to stay in a matter of clicks.

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