A poolside area with lounge chairs and umbrellas, surrounded by a forested landscape.

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Castiglione del Bosco villas

Exterior

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (67 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is AED 565
AED 653 total
includes taxes & fees
19 Jul - 20 Jul
Il Poggio dell'Eremita
Exterior

Elegant and spacious two-storey villa of 142 m2 composed on the ground floor of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.On the first floor we find a double bedroom w

Elegant and spacious two-storey villa of 142 m2 composed on the ground floor of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.On the first floor we find a double bedroom w
Trequanda
The price is AED 1,156
AED 1,411 total
includes taxes & fees
25 Jul - 26 Jul
Elegant and spacious two-storey villa of 142 m2 composed on the ground floor of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.On the first floor we find a double bedroom w
Property grounds

Charming Tuscany Villa w/ Private Infinity Pool

Charming Tuscany Villa w/ Private Infinity Pool
Castel del Piano
The price is AED 1,585
AED 2,084 total
includes taxes & fees
14 Jul - 15 Jul
Charming Tuscany Villa w/ Private Infinity Pool
Exterior

Val d'Orcia Historic Farmhouse: 19th century dwelling with Pool and View. 10pl for groups

Val d'Orcia Historic Farmhouse: 19th century dwelling with Pool and View. 10pl for groups
Montenero
The price is AED 1,423
AED 2,727 total
includes taxes & fees
18 Jul - 19 Jul
Val d'Orcia Historic Farmhouse: 19th century dwelling with Pool and View. 10pl for groups
Property grounds

Villa I Girasoli in Montepulciano with Swimming pool

Villa I Girasoli in Montepulciano with Swimming pool
Montepulciano
10.0 out of 10, Exceptional, (2 reviews)
"We loved our stay at the villa. Alex and Gabrielle were very helpful before and during our stay, answering all our questions and being very responsive. The view out our front window was incredible along with the front porch and pool overlooking their vineyard and rolling hills. The house was perfect for our needs. Very clean, well kept, and an authentic Tuscan villa experience. And, their own wine is fabulous!"
United States
Julie V.
The price is AED 3,270
AED 3,270 total
includes taxes & fees
12 Aug - 13 Aug
Villa I Girasoli in Montepulciano with Swimming pool
Exterior

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning
Siena
The price is AED 843
AED 851 total
includes taxes & fees
10 Aug - 11 Aug
Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning
Pool

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Siena
The price is AED 22,887
AED 22,887 total
includes taxes & fees
14 Jul - 15 Jul
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Exterior

Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi

Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
The price is AED 6,256
AED 6,530 total
includes taxes & fees
14 Jul - 15 Jul
Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
Exterior

Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Rapolano Terme
9.0 out of 10, Wonderful, (4 reviews)
"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.
The price is AED 3,068
AED 4,107 total
includes taxes & fees
18 Jul - 19 Jul
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Property grounds

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is AED 18,207
AED 20,304 total
includes taxes & fees
14 Jul - 15 Jul
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Exterior

Red Heart - relax with those you love in Tuscany.

Red Heart - relax with those you love in Tuscany.
Trequanda
The price is AED 2,306
AED 3,811 total
includes taxes & fees
14 Jul - 15 Jul
Red Heart - relax with those you love in Tuscany.
Exterior

Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is AED 7,195
AED 8,122 total
includes taxes & fees
26 Jul - 27 Jul
Villa Torre Among the Hills of Siena
Property grounds

Villa 'In Antico Borgo Medievale' with Mountain View, Wi-Fi and Air Conditioning

Villa 'In Antico Borgo Medievale' with Mountain View, Wi-Fi and Air Conditioning
Porrona
The price is AED 2,717
AED 3,019 total
includes taxes & fees
14 Jul - 15 Jul
Villa 'In Antico Borgo Medievale' with Mountain View, Wi-Fi and Air Conditioning
Interior

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Vico dʼArbia
10.0 out of 10, Exceptional, (1 review)
"Lovely house in the Montechiaro property, very close to Siena, but far enough to enjoy the night sky in Tuscany. Communication was great."
United States
Marina O.
The price is AED 4,981
AED 5,908 total
includes taxes & fees
26 Jul - 27 Jul
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Outdoor dining

Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi

Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi
Murlo
10.0 out of 10, Exceptional, (1 review)
"Our stay at this property was absolutely excellent! The home was spotless, beautifully decorated, and even more spacious than the photos showed. Every amenity listed was fully functional, and the brand new swimming pool was amazing. The location was perfect— isolated peaceful and quiet, yet just a short drive from the Buonconvento .The host was wonderful to work with. Communication was lightning-fast, and the check-in and checkout instructions were crystal clear. They truly went above and beyond...
United States
martina p.
The price is AED 12,579
AED 13,233 total
includes taxes & fees
9 Aug - 10 Aug
Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi
Property grounds

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Montalcino
The price is AED 22,759
AED 24,856 total
includes taxes & fees
14 Jul - 15 Jul
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Pool

Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi
Torrita di Siena
The price is AED 13,698
AED 13,707 total
includes taxes & fees
20 Jul - 21 Jul
Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi
Exterior

Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w
Trequanda
The price is AED 1,086
AED 1,325 total
includes taxes & fees
8 Aug - 9 Aug
Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w
Exterior

Elegant and spacious ground floor villa of 142 m2 located in a private area of ​​the estate suitable for those with mobility difficulties. Composed of a large living room with fireplace, kitchen complete with dishwasher, microwave, electric oven, mok

Elegant and spacious ground floor villa of 142 m2 located in a private area of ​​the estate suitable for those with mobility difficulties. Composed of a large living room with fireplace, kitchen complete with dishwasher, microwave, electric oven, mok
Trequanda
The price is AED 1,472
AED 1,796 total
includes taxes & fees
8 Aug - 9 Aug
Elegant and spacious ground floor villa of 142 m2 located in a private area of ​​the estate suitable for those with mobility difficulties. Composed of a large living room with fireplace, kitchen complete with dishwasher, microwave, electric oven, mok
Terrace/patio

Chalet "Villa Falco" with Shared Pool, Private Terrace & Wi-Fi

Chalet "Villa Falco" with Shared Pool, Private Terrace & Wi-Fi
Trequanda
The price is AED 3,606
AED 3,618 total
includes taxes & fees
8 Aug - 9 Aug
Chalet "Villa Falco" with Shared Pool, Private Terrace & Wi-Fi
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 Castiglione del Bosco Hotel Reviews

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"I am looking forward to my next stay at this magical hotel! Every single staff member was lovely and kind, and always helpful with questions you may have. The rooms were beautiful, clean, and well stocked. The garden terrace in the morning for breakfast was wonderful and the breakfast itself, was excellent. The mourning doves and turtles in the garden were an unexpected delight! If you want a magical place to stay while you're in the beautiful town of Siena, I would recommend this place a thousand times over!"
Heather 4-night trip
Posted 7 hours ago
Palazzo Ravizza

Frequently asked questions

How much do villas in Castiglione del Bosco cost?
Rates for villas in Castiglione del Bosco range between AED 653 and AED 24,856 per night. Whatever your budget, you can find a place that fits the bill 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 Castiglione del Bosco?
Pack your suitcase and pick from 536 villas in Castiglione del Bosco. For a family escape, a getaway with pals and everything in between, Expedia can help you find the right place in a few simple clicks.
Why book your villa in Castiglione del Bosco with Expedia?
Reserving a villa in Castiglione del Bosco is as easy as entering your travel dates and picking the option that has what you need. Searching for something luxurious or low cost, or a stay that also includes free WiFi? Use Expedia's search filters to narrow your results and find the perfect pad.
How can I find cheap villas in Castiglione del Bosco?
With Expedia's user-friendly filter tool, locating cheap villas in Castiglione del Bosco is a cinch. To discover properties that'll make your wallet smile, refine your search results by budget, amenities and star rating.