Villas in Siena

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Check prices for these dates

Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21
In one month
Jan 2 - Jan 4
In two months
Jan 30 - Feb 1

Villas in Siena

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

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

Vico dʼArbia
$1,117 nightly
The price is $1,121
Dec 8 - Dec 9
Total with taxes and fees
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Outdoor dining
Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany

Vico dʼArbia
$1,586 nightly
The price is $1,591
Dec 8 - Dec 9
Total with taxes and fees
Villa Capanna: A Window onto Tuscany
Exterior
Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena

Vico dʼArbia
$1,586 nightly
The price is $1,591
Dec 10 - Dec 11
Total with taxes and fees
Villa Torre Among the Hills of Siena
Exterior
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

Montalcino
$7,510 nightly
The price is $7,510
Dec 8 - Dec 9
Total with taxes and fees
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Pool
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Siena
$6,966 nightly
The price is $6,966
Dec 8 - Dec 9
Total with taxes and fees
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Exterior
Il Poggio dell'Eremita

Il Poggio dell'Eremita

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 8 - Dec 9
Total with taxes and fees
Il Poggio dell'Eremita
Pool
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

Gaiole in Chianti
$7,510 nightly
The price is $7,510
Dec 8 - Dec 9
Total with taxes and fees
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Pool
panoramica casa con piscina privata

panoramica casa con piscina privata

siena
7.0 out of 10, Good, (10)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
United Kingdom
Olivier B.
$175 nightly
The price is $175
Dec 15 - Dec 16
Total with taxes and fees
panoramica casa con piscina privata
Pool
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Montespertoli
10.0 out of 10, Exceptional, (1)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
$1,781 nightly
The price is $1,784
Dec 9 - Dec 10
Total with taxes and fees
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Terrace/patio
Antico Brunello

Antico Brunello

Montalcino
$7,684 nightly
The price is $8,464
Dec 8 - Dec 9
Total with taxes and fees
Antico Brunello
Exterior
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Montespertoli
10.0 out of 10, Exceptional, (12)
"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"
United States
Elise D.
$1,658 nightly
The price is $1,663
Dec 9 - Dec 10
Total with taxes and fees
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Terrace/patio
"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi

"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi

Gaiole in Chianti
10.0 out of 10, Exceptional, (7)
"Country location but easy access to a great local winery/restaurant and the town of Gaiole."
Canada
russ h.
$665 nightly
The price is $669
Dec 8 - Dec 9
Total with taxes and fees
"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi
Pool
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Radda in Chianti
10.0 out of 10, Exceptional, (1)
"Pros: Świetna lokalizacja i przyjemne otoczenie domu. Dom położony na wzniesieniu z którego roztaczał się piękny widok. Cons: Osoba opiekująca się domem nie mówiła po angielsku co utrudniało komunikację. Nie byliśmy świadomi że dom podzielony jest na 2 części góra i piwnica w której były dodatkowe 3 pokoje. Uszkodzona pralka która nie dopierała pranych ubrań - brudna woda z zanieczyszczeniami które dodatkowo brudziły ubrania."
Poland
Anonymous traveler
$2,045 nightly
The price is $2,050
Dec 10 - Dec 11
Total with taxes and fees
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Outdoor spa tub
Villa Dei Pavoni - Luxury Villa on top of hills in Florence

Villa Dei Pavoni - Luxury Villa on top of hills in Florence

Toscana
10.0 out of 10, Exceptional, (1)
"The host was amazing! The property was beautiful. All was seamless! All of our needs were met. Highly recommend! "
United States
Leopard I.
$2,370 nightly
The price is $2,370
Dec 8 - Dec 9
Total with taxes and fees
Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Exterior
Red Heart - relax with those you love in Tuscany.

Red Heart - relax with those you love in Tuscany.

Trequanda
$1,064 nightly
The price is $1,068
Dec 9 - Dec 10
Total with taxes and fees
Red Heart - relax with those you love in Tuscany.
Exterior
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Montespertoli
10.0 out of 10, Exceptional, (38)
"Excellent in every way. Highly recommend"
United States
Ed M.
$1,729 nightly
The price is $1,734
Jan 7 - Jan 8, 2026
Total with taxes and fees
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Exterior
Villa con Piscina, Sauna, Jacuzzi

Villa con Piscina, Sauna, Jacuzzi

Città Metropolitana di Firenze
6.0 out of 10, (2)
"Beautiful property, highly recommended. "
United States
Magdalena
$689 nightly
The price is $695
Dec 8 - Dec 9
Total with taxes and fees
Villa con Piscina, Sauna, Jacuzzi
Exterior
Villa "Arnilù" with Private Pool & Wi-Fi

Villa "Arnilù" with Private Pool & Wi-Fi

San Gimignano
$5,833 nightly
The price is $5,839
Jan 5 - Jan 6, 2026
Total with taxes and fees
Villa "Arnilù" with Private Pool & Wi-Fi
Terrace/patio
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Impruneta
10.0 out of 10, Exceptional, (3)
"Pictures do not do it justice, this house and location is absolutely beautiful. Very comfortable beds, clean house, beauty views, nice fireplace.owner goes above and beyond to make you feel welcome. She had her local wine, cooked us a delishes breakfast, and also brought her olive oil to do tasting. We will definitely be back, i thank you for an amazing experience and a beautiful house."
United States
Lidija M.
$523 nightly
The price is $523
Dec 8 - Dec 9
Total with taxes and fees
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Exterior detail
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

Castellina in Chianti
$6,055 nightly
The price is $6,055
Jan 1 - Jan 2, 2026
Total with taxes and fees
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
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 Siena Hotel Reviews

Hotel Italia

Hotel Italia

10/10 Excellent
"This was a short stay for us in Siena. A great hotel. Friendly staff and the best bargain best breakfast we have had in Italy. Highly recommended"
Phil 1-night trip
Posted 3 days ago
Hotel Italia

Find out more about Siena

Siena Villas information

Number of reviews
97
Accommodation
85 Villas
Lowest Price
$165
Highest Price
$8,464

Frequently asked questions

How much do villas in Siena cost?
You can expect to pay between $165 and $8,464 per night for villas in Siena. Whatever your budget, the perfect getaway is only clicks 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 Siena?
Siena has 85 villas to select from. Find your ideal stay quickly and easily by checking the "Villa" box under the "Property type" tab in our filter tool.
Why book your villa in Siena with Expedia?
Booking a villa in Siena is as simple as working out your travel dates and selecting an option that meets your needs. Searching for something luxurious or low cost, or a property that also comes with free WiFi? Use Expedia's search filters to narrow your results and find the ideal fit.
How can I find cheap villas in Siena?
Expedia is here to help you easily source cheap villas in Siena. Use our convenient filter tool to select amenities, budget and star rating to refine your search and find the best place to stay in a matter of clicks.
What is there to do near my villa in Siena?
You'll find loads of terrific things to fill your days in Siena. Drop by big attractions like Museo dell'Acqua, Accademia Musicale Chigiana and Basilica dell'Osservanza. Palasport Mens Sana, Porta Romana and San Spirito are also visited by many.

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