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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Villas in Siena and around

Spacious villa with stunning pool, luscious gardens
Outdoor dining

Spacious villa with stunning pool, luscious gardens

The price is €1,753
includes taxes & fees
31 Aug - 1 Sept
Spacious villa with stunning pool, luscious gardens
VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
Pool

VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino

The price is €6,450
includes taxes & fees
22 Aug - 23 Aug
VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
Il Poggio dell'Eremita
Exterior

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (53)
"Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular."
The price is €156
includes taxes & fees
12 Sept - 13 Sept
Il Poggio dell'Eremita
panoramica casa con piscina privata
Pool

panoramica casa con piscina privata

7.0 out of 10, Good, (9)
"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....
The price is €154
includes taxes & fees
1 Sept - 2 Sept
panoramica casa con piscina privata
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Pool

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

The price is €5,983
includes taxes & fees
22 Aug - 23 Aug
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Outdoor pool

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

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! "
The price is €2,094
includes taxes & fees
24 Aug - 25 Aug
Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Antico Brunello
Outdoor pool

Antico Brunello

The price is €7,270
includes taxes & fees
22 Aug - 23 Aug
Antico Brunello
Villa con Piscina, Sauna, Jacuzzi
TV, fireplace

Villa con Piscina, Sauna, Jacuzzi

10.0 out of 10, Exceptional, (1)
"Beautiful property, highly recommended. "
The price is €627
includes taxes & fees
17 Sept - 18 Sept
Villa con Piscina, Sauna, Jacuzzi
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Pool

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

The price is €6,450
includes taxes & fees
22 Aug - 23 Aug
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
Interior

Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.

9.8 out of 10, Exceptional, (21)
"We staid there for a week, great with kids (pool) and good location in the countryside if you have car (30m from Florence, 15m from San Gimignano, 35 from Siena)"
The price is €610
includes taxes & fees
6 Sept - 7 Sept
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
Villa Cicogna Private Villa, sleeps 2 -10 guests
Pool

Villa Cicogna Private Villa, sleeps 2 -10 guests

10.0 out of 10, Exceptional, (6)
"Our family stayed here for a local wedding and enjoyed the charm of this quiet town and comfortable villa. The hosts were super responsive and welcoming, making sure we had everything we needed for a pleasant stay. Our toddler loved running around and swimming every day in the pool. The location is perfect to drive to nearby cities with parking provided. Would love to visit again!"
The price is €130
includes taxes & fees
24 Aug - 25 Aug
Villa Cicogna Private Villa, sleeps 2 -10 guests
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
Pool

Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning

10.0 out of 10, Exceptional, (1)
The price is €3,081
includes taxes & fees
5 Sept - 6 Sept
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Outdoor pool

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

10.0 out of 10, Exceptional, (38)
"Excellent in every way. Highly recommend"
The price is €1,747
includes taxes & fees
25 Aug - 26 Aug
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Beautiful Tuscan home between Florence & Siena
Outdoor dining

Beautiful Tuscan home between Florence & Siena

10.0 out of 10, Exceptional, (5)
"Property was just as listed. Clean, large, and a great location for wine tasting, local restaurants, and more. The owners were super helpful in planning some local outings. Highly recommended. "
Beautiful Tuscan home between Florence & Siena
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Fridge, microwave, oven, stovetop

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

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!"
The price is €2,014
includes taxes & fees
19 Sept - 20 Sept
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Pool

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

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."
The price is €2,066
includes taxes & fees
4 Sept - 5 Sept
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi
TV, fireplace

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

10.0 out of 10, Exceptional, (7)
"Country location but easy access to a great local winery/restaurant and the town of Gaiole."
The price is €1,926
includes taxes & fees
19 Sept - 20 Sept
"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi
Exclusive Villa with Concierge service and heated pool on the Florentine hills
Outdoor dining

Exclusive Villa with Concierge service and heated pool on the Florentine hills

10.0 out of 10, Exceptional, (103)
"Our host (Cate), along with her sister and mother, were fantastic. Very responsive, easy to get ahold of and worked very hard to ensure our visit was amazing. Cate was onsite and worked closely with the catering company and made sure all went well.."
Exclusive Villa with Concierge service and heated pool on the Florentine hills
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Terrace/patio

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

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

Hotel Chiusarelli

10/10 Excellent
"On our last night there the gentleman in the foyer was amazing thankyou "
cheryl 2-night trip
Posted 2 days ago
Hotel Chiusarelli

Frequently asked questions

How much do villas in Siena cost?
You can expect to pay between and 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 92 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.