A historic town with a prominent tower and a rainbow arching over it.

Villas in Province of Siena

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Top Cities in Province of Siena

A historic town with tightly packed buildings, a prominent tower, and a church.
VillasVillas

Siena

Siena

Our top choices for Province of Siena villas

Exterior

Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany

Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
San Gimignano
10.0 out of 10, Exceptional, (84 reviews)
"From the minute we arrived to the day we left we found the villa fantastic, and the owners were very helpful and really went out of their way to make our stay lovely."
United Kingdom
Ian S.
Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
Exterior

Enchanting Tuscan Villa / Private Estate / Heated Pool / Panoramic Views

Enchanting Tuscan Villa / Private Estate / Heated Pool / Panoramic Views
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (58 reviews)
"Excellent property in a very peaceful location. Bird song was wonderful to hear. Very well organised booking and local staff to help."
United Kingdom
Mike T.
Enchanting Tuscan Villa / Private Estate / Heated Pool / Panoramic Views
Outdoor pool

Montalcino: Private villa in the heart of Tuscany, private pool, A/C

Montalcino: Private villa in the heart of Tuscany, private pool, A/C
Montisi
10.0 out of 10, Exceptional, (62 reviews)
"Host very helpful. plenty of room inside and out. Beautiful setting."
United States
David A.
Montalcino: Private villa in the heart of Tuscany, private pool, A/C
Outdoor pool

Private villa in the heart of chianti with view of siena

Private villa in the heart of chianti with view of siena
Fonterutoli
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful villa and stunning location. The host was very responsive and helpful. I would love to return someday. "
United States
Wendy F.
Private villa in the heart of chianti with view of siena
Outdoor dining

Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, AC, WiFi

Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, AC, WiFi
San Gimignano
10.0 out of 10, Exceptional, (113 reviews)
"Our stay was absolutely amazing and Barbara is such a kind and attentive host! Barbara makes the most delicious meals we had in Italy."
United States
Olivia B.
Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, AC, WiFi
Outdoor dining

FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI

FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Vagliagli
10.0 out of 10, Exceptional, (72 reviews)
"Beautiful home and great host"
United States
Dean B.
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Property grounds

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Monteriggioni SIENA
9.8 out of 10, Exceptional, (60 reviews)
"Great property "
Denmark
Sara B.
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Exterior

Villa Costa, Stunning Villa in the heart of Tuscany.

Villa Costa, Stunning Villa in the heart of Tuscany.
Siena
10.0 out of 10, Exceptional, (36 reviews)
"This villa's stunning views and the hospitality of the hostess and all the people of Radicondoli was exceptional. I would book this villa again."
United States
steven a.
Villa Costa, Stunning Villa in the heart of Tuscany.
Exterior

Beautiful private villa for 4 people with A/C, WIFI, pool, TV and terrace

Beautiful private villa for 4 people with A/C, WIFI, pool, TV and terrace
Asciano
9.8 out of 10, Exceptional, (30 reviews)
"Mooie woning met een grote tuin en fijn zwembad. [English translation courtesy of Easy Reserve] Beautiful home with a large garden and lovely pool."
United States
Ellen E.
Beautiful private villa for 4 people with A/C, WIFI, pool, TV and terrace
Exterior

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Castellina in Chianti
10.0 out of 10, Exceptional, (65 reviews)
"Gorgeous property - we had a wonderful stay "
United Kingdom
Michelle D.
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Outdoor dining

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Siena
9.4 out of 10, Exceptional, (73 reviews)
"The villa was clean, spacious and very comfortable. The views were amazing!"
Canada
Aysun P.
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Exterior

Villa with private pool on 25 acres in the heart of Chianti, close to Siena

Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Pievasciata
9.8 out of 10, Exceptional, (79 reviews)
"Excellent location to go exploring the Chianti region! Great old villa well away from everything."
United States
Scott H.
Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Exterior

Villa Podere Belvedere

Villa Podere Belvedere
Pienza
9.8 out of 10, Exceptional, (14 reviews)
"Thank you for making our trip so enjoyable - great hospitality!"
United States
Moleek D.
Villa Podere Belvedere
Exterior

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Siena
10.0 out of 10, Exceptional, (20 reviews)
"The place was absolutely beautiful, immaculately clean & super relaxing.Communication was excellent.Exceeded our expectations! Highly recommend and I can’t wait to stay here again."
United States
Elizabeth b.
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Outdoor pool

panoramica casa con piscina privata

panoramica casa con piscina privata
siena
7.0 out of 10, Good, (10 reviews)
"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.
panoramica casa con piscina privata
Interior

Luxury converted barn with hilltop views in chianti wine region, Tuscany

Luxury converted barn with hilltop views in chianti wine region, Tuscany
Castellina in Chianti
10.0 out of 10, Exceptional, (98 reviews)
"One of the best vrbo we have experienced. The location was perfect to explore the Tuscany Chianti region. Host was accommodating and had the best recommendations from restaurants to vino! "
United States
Phil V.
Luxury converted barn with hilltop views in chianti wine region, Tuscany
Interior

Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Siena
10.0 out of 10, Exceptional, (15 reviews)
"This is a superb property and location. Our hosts were great - super helpful and communicative. We were there on a cycling weekend and it met our every need. Highly recommended. Thanks to Anna and Mario for hosting us. "
United Kingdom
Lindsay D.
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Pool

Villa Sarteano - Villa with private pool

Villa Sarteano - Villa with private pool
Sarteano
9.8 out of 10, Exceptional, (16 reviews)
"Perfect!"
United Kingdom
Johannes W.
Villa Sarteano - Villa with private pool
Exterior

Rocca di Cetona, a Luxury Castle with Pool in Tuscany

Rocca di Cetona, a Luxury Castle with Pool in Tuscany
Cetona
10.0 out of 10, Exceptional, (10 reviews)
"The bedrooms are spacious and comfortable, the multiple dining areas were so conducive to our large group and the pool and grounds were beautifully maintained. We loved everything about our stay."
United States
Michael
Rocca di Cetona, a Luxury Castle with Pool in Tuscany
Exterior

Relax in the green, in the municipality of Monteriggioni just 7 km from Siena

Relax in the green, in the municipality of Monteriggioni just 7 km from Siena
Monteriggioni
10.0 out of 10, Exceptional, (6 reviews)
"This was the epitome of staying in an authentic Villa, with amazing views of the Tuscany countryside. "
United States
Donna
Relax in the green, in the municipality of Monteriggioni just 7 km from Siena
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 Province of Siena Hotel Reviews

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"This is a traditional and historic building with high ceilings and a beautiful garden overlooking the surrounding countryside.It is not a modern contemporary hotel, but the rooms are lovely, the garden was beautiful and a good breakfast too. There is a small bar in the evening, but no restaurant for an evening meal, but frankly you will likely want to explore and eat out at one of the many restaurants in the old town. A great find."
David 4-night trip
Posted 2 hours ago
Palazzo Ravizza