Villas in Province of Siena

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Top Cities in Province of Siena

VillasVillas

Siena

Siena

Our top choices for Province of Siena villas

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
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
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, (71 reviews)
"Beautiful home and great host"
United States
Dean B.
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
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
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.
Outdoor dining

Exclusive Farmhouse Pool & View of San Gimignano

Exclusive Farmhouse Pool & View of San Gimignano
Toscana
9.4 out of 10, Exceptional, (3 reviews)
"Place was very nice, clean with great views. Beds were comfortable. Communication with owner was not great and some amenities and customer service were average. Emailed owner about WiFi issue, HVAC unit error code and remotes and whether water was potable, no response. Also would’ve have been nice to have toaster/oven/microwave. "
United States
David A.
Exclusive Farmhouse Pool & View of San Gimignano
Exterior

Stunning private villa for 4 guests with A/C, pool, WIFI, TV and terrace

Stunning private villa for 4 guests with A/C, pool, WIFI, 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.
Stunning private villa for 4 guests with A/C, pool, WIFI, TV and terrace
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

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, (19 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
Exterior

Relax in a private Tuscan Villa with pool and open hill views

Relax in a private Tuscan Villa with pool and open hill views
Montefollonico Torrita di Siena SI
10.0 out of 10, Exceptional, (50 reviews)
"I have rented many villas and this stay was up there among the best. Wonderful villa, everything was clean and worked properly and I can’t emphasize enough how great the location was. When you stay there go to Casa Newton for cocktails, beautiful boutique hotel a six minute drive away. "
United States
Alan H.
Relax in a private Tuscan Villa with pool and open hill views
Exterior

BEAUTIFUL VILLA with private Pool in the heart of Chianti

BEAUTIFUL VILLA with private Pool in the heart of Chianti
castelnuovo berardenga
10.0 out of 10, Exceptional, (27 reviews)
"Great villa great view fantastic hostage "
Germany
Markus B.
BEAUTIFUL VILLA with private Pool in the heart of Chianti
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

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
San Gimignano
10.0 out of 10, Exceptional, (115 reviews)
"We very much enjoyed our stay. Alessandro was very welcoming and had many good suggestions. The views were incredible, both from the home and on the walk to the village. The location was perfect!"
United States
Suzanne H.
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
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
Pool

Villa Sarteano - Villa with private pool

Villa Sarteano - Villa with private pool
Sarteano
9.8 out of 10, Exceptional, (15 reviews)
"Perfect!"
United Kingdom
Johannes W.
Villa Sarteano - Villa with private pool
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

Hotel Minerva

Hotel Minerva

8/10 Good
"Very good location . Terrace was great!"
Amy 1-night trip
Posted less than an hour ago
Hotel Minerva