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

Villas in Province of Siena

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Top Cities in Province of Siena

Our top choices for Province of Siena villas

1. 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, (70 reviews)
"Beautiful house in perfect location with stunning views. Luigi was a very welcoming and helpful host"
United States
Mark G.
Montalcino: Private villa in the heart of Tuscany, private pool, A/C

2. PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
chiusi
10.0 out of 10, Exceptional, (61 reviews)
"We had a very nice stay and a well organized pizza night in the villa. Glad to come again:) "
Germany
Florian Maria W.
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

3. 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, (124 reviews)
"Great location. Loved walking to town!"
United States
Todd C.
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

4. Gorgeous view on vineyards, Stone Tuscan private Villa

Gorgeous view on vineyards, Stone Tuscan private Villa
Toscana
10.0 out of 10, Exceptional, (133 reviews)
"We had a very relaxing stay at the Villa. The pool was perfect for us with amazing views. Great location for visiting Siena"
United States
Nicola S.
Gorgeous view on vineyards, Stone Tuscan private Villa

5. Podere Il Boschetto - Luxury Estate in Siena

Podere Il Boschetto - Luxury Estate in Siena
Siena
9.8 out of 10, Exceptional, (43 reviews)
"Absolutely Wonderful Place to stay!! Our Hosts were excellent and very nice! Barbara and Michele were very informative and had great suggestions!! Location made you feel like you were in a Fairytale. Clean, spacious and had everything you needed. Just take short walk to town for groceries/restaurants or you can take the bus. The bus stop is right at the gate of your Villa!!"
United States
Nicole M.
Podere Il Boschetto - Luxury Estate in Siena

6. 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.

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

Beautiful private villa for 4 people with WIFI, A/C, pool, TV and terrace
Asciano
10.0 out of 10, Exceptional, (32 reviews)
"Absolutly a wonderful vacation we had at Pierce di Sant Ippolito. The host family is very friendly and are ready to help and recommend trips and places. Perfect for Four persons. The small privat ovned Church is old and very nice. Would very much like to come back."
United States
Lars Dahl J.
Beautiful private villa for 4 people with WIFI, A/C, pool, TV and terrace

8. Villa Simo: exclusive use, private pool, 25 acres in Chianti, close to Siena

Villa Simo: exclusive use, private pool, 25 acres in Chianti, close to Siena
Pievasciata
9.8 out of 10, Exceptional, (81 reviews)
"The house and surroundings are amazing, we had a wonderful stay and the hosts were great and so easy to communicate with."
United States
Jessica K.
Villa Simo: exclusive use, private pool, 25 acres in Chianti, close to Siena

9. Villa Sabrina by PosarelliVillas

Villa Sabrina by PosarelliVillas
San Gimignano
10.0 out of 10, Exceptional, (98 reviews)
"Loved Villa Sabrina, location was brilliant and owners discrete. Probably helped that it was 35 so pool and A/ C a blessingSan G about 15 min drive but a lovely hours walk across hills. Also easily visited Volterra, Siena and Florence. Highlight of trip Antinori Chianti Classico vineyard"
United States
Mark G.
Villa Sabrina by PosarelliVillas

10. Hilltop house in the heart of Tuscany with private pool

Hilltop house in the heart of Tuscany with private pool
Montisi
9.8 out of 10, Exceptional, (100 reviews)
"A hidden gem with a stunning view over the Crete Senesi. Photographs do not do it justice."
United States
André W.
Hilltop house in the heart of Tuscany with private pool

11. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (74 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is AED 569
AED 626 total
includes taxes & fees
17 Nov - 18 Nov
Il Poggio dell'Eremita

12. An exclusive getaway at a Tuscan winery: a charming villa with a pool and breathtaking views.

An exclusive getaway at a Tuscan winery: a charming villa with a pool and breathtaking views.
Radda in Chianti
10.0 out of 10, Exceptional, (17 reviews)
"One of the best proprties we have ever stayed at. The house and grounds are well appointed and pristine. Samanta and Franco go above and beyond to make your stay memorable. We loved every minute of our visit! We hope to return when the weather is nicer and stay longer so we can enjoy the pool. Don’t miss the wine tour and tasting - it was such a great learning experience and you can taste the love they have for their vineyard in the wines. Simply exceptional in every aspect."
United States
Reed F.
An exclusive getaway at a Tuscan winery: a charming villa with a pool and breathtaking views.

13. Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!

Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
San Gusme
9.8 out of 10, Exceptional, (103 reviews)
"We had a great stay , location was good for days out, our only concern was the property wasn’t suitable for anyone who had mobility issues, one of our party did and the stairs without handrails was a challenge also the pathways, we should have checked ahead of our visit"
United States
Annie B.
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!

14. Villa with private pool and panoramic view in beautiful Val d'Orcia

Villa with private pool and panoramic view in beautiful Val d'Orcia
San Giovanni d'Asso
9.8 out of 10, Exceptional, (14 reviews)
"Wonderful stay in the Tuscan countryside! We spent a week here with our 3 teenage children and it was the perfect blend of relaxing by the pool and visiting nearby beautiful hilltop towns (Montalcino, Pienza and Montepulciano) along with Sienna, Communication about our arrival with Jo was very easy and we loved the welcome basket of goodies on arrival! The villa had everything we needed - pool towels, umbrellas, loungers - along with dishwasher and laundry powder, olive oil, herbs and spices....
United States
Sarah J.
Villa with private pool and panoramic view in beautiful Val d'Orcia

15. 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, (100 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

16. 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, (64 reviews)
"You couldn’t beat the location, very central to other towns and easy to find. Hosts were so nice and kind and very helpful. It was really nice to come back to the pool after a day of exploring. The whole property was immaculate. We would definitely come back!"
United States
Nancy R.
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

17. Villa in Montalcino, exclusive for you, stunning view!!!

Villa in Montalcino, exclusive for you, stunning view!!!
Montalcino
10.0 out of 10, Exceptional, (95 reviews)
"Lovely villa in a beautiful location. "
United Kingdom
helen S.
Villa in Montalcino, exclusive for you, stunning view!!!

18. VILLA SARAH LUXURY SAN GIMIGNANO, 5 EN SUITE ROOMS , SWIMMING POOL, SPA.

VILLA SARAH LUXURY SAN GIMIGNANO, 5 EN SUITE ROOMS , SWIMMING POOL, SPA.
San Gimignano
10.0 out of 10, Exceptional, (49 reviews)
"Thank you Caterina and Carolina for a great stay. Loved our chef Fabio who helped us prepare one meal and cooked another for us. Rooms and view are better than the pictures! "
United States
Robert J.
VILLA SARAH LUXURY SAN GIMIGNANO, 5 EN SUITE ROOMS , SWIMMING POOL, SPA.

19. The timeless elegance with private pool

The timeless elegance with private pool
Poggibonsi
9.6 out of 10, Exceptional, (4 reviews)
"A beautiful Villa in the heart of Tuscany. The pool was a refreshing relief after busy days."
United States
John A.
The timeless elegance with private pool

20. Villa Dipendenza, Historic Holding with wonderful swimming pool

Villa Dipendenza, Historic Holding with wonderful swimming pool
murlo - siena, tuscany
10.0 out of 10, Exceptional, (43 reviews)
"Even better than we picturedThis place exceeded our expectations — a beautiful, scenic property that was the perfect break from the big cities. The hosts were friendly and helpful throughout our stay. The rooms were spacious and cool, and the outdoor area was ideal for enjoying dinner al fresco. The infinity pool and lounging area were an absolute highlight — stunning views and the perfect spot to relax between exploring the region.A special highlight: the cooking class with the owner's son. We...
United States
Crystal V.
Villa Dipendenza, Historic Holding with wonderful swimming 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

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