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

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

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

Outdoor pool

1. 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 pool

2. Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany

Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany
Pienza
9.6 out of 10, Exceptional, (20 reviews)
"The view from the house is spectacular! What a great spot for a group of friends or a large family. Close to vineyards and shopping. We love sitting on the back patio having dinner. The dog and cats were an extra. Lily and her husband were very helpful and we really enjoyed having the meals cooked by the chef while we were there. The last night with the fish was the best!"
United States
julie l.
Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany
Property grounds

3. 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, (61 reviews)
"This was a wonderful stay for my wife and I in Tuscany. Paola and Gianfranco were there to welcome us at the time we said we would arrive, and showed us all of the details of the accommodation. It was well equipped and very comfortable, and the automatic gates to the garden made the accommodation and covered parking very secure. Although we did not speak the same language Gianfranco helped us with a map of his recommended tourist routes and towns. We would highly recommend this rental and...
United States
Terence I.
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Exterior

4. 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 pool

5. Tuscan oasis overlooking Montepulciano, Villa with pool and exclusive garden

Tuscan oasis overlooking Montepulciano, Villa with pool and exclusive garden
Toscana
Tuscan oasis overlooking Montepulciano, Villa with pool and exclusive garden
Exterior

6. Charming Tuscany Villa with magical Garden, shared pool, Chianti Area

Charming Tuscany Villa with magical Garden, shared pool, Chianti Area
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (57 reviews)
"Definitely will visit again!"
United States
Mark S.
Charming Tuscany Villa with magical Garden, shared pool, Chianti Area
Exterior

7. 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, (60 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
Terrace/patio

8. 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, (59 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
Exterior

9. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (69 reviews)
"This was the perfect spot for our Tuscany 4 day visit. Put us right in the middle of where we wanted to visit.The house is exactly what we wanted for a visit. It’s not a 5 star luxury resort. It is house that we envisioned while visiting Tuscany. Very clean, Fabrizio is great (and he has Google translate down ;-) ). "
Canada
Joe B.
Il Poggio dell'Eremita
Outdoor dining

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, (96 reviews)
"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."
United States
Timothy C.
Hilltop house in the heart of Tuscany with private pool
Exterior

11. 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, (22 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 dining

12. 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, (46 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.
Interior

13. 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)
"A beautiful place in the heart of Chianti. Definitely off the beaten path, so need a vehicle to get there. Close to good wineries. Castellini in Chianti was a quaint village to shop at and eat in. Pool was nice, but wasn’t heated, so couldn’t take advantage of it in late April. Dinner with Serena was worth it."
United States
Denise A.
Luxury converted barn with hilltop views in chianti wine region, Tuscany
Pool

14. 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
Terrace/patio

15. Gorgeous view on vineyards, Stone Tuscan private Villa

Gorgeous view on vineyards, Stone Tuscan private Villa
Toscana
10.0 out of 10, Exceptional, (127 reviews)
"Great location."
United States
Kim B.
Gorgeous view on vineyards, Stone Tuscan private Villa
Outdoor pool

16. 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
Outdoor pool

17. The timeless elegance with private pool

The timeless elegance with private pool
Poggibonsi
9.4 out of 10, Exceptional, (3 reviews)
"Everything was smooth upon arrival. Aida and her family are the absolute sweetest and helpful people. The villa is so charming and lovely. We all enjoyed our stay there so much. "
Sweden
Shiva H.
The timeless elegance with private pool
Property grounds

18. Villa with unique view of Siena with private pool

Villa with unique view of Siena with private pool
Ascarello
9.8 out of 10, Exceptional, (10 reviews)
"We had a wonderful stay at this villa. The views were absolutely breathtaking and made every meal on the terrace feel magical. The location was perfect, close enough to the city that we even enjoyed a leisurely run there some mornings. It was also very easy to access by car, and the hosts were incredibly helpful and responsive throughout our stay. We would happily stay here again."
United States
Amber K.
Villa with unique view of Siena with private pool
Exterior

19. Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.

Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Radda in Chianti
10.0 out of 10, Exceptional, (14 reviews)
"Our stay could not have been better. The Villa is wonderful, very comfortable and beautiful in every way. Samanta and Franco are great hosts and made our time at their villa just perfect. I could go on and on about every aspect, but it would be a long list of superlatives. "
United States
Tom B.
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Exterior

20. 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, (7 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

Hotel Athena

Hotel Athena

10/10 Excellent
"Wonderful hotel in great location just a short walk from the centre but quiet and peaceful in the evening. Fabulous helpful staff. Breakfast always fresh and lots of choice. We used the terrace restaurant once and it was fabulous - what amazing views! Highly recommended for a short or longer stay"
Richard 7-night trip
Posted 8 hours ago
Hotel Athena

Find out more about Province of Siena

Vacation Like a Royal in a Province of Siena Villa

Long ago in ancient Rome, villas were made for upper-class members of society to escape the heat of the city in the surrounding hills or the beaches. These luxurious getaways hosted feasts and offered refined tastes to all their visitors. Back then, villas were seen as a mark of wealth and status—something only the elite could achieve. Now thanks to Expedia, you can stay at one for a price you won't believe. You've probably seen shared photos of friends or relatives staying at a fancy villa and wondered, "How in the world did they afford this?" Now you can see these stays aren't out of reach, and are more doable than ever with our team working as your booking agent.

Stay in a Province of Siena Villa for Your Next Vacation

When you are on holiday, the last thing you should worry about is getting separated at a resort, or having to cancel your "fun in the sun" day because the pool is too packed. We can help you get the most out of your visit to Province of Siena without having to hurry to make reservations for lounge chairs or at the nearby bistro. Our charming villas will leave you feeling refreshed, because you will feel like you are actually on a break, rather than a stressful trip. Staying in one of our unique properties is the perfect way for you and your family to enjoy a relaxing getaway. Just think: You can do just about anything you want on a villa property. Isn't that the life?

Book Your Stay in Province of Siena Today

Where you stay in Province of Siena is all based on your personal needs for your holiday. It can be a home away from home...or, if you are craving seclusion, you can choose to stay in a luxury getaway villa. Forget about resorts blaring music at all hours of the night—the party is over when you go to bed. Not familiar with the area? Don't worry; some of our villa rentals have concierge services available if you need someone to help pick the perfect activities and restaurants while you're in Province of Siena. So, when you're ready, Expedia will be here to help you book your perfect villa holiday.

Province of Siena Villas information

Number of reviews
662
Accommodation
1127 Villas
Lowest Price
Highest Price

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