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Check prices for these dates

Next weekend
14 Nov - 16 Nov
In two weeks
21 Nov - 23 Nov
In one month
5 Dec - 7 Dec
In two months
2 Jan - 4 Jan

Featured Villas in Province of Siena

Outdoor pool
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
10.0 out of 10, Exceptional, (9)
"We were a group of 12 retired friends staying at Villa Santa Chiara for a few nights. The entire checkin/out process was very easy. Anna and Mario allowed us a late checkout which was very helpful. The location is a short but uphill walk to the city center. The accommodations were perfect for us and we especially enjoyed sitting outside by the pool or by the gazebos. All 12 of us loved the location, the quality of the accommodations and especially the helpfulness of the owners. This would be our...
United States
Michael O.
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Outdoor pool
Villa in Montalcino, exclusive for you, stunning view!!!
Villa in Montalcino, exclusive for you, stunning view!!!
10.0 out of 10, Exceptional, (86)
"We were a group of 4 couples and found there was plenty of room for all of us. The property as better in person than we had expected. We had a car so it was really easy to get around and see all the towns nearby. Very beautiful property with great vistas. So relaxing to hang out at the pool or the deck."
Canada
Elfrieda S.
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor dining
Hilltop house in the heart of Tuscany with private pool
Hilltop house in the heart of Tuscany with private pool
9.8 out of 10, Exceptional, (94)
"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
Il Poggio dell'Eremita
Il Poggio dell'Eremita
10.0 out of 10, Exceptional, (57)
"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."
United States
Vivian K.
The price is AU$247
includes taxes & fees
8 Nov - 9 Nov
Il Poggio dell'Eremita
Outdoor pool
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!
10.0 out of 10, Exceptional, (58)
"This was a stunning property and we thoroughly enjoyed our time enjoying the pool and the beautiful yard. Luigi was very helpful and quick to respond with any questions we had. The little village of Montisi is cute and we enjoyed walking there in the mornings. The location is a short drive to other towns and some of the best wines in Tuscany. It was very hot the week we were there - a few nights we found it difficult to sleep. Overall it is a beautiful location and Luigi was a fabulous host....
Canada
Neysa D.
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!
Pool
Private villa in the heart of chianti with view of siena
Private villa in the heart of chianti with view of siena
10.0 out of 10, Exceptional, (3)
"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
Exterior
Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool
Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool
10.0 out of 10, Exceptional, (56)
"What a beautiful place! Communication with Sheri prior to arriving was excellent and we were met in the local town to be escorted to the property. The house is of the highest quality, spotlessly clean with facilities of an excellent standard. A perfect mix of traditional construction with modern fixtures and fittings. The fresh fruit, vegetables, wine and extra provisions that were provided were very much appreciated. Such a tranquil setting to relax in amongst the vineyards. We were lucky...
United Kingdom
Neil M.
Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool
Outdoor dining
Villa with private pool, air conditioning near wineries at 3km from village
Villa with private pool, air conditioning near wineries at 3km from village
9.4 out of 10, Exceptional, (46)
"Thank you for your amazing hospitality and sharing your beautiful space with us. We felt welcomed and at home the entire time we were here. We enjoyed exploring all the Tuscan towns and enthralled by the beauty of the countryside. The pool was a favourite for our children and we loved seeing the different wildlife; porcupines, wild boars, and coyotes. The dinner that Leonardo cooked for us was an absolute highlight and HIGHLY recommend this to any other guests who wish to indulge. Thank you so...
Canada
Kevin H.
Villa with private pool, air conditioning near wineries at 3km from village
Property grounds
VILLA SARAH LUXURY SAN GIMIGNANO, 5 EN SUITE ROOMS , SWIMMING POOL, SPA.
VILLA SARAH LUXURY SAN GIMIGNANO, 5 EN SUITE ROOMS , SWIMMING POOL, SPA.
10.0 out of 10, Exceptional, (45)
"What an amazing week at Villa Sarah! Every aspect, from the house to the view to the surroundings and to our gracious hosts exceeded our expectations. If there were 10 stars, we would give it 10 stars!"
United States
pamela s.
VILLA SARAH LUXURY SAN GIMIGNANO, 5 EN SUITE ROOMS , SWIMMING POOL, SPA.
Exterior
Villa Costa, Stunning Villa in the heart of Tuscany.
Villa Costa, Stunning Villa in the heart of Tuscany.
10.0 out of 10, Exceptional, (36)
"Our group of 8 lovers of food and wine thoroughly enjoyed the comfortable and spacious villa, isolated on a hilltop amongst the sheep and with 360 degree views of the Tuscan countryside and the charming small village of Radicondoli. Perfect for visiting many fascinating villages, towns, and cities of Tuscany, preparing meals of pasta and truffles with local wines, sampling freshly-pressed olive oil from nearby producers, and tasting at generations-old wineries. The one glitch we had was a...
United States
Gregory L.
Villa Costa, Stunning Villa in the heart of Tuscany.
Terrace/patio
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
10.0 out of 10, Exceptional, (113)
"A true Tuscany experience. Fantastic place to stay. Highly recommendable for family holiday. We all loved the welcome dinner which Francesca, our host, prepared for us. And her team, Best of Mas, was very helpful and responsive. It was a lovely stay!"
Germany
Le L.
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Outdoor pool, pool loungers
Secluded villa between Chianti vineyards, private pool, tennis, large garden
Secluded villa between Chianti vineyards, private pool, tennis, large garden
10.0 out of 10, Exceptional, (44)
"Amazing villa! Views were stunning! Villa had everything you could hope for or imagine! We were a group of three couples traveling together. Layout of bedrooms was perfect, with each having its own bathroom. Extremely well equipped kitchen. The week we were there was a bit cool, and having the huge fireplace made things extra special. Host's recommendations for restaurants and private chefs were excellent. Huge huge appreciation to Mina (one of the private chefs). Her pasta was the best we had...
United States
Stephen W.
Secluded villa between Chianti vineyards, private pool, tennis, large garden
Outdoor dining
Winery Villa in the heart of Nobile Vineyards.
Winery Villa in the heart of Nobile Vineyards.
10.0 out of 10, Exceptional, (14)
"The house is amazing, it’s a beautiful property and Barbara was very helpful. We wish we could have stayed longer!"
United States
Justin B.
Winery Villa in the heart of Nobile Vineyards.
Seasonal outdoor pool
Luxury Villa Basilio Chianti
Luxury Villa Basilio Chianti
Luxury Villa Basilio Chianti
Outdoor dining
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
10.0 out of 10, Exceptional, (107)
"Beautiful home, beautiful views. "
United States
James D.
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Exterior
BEAUTIFUL VILLA with private Pool in the heart of Chianti
BEAUTIFUL VILLA with private Pool in the heart of Chianti
10.0 out of 10, Exceptional, (27)
"We celebrated our baby turning 1 with family and friends and this property was an absolute dream! It comfortably fit our large group! We had a private chef host a dinner for us that Alessandro requested which was incredible! We are grateful for the family memories and would 100% return! Thank you for being such a great host! "
United States
Emily A.
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Outdoor pool, a heated pool
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
10.0 out of 10, Exceptional, (68)
"House was great and so were the hosts. Called a few times for questions or dinner ideas, made reservations for us and just great all around. Will highly recommend to friends"
United States
pam F.
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Exterior
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
10.0 out of 10, Exceptional, (108)
"We couldn't be more pleased with our stay and this outstanding Tuscan Farm house. The apartment itself was even better than the pictures and the views were straight out of a painting. We had two breakfasts and two suppers prepared by Barbara which were better than restaurant quality. What made this stay even more special was our host, Barbara, her father and her nona Vera! Out of all my VRBO experiences, this has been the best by far. We all wish to return. "
United States
Sandra T.
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
Outdoor pool
Il Boschetto an oasis of peace and nature in Siena
Il Boschetto an oasis of peace and nature in Siena
9.8 out of 10, Exceptional, (38)
"The rooms are spacious and well equipped and the house can easily accommodate 10 people. The property is located in a wealthy enclave of Siena minutes from town yet it is completely private. The views are breathtaking and the property is gorgeous."
United States
Carlton J.
Il Boschetto an oasis of peace and nature in Siena
Pool
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
10.0 out of 10, Exceptional, (81)
"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
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

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Beautiful place and a very nice staff. "
Michael 1-night trip
Posted 4 days ago
Grand Hotel Continental Siena – Starhotels Collezione

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
865
Accommodation
1219 Villas
Lowest Price
AU$247
Highest Price
AU$247

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