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Villa vacation rentals in Province of Siena

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Popular amenities for Province of Siena villa rentals

Private villa rentals

Superhost
Villa in Chiusi
4.67 out of 5 average rating, 3 reviews

Tuscany 2 Villas sleeps 12 private heated pool

PiotrRating, 5 stars46 months ago
In reality villas present themselves a lot prettier than in photos on website. The area and surroundings are beautiful, calm and quite. Place is perfect as exit basis for exploring and sightseeing Tuscany. Rooms and beds are adequately big and clean. Kitchen and utensils are in sufficient quantity. Pool is clean, water warm. There’s no need for a battle for lawn chairs. Jacopo is very helpfull, communicative, serves his help everyday. The place is worthy of recommendation. We spent our holiday time comfortably in quaint area. All the best!
Guest favourite
Villa in Sodo
4.95 out of 5 average rating, 22 reviews

The House of the Sole del Sodo

ClaireRating, 5 stars7 months ago
We chose Il Sole del Sodo because it had 6 en-suite rooms, a pool, was close to a town and a train station and had a well- regarded host who could provide extras like breakfast, dinners, cooking classes and olive oil tastings e.g. Claudia! While rustic, the villa’s charm and peaceful spaces draw you right in and Claudia’s hospitality is unsurpassed. The villa fronts to the road to Cortona and backs to a field of sunflowers. Our family and friends dined on the private patio and found a back way to walk up to Cortona for exercise. A unique and wonderful experience!
Guest favourite
Villa in Castiglion Fiorentino
5 out of 5 average rating, 18 reviews

Villa Degli Olivi

MargaretRating, 5 stars7 months ago
The villa was perfect for our family of 6 adults and 4 children. Swimming pool with toys outstanding. Pizza oven and bbq fun to use and a beautiful peaceful garden. Walking distance into Castiglion which is a beautiful old town. Would love to return.
Top guest favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 21 reviews

Montemarcoli

RobertRating, 5 stars4 weeks ago
Our stay at Villa Montemarcoli was fantastic. So peaceful. No noice from cars and really no air traffic noise whatsoever. Just the birds singing. Just want to mention you will need to drive to everything but the roads are so beautiful you won’t mind! I would recommend a small SUV or car with all wheel drive as the villa is located up a gravel road and roads in the area can be narrow and parking can be tight in places. I would definitely recommend Brigitta’s Villa and hope to come back again someday 😎🍷
Superhost
Villa in Provincia di Siena
4.77 out of 5 average rating, 30 reviews

Villa Limone - 3 bedroom villa in Tuscany

LorenzoRating, 5 stars1 week ago
We had a great time , the rooms were clean , the lovely place surrounded by greenery
Guest favourite
Villa in Toscana
4.88 out of 5 average rating, 60 reviews

Chianti Villa at Mulino del Cerchiaio

MathildeRating, 5 stars7 months ago
Thank you!! We enjoyed our vacation with 9 friends! A little humid because of the weather, but the place is ideal in summer and comforting by the fire when the good weather is not present!
Superhost
Villa in Montepulciano
5 out of 5 average rating, 3 reviews

Terra Antica Suites & Villas - Villa Vino - Private Jacuzzi

HeatherRating, 5 stars5 months ago
Our stay at Terra Antica was a dream. The location is perfect and the property and villa are exceptional. We were close enough to town to get to restaurants and shopping and then come back for some quiet relaxing time. There are numerous wineries to visit in the area. Day trips to other local towns are easy to do as well. The private jacuzzi was an extra bonus & we used it several times during our stay. We will be back again!
Top guest favourite
Villa in Cavriglia
4.99 out of 5 average rating, 128 reviews

Villa Poggio in Mandria in Chianti

EmilyRating, 5 stars7 months ago
We spent a week at Villa Poggio a Mandria as part of a group of six adults and had the most incredible and magical time. The photos do not do justice to how extraordinary the villa and surrounding area are — it’s nestled in an olive grove near the top of a hill just a short walk from a medieval village (Montegonzi), with utterly spectacular views in every direction. It could not be more peaceful or breathtaking. The villa was spotless, gorgeous and fully equipped, with tons of space for everyone. We had an unforgettable day with Lorenzo (contact available through Claudia and Leonardo), a local tour guide and chef who took us on an amazing wine tour and then cooked us the best meal ever that evening. And Claudia and Leonardo are the kindest, most responsive hosts, always available to answer any questions we had and even baking us a beautiful cake one evening! We can’t recommend Villa Poggio a Mandria enough. We had an unforgettable trip that truly felt like a dream. Thank you!

Luxury villa rentals

Guest favourite
Villa in Montepulciano
4.91 out of 5 average rating, 122 reviews

Villa in Montepulciano with a Pool

LindaRating, 5 stars3 weeks ago
We had a wonderful time in Tuscany! We were able to make use of the pool on the first day with our two boys, 7 and 4. We visited Pienza, Montepulciano and Montelccino. We also purchased two of the wines from the estate. Alex made everything very easy and was a great host!
Superhost
Villa in Greve in Chianti
4.83 out of 5 average rating, 29 reviews

Romantic Villa with private pool and fabulous view

RobertRating, 5 stars1 week ago
We absolutely enjoyed our stay. It felt like home from day one. The views are phenomenal; the garden is peaceful and fragrant. The kitchen is a delight to cook in. We walked into the beautiful village of Panzano multiple times (some hills which helped us burn off the pasta calories!). We didn’t want to leave.
Top guest favourite
Villa in Monteriggioni
4.97 out of 5 average rating, 152 reviews

Villa of the 2 Olive Trees (Abbadia Isola)

RodolfoRating, 5 stars1 month ago
I recently stayed at this B&B and the experience was really positive. The property is cozy and well cared for, with clean and comfortable rooms. The atmosphere is familiar and relaxing, ideal for both a short stay and a longer vacation. The strength is definitely the hospitality: the owners are kind and helpful, always ready to give advice on what to visit in the dintori Vote: ⭐⭐⭐⭐⭐ Recommended for anyone who wants to feel at home even away from home!
Guest favourite
Villa in Colle di Val d'Elsa
4.95 out of 5 average rating, 22 reviews

Villa l'elsa beautiful country home with view - vi

KelseyRating, 5 stars5 days ago
A great place for a large group! Loved the outdoor space and view. A truly beautiful home. An overall great stay. Tentative manager. Pros: - Spacious house - Many rooms - Outdoor space - Games/kids supplies - Charging Adapters - Washer & Dryer - Many bathrooms Cons: - Not a self check-in. It was stressful coordinating with the manager while trying to travel and coordinate with our large group. - Hot tub wasn’t clear on how to heat and we would have loved to have it full and warm for arrival after a long travel day for us and the kids. - Downstairs bed was very firm. - We didn’t have enough dishwasher pods, toilet paper or paper towels for our group so we had to buy some. I feel that should be included.
Guest favourite
Villa in Castiglion Fiorentino
4.95 out of 5 average rating, 43 reviews

Villa il Laghetto with Infinity Pool in Tuscany

NataliyaRating, 5 stars4 days ago
Our big family had the most amazing stay at Alessandro and Elisa's. It was a special occasion for us, and thanks to the hosts we enjoyed our stay to maximum: the food was great, the communication was smooth, the location is beautiful and the house is very spacious.
Top guest favourite
Villa in San Gimignano
4.97 out of 5 average rating, 37 reviews

Exclusive villa private pool Florence and Sienna

NolitaRating, 5 stars1 week ago
I cannot recommend Serena’s place enough. We were impressed as soon as we drove in the gate. The house was beautifully decorated, and so big and spacious for our big group of 14 people, one toddler who absolutely loved walking through the grass and endless space to run around in a safe environment. This house is super clean, and updated throughout. It has eveything you could need, including dishes and cooking supplies. This house was very comfortable and so relaxing, nature everywhere, beautiful areas to walk around and take in the spectacular scenes all around. Endless fun for our children also, volleyball net, pool table and pool. Serena was contactable all the time, sending us endless recommendations, one of which we got a private chef Sergio to the house who I highly recommend for anyone else staying. He gave us a beautiful Italian night with amazing food we really appreciated and enjoyed. Serena thank you so much for everything we will be back to your beautiful villa in the future
Guest favourite
Villa in Radicondoli
4.98 out of 5 average rating, 50 reviews

Fabulous Villa in the heart of Tuscany

MarthaRating, 5 stars8 months ago
This is a lovely house in a beautiful setting. The whole family are very generous and kind. Highly recommend.
Guest favourite
Villa in Montalcino
5 out of 5 average rating, 7 reviews

VILLA IN THE HILLS OF VAL D'ORCIA

AlethiaRating, 5 stars17 months ago
Beautiful and tranquil countryside retreat and welcoming hostess. Stayed with friendsfor my birthday weekend and we enjoyed so much hanging out by the fire in the evening and enjoying the fresh morning air around the garden before breakfast. Just wish we could have stayed longer!

Villa rentals with a pool

Guest favourite
Villa in Monte San Savino
5 out of 5 average rating, 7 reviews

Private villa with pool

BeatrizRating, 5 stars1 month ago
The owners are a lovely couple who cared for us very well, the house is beautiful, very clean, we didn't get cold and we didn't miss anything. The views seen from the house are wonderful!! Highly recommended if you want to visit Tuscany
Top guest favourite
Villa in Località Poggio Olivo
4.98 out of 5 average rating, 59 reviews

Beautiful villa with swimming pool in Tuscany

Harm JanRating, 5 stars6 days ago
What a lovely week we had in the vacation home. Very neat and wonderful the space around you, just outside the city but feeling like you're outside. And the view, enchanting. Very friendly people who want to do everything for you. And then even more luxury, the pool. Wonderful to cool in. All in all, really great! Highly recommend.
Superhost
Villa in Campagnatico
4.8 out of 5 average rating, 5 reviews

Charming villa on two levels - Casa Lola

SofiaRating, 5 stars9 months ago
Mel is a fantastic host and the place is exactly like in your most vivid Tuscany dreams.:) It's not our first time here and we absolutely loved everything about the place. We booked all three homes available at Mel's place and had an unforgettable week with the entire family - highly highly recommended! Thank you, Mel for being absolutely fabulous!✨
Guest favourite
Villa in Montevarchi
4.91 out of 5 average rating, 43 reviews

Villa Pongina - Tuscany - private pool - air with

RonjaRating, 5 stars7 months ago
This villa was absolutely perfect for what I was hoping for. It was even better than the pictures, and the surroundings were beautiful. We loved the secluded feel of the villas, and the size of the villas was perfect for our group. Serena was super helpful and very flexible, so I can't recommend this place enough!
Guest favourite
Villa in Castiglion Fiorentino
4.95 out of 5 average rating, 39 reviews

Villa Il Sogno di Pietro, private pool and AC

SheebaniRating, 5 stars7 months ago
We loved our stay at this beautiful place! It was extremely peaceful and our family had a great time!
Top guest favourite
Villa in Monte San Savino
4.99 out of 5 average rating, 70 reviews

CHARMING TUSCANY VILLA PRIVATE POOL

Tsz Kwan CarrieRating, 5 stars6 months ago
Francesco is nice:) He brought us welcome pizzas and dessert. His response is instant. The place is quiet which provide you completely private place. Just a bit far from town if you cannot drive yourselves. If you have cars, it is not a problem, just few minutes drive from town. The place looks exactly the same as the pictures, clean and tidy. Definitely enough space for 8 adults. Recommend.
Superhost
Villa in San Gimignano
4.79 out of 5 average rating, 24 reviews

Elisa Villa

DominiqueRating, 5 stars6 months ago
Beautiful house in the vines surrounded by sumptuous hillsides in an incredible postcard setting. Perfect for gatherings for families or with friends. The location is ideal to radiate between Siena, Florence and Chianti or resting while enjoying the pool. Elisa, always attentive, is very responsive and will respond almost without delay.
Guest favourite
Villa in Montevarchi
5 out of 5 average rating, 13 reviews

Tuscan villa with private pool and stunning views

BarbaraRating, 5 stars8 months ago
We had a wonderful week at Sergio's family's villa. Massimo met us with Sergio on our arrival and showed us around the villa. The villa is located in the beautiful Tuscan countryside about 3 miles (10 minutes drive) from Montevarchi which has a great selection of supermarkets including a huge Coop with the best cheese counter we have ever seen. Sergio's family gave us a great number of recommendations from restaurants to local sights etc. One restaurant we particularly liked was Le Mura del Cassero in Montevarchi. We had a couple of trips, one to Siena by car and another to Florence by train. Both very accessible. The pool at the villa is wonderful (Massimo checked it every morning before we even surfaced) and Sergio and Massimo were the kindest hosts. They gave us a huge fruit bowl, prosecco, beers, pastries, home produced olive oil and their own delicious wine...truly lovely generous people. We would definitely recommend this villa to others!

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