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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

La Casa del 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
Siamo stati benissimo , le stanze erano pulite , il posto incantevole immerso nel verde
Guest favourite
Villa in Toscana
4.88 out of 5 average rating, 60 reviews

Chianti Villa Mulino del Cerchiaio

MathildeRating, 5 stars7 months ago
Merci !! Nous avons bien profité de nos vacances entre copines à 9 ! Un peu d’humidité du fait du temps, mais l’endroit est idéal en été et réconfortant au coin du feu quand le beau temps n’est pas présent !
Superhost
Villa in Montepulciano
5 out of 5 average rating, 3 reviews

Terra Antica Suite & Ville - 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 a 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 a Montepulciano con Piscina

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 dei 2 Ulivi (Abbadia Isola)

RodolfoRating, 5 stars1 month ago
Ho recentemente soggiornato in questo B&B e l’esperienza è stata davvero positiva. La struttura è accogliente e ben curata, con camere pulite e confortevoli. L’atmosfera è familiare e rilassante, ideale sia per un breve soggiorno che per una vacanza più lunga. Il punto di forza è sicuramente l’ospitalità: i proprietari sono gentili e disponibili, sempre pronti a dare consigli su cosa visitare nei dintori Voto: ⭐⭐⭐⭐⭐ Consigliato a chiunque voglia sentirsi come a casa anche lontano da casa!
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, 42 reviews

Villa il Laghetto with Infinity Pool in Tuscany

AndreaRating, 5 stars1 week ago
La villa di Alessandro è un’angolo di paradiso immerso nel verde della campagna toscana. Raramente ho trovato una villa così bella, curata e pulita, con spazi verdi assolutamente strepitosi. Alessandro e sua moglie sono degli host fantastici, sempre pronti e reattivi per qualsiasi esigenza. Non posso che ringraziarli per la magnifica ospitalità e per la splendida esperienza.
Superhost
Villa in Volterra
4.87 out of 5 average rating, 31 reviews

Le Campore - Stunning view over the Tuscany hills

MattRating, 5 stars6 months ago
Amazing views, lovely accommodation, helpful and friendly host. The driveway is a real challenge and needed more-than-basic hire cars (VW Golf was fine, Fiat Panda struggled), but was manageable. Would love to come again
Top guest favourite
Villa in Siena
4.93 out of 5 average rating, 58 reviews

Villa Nannini Siena

MelissaRating, 5 stars5 days ago
Roberta’s house was amazing! We thoroughly enjoyed our stay and our only regret was that we weren’t there longer. Our 3 year old also didn’t want to leave. The house is exactly as described and pictured and is large, great for families or groups of friends. Roberta has also catered for children so well, with a kids bunk bed room, a playroom and a cubby house outside and there is also a portacot and high chair. The backyard is fully fenced for safety of children, so they can play in the backyard freely. The pool is amazing with a beautiful view. Roberta was friendly, accommodating and responsive and provided us with a suggestion for dinner when we arrived. The location is a lovely quiet spot and I would recommend having a car to get around. Thank you again for our stay Roberta, we loved it and can’t wait to come back. We highly recommend this property.
Guest favourite
Villa in Montalcino
5 out of 5 average rating, 7 reviews

VILLA NELLE COLLINE DELLA 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
Los dueños son una pareja encantadora que nos atendieron muy bien, la casa preciosa, muy limpia, no pasamos nada de frío y no nos faltó de nada. Las vistas que se ven desde la casa son maravillosas!! Muy muy recomendable si queréis visitar la Toscana
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
Wat hebben we een mooie week gehad in het vakantiehuis. Zeer netjes en heerlijk de ruimte om je heen, net buiten de stad maar het gevoel alsof je buitenaf zit. En het uitzicht, betoverend. Hele vriendelijke mensen die alles voor je willen doen. En dan nog meer luxe, het zwembad. Heerlijk om in af te koelen. Al met al, echt super! Echte aanrader.
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 con

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, piscina privata e AC

ChanitahRating, 5 stars7 months ago
Het huis was prachtig. Bijna alles was geweldig een paar kleine puntjes. De keuken wat klein voor een grote groep. Er miste schaaltjes voor bijvoorbeeld yoghurt… of die hebben wij niet gevonden. Er was een stopcontact in een slaapkamer wat onveilig en er miste een douchegordijn in de gedeelde badkamer. Maar verder was het geweldig alles heel schoon en groot prachtige zwembad met tuin eromheen. Erg genoten
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

Villa Elisa

DominiqueRating, 5 stars6 months ago
Superbe maison dans les vignes entourée de somptueux coteaux dans un incroyable cadre de carte postale. Parfait pour se retrouver en famille ou entre amis. L'emplacement est idéal pour rayonner entre Sienne, Florence et le Chianti ou se reposer en profitant de la piscine. Elisa, toujours à l'écoute, est très reactive et répondra quasiment sans délai.
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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