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Vacation home accommodations in Province of Siena

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Popular amenities for Province of Siena vacation houses

Family-friendly vacation houses

Top guest favourite
Vacation home in San Donato In Poggio
4.98 out of 5 average rating, 134 reviews

Chianti Penthouse with panoramic View & Pool

Jens & KatjaRating, 5 stars2 weeks ago
Our stay in Tuscany was absolutely unforgettable! The peaceful surroundings and stunning views made it the perfect getaway. The small village nearby was charming, with some fantastic restaurants and a supermarket just a short walk away. The scenery all around was simply breathtaking. Giada was super friendly and incredibly responsive — they even helped us rent bikes, which made exploring the area even more special. Everything was clean, well-equipped, and comfortable. We had a wonderful time and would love to come back!
Superhost
Vacation home in Siena
4.84 out of 5 average rating, 75 reviews

"Lisa" apartment with fireplace

MarcusRating, 5 stars8 months ago
We had a great week at Lisa's place. Extremely clean, very well maintained facility, great pool and all staff always very helpful. Highly recommend especially because of the proximity to Siena. Fantastic city!
Superhost
Vacation home in Asciano
4.88 out of 5 average rating, 98 reviews

Charming home Crete Senesi

NadezhdaRating, 5 stars4 days ago
The house and the location are amazing! Emiliano is super nice host. I strongly recommend it.
Guest favourite
Vacation home in Panzano
4.94 out of 5 average rating, 54 reviews

Antico Chianti Residence

LinaRating, 5 stars3 months ago
Nice and clean apartment. Good beds. In the middle of Panzano
Superhost
Vacation home in Villa Parigini
4.88 out of 5 average rating, 8 reviews

Near Siena (6 km), swimming pool and terrace

Paul LudvigRating, 5 stars8 months ago
Great location close to Siena and good size for a large family
Superhost
Vacation home in Rapale
5 out of 5 average rating, 8 reviews

Borgo Rapale – Jacopo

LaurenRating, 5 stars11 months ago
Nice relaxing place off the beaten path, beautiful views. Well cared for. You can walk around their vineyards and Olive Grove, and even buy local wine from the host.
Top guest favourite
Vacation home in San Gimignano
4.91 out of 5 average rating, 226 reviews

Appartamento Margherita Tuscan home

CharlotteRating, 5 stars1 week ago
We had a great time at Stefania's family apartment, both quiet and conveniently located. The view is beautiful, especially at sunrise. The apartment is well appointed and the terrace very nice. We enjoyed alternating the days of visiting and resting in this typical San Gimignano setting. Stefania is a perfect host: helpful, available and discreet. His attachment to this family apartment deeply touched me and reminded me of the holiday memories in my own family home that we no longer have today. A place full of soul that we would recommend without hesitation!
Superhost
Vacation home in Siena
4.86 out of 5 average rating, 14 reviews

Borgo dei Fondi, Apt. Loggia

KimRating, 5 stars10 months ago
David and Vittoria take great care to ensure a positive experience at their beautiful Tuscany home. David welcomed us after our harrowing day in Pisa and we felt at ease and welcomed immediately. Borgo dei fondi is the quintessential Tuscany home, peaceful, beautiful, surrounded by nature, with relaxing and fun amenities like the pool, bbq and outdoor patio. It was the perfect place to come home to and relax after day trips to Florence and Siena and equally wonderful to just stay put for a day and enjoy the tranquility. We highly, highly recommend staying here.

Vacation home rentals with a patio

Superhost
Vacation home in Torrita di Siena
4.81 out of 5 average rating, 16 reviews

Pian'D'olmo, an ancient farmhouse in the heart of Tuscany

AnnieRating, 5 stars7 months ago
We had a vision and dream of staying in a Tuscan villa in the country and it exceeded all our expectations.
Guest favourite
Vacation home in Monticiano
5 out of 5 average rating, 36 reviews

Casa Dani with private pool

LeasaRating, 5 stars7 months ago
Beautiful accomodation and very clean. Loved that we could walk into town for essentials and to eat and drink. Pool and outside area is stunning . Dani helped when we needed coal and was on hand for help. The accomodation has absolutely everything you need in the kitchen as well as hair dryer, towels for bathing and pool, extra pillows and blankets . We would absolutely recommend.
Superhost
Vacation home in Lilliano
4.83 out of 5 average rating, 6 reviews

Cosy house with private pool

LucasRating, 5 stars8 months ago
Very nice house. Very nice welcome from our host's in-laws. They were always available and thoughtful although they only speak Italian. The location of the accommodation is ideal between Siena and Florence. Lots of pretty villages nearby.
Top guest favourite
Vacation home in Petrignano del Lago
4.97 out of 5 average rating, 63 reviews

Fontarcella, H&R- mediterranean home with jacuzzi

עפריRating, 5 stars1 week ago
The stay was excellent, thinking about the little details, great kitchen and activities equipment The host was in touch with us all the time and responded quickly to any questions and gave recommendations on what to do in the area Everything was clean and tidy and very beautiful, great value for the price!
Top guest favourite
Vacation home in Poggibonsi
4.97 out of 5 average rating, 39 reviews

Ellerone 20, an old barn in Chianti

yamiRating, 5 stars6 months ago
In one word amazing ! in two words highly recommend ! we where 5 adults and the place was warm and welcome . full kitchen , absolutely amazing view and private . Thanks sara for all your help !
Top guest favourite
Vacation home in Monticchiello
5 out of 5 average rating, 17 reviews

Elegant farmhouse overlooking Pienza

KrisRating, 5 stars1 week ago
Gorgeous home in Monticchiello with breathtaking views. Pictures do not do it justice! Truly one of the most beautiful properties and homes we’ve ever stayed in. There was plenty of space for our group of 5 to spread out and relax. Enjoyed amazing nights together cooking in the beautiful farmhouse kitchen. There was everything we needed to feel right at home. Laura was an excellent host and greeted us with a warm welcome. She checked in throughout our stay to make sure we were comfortable and answered all our questions in a timely manner. You must follow her exact instructions for getting to the house as GPS can take you down some bad roads if you are not paying attention. Still dreaming of this home and cannot wait to return!

Vacation home rentals with a washer and dryer

Guest favourite
Vacation home in Chianciano Terme
5 out of 5 average rating, 88 reviews

The Eagle and the Olive Tree

Michael RobertRating, 5 starstoday
Amazing place to spend time. Great hosts and fantastic location
Superhost
Vacation home in Laterina
4.7 out of 5 average rating, 10 reviews

Apartment with pool and restaurant

RicardoRating, 5 stars8 months ago
Location was very nice, easily reachable by car and train is close. House had AC and the pool was great even though the space is shared. Also they always restocked us with toilet paper and other amenities when we asked for, only need to bring some minor stuff for cooking like oil and salt/pepper. No oven but assides from that we cooked alot of big meals for everyone and the experience was fantastic Cool place to stay!
Top guest favourite
Vacation home in Monteroni d'Arbia
4.9 out of 5 average rating, 68 reviews

White lily with a view of Siena

CarolineRating, 5 stars1 week ago
This was the second time we stayed in one of Marta‘s apartments! I think that says it all already. We are just in love with the location and the apartments always make you feel at home right away! Thank you again Marta for hosting us (and the delicious vino 🍷😄). We will be back 100%!
Superhost
Vacation home in Ulignano
4.73 out of 5 average rating, 11 reviews

★ Romantic apartment & stunning view of Tuscany ★

AndrewRating, 5 stars10 months ago
A great peaceful location with excellent pool area and gardens, but also well placed to visit Florence, Siena and San Gimignano. A car is necessary and it is easy to get around the Tuscan hills from here. Giorgia greeted us on arrival and responded very quickly to our questions during the week. Bug spray is essential. All in all we had a wonderful holiday.
Guest favourite
Vacation home in Vitignano
5 out of 5 average rating, 27 reviews

Podere Vittoria Apartment: Heart of Chianti

WinnieRating, 5 stars1 week ago
we had such a wonderful time at Tuscany and a lot of it was because of this airbnb. this place has such a serene garden and backyard space and it's awesome to be so close to nature. Edoardo was extremely helpful and welcoming making this place homey. most of the times I asked a question and got an answer from him in seconds. I'd love to take my family back and stay here again.
Guest favourite
Vacation home in Siena
4.9 out of 5 average rating, 40 reviews

Apartment in historic Villa in Siena_"IL MANGIA"

YuRating, 5 stars1 month ago
This was such a wonderful experience, enjoyed the beautiful courtyard for 4 days, clean rooms, quaint and textured furnishings and set up, it does have a warm home feel.Many times I want to be lazy in the room, enjoy the sunshine of the courtyard, and enjoy all the amenities provided in the room.I highly recommend this homestay, take a bus at the door for a few minutes to the ancient city of Siena, we go up each time to the ancient city on foot, you can enjoy the pastoral scenery of Tuscany all the way, thank you Cristina and her brother for their warm and thoughtful service, and the opportunity to come back here later.
Guest favourite
Vacation home in Campagnatico
4.85 out of 5 average rating, 13 reviews

Cozy Cottage with a beautiful view - Casa Luciano

ThomasRating, 5 stars4 weeks ago
We had a very nice time at Casa Luciano! Unfortunately, we could not use the great pool in March (although ice bathing is becoming more and more popular;-)). The area is very nice and quiet. We were able to hike, explore Campagnatico and other places. Once we were able to enjoy the good food at Vecchia Oliviera. (Attention: Pizza is only available from about May) We also supported the village shop properly. It has a decent selection for the size. Thank you Mel for the always timely assistance with questions and problems! We will recommend the accommodation and may also be able to vacation here during the pool time.
Superhost
Vacation home in Colle di Val d'Elsa
4.72 out of 5 average rating, 29 reviews

Tower House of the 1000

GabrieleRating, 5 stars5 days ago
A helpful and friendly host, the house is located in Colle Alta and is not equipped with an elevator and even reaching Colle Alta is not very easy because it is very uphill. But there's a breathtaking view and the location is right in the center. The apartment is equipped with two bathrooms and both a dishwasher and a dryer. We had a great time.

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