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Villa holiday rentals in San Casciano In Val di Pesa

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Popular amenities for villa rentals in San Casciano In Val di Pesa

Private villa rentals

Superhost
Villa in Cerbaia
5 out of 5 average rating, 12 reviews

Villa Feudo, incredible villa with private pool an

PatriciaRating, 5 stars1 month ago
The house is beautiful, quiet, and very well maintained. The rooms are comfortable. We spent a wonderful few days there. The service from our host, Monica, was excellent. She helped us coordinate transfers, tickets to some services, restaurant reservations, and wine and village tours. We hired a private chef, Federico (highly recommended). Every meal was incredible. He cooked delicious dishes; each day was an unforgettable experience. The only thing I wouldn't recommend is extra cleaning. If it's necessary, it's important to supervise it closely. Be very specific about what is expected. The cost of the service depends on the number of people cleaning and the hours it takes (something they don't specify). It cost us $110 (not including changing sheets and towels).
Top guest favourite
Villa in Panzano
4.93 out of 5 average rating, 75 reviews

Luxury Villa on Chianti Wine Estate

StevenRating, 5 stars1 month ago
Wonderful stay at the Villa among the vineyards in Panzano. Vicky, the host, is the owner of Le Fonti winery with the villa surrounded by their vineyards and olive groves. The view from the villa is absolutely stunning. The town of Panzano is very cute. We bought groceries at the Coop and made breakfast each morning, gathering in the cozy well equipped kitchen. There is a courtyard immediately outside the doors of the villa with a large table, and again amazing views. Our time in the villa was so relaxing! Though we went to several wineries, a highlight was a very personal tour of the winery, wine making process and wines by Vicky at Le Fonti. She spent time discussing/pouring the different wines, even bringing over the same wine from different years to show us the difference the weather/grape stress influences the final taste. Overall exactly what we wanted from a Tuscan experience and really enriched by an extremely friendly and knowledgeable host.
Guest favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 6 reviews

Casanova of Bricciano

PeterRating, 5 stars2 weeks ago
What a fabulous setting and location. Perfect to explore the Chianti region and beyond. It’s roomy, everything you need is there, beautiful pool and a view to cherish. Dining on the terrace is a wonderful experience and with a vinyard with lovely wines available right next door what more do you need from a Tuscan holiday. All hosted perfectly by Fabio and Andrea. Very highly recommended.
Guest favourite
Villa in Asciano
4.93 out of 5 average rating, 88 reviews

Casa Bianca, a gorgeous Tuscan home in Crete Senesi

JulieRating, 5 stars1 week ago
Photos do not do justice to the amazing views. Very special place.
Top guest favourite
Villa in Rignano sull'Arno
5 out of 5 average rating, 15 reviews

villa "La Fonticina"

KathyRating, 5 stars1 week ago
Incredible host and property. We feel fortunate to have had the opportunity to stay here. Cesare was beyond helpful with recommendations and flexible with our check in. Secluded, peaceful and a great place for making memories during our travels around Italy.
Superhost
Villa in Gambassi Terme
4.85 out of 5 average rating, 152 reviews

Il Leccio - Tuscany home near San Gimignano

MilaRating, 5 stars3 weeks ago
The magnificent view can be enjoyed both as a couple and with friends. It is very quiet and everything has been thought of: outside there are very comfortable seating options, a grill and pool. The garden smells of jasmine everywhere. There is nothing missing inside either. The house is perfect and is in the perfect location. After a 20-minute drive, you will reach San Gimignano. Simply a dream and always worth a trip 😍
Guest favourite
Villa in Pescia
4.82 out of 5 average rating, 67 reviews

Romantic and Luxury Cottage Nanni with Pool

JackRating, 5 stars1 month ago
This is the best Airbnb I have ever stayed at. I highly recommend staying here. The villa is beautiful and the surroundings are stunning. The villa, immaculate and well decorated, is perfect for relaxing, with lots of different areas inside and outside to sit or recline, and the pool is perfect for a dip. The owners are really friendly, very helpful and were extremely accommodating to all our needs. The local town of Pescia is pleasant and has all of the amenities you will need to make your stay comfortable, such as a very smart supermarket (Esselunga) just a 3 minute drive away. Pisa, Florence, Lucca and Siena are all within driving distance, or you can take a train from Pescia. I do recommend hiring a car, as this allowed us to take smaller trips to some places that became our favourties, such as Monte Carlo, that would have not been possible without a car. This Airbnb is ideal for couples, romantic holidays, relaxing and exploring Tuscany. Again, it's the best I've ever stayed at!
Superhost
Villa in Greve in Chianti
4.89 out of 5 average rating, 84 reviews

Put down your luggage, this is just the beggining!

CliveRating, 5 stars9 months ago
The villa is situated on the outskirts of Greve in Chianti. For us it was a perfect location - enjoy country views yet walkable to the town centre for restaurants and shops. Four double rooms, each with an ensuite/shower. Everything you need for a great time - swimming pool, terrace with built in BBQ. Kitchen is well equipped with dishwasher, large fridge freezer and large range cooker. Kitchen table was ideal as we could all fit round and it made the kitchen the social hub as we used the comfy lounge for those quieter moments. Definitely recommend. We would be happy to go back.

Luxury villa rentals

Guest favourite
Villa in Greve in Chianti
4.91 out of 5 average rating, 22 reviews

Il Castellaccio Villa

MelissaRating, 5 stars3 weeks ago
We were a group of 8 staying at Villa Il Castellaccio and it was the most amazing experience. Leonardo was very helpful leading up to our stay helping plan a night with a private chef dinner. The food was some of the best we had! The Villa was private, more than enough space for our group and the grounds around the pool was always pristine. We highly recommend staying at this wonderful place. Our group already discussed coming back again and staying longer. Thank you Leonardo!
Top guest favourite
Villa in Montecucco
4.91 out of 5 average rating, 43 reviews

Villa Angiolina

PamelaRating, 5 stars6 days ago
Laura was an amazing host and made sure we knew all the details of the house and was very responsive if we had a question. The house itself is gorgeous and so are the surroundings. Highly recommend staying here as a home base in the Tuscany area! We visited many surrounding cities as well as a winery 40 minutes south. We would also recommend the restaurant Nuevo Ranch right done the street! Wonderful!
Superhost
Villa in Bottai
4.91 out of 5 average rating, 23 reviews

Villa up the Certosa hill of FLR

JeffRating, 5 stars1 month ago
Our family vacation to Villa Berni in Bottai was phenomenal, and it all started with the accommodations. Alessandro's brother, Enrico, met us as planned and gave us a tour of the villa. As requested, they provided 2 cribs for our grandbabies. With 6 bdrms and 5 bath, each couple had their own space, and the babies had their own rooms too. It was conveniently located taking 20 minutes to the Florence city center and other local towns provided everything we needed. Our favorite part of the villa was the garden courtyard. We had morning coffees and evening cigars/drinks. A bonus was the tortoises which the babies loved finding each morning to feed them strawberries. Part of the family farm, Enrico gave us a tour of the olive grove and farm animals. He even staged eggs for the grands to collect. Our last night, we arranged pro chefs to prep an authentic Tuscany dinner. This kitchen met their needs, and we ate in the courtyard. We couldn't ask for more...Thanks for hosting us!
Top guest favourite
Villa in Barberino Tavarnelle
5 out of 5 average rating, 36 reviews

Valluccia 51

FlorisRating, 5 stars1 month ago
We had an amazing time in the villa from Tommaso. It has all the amenities that you expect from a villa in this price class. The view looking over the valley is beautiful. The communication with the host was very pleasant and swift. As an example; The existing tv got broken in the evening and the next morning Tomasso installed a new one with all the modern features like Apple Airplay. Since the weather was not great the first days you can imagine that this was very nice to have a good working tv. Anyone who is considering renting a villa in the surrounding of San Donato, I highly recommend this villa from Tommaso.
Superhost
Villa in Greve in Chianti
4.84 out of 5 average rating, 31 reviews

Romantic Villa with private pool and fabulous view

ReubenRating, 5 stars4 days ago
Most beautiful villa with so much charm! Fantastic location as well, easy to explore Florence, Siena, San Gimignano, as well as all the surrounding wineries and countryside. The villa was so lovely that we decided to spend 2 days in the villa, chilling at the pool drinking wine and having tapas! Janine is a great host with many recommendations of what to do in the local area. Highly recommended to stay here to experience Tuscany!
Superhost
Villa in San Gimignano
4.79 out of 5 average rating, 19 reviews

Exclusive Farmhouse Pool & View of San Gimignano

AlineRating, 5 stars1 month ago
This property exceeded our expectations with spectacular views and peaceful, natural surroundings! The host was friendly and responsive. The proximity to San Gimignano and other Tuscan destinations was convenient. Each day felt magical! Just sitting on the patio was amazing! An unforgettable destination and experience!
Top guest favourite
Villa in Loro Ciuffenna
4.98 out of 5 average rating, 50 reviews

The Lazy Oak

JarrettRating, 5 stars2 weeks ago
There are very few times when a stay not only lives up to expectations, but exceeds them. Our stay at the Lazy Oak did just that. There are no adjectives to truly describe the beauty of the villa and the surrounding countryside. Sitting at the infinity pool, looking out over the olive groves before a dinner prepared in house by a Tuscan chef as the sun sets will go down as one of the greatest days of our lives. We visited the nearby town twice for gelato but the truth is we did not want to leave the property! If you are looking for a peaceful quintessential Tuscan vacation in the countryside, look no further than the Lazy Oak. Mario is on property to tend to any needs but keeps to himself unless called upon. We actually loved his company and called him over to talk on multiple occasions…with the help of Google translation of course. Thank you Mario and Alesandro for an unforgettable stay. We hope to see you again in the future.
Superhost
Villa in Galluzzo
4.73 out of 5 average rating, 11 reviews

Tenuta del Podestà villa di charme in Firenze

BrianRating, 5 stars8 months ago
David’s place embodies elegance and tranquility. Beautiful interior with intricate touches. The backyard was huge and our pup enjoyed running around on it. It’s as described in the pictures. David was also a very kind host. Responsive to our questions and insightful when it came down to recommendations. Highly recommend to anyone considering booking!

Villa rentals with a pool

Guest favourite
Villa in Certaldo
4.89 out of 5 average rating, 18 reviews

Villa Gelsomino, your dream in Tuscany

LenaRating, 5 stars2 months ago
We were traveling with a group of 4 couples and three toddlers. And loved the place. Each couple had their own bathroom and everything was super clean. The entire complex was very well maintained. There was a tennis court, a football field, foosball, volleyball and a great children's playground. The facility cannot be better equipped. In addition, the location of the property is perfect for exploring Tuscany. We were completely satisfied and would come back right away.
Guest favourite
Villa in Gambassi Terme
4.96 out of 5 average rating, 54 reviews

Villa Via Francigena

BettyRating, 5 stars4 days ago
Beautiful surroundings, peaceful, beautiful pool! Extremely well-appointed kitchen. Hosts responded immediately if we had any questions.
Top guest favourite
Villa in Figline e Incisa Valdarno
5 out of 5 average rating, 18 reviews

Mathis House Best View in Chianti, Exclusive Pool

LaylaRating, 5 stars1 month ago
We were already contacted by Emanuele in advance. He sent us the directions so we can easily find the house. We were very warmly welcomed with regional specialties and wine. The stay was great, we felt very comfortable. During the stay we received a lot of tips regarding food and excursion options from Emanuele. He was very helpful and always available. I'm sure we'll be back.
Superhost
Villa in Monsanto I
4.97 out of 5 average rating, 29 reviews

La Cipresseta Estate | Cipresso House

Marie LouiseRating, 5 stars3 weeks ago
Really nice place. Sweet and super helpful hostess. We are coming back
Top guest favourite
Villa in Volterra
5 out of 5 average rating, 23 reviews

Romantic Villa with private pool - "Il Pollaio"

ErinRating, 5 stars3 weeks ago
A beautiful home to base ourselves in while exploring Tuscany. Lovely country surrounds. House has everything you need, spacious. Gorgeous terraces and pool. Enjoyed Volterra, San Gimignano and Siena but always great to come back to our Tuscan home! Silvia gave fantastic recommendations - pasta making at Ristorante de Beppino and in house chef Beppe highlights. Also loved Monterosola winery tasting. Very highly recommend. One of the best!
Top guest favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 24 reviews

Montemarcoli

TorbjørnRating, 5 stars2 weeks ago
We had an amazing stay at the villa. A modern house in a quiet environment with beautiful views. Brigitta was very helpful and responded quickly to our inquiries both before and during the stay.
Top guest favourite
Villa in Montaione
4.96 out of 5 average rating, 25 reviews

Private Villa with semi-Olympic pool and Tennis

JosephineRating, 5 stars4 weeks ago
absolutely amazing!! Francesca made us feel right at home. the place was amazing and we definitely want to come back. the property is beautiful and great if you want to play tennis , ping pong, or swim… super fun. Francesca was so sweet, gave us great recommendations, and helped us with all our questions. She even graciously helped our grandma get a doctor to see her when she sick. 10/10 amazing !
Guest favourite
Villa in Lucignano
4.88 out of 5 average rating, 24 reviews

Unique Villa in Tuscany

KeithRating, 5 stars1 week ago
A stunning property, completely private and quiet. Large outdoor heated pool was well maintained with perfect outdoor eating and sitting areas. We ate out on the terrace every night. Luc recommended the closest Osteria which we all loved, and also recommended the spot to see those iconic views of Tuscany with the avenues of cypress trees. All 6 of us had joyful experience. Highly recommended.

Destinations to explore