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Villa holiday rentals in Castiglione del Lago

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Popular amenities for Castiglione del Lago villa rentals

Private villa rentals

Guest favourite
Villa in Castiglion Fiorentino
4.98 out of 5 average rating, 66 reviews

Tuscany Villa Mammi

SebastianRating, 5 stars1 week ago
Absolutely brilliant place. Very charming, spacious and calm. Beautiful view, pool, and outdoor area. Simone is very kind and highly responsive. We stayed here 6 adults and had a wonderful time. Highly recommended for both friends and families.
Top Guest favourite
Villa in La Cima
4.94 out of 5 average rating, 32 reviews

- 20% Last Minute 21June-2July Lake View Villa

MariaRating, 5 stars4 days ago
Stunning location high up over the lake, beautiful views from the balcony, and the most peaceful and private place I have stayed. The villa has a rustic feel and is well equipped with everything you could need, but the outstanding features are the fabulous pool and picturesque garden, full of butterflies and bees! We would love to come back!
Superhost
Villa in San Casciano dei Bagni
5 out of 5 average rating, 4 reviews

Podere la Piscina Termale - RestArt

GloriaRating, 5 stars1 month ago
Perfect stay from start to finish. The villa was immaculate and the staff who checked us in were fast, considerate and friendly. They informed us of extra services that we ended up using in the end like we organised a dinner with their private chef on our last night and it was amazing. The thermal pool and sauna were TOP! Highly recommend and will book again!
Guest favourite
Villa in Passignano sul Trasimeno
4.88 out of 5 average rating, 32 reviews

Villa with panoramic pool • Lake Trasimeno

MelanieRating, 5 stars1 week ago
An amazing hideaway in the hills! Takes you into holiday mode & switching off in the beautiful setting surrounded by nature & incredible views. So glad we booked & would love to go back again. Paulo, and family, were so helpful, kind & responsive. The area whilst quiet is very welcoming to tourists & we met many friendly people who would always help us out on our way. The house itself is stunning & huge. The bathrooms are dated but they work fine & everything functions as it should so it really isn’t a problem so don’t be put off by that. The linens are incredible & the beds very comfortable. Air conditioning works well. Kitchen well equipped & house has an abundance of space and beautiful furniture to relax in, inside and out. Honestly the scenery outside was incredible & we spent every minute we could outside which is a shame only because the house was also beautiful. The pool was fabulous & it was hot enough that heating wasn’t needed.Didn’t use sauna or spa,needed longer! Miss it!
Top Guest favourite
Villa in Monticchiello
4.97 out of 5 average rating, 73 reviews

Villa with garden. The Cardinal's Garden.

ShaneRating, 5 stars3 weeks ago
Great place to stay. Excellent communication, went above and being to ensure our stay was exceptional. Deborah even bought a pasta machine for us to use for our evening meal - which was really appreciated. It was a great week.
Guest favourite
Villa in Buonconvento
5 out of 5 average rating, 12 reviews

Beautiful tuscan country house

AlexRating, 5 stars4 days ago
An incredible, beautiful house where you’ll feel right at home. The villa is spacious and welcoming, perfect for cooking and relaxing with friends. My only suggestions would be the need for fans in the bedrooms as without AC it gets quite warm during those hot evenings.
Top Guest favourite
Villa in San Venanzo
4.91 out of 5 average rating, 125 reviews

Casa Boschetto, villa with private pool

StephanieRating, 5 stars1 week ago
Was a beautiful respite for our family while travelling between Rome and Florence. It comfortably fit eight of us including the grandparents and younger children. We enjoyed a day trip to Assisi and spent time by the pool. Quiet but about an eight minute drive to a nearby town. Just a tip, use Apple maps instead of Google Maps. Google wanted to send us down an overgrown path.
Guest favourite
Villa in Magione
5 out of 5 average rating, 5 reviews

Villa Polvese Luxury Lake side Villa

YvetteRating, 5 stars9 months ago
The villa is the most beautiful place we stayed at during our 20 day trip through Europe. It’s a bit on a splurge in price but very much worth it. The views from the villa of the pool and the lake are breathtaking. The house is very beautiful, everything was functioning properly and the kitchen is great to cook in. We stayed in and cooked dinner one night and it was great. We also took advantage of the Complimentary olive oil tasting that is included with the stay and that was also of fun. Our guide said was so knowledgeable! I can’t say enough good things about this place. It was a much needed break during our busy vacation.

Luxury villa rentals

Top Guest favourite
Villa in Marsciano
5 out of 5 average rating, 14 reviews

Luxury Villa in Umbria with Private Pool

SandraRating, 5 stars8 months ago
We very much enjoyed our stay here!! So beautiful, very peaceful! Super clean, fantastic host that gave us great recommendations!! Really made our Umbria stay very special!
Superhost
Villa in Pergo
4.5 out of 5 average rating, 20 reviews

Villa La Pieve

AndrewRating, 5 stars2 months ago
Denyse’s place is lovely, very peaceful and as described in the listing. We visited in mid April during a rainy week so didn’t get to try the pool but it looks lovely. The house itself is a converted chapel and the recent renovations are very nice. The area is quiet but a short drive to Cortona and an hour from the Brunello wine region. All in all a very nice stay thank you Denyse!
Guest favourite
Villa in Collazzone
4.94 out of 5 average rating, 51 reviews

VILLA ROSETO-TODI

JeremyRating, 5 stars3 days ago
Amazing property! Better than the photos. 5 bedrooms each with their own bathroom. Beautiful property amongst the olive trees. Enjoyed relaxing days by the pool, Floriana’s own Prosecco and the private pasta cooking class! Amazing stay!
Superhost
Villa in Chiusi
4.89 out of 5 average rating, 9 reviews

Villa Febea - Villa Febea 16

HelenaRating, 5 stars1 month ago
Villa Febea is the most magical place, perfect for a large family gathering and celebration. It is gorgeous, comfortable, practical and in a great location. We were given first-class treatment and felt at home and well taken care of. We were given guidance and advice on the planning of our stay over the course of many months, so when we arrived at the villa, everything fell into place perfectly. The owners offer a large selection of services and excursions and can help with just about anything. We had fantastic dinners organized for us at the villa, and we highly recommend the pasta making class followed by dinner, which was one of many highlights. We loved the place, the staff and our whole experience. A holiday and celebration to remember forever!
Superhost
Villa in Castiglione d'Orcia
5 out of 5 average rating, 11 reviews

#1 Luxe Farmhouse, Hilltop Views, Saltwater Pool

MiaRating, 5 stars1 month ago
We were looking for a villa that had plenty of space for my husband and I with our 3 adult kids and this villa was perfect! We all had our own bedrooms and private bathrooms. The villa was in the idyllic peaceful Tuscan countryside surrounded by rolling hills, wine vineyards and olive trees with distant views of castles. It is absolutely gorgeous! Alessandro, the owner of the villa met us upon check in. The property has been in his family for hundreds if years. He was incredibly kind and generous, leaving an abundant amount of fruit, several bottles of wine from his vineyard and beautiful fresh flowers in every room. He was always available to answer any questions and make recommendations. Anke, the property manager, was excellent and responsive. Promptly answering my questions prior to the trip and proactively giving us wonderful recommendations. Highlights were truffle hunting Il Podere Castle, Umbria Olive oil tour and Banfi Castle wine tasting. Memories to last a lifetime! ❤️
Guest favourite
Villa in Pergine Valdarno
4.95 out of 5 average rating, 87 reviews

La Vignaccia (Farmhouse) - villa w/private pool

DominicRating, 5 stars1 month ago
La Vignaccia is wonderful. We were a family of 6 adults plus a baby, and the set up was great for spending time together but also having plenty of space. The kitchen is well equipped for cooking for a large group and the many private spaces were very relaxing. Working remotely was possible with the wifi but not super strong for calls. However there is 5G around the house, so hot spotting from a window worked fine.
Top Guest favourite
Villa in Monte San Savino
4.99 out of 5 average rating, 77 reviews

CHARMING TUSCANY VILLA PRIVATE POOL

AmitRating, 5 stars1 day ago
Sometimes you’re lucky to find a great place, and other times a great host—but with this villa, we hit the jackpot and got both. From the moment we booked, Francesco was in touch and incredibly attentive. He went above and beyond to help us celebrate a birthday in our group, organizing flowers, balloons, and a cake for the occasion. He welcomed us in person with a fresh pizza, a fantastic bottle of wine, and garden picked plums. Every morning, he delivered the best pastries we had in Italy and offered excellent recommendations for restaurants and wineries. Villa Tonacato, a charming residence, itself is a private, beautifully maintained property with modern updates, including a well-equipped kitchen, stylish bathrooms, and thoughtful amenities. It’s about a 10–12 minute drive from the charming town of Monte San Savino, which has a lively restaurant scene worth exploring. We had a fantastic stay and are already looking forward to coming back.
Superhost
Villa in San Leo Bastia
4.92 out of 5 average rating, 13 reviews

Villa Elisa | Private Pool, Air/Co & Amazing View

Carlos Rating, 5 stars8 months ago
Villa Elisa is the best place I have stayed so far. Its construction style is old and special, the care of the Villa is down to the details, whether it is the exterior or interior, everything works is impressive even though some parts of the house are original from that time such as the doors, the windows, the floor tiles,The view is magnificent, magical whether with the radiant sun, under a torrential rain, under the clouds, under the mist or under the stars with the moon as a companion.Absolutely everything in detail and scrupulously organized, all thanks to its hosts Luciano and Christina. Now I will make an important section, if the Villa is majestic, they are also splendid and kind; I had the pleasure and pride of meeting them personally, people like few I have ever met and who are now scarce. Natural, simple and kind, always at hand unconditionally for whatever was needed.I recommend this place to everyone who wants to enjoy a great place and excellent company and 100 percent.

Villa rentals with a pool

Top Guest favourite
Villa in Località Poggio Olivo
4.98 out of 5 average rating, 63 reviews

Beautiful villa with swimming pool in Tuscany

HannahRating, 5 stars2 days ago
Our stay was incredible. The pictures don’t do justice for the view and the house. We look forward to staying here again!
Superhost
Villa in Castiglion Fiorentino
4.8 out of 5 average rating, 5 reviews

Ortaglia di Sotto Farm

FrankRating, 5 stars2 weeks ago
We spent an unforgettable week in the beautiful setting of this villa. Two families, a baby, a dog - all happy. The kitchen is super-equipped and we had Tuscan barbecues with Florentine steaks and sausages by the pool - wonderful. On the occasion of our silver wedding anniversary, private chef Elena prepared a fantastic Tuscan lunch for us under the pool pergola - unforgettable! Leonardo was also extremely welcoming and helpful from the first contact. It is thanks to him that we made a really good impression with our American family. Thank you so much for everything - Castiglion Fiorentino forever!!!
Guest favourite
Villa in Umbertide
4.93 out of 5 average rating, 15 reviews

Villa Comunaglia - Design Villa with Private Pool

RobinRating, 5 stars2 weeks ago
Andrea's property tucked into the beautiful hills on the Umbria countryside was truly incredible. The property had every amenity and many areas to soak up the sun and the views. It was probably the best BBQ view I've ever seen. The property was a bit further than we thought it was initially and you definitely need a car to get up the steep roads, but the quality of the host and the home made our stay unforgettable. Thank you Andrea & Giovanni
Top Guest favourite
Villa in Colombella
5 out of 5 average rating, 95 reviews

Torre Villa Belvedere Luxury & Relax with pool

MaximilianRating, 5 stars3 weeks ago
We had a fantastic stay! The house was beautifully equipped with everything we needed — from the kitchen to the bedrooms, every detail was thoughtfully arranged. The garden was absolutely lovely, perfect for relaxing in the sun or enjoying a meal outdoors. The pool was a real highlight — clean, spacious, and a great way to cool off during the day. What truly made the stay special was the warm hospitality of our hosts. They were welcoming, helpful, and made us feel completely at home from the very first moment. Highly recommended — we would love to come back!
Superhost
Villa in Seggiano
5 out of 5 average rating, 8 reviews

Case Bianchi

JulianeRating, 5 stars3 weeks ago
We had a great time! Super clean and spacious house with a nice outdoor area. Constanze was always super helpful and responded quickly. But be aware, you need a car and restaurants and supermarkets are not in walking distance. Thanks a lot for having us.
Top Guest favourite
Villa in Montone
4.95 out of 5 average rating, 19 reviews

Villa San Lorenzo | Private Pool, AC & Jacuzzi

Ólafía Svandís GrétarsdóttirRating, 5 stars2 weeks ago
Beautiful house in beutiful country side with spectacular view. My family couldn't get enough of it and we started all mornings sitting on the veranda with our morning coffee looking at this beutiful view. We loved the pool and our grandchildren too. We will be back.
Top Guest favourite
Villa in Marciano della Chiana
4.95 out of 5 average rating, 78 reviews

La Bacaia

JorgeRating, 5 stars2 weeks ago
We thoroughly enjoyed our stay. The house is conveniently located in the heart of the Valdichiana with easy and clear access to the surrounding towns. The grounds were beautifully landscaped with a combination of olive trees, grapevines, flowers and even herbs like rosemary, basil and mint that we used in our cooking. The rooms were spacious and very private. Our group of 6 were more than comfortably accommodated, each with its own bathroom and AC units that worked well. The two kitchens served us well. We mainly utilized the outside kitchen as the weather throughout our stay was perfect. The kitchens were well stocked with all of the necessary cooking items. There were some items that we needed to purchase at the local supermarket, including shower gel, paper towels, napkins, etc. For a one week stay we would recommend extra towels, especially for the pool. Overall, I would highly recommend La Bacaia as a base to fully enjoy your Tuscan vacation.
Guest favourite
Villa in Cortona
5 out of 5 average rating, 11 reviews

Country house in Cortona with swimming pool

ArminderRating, 5 stars3 weeks ago
We stayed at Claudia’s for my 40th and we had the best time. The home is absolutely beautiful and has a sweet charm. The most quaint outdoor space and garden with pool. The home had a fully equipped kitchen and bathrooms in each bedroom. She was so very kind and always responsive anytime I messaged her before the trip and during. She made us a delicious dinner and desert. My group also requested for her to make a cake for my birthday and we enjoyed the best tiramisu. We loved our stay here and would come again!

Destinations to explore