
Villa holiday rentals in Asciano
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Top-rated villa rentals in Asciano
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Private villa rentals

Stunning Tuscan Villa & Panoramic Infinity Pool
This was our second time visiting Mogens and Suzie's beautiful home in Cortona. One reason for coming back was the sheer beauty of the property and the proximity to fantastic medieval towns with incredible history that endures even now. For wine enthusiasts, there are tons of wine tasting opportunities with lunch, dinner or just great wine. Another reason for our return visit was an opportunity to spend time again with Mogens and Suzie, by far the best AIRBNB hosts we have ever encountered. They do everything imaginable to make your time as enjoyable as possible and to say that they go the extra mile would be a gross understatement. We can't wait to come back a third time.

Villa with pool in Chianti Area
Our stay at Mariella's beautiful home was a highlight of our five week trip throughout Italy. Peacefully situated between Florence and Siena, this villa offers a welcoming respite from the hustle and bustle of the cities. It was also super convenient to the vineyards throughout Chianti. Waking up every morning to the sunrise views over the valley and enjoying a glass of wine in the evening were the perfect beginning and ending to each day. The pool was even larger than we imagined and provided days of entertainment sprinkled in during a week of sightseeing and wine tasting. I cannot recommend this home, location, or host enough. You will NOT be disappointed!

Charming villa 15' walk to center stunning view
Wonderful villa with a beautiful outdoor area- fruit trees, roses, and flowers. We enjoyed the wine, snacks and fresh fruit the host had for us upon arrival. This was our last stop in Italy. Bedding, mattresses and AC has not been great in the places that we have stayed, and never was there a fan. This villa had a comfortable bed , great ac, and a ceiling fan in the bedroom. My husband said his best night sleep the entire trip. We were missing our dogs and cats and we loved having theirs visit us daily! The hosts were traveling so we didn’t get the chance to meet them. They regularly checked in on us to make sure everything was good and provided local recommendations. Given the reviews and accommodation, I’m sure they are amazing! If you’re ever in Florence, this place is worth the stay.

Villa Il Tollino
We had a wonderful stay at this place! Ginacarlo and Gabriella are extremely friendly hosts who have a lot of helpful recommendations and are always very responsive. Moreover, they not only brought us homemade pizza, sweet treats, fruits and wine, they also brought toys for our 1.5year old daughter! The home is clean and has everything you need for your stay. The views from the patio of the surroundings are amazing!! The entire area is also very peaceful and relaxing and close to many interesting locations (Siena, Arezzo, Montepulciano etc). We highly recommend this place and would come back again!

Sestuccina
Beautiful place to stay! • Super nice location (lots of nature and very quiet) • Communication always runs smoothly • Great restaurants and delicious ice cream within 5 minutes' drive • Equipment exactly as specified I would recommend it again and again! Luciano and Brigitta are great hosts 😊

Luxury Tuscan countryside villa with pool/WiFi/AC
I cannot say enough about our trip to Martino’s villa. What a lovely villa in the cute town of San Casciano dei Bagni. We had a great family vacation, enjoying some of the smaller towns and a visit to Montepulciano . We enjoyed Eleanor’s cooking for us two nights- what an amazing chef! Martino was very responsive and helpful when we needed something. I hope we can return one day!

Villa with garden. The Cardinal's Garden.
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.

Villa Sunkiss: Luxury Farmhouse with Tuscan Flair
The Villa is absolutely beautiful in a great location with spectacular mountain views and sunsets. The Villa is even better than the pictures, extremely clean, beautifully decorated, quiet, peaceful with all modern luxuries. Our host Silvana was awesome and was excellent and clear in all communications. The owners were very warm and friendly. If you are looking for a quiet escape in the Tuscany region, look no further. We will certainly be back in the future. I highly recommend scheduling a private chef to indulge you in great Italian food at the villa. Our chef Mariella was wonderful and the food was incredible. Awesome stay and experience all around.
Luxury villa rentals

Fabulous Farmhouse with Pool & 360 Panoramic View
Caroline's villa was absolutely stunning. We visited as a family of 8 adults and it was even more beautiful in person. It's completely private with amazing views all around. It's also in a great location to visit other picturesque villages nearby with a car. The pool was a great addition to combat the Tuscan heat. As this is in the countryside, be aware that there will be insects and wildlife. We came across a snake and a scorpion, but that's not an issue with the house, but rather the natural environment. The property manager Bianca greeted us upon arrival. She was super friendly and helpful with tips. And Caroline left us super detailed recommendations for restaurants, itineraries, and wineries. She was always available and friendly. We had an amazing time and would definitely visit again!

Villa Nobile - Private Jacuzzi
Our stay at Villa Nobile was exceptional. The villa provided the perfect balance of privacy, surrounded by olive trees and vineyards, while offering the comforts and services of a resort. From the seamless transfer arrangements coordinated by Mario to the attentive staff who ensured every detail was taken care of, the hospitality was outstanding. The wine tasting upon arrival was a wonderful introduction to the region, and the fresh, thoughtfully prepared breakfasts each morning were a delight. Having dinners prepared for us and placed in the refrigerator after days spent exploring the town and local wineries was an added convenience we truly appreciated. The breathtaking sunrises and sunsets made our time here even more memorable. We are grateful for such a wonderful experience and look forward to returning.

Capanna Di Elfo
The property was comfortable, spacious and spotlessly clean. The owners of the property , Claudio and Angelica, are helpful and delightful. However, the “host” BoMVillas , who acts as a middleman, was rude and disrespectful when we had a miscommunication. I would not make another booking that was offered by BoMVillas.

villa "La Fonticina"
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.

The Lazy Oak
The Lazy Oak Villa is everything we dreamed of and more for our honeymoon. The house is beautiful, well furnished and feels so homely and comfortable. The surroundings are simply stunning; the view from the house and pool never get old! Mario and Alessandro were super helpful, offering to help us book restaurants and vineyards if needed. Mario keeps to himself so still feels very private but is happy to help with anything and it was nice to see him around (with his cute little dog!) and know he was about if we needed anything. Couldn’t recommend the Lazy Oak Villa more, and we’re already talking about when we could come back!! Thank you Mario and Alessandro!
Le Maggioline Your Tuscany country house
Olga's villa is absolutely stunning. Our family of 9 had the most wonderful visit. We enjoyed cooking in the beautiful and well appointed kitchen, eating outside on the terrace, swimming in the pool, and relaxing outside on the terrace, enjoying the peaceful beauty and breathtaking views of Tuscany. Olga's place is truly special. Olga was very communicative, helpful and kind. We highly recommend her villa to others.

Tuscany Villa With Pool & Magnificent Garden
Barbara’s place was above and beyond our expectations in every way! If you are looking for a place to stay in this general area, don’t hesitate! Barbara was a wonderful host and all the instructions were very clear. The kitchen is very well stocked and we cooked all of our dinners there as we were traveling with a baby. We spent a lot of time hanging out as a family and there was more than enough room for us and both sets of grandparents. The home is very well situated and we loved exploring. There are so many great restaurants in the area. I can’t over state the beauty of the area and the house itself…my family is already dreaming about coming back!

Villa Isabella
Christina’s home was beautiful. She was an amazing host, getting us last minute reservations at restaurants and doing a cooking class with us on our last night that was fun and delicious!
Villa rentals with a pool

Villa La Gemma
I was genuinely impressed by this place. So beautiful! The pool is incredible, they had prosecco and limoncello for us and provided several supplies for a successful stay. I would 100000% come back here!

Villa Le Tortore private luxury pool relaxation Siena
We spent six nights in June at this gorgeous house. Thiago was so welcoming and the house was pristine and comfortable with great air conditioning. We loved relaxing and cooling off in the pool which was clean and well maintained. Siena is beautiful and about 15 minutes walk from the house. We loved our stay, it was perfect for our family holiday. Thank you Thiago!

Tuscany Villa Mammi
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.

Vakantievilla Farmhouse Dolci Hills
This was the finest AirBNB home that we've ever stayed in. Every room was immaculate, the views were incredible (private and among vineyards, you can see for miles), every appliance and fixture seemed new. Everything was anticipated to make the stay perfect.....a refrigerator, bathroom and shower at the beautiful pool, pool towels in each bedroom, etc. As soon as you walk into this house, you are going to go "wow", and for good reason. Francesca came and cooked us a delicious local dinner and did some light grocery shopping for us.....all for an unreasonably LOW fee. We had another chef team come in on another night. We also visited a local winery where we had a fantastic, private wine tasting tour and lunch (Tenuta Vitalonga) and followed that up with touring Orvieto and having dinner at a very unique restaurant (Le Grotte del Funaro). Make sure you have a car or are using a bus/limo service for your transportation, nothing is walkable from this beautiful private house.

Pasqui Villas : Tribbio private house pool WiFi
We stayed at this Villa for just under a week with 2 families and had the most amazing time. It was absolutely perfect. SO much space (2 kitchens, 3 living rooms, 7 bathrooms!!!!) The pool and grounds around the home are stunning and they take such great care of it. You can tell this is a family home that Federica and her family take great pride in. Federica and her son welcomed us at the villa and they were super responsive before and during our stay. They also recommended a lot of things like a driver for a wine tour, chef that came and cooked for us a couple nights (so delicious), etc. Am very sad to not be at this dreamy villa anymore and hope to go back at some point in the future. Highly recommend!!

La Bacaia
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.

Romantic Villa with private pool - "Il Pollaio"
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!

Villa Fortuna with Hot-Tub and pool near Tuscany
A Perfect Holiday – Like Heaven on Earth! This place exceeded all our expectations. A stunning and peaceful location with breathtaking views over the valley, lake, and mountains. The house and garden were beautifully maintained, and the accommodation was very clean and comfortable. A special thank you to Mrs. Lesley, who was an invaluable help throughout our stay. She provided us with plenty of useful tips and advice on various matters, such as train tickets and local attractions. Thanks to her, we were also able to arrange a wonderful dinner at the villa – truly an unforgettable experience. We wholeheartedly recommend this place – if we could give it 150%, we absolutely would!
Quick stats about villa rentals in Asciano
Total rentals
80 properties
Nightly prices starting at
$151 NZD before taxes and fees
Total number of reviews
610 reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
70 properties have a pool
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- Lake Bolsena
- Basilica of Santa Maria Novella
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Kite Beach Fiumara
- Marina di Grosseto beach
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Teatro Verdi
- Palazzo Vecchio
- The Boboli Gardens
- Cala Di Forno