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Villa holiday rentals in Pitigliano

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Popular amenities for Pitigliano villa rentals

Private villa rentals

Top Guest favourite
Villa in Paciano
5 out of 5 average rating, 6 reviews

Fontanaro/Sangiovese – Pool & Steps to Village

ChristianRating, 5 stars10 months ago
Country slow living at its best combined with outstanding hospitality. Our vacation started right after we entered the apartment which was exactly as described and cleaned to perfection. We immediately got recommendations on possible activities in the region and were actively supported during support with any request we had. We highly recommend this place to anyone looking for some relaxation in a peaceful environment.
Top Guest favourite
Villa in Cinigiano
5 out of 5 average rating, 45 reviews

Scacciapensieri. Cottage in Tuscan Country

KoenRating, 5 stars1 month ago
Great holiday home with beautiful views over the Tuscan hills. No less than 3 spacious bedrooms with great beds. A nice covered terrace with the same beautiful view where you can have delicious breakfast or dinner. The private swimming pool is of course also fantastic, our children enjoyed this. Gabriele is a very friendly proactive host who sent all nice tips and useful info in advance and awakened our self upon arrival. Despite the slightly inclement weather during the week we were there, there is plenty to do and visit in the area, when the weather is nice you can also go to the coast. I would highly recommend this stay and hope to come back someday!
Top Guest favourite
Villa in Chiusi
4.99 out of 5 average rating, 84 reviews

Spacious Panoramic Villa: Perfect to Visit Tuscany

ChristianRating, 5 stars2 weeks ago
I honestly can't say enough positive things about this beautiful villa/property and the host (Andrea). It exceeded all expectations. The pictures are beautiful, but it truly doesn't do justice to the real thing. The villa is huge with 4 very spacious bedrooms / 3 full baths that provides tons of space. The living room is huge with an incredible view and so much other room (dining, sitting area, etc). The outside patio is unbelievable with a view to die for. Has a private garage for a car if you drive and washing machine. Kitchen is good size with full-size appliances if you choose to cook. Air conditioning in all rooms! Andrea was an exceptional host and extremely accommodating. He met us when we arrived and gave us a personal tour and also left us with a delicious bottle of wine! If you take a train to Chiusi (we did), you will have to get a taxi from the station to the villa (~10 minute drive). Chiusi historic center is a very easy 5-minute uphill walk from the villa. 5 *
Guest favourite
Villa in Vitorchiano
4.97 out of 5 average rating, 29 reviews

Poggio Pasquale Eco Lodge Boutique

AntoniaRating, 5 stars1 month ago
This place is magical! It’s even better than the pictures, it’s a little oasys of green and beauty. The house is like a cozy cottage surrounded by majestic oaks, lush green and with a gorgeous sunset! There’s lots to do in the surroundings, Vitorchiano, Villa Lante, the Moutan botanical garden and more. Federica is extremely kind and responsive, she always helped and was very flexible. We loved the place and hope to come back soon!
Guest favourite
Villa in Attigliano
5 out of 5 average rating, 19 reviews

Villa dei Tigli

DavidRating, 5 stars1 month ago
We had an amazing time with our dog (galgo/spanish greyhound). You couldn't wish for a better place to be on holidays with a dog. Huge area with a high-fence. A dream. Letizia was always helpful and responsive. We're definitely looking to come back.
Top Guest favourite
Villa in San Quirico d'Orcia
4.98 out of 5 average rating, 47 reviews

Tuscan villa in the heart of the Val d'Orcia

UlrikeRating, 5 stars6 days ago
I would love to give 6 stars! Tommaso's accommodation is at least as beautiful as in the photos. The house has a wonderful atmosphere and a very pleasant living environment. It is extremely tasteful and cozy and we immediately felt very comfortable there. Everything you need is available and upon our arrival everything was sparkling clean. We were particularly pleased with the view from the terrace and from the covered dining area: you are surrounded by an (organic) olive grove and can see over the surrounding valley to the green, rolling hills of Tuscany up to Monte Amiata. In the area, there are some very interesting typical Tuscan towns such as Pienza and Montalcino - we have also "hiked" these; on the other hand, it is not far to larger cities such as Siena and Montepulciano. A trip to the sea is also easily feasible. Tommaso and Laura were always available, helpful and accommodating. We're thrilled!
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 Civitella d'Agliano
5 out of 5 average rating, 28 reviews

Casa Braeside: A private villa in the countryside

TerryRating, 5 stars1 month ago
VERY rural location,which we loved,but if you are not used to country living and driving on country roads,the location could be intimidating.We were there in April,too early to be able to use the pool,but we did use the charcoal grill and ate outside several times. The surroundings are spectacular and you can hike up to the charming town of Civitella D'Agliano. There are grocery stores available as well as several pizzerias.We used it as a base for day trips to Umbria and Tuscany. We had a lovely 12 days here!

Luxury villa rentals

Superhost
Villa in San Venanzo
4.95 out of 5 average rating, 55 reviews

Casale La Sperella - Entire Stonehouse

MertRating, 5 stars2 weeks ago
Manfredi was the best host possible! We truly enjoyed every second with our family. At first the location was difficult to find, but thanks to his excellent and rapid responses we could find the house easily! The house is even more beautiful in person, the photos don’t do justice to the sheer beauty of the property and the surroundings. A must visit when in the region! Thank you Manfredi for this excellent stay!
Superhost
Villa in Porto Ercole
5 out of 5 average rating, 11 reviews

Villa Isolotto, by the sea at Argentario

GiuseppeRating, 5 stars9 months ago
Isabella’s place is beautiful and peaceful. The villa is exactly as in the picture and offer lots of common spaces were to relax and play, it is super clean and very well decorated, feels like home. The garden and the view are to die for. Waking up in the morning and see the sunrise over the sea was pure magic. The direct access to the sea was definitely a plus and we really enjoyed it . We recommend this place with no hesitation and we really hope to come back again. This place is a true gem, you won’t be disappointed and Isabella is a great host. Thank you for having us!
Superhost
Villa in Bagni, Orvieto
5 out of 5 average rating, 10 reviews

Hilltop Villa in the dreamy Orvieto countryside

SerenaRating, 5 stars35 months ago
My family and I we had a wonderful holiday in this beautiful villa, surrounded by the magical atmosphere of the Umbria countryside. There is nothing we can complain about,everything was perfect,the swimming pool added a plus especially during the 2022 July’s heat wave! The pool was well maintained and daily cleaning service was provided by the owner’s handy man. We really hope to come back next year and make more unforgettable memories at the Hilltop Villa-Orvieto
Top Guest favourite
Villa in San Giovanni d'Asso
5 out of 5 average rating, 25 reviews

Pasqui Villas : Tribbio private house pool WiFi

EmilyRating, 5 stars2 weeks ago
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!!
Superhost
Villa in Talamone
4.88 out of 5 average rating, 75 reviews

Villa Il Molinaccio with terrace and private beach

SamanthaRating, 5 stars2 weeks ago
Stunning property, with incredible views and the cutest town just a short walk away. We loved it so much we even extended for another night! Highly recommend.
Guest favourite
Villa in Orvieto
4.91 out of 5 average rating, 33 reviews

Spectacular villa with a view and infinity pool

HollyRating, 5 stars2 weeks ago
The villa was peaceful and spacious. We felt very comfortable there for our month’s stay. It had wonderful views of Orvieto and the surrounding hills. Pia, Alessandro and Theresa were also great and very helpful.
Superhost
Villa in Orvieto
5 out of 5 average rating, 3 reviews

Hadrian's Villa Collombroso

Ben & KimRating, 5 stars13 months ago
I cannot recommend Villa Collombroso enough. We had such a wonderful 3+ week stay here with our two kids and family friends. Everyone was comfortable and at ease. We felt relaxed on the property and loved walking to see chickens. Everything was truly lovely and Taira and Gina made our experience excellent. We had a private meal cooked by Taira and did pizza making which were some of the best experiences! We enjoyed having a rental car and the access to drive into Orvieto easily but also quick day trips to Siena, Perugia, Assisi, Bolsena, and Lago Trasimeno. We used the train to get easily into Rome, Florence, and Venice. Thank you for such a wonderful stay!
Superhost
Villa in Chiusi
4.89 out of 5 average rating, 9 reviews

Villa Febea - Villa Febea 16

HelenaRating, 5 stars3 weeks 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!

Villa rentals with a pool

Guest favourite
Villa in Lugnano in Teverina
4.93 out of 5 average rating, 29 reviews

Villa Camporiccio

Anne-MariRating, 5 stars2 weeks ago
We loved spending a week at this beautiful villa, which seems to have been renovated quite recently with wonderful taste, suiting an Italian countryside villa. And the views, breathtakingly beautiful! Everything was even better than in the pictures. We especially enjoyed the pool, the outdoor dining arkea and the kitchen. Perfect for our group of four friends! The villa is a few kilometers from the closest shops, restaurants etc. so you need a car to get around. There were many towns and villages nearby which we enjoyed exploring. All in all a very enjoyable holiday in a beautiful location!
Guest favourite
Villa in Paciano
4.93 out of 5 average rating, 29 reviews

Villa Giara - Pool with a view. Trasimeno Lake

ChristopheRating, 5 stars9 months ago
Our stay in Paciano exceeded our expectations. The place is perfect, quiet and offers beautiful views of the valley and lake. The house is fully equipped, nothing to plan and our hosts were super available and provided good advice (thanks for the recipes). Amenities and shops 15 min drive. Ideally located between Rome, Florence, Pisa and Siena. No complaints, it was a very nice surprise, thanks to Maria Pia and Dante.
Top Guest favourite
Villa in Località Poggio Olivo
4.98 out of 5 average rating, 62 reviews

Beautiful villa with swimming pool in Tuscany

KimberlyRating, 5 stars2 weeks ago
The villa, grounds and hosts were fabulous! The views were amazing, the villa extremely clean and well appointed, the pool absolutely delightful, and the surrounding towns and wineries fantastic to explore. Supermarket very close.
Top Guest favourite
Villa in San Casciano dei Bagni
5 out of 5 average rating, 15 reviews

Tuscan farmhouse in San Casciano dei Bagni

DanielRating, 5 stars1 week ago
We had a great time! If you are looking for a quiet place where you can disconnect from everyday life and relax, this is the right place.
Superhost
Villa in Grosseto
4.88 out of 5 average rating, 25 reviews

Cheerful Villa with Pool First Floor

FernandaRating, 5 stars9 months ago
Ilaria’s villa is a comfortable and stylish base from which to explore all the wonders that Maremma has to offer. We are a family of four, and after a couple of weeks in Italy, the kids were craving home-cooked meals, so we spent several hours in the kitchen and dining areas. It was delightful to cook while listening to the kids having fun in the pool. The beds were very comfortable and inviting. The villa is conveniently located near the old town center and several supermarkets. Since we were keen to visit Porto Ercole, Alberese, and Saturnia, we didn’t dedicate as much time to Grosseto as we should have. The old center has a very mellow vibe, and everyone we met was very friendly and welcoming. We wished we could have stayed longer. Finally, I want to say a big thank you to Ilaria for being so accommodating and kind. We are already looking forward to returning to your place.
Top Guest favourite
Villa in Cetona
5 out of 5 average rating, 12 reviews

Country Charm & Jacuzzi

GaryRating, 5 stars1 week ago
An Unforgettable Stay with the Best Host Ever! Flaminia is truly the best host we’ve ever had the pleasure of meeting. From the moment we arrived, she made us feel completely at home. She’s incredibly helpful—always available and willing to assist with anything we needed, no questions asked. Her warm, down-to-earth personality made our stay not only comfortable but genuinely special. What made the experience even more memorable was her recommendation to try her father’s amazing Roman cuisine, perfectly paired with local wines. It was an unforgettable meal and a true highlight of our trip. The farmhouse itself is beautifully located in the heart of Tuscany. It’s the perfect base for exploring nearby cities and the stunning countryside. Thanks to the central location, we were able to easily travel around and soak in all the beauty Tuscany has to offer. Flaminia went above and beyond in every way
Top Guest favourite
Villa in Cortona
4.91 out of 5 average rating, 65 reviews

Villa Le Vigne, 8 pax, private pool, Top Comfort

LouisRating, 5 stars1 month ago
This property is incredible! Gigi was a great host and made us some great dinner reservations. This is a must visit if you like the area and have a big group.
Top Guest favourite
Villa in Arcidosso
5 out of 5 average rating, 5 reviews

Villa toscana in pietra

KayRating, 5 stars1 week ago
Wow, what a wonderful experience. My husband and I chose Marco and Marta’s Villa to renew our 30th Anniversary vows. It was a magical experience that we will treasure forever. We had our boys with us to celebrate and the Villa was perfect for all five of us. It was so cozy and the bedrooms were spacious. The kitchen had everything we needed to cook our Tuscan dinners including all the amenities. Marco and Marta had their wine and olive oil for us to enjoy during our stay. The wine was amazing and the olive oil so yummy. The yard was spectacular overlooking the Tuscan mountains with the lovely pool to enjoy daily and outdoor seating to savor those beautiful daily sunrises and sunsets. Marta and Marco were perfect hosts and went out of their way to help make our anniversary extra special. It was a true Tuscan experience and we highly recommend their Villa. It was everything we expected and much much more. We will definitely be back to stay in the future!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Grosseto
  5. Pitigliano
  6. Villa rentals