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House vacation rentals in Castel del Piano

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Popular amenities for Castel del Piano house rentals

House rentals with a pool

Superhost
A rustic villa is surrounded by greenery, featuring a clear swimming pool bordered by lounge chairs. Stone walls and arched windows create a charming exterior. A well-maintained garden enhances the tranquil setting, while the sky reveals scattered clouds and sunlight.
Home in San Giovanni d'Asso
4.77 out of 5 average rating, 52 reviews

Tuscan Villa Poggetto Montalcino

SamRating, 5 stars7 months ago
Villa poggetto was a beautiful and quiet retreat. Our family used it as a base for seeing other parts of Tuscany and hired a car so it was perfect. It has basic amenities and the pool is in great condition. Only critique is the doors don’t lock well (not really a concern as the area is quiet) and as it is rural there are animals around such as mice and cute local cats. Gastone was a great host who allowed us to check in at 11pm when we were running late. He is very responsive and kind.
Top guest favorite
The exterior of Villa Pergo is revealed, showcasing a historic stone facade under a clear blue sky. A spacious gravel area is visible, surrounded by lush trees and potted plants, providing ample parking and outdoor space.
Home in Pergaccio
5 out of 5 average rating, 46 reviews

Villa Pergo is an ancient charming country villa

TerriRating, 5 stars7 months ago
Based on the previous wonderful reviews of Antiqua degli D’ulivi, a year ago we booked a three week stay in the outskirts of Cortona in Pergo. We had our kids, grandkids and dear friends with us and as we drove through the gates into the Villa, we entered a magical place filled with generosity, laughter, relaxation, wonderful food, a refreshing pool and golden light. Massi was always there to help us with any questions we had and refill our olive oil bottle with the amazing green liquid made from his olives. We enjoyed the most delicious lunch with his family and they also were such giving, lovely people. We learned so much about Italy and Tuscany from them: porcini mushrooms, Perugia soccer teams, local markets, hot springs near Montepulciano, nearby restaurants, vineyards, hikes and more. We highly recommend an extended stay at this Tuscan home—we were so fortunate to experience it for three glorious weeks. The memories will be long lasting and always treasured. Mille Grazie to Massi
Superhost
The exterior of the property showcases a charming casale with rustic stone walls and large windows. A swimming pool is positioned in front, surrounded by a well-maintained lawn. A gazebo offers shaded seating, and sun loungers invite relaxation under the sunny sky.
Home in Città della Pieve
5 out of 5 average rating, 4 reviews

Casa Arcobaleno – Città della Pieve

MarkRating, 5 stars8 months ago
Such a lovely villa. Beautifully arranged with perfect amount of space for our group of 8. The villa has everything you need. The pool was lovely and warm even without being heated. Margherita, the local host, was amazing - so helpful. Would definitely come back.
Superhost
The rustic stone farmhouse is set against a vibrant sky, surrounded by lush greenery and offering an inviting entrance. The property features a well-maintained garden that enhances the tranquil nature of the location.
Home in Scansano
4.77 out of 5 average rating, 47 reviews

The Farmhouse in the heart of Maremma

GuusRating, 5 stars8 months ago
Ginevra was very friendly and forthcoming. Communication was smooth and prompt. Nice place, surely recommended!
Top guest favorite
A tranquil swimming pool is surrounded by stone decking, complemented by sun loungers in a serene garden setting. Olive trees provide a natural backdrop, while a rustic building and landscaped areas are visible nearby.
Home in Serre di Rapolano
4.97 out of 5 average rating, 74 reviews

L'Olivo - detached villa with swimming pool

MartaRating, 5 stars7 months ago
Amazing place in a quiet area with a beautiful view of the countryside. Climate cottage equipped with everything you need. Together with our dogs we felt like at home. Bruna is an incredibly warm and helpful person. Thank you for a wonderful time.
Top guest favorite
Home in Città della Pieve
4.97 out of 5 average rating, 77 reviews

Casale with pool -Ad Galli Cantum- Vesper

ChrisRating, 5 stars5 months ago
We loved Elena’s place and wish we could have stayed longer to just relax and soak it in. The property is beautiful - the pictures on the listing don’t do it justice. Elena provided a couple of restaurant recommendations that were spot on. We would definitely return!
Top guest favorite
Home in Pereta
5 out of 5 average rating, 52 reviews

Bel Casale with sea view and the mediaeval village

JessicaRating, 5 stars7 months ago
Absolutely stunning setting! The house is very beautiful and the sunset is incredible. It was comfy, clean and we could easily have stayed much longer. The kids loved exploring the yard and wandering around all the beautiful olive trees. Paola was so helpful with local recommendations and always responsive! The house had all the essentials, which was great as there isn’t exactly a supermarket down the road. It was a really special stay. Thank you for having us!
Guest favorite
A spacious living room features a vaulted ceiling with terracotta tiles. Glass doors open to a scenic outdoor area, inviting natural light. Comfortable seating includes a light-colored sofa with decorative pillows and woven chairs, complemented by framed botanical art on the walls.
Home in Asciano
4.96 out of 5 average rating, 45 reviews

Tuscan farmhouse near Siena + Cortona, heated pool

RobRating, 5 stars7 months ago
We absolutely loved the home and location! There were nine of us and everyone had their own space and bathroom. The home was very clean and decorated beautifully. Amanda was a fabulous host. She was very responsive with all communication and helpful with places to see in the region. The location was excellent for traveling all around Tuscany and it was very peaceful. We can't wait to go back!

Weekly house rentals

Superhost
The exterior of a charming residence is visible, featuring a winding pathway leading to a quaint patio area. A small table and chairs are set for outdoor relaxation, surrounded by lush greenery and colorful flowers. The building's façade is complemented by rustic shutters.
Home in Contignano
4.77 out of 5 average rating, 31 reviews

Noi 2 Vacanze - Dario's House

LaurenceRating, 5 stars7 months ago
The views are beautiful. Peaceful neighborhood. However, the kitchen is missing several items for cooking.
Superhost
A spacious dining area is illuminated by natural light filtering through open doors. A large wooden table is surrounded by several chairs, and a matching sideboard displays glassware. Soft curtains frame the doorways, enhancing the charming countryside feel.
Home in Lucignano
4.78 out of 5 average rating, 9 reviews

Beautiful property between Siena and Arezzo

TimRating, 5 stars20 months ago
we had a very nice stay. The entire accommodation was very clean. Highly recommend taking something against the mosquitoes. the only criticism was the chairs on the terrace, as 2 have shackled heavily, there should be a replacement here.
Superhost
A stone villa is framed by lush greenery, showcasing a welcoming entrance with an ornate gate. Large windows with green shutters invite natural light into the home. A small balcony is visible on the upper level, adding to the charm of the exterior.
Home in Montefollonico
4.89 out of 5 average rating, 18 reviews

[15 min da Montepulciano] Villa Chiara

JoeRating, 5 stars7 months ago
Great location and the 2 full size bathrooms were nice!
Guest favorite
Home in Montebenichi
4.88 out of 5 average rating, 17 reviews

The Montebenichi Dovecote

StephenRating, 5 stars1 week ago
We had an incredible stay at this beautiful villa in the rolling hills of Tuscany. Perched on a mountain, the property offers stunning views over the countryside, with gorgeous gardens and an authentic Tuscan feel throughout. The villa itself was spacious, comfortable, and full of charm. The location was perfect — peaceful and private, yet central to many of the places we wanted to visit, including Florence, Montepulciano, Siena, and San Gimignano. Christina, our contact person, was a great communicator. She was also on time, very helpful and pleasant to be around. She provided us with great insights about the area and the property. The location was excellent for us to use the e-bikes that we rented. We had breathtaking rides around the area. There was an excellent grocery store, Conrad’s in Bucine with a very tasty restaurant in the same Plaza. It was the perfect rustic home base with lots of charm the Tuscan experience for exploring the region, and we would absolutely stay again
Guest favorite
Home in Colle di Val d'Elsa
4.95 out of 5 average rating, 59 reviews

Countryhometuscany - House with Garden -

DavidRating, 5 stars2 weeks ago
There aren't enough words to describe this experience. We loved staying here and loved the house; you have everything you need. The garden is great if you have dogs, and it's really quiet and cozy. Tesa and Giovani are amazing hosts and we are very happy that we met them. We will get back next year for sure.
Superhost
The image features a sparkling pool in the foreground, bordered by a carefully landscaped garden. A comfortable seating area with lounge chairs is positioned nearby, while a large umbrella provides shade. The stone building in the background is adorned with greenery and showcases a charming terrace.
Home in Lisciano Niccone
4.69 out of 5 average rating, 49 reviews

Casa Trasimonte | country house with private pool

CarinaRating, 5 stars9 months ago
We had an amazing week in Casa Trasimonte, where we enjoyed the house, the pool, the terrace and the view. The house is richly equipped, so we ate a lot at home. We also ate at the local restaurant Lo Scoliotto, where the view and food are good. In Tuoro, we ate with great views of the lake. Largo Trasimeno itself was a bit of a disappointment. Not to look at (really beautiful), but not inviting to bathe. We did great walks in the mountains around the house and met a beautiful animal diversity. All in all, a great recommendation from us.
Top guest favorite
A spacious living area features a combination of light-colored furniture and decorative elements. Natural light enters through multiple windows adorned with sheer curtains. A cozy seating arrangement includes comfortable chairs and a sofa, with a decorative table in the center.
Home in Montepulciano
4.97 out of 5 average rating, 36 reviews

A moment of relaxation

RiccardoRating, 5 stars1 week ago
As soon as we entered, the feeling was that of being at home. Spacious, clean and equipped with everything you need. In addition, Francesca was very nice to leave us a fantastic and abundant breakfast. Also recommended for the location.
Guest favorite
Home in Castiglione del Lago
5 out of 5 average rating, 25 reviews

Bliss out in Historic Farmhouse on Organic Wine Estate with Tennis and Pool

ChristopherRating, 5 stars6 months ago
We had a fantastic stay with a group of four adults and five kids. Accommodations were immaculate, private chefs were decadent and delicious, and fantastic wine. The grounds were just lovely as well and we enjoyed having a fire in the fire place every evening. That you for a lovely stay!

Private house rentals

Superhost
Home in Ville
4.79 out of 5 average rating, 29 reviews

Independent Tuscan Villa Siena with Pool (7+1)

RonRating, 5 stars7 months ago
We stayed for a week and had a wonderful time. The house is well maintained and exactly as per the description provided. Giovanna and her family are highly responsive and responded instantly to any queries we had. We would highly recommend anyone wanting to go to the Toscana to stay at this wonderful house.
The living and dining area is characterized by rustic wooden beams and terracotta flooring. A wooden dining table is set for meals, while a comfortable seating arrangement faces a fireplace. Natural light enters through a large arched window, complemented by a television in the corner.
Home in Castellina Chianti SI
5 out of 5 average rating, 4 reviews

Capanna di Sotto by Interhome.

AntjeRating, 5 stars8 months ago
we immediately felt comfortable 7 d enjoyed the stay very much. A ideal starting point for excursions.
The exterior of the rustic stone house features a spacious terrace with tiled flooring and a wooden pergola. Lush greenery surrounds the area, and vibrant flowers add color to the landscape. The entrance is framed by opened double doors, inviting guests to explore.
Home in Cortona
4.87 out of 5 average rating, 15 reviews

Lucia by Interhome

ChristophRating, 5 stars7 months ago
The terrace was great, and the entire place had a quiet and peaceful feeling.
Top guest favorite
A modern kitchen features a central island with an induction cooktop and seating for several guests. Gray cabinetry complements stainless steel appliances, including an oven and refrigerator. Natural light fills the space, highlighting the open-concept layout that connects to the living area.
Home in Castiglion Fiorentino
5 out of 5 average rating, 17 reviews

Volpe by Interhome

MartinRating, 5 stars6 months ago
It was an absolute delight to stay at this gem of a property. We booked for 10 days and had a chance to enjoy and explore the surrounding areas. The house is spotless, comfortable, spacious, and fully equipped with modern appliances. So it has exceeded our expectations and would love to book it again in the future. Our host Alberto, is welcoming and very friendly, making the process of checking in and out quite seamless. My overall impression is 10/10.
The outdoor area features a private swimming pool surrounded by a landscaped lawn, with several sun loungers positioned for relaxation. The pool is framed by natural stone, and lush greenery provides a serene backdrop under a partly cloudy sky.
Home in Roccastrada
4.92 out of 5 average rating, 13 reviews

Casa la Selvolina, by Interhome

IrisRating, 5 stars7 months ago
La Selvolina is a great place to unwind and enjoy the surroundings, but also the lovely pool. The house is nice, the kitchen very complete. Everything is available for a wonderful stay. If you have any questions, there was always a quick and very friendly response, which we experienced as very pleasant and welcome. La Selvolina is a wonderfully quiet place, about a 30 minute walk (up the mountain) or 5 minutes by car to Roccastrada. If you're lucky, you could see deer in the garden and hear the owls at night. It is advisable to have an SUV because the road is not paved.
An inviting outdoor area is adorned with vibrant flower pots in various colors, arranged along a stone path. Wooden shelves display additional potted plants, while a playful decorative figure adds a touch of whimsy to the garden's welcoming ambiance.
Home in Castel del Piano
4.79 out of 5 average rating, 52 reviews

La Casa di Miria

KevinRating, 5 stars6 days ago
Absolutely stunning home. I have nothing negative to say. The host was amazing, she was super nice, responsive and kind. 100% Reccomend to everybody.
Guest favorite
A spacious hydro massage bath is situated in a natural stone vaulted area, complemented by a wooden floor. A door leads to an outdoor terrace area with lounge chairs, while a drink holder and ice bucket are positioned beside the bath.
Home in Seggiano
4.94 out of 5 average rating, 122 reviews

The Wellness Suite by Interhome

LucaRating, 5 stars3 weeks ago
Wonderful experience and wonderful accommodation, we will be back soon
The image captures a rustic landscape of a stone-built house nestled among greenery. A mix of trees and shrubs is visible, with a backdrop of rolling hills and a cloudy sky. The natural setting provides a sense of tranquility and seclusion.
Home in Cortona
5 out of 5 average rating, 4 reviews

Il Feudo by Interhome

GillRating, 5 stars8 months ago
A fabulous place to relax surrounded by beautiful scenery.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Grosseto
  5. Castel del Piano
  6. House rentals