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House vacation rentals in Val di Chiana

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Popular amenities for Val di Chiana house rentals

House rentals with a pool

Guest favorite
A large terracotta vase is positioned beside a stone building, partially shaded by a lush tree. Surrounding greenery complements the natural setting, with a clear blue sky visible overhead, featuring a few scattered clouds.
Home in Civitella in Val di Chiana
4.93 out of 5 average rating, 45 reviews

Casa Fattore - Tuscan countryside house

LunaRating, 5 stars7 months ago
The stay at the Capocontro estate was very satisfactory. The entire old village is a jewel set in the greenery, with spectacular views of the woods of the Val di Chiana. The place is tidy and clean, picturesque and elegantly retro. Piero and Lella are very available in communications and suggestions of places to visit and eat. We loved the peace and quiet of the place, as well as the pool with a view. We stopped little and the weather was a little capricious, otherwise we would have enjoyed the exteriors of the farm more. Only small mole: the dishes and the fridge were not really immaculate, but nothing that can't be resolved with a sponge shot. Highly recommended for both a short and long stay, so you can enjoy the quiet of the place and visit the surroundings.
Superhost
A spacious outdoor area features a large swimming pool surrounded by well-maintained grass. The pool area includes several white lounge chairs and is complemented by a nearby shaded seating space. Rustic stone buildings are visible in the background, amidst lush greenery.
Home in Todi
4.94 out of 5 average rating, 32 reviews

Villa in Umbria with pool

MichaelRating, 5 stars8 months ago
Antonio is a very nice host who always takes care of the house and his guests. The 4 apartments were very good and also convenient for our group vacation. Parking is more than enough on the property as cars are also mandatory to get to the house. Furthermore, the pool is very good and also very large. Enough space to have fun. Antonio came several times to clean the pool, which was very good. Other shade options such as umbrellas or another pavilion would be good, otherwise you have to take them with you beforehand.
Top guest favorite
A well-maintained outdoor area features a private pool surrounded by a lush green lawn. A cozy villa can be seen in the background, complemented by tall trees and a relaxing ambiance. Lounge chairs are positioned near the pool, inviting leisure under the partly cloudy sky.
Home in Reggello
5 out of 5 average rating, 44 reviews

Villa in Tuscany - Reggello, with Swimming Pool and WiFi.

MicheleRating, 5 stars1 week ago
Very nice place to stay in the hills of Tuscany. A little remote but we appreciated that. Many restaurants nearby with really very good food and absolutely good prices. Accommodation with large garden, pool, air conditioning and heating. Well-kept and clean. Chickens whose eggs we were allowed to collect. Magena was always available, very friendly and helpful. Many wineries in the area where you can eat and drink. We will be back. Thanks Magena and Eduardo
Superhost
Home in Umbertide
4.81 out of 5 average rating, 37 reviews

Private villa with pool and breathtaking views

SophieRating, 5 stars8 months ago
Anna’s house is stunning and tucked away in such a beautiful quiet location. The people who take care of the house were kind and our two year old loved him. Would highly recommend anyone who wants a quiet get away from the hustle and bustle of life to stay here.
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 stars7 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 outdoor pool area features a rectangular pool surrounded by a spacious wooden deck. Sun loungers and beach umbrellas are placed around the pool, with vibrant flowers adding color to the scene. A panoramic view of the surrounding hills can be seen in the background.
Home in Canneto
4.92 out of 5 average rating, 25 reviews

Elegant Accommodation in Villa with Swimming Pool in Perugia

AndrewRating, 5 stars8 months ago
Wonderful stay. Great layout for us (2A, 2C, 1I) and a fantastic swimming pool. Roberta was lovely and we communicated via messaging app given language differences. Roberta and family were quiet in the ground floor apartment and the upstairs rental were equally nice. We barely had to share the pool. Great location for day trips to Florence, Sienna and Assisi.
Guest favorite
The villa is set within a spacious green garden, surrounded by lush trees and rolling hills. Stone architecture is complemented by climbing plants, while terracotta roofs add warmth. The inviting outdoor space features well-maintained grass, creating a tranquil environment perfect for relaxation.
Home in Ficulle
4.96 out of 5 average rating, 23 reviews

Big Breathtaking PoolVilla bw Rm/Fl

PatrickRating, 5 stars8 months ago
Beautiful large house with great views and an amazing pool area. A little remote, at the end of a long and steep gravel road, but completely worthwhile. Great hosts, very attentive to their guests' every need.
Guest favorite
A private pool area is framed by lush greenery and blooming flowers. Two lounge chairs and a small table are arranged on a stone patio under a large umbrella. The bright yellow house is partially visible, showcasing an upper balcony.
Home in Cortona
4.96 out of 5 average rating, 57 reviews

"Casa Elisa", house with swimming pool at the foot of Cortona

AlessandroRating, 5 stars4 months ago
I had an unforgettable stay at Casa Elisa, located at the foot of the beautiful Cortona. The atmosphere is magical: a perfect fusion of Tuscan tradition and modern comfort. The rooms are elegant and quite spacious, tastefully furnished and equipped with all the necessary comforts. The garden with pool is an oasis of tranquility, ideal to relax with a good book or to enjoy an aperitif at sunset. But it's the warmth and hospitality of Elisa's family that makes the stay really special. Their availability in providing information about places to visit and recommended restaurants makes all the difference. I highly recommend Casa Elisa to anyone who wants to discover the beauty of Tuscany, living an authentic and unforgettable experience.

Weekly house rentals

Guest favorite
The living area features wooden beams across the ceiling and a cozy seating arrangement with a sofa and a bench. Large glass doors open to a garden, allowing natural light to fill the space. Decorative items are displayed on the shelves nearby.
Home in Figline e Incisa Valdarno
4.91 out of 5 average rating, 44 reviews

POMEGRANATE CAMPOPINETA

AmandaRating, 5 stars6 months ago
Alessandra’s place was an absolute dream. It’s picturesque with the most gorgeous view of Tuscany hills in a rustic styled rental. She was extremely helpful and attentive during our stay! Would definitely come back here next time we visit!
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!
Top guest favorite
An appealing stone villa is framed by lush greenery and manicured hedges. A circular stone fountain is centered in a gravel area, surrounded by shrubs and trees. The sky is partly cloudy, providing a gentle light that enhances the natural beauty of the setting.
Home in Castelfranco Piandiscò
4.96 out of 5 average rating, 82 reviews

Villa close to Florence amazing view private pool

Ane ElineRating, 5 stars7 months ago
Had a week here with good friends. Enjoyed the beautiful house and the area. Great for a slow, calm getaway!
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!
Guest favorite
Home in Montebenichi
4.88 out of 5 average rating, 17 reviews

The Montebenichi Dovecote

StephenRating, 5 stars5 days 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
Superhost
A spacious dining area is highlighted by a large wooden table surrounded by chairs. Exposed wooden beams and an arched window frame contribute to the rustic charm. A glass door allows natural light to illuminate the room, revealing a comfortable seating area in the background.
Home in Molino Vitelli
5 out of 5 average rating, 3 reviews

2 / 8px house on Tuscan Borders

ElizabethRating, 5 stars2 weeks ago
Andrea's place was perfect for our short two night stay in the Niccone Valley, or fav area in Umbria. We were there in cooler weather and the floor heating took a bit to come on but once it did we were comfortable. I think it would be a great place in the warmer weather as the pool looked wonderful. The Niccone Valley is somewhat remote but with the location of this property you had the best of both worlds quick access to Umbertide and yet embedded in the valley. Would love to return in the warmer weather. Thank you Andrea!
Top guest favorite
The exterior of the two-story stone villa is framed by olive trees and garden flowers. Balconies with flower boxes adorn the upper level, while wooden shutters provide a rustic charm. Lush green space surrounds the property, enhancing its natural setting.
Home in Monte del Lago
4.97 out of 5 average rating, 30 reviews

Villa Profumo di Salvia. Lakefront

AndrewRating, 5 stars6 months ago
We had a wonderful stay. Silvia was very responsive, and she even brought us pizza upon our late arrival! The grounds are gorgeous and the views were incredible. The villa itself was spacious, clean, and exactly as described in the listing. Highly recommended.

Private house rentals

Guest favorite
A living room area features a yellow leather sofa adorned with colorful cushions. A patterned rug covers the tiled floor. Large windows provide natural light, and an archway leads to a dining area with wooden furniture and a view into the well-equipped kitchen.
Home in Radda in Chianti
4.85 out of 5 average rating, 177 reviews

Tuscany House "La Querce Sola"

EricRating, 5 stars1 week ago
Rosanna and her country house are as great as all the reviews say. The house is spacious, comfortable, clean, quiet, charming with beautiful views of the surrounding hills. Great place to relax with family. If you intend to use the oven ask for instructions, it works fine but the operation wasn’t intuitive for us. Also bring plenty of bottled water, the house supply is fine for washing but not for drinking/cooking. Rosanna gave us great recommendations for dining and sightseeing in the Radda/ Castellina area, great place at a reasonable rate!
Superhost
A two-story stone house is surrounded by lush greenery, featuring flowering shrubs and trees. Large windows are framed by wooden shutters, allowing natural light to brighten the interior. The tranquil garden provides a serene outdoor space for relaxation.
Home in Monte San Savino
4.83 out of 5 average rating, 200 reviews

In Tuscany between Siena Arezzo, near Chianti

FrancesRating, 5 stars1 day ago
We had a perfect break in Lorenza’s lovely house. It was extremely spacious and exceptionally clean. The garden is beautiful and well maintained with lots of areas to sit in and enjoy the peaceful environment. Our dogs loved their walks in the woods nearby and they enjoyed meeting all the feline residents! Lorenza and her husband are a lovely friendly couple who have put a lot of thought into ensuring their guests have a great holiday.
Guest favorite
Home in Civitella Paganico (GR)
4.94 out of 5 average rating, 18 reviews

Podere Vignali by Interhome

SimoneRating, 5 stars7 months ago
Really beautiful place and beautiful surroundings. All communication went smoothly. Very clear instructions and descriptions sf amenities. The host will be in touch with you a few dsge before arrival and check in was super easy.
A rustic stone farmhouse is framed by a gravel courtyard, punctuated with potted plants and vibrant flowers. The structure features an arched entrance, wooden doors, and a tile roof. A shaded area is provided by nearby trees, enhancing the serene setting.
Home in Radda in Chianti
5 out of 5 average rating, 9 reviews

Le Bonatte by Interhome

CarlRating, 5 stars7 months ago
Joy (the owner) is a joy! She is one of the best hosts we’ve had on this platform. Flexible checking, due to delayed flight. Rooms were bigger than anticipated and beautiful. Lovely rustic Tuscan charm of a property. Plenary of recommendations at the property for local restaurants and activities. Can’t recommend this property enough!
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 stars5 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.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Arezzo
  5. Val di Chiana
  6. House rentals