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House holiday rentals in Castiglion Fiorentino

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Popular amenities for house rentals in Castiglion Fiorentino

House rentals with a pool

Superhost
Home
4.8 out of 5 average rating, 81 reviews

House with pool among olive trees plantation

KarolinaRating, 5 stars7 months ago
The apartment is located in the picturesque surroundings. It takes quite a while to get there up the hill, but the views reward it! The place was clean and well-prepared for our stay. Good spot if you look for some peace and quiet and want to stay away from the noise!
Top guest favourite
Home
5 out of 5 average rating, 44 reviews

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

MicheleRating, 5 stars5 days ago
Very nice place to stay in the hpgel of Tuscany. A little remote but we appreciated that. Lots of restaurants around the area with really very good food and absolutely good prices. Accommodation with a large garden, pool, air conditioning and heating. Well-maintained and clean. Chickens whose eggs we were allowed to get. Magena true always available, very friendly and helpful. Many wineries in the area where you can eat and drink. We'll be back. Thanks Magena and Eduardo
Superhost
Home
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 favourite
Home
5 out of 5 average rating, 46 reviews

Villa Pergo is an ancient charming country villa

TerriRating, 5 stars6 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
Top guest favourite
Home
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.
Guest favourite
Home
4.96 out of 5 average rating, 45 reviews

Tuscan farmhouse near Siena + Cortona, heated pool

RobRating, 5 stars6 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!
Superhost
Home
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 favourite
Home
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 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 amenities. The garden with swimming pool is an oasis of tranquility, ideal for relaxing with a good book or enjoying a sunset aperitif. But it is the warmth and hospitality of Elisa's family that makes the stay really special. Their availability in providing information on places to visit and recommended restaurants makes a 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 favourite
Home
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
Home
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
Home
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
Home
4.75 out of 5 average rating, 60 reviews

Casa Belvedere with Pool

GeoffreyRating, 5 stars7 months ago
The photos do not capture beauty and character of this place. Very comfortable and high spec renovation of the historic farmhouse ... spacious, relaxing, huge pool, bedrooms stayed cool even as temperature reached 30+ degrees. Great restaurant just round the corner, and top wineries nearby. Fantastic weekend was had, thank you Maurizio!
Superhost
Home
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 favourite
Home
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 favourite
Home in Montebenichi
4.88 out of 5 average rating, 17 reviews

The Montebenichi Dovecote

StephenRating, 5 stars3 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
Home
4.85 out of 5 average rating, 206 reviews

Gaiole in Chianti Poggio Casabianca

MonicaRating, 5 stars5 months ago
What a great getaway!! We hope to make it back soon!

Private house rentals

Guest favourite
Home
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!
Home
5 out of 5 average rating, 4 reviews

Olindia by Interhome

TimRating, 5 stars19 months ago
I stayed at the adorable place with my family for a week. Upon arrival, the host gave us the key and showed us everything. We especially liked the large pool and the breathtaking view of Lake Trasimeno from the upper floor of the house. We had a very nice week in Umbria and explored the surroundings in day trips. If you have any questions or problems, the host has always been kindly helped. We like to come back
Guest favourite
Home
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.
Superhost
Home
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.
Home
5 out of 5 average rating, 9 reviews

Le Bonatte by Interhome

CarlRating, 5 stars6 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!
Home
5 out of 5 average rating, 8 reviews

Pianelli by Interhome

DiegoRating, 5 stars22 months ago
The stay was amazing, the Host Luciano was very nice and forthcoming about any inquiry we had. I can recommend the place to anybody who wants to have a nice, chill time in the hills of central Tuscany.
Home
4.87 out of 5 average rating, 15 reviews

Lucia by Interhome

ChristophRating, 5 stars6 months ago
The terrace was great, and the entire place had a quiet and peaceful feeling.
Top guest favourite
Home
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.

Quick stats about house rentals in Castiglion Fiorentino

  • Total rentals

    10 properties

  • Nightly prices starting at

    £38 before taxes and fees

  • Total number of reviews

    190 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Wifi availability

    10 properties include access to wifi

Destinations to explore