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House vacation rentals in Cortona

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Popular amenities for Cortona house rentals

House rentals with a pool

Guest favorite

Home in Civitella in Val di Chiana

4.93 out of 5 average rating, 45 reviews

Casa Fattore - Tuscan countryside house

LunaRating, 5 stars4 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

Home in Todi

4.94 out of 5 average rating, 32 reviews

Villa in Umbria with pool

MichaelRating, 5 stars5 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.
Superhost

Home in Umbertide

4.81 out of 5 average rating, 37 reviews

Capanna: Scenic Umbria Villa for 8. Private Pool

SophieRating, 5 stars5 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

Home in Città della Pieve

5 out of 5 average rating, 4 reviews

Casa Arcobaleno - Citta della Pieve

MarkRating, 5 stars4 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

Home in Cortona

4.75 out of 5 average rating, 4 reviews

Little Poventa

ShelleyRating, 5 stars4 months ago
casale polenta exceeded our expectations. beautiful property and accommodations.
Guest favorite

Home in Monte San Savino

4.99 out of 5 average rating, 69 reviews

CHARMING TUSCANY VILLA PRIVATE POOL

Tsz Kwan CarrieRating, 5 stars3 months ago
Francesco is nice:) He brought us welcome pizzas and dessert. His response is instant. The place is quiet which provide you completely private place. Just a bit far from town if you cannot drive yourselves. If you have cars, it is not a problem, just few minutes drive from town. The place looks exactly the same as the pictures, clean and tidy. Definitely enough space for 8 adults. Recommend.
Guest favorite

Home in Todi

5 out of 5 average rating, 37 reviews

Apartment in villa and pool 10 minutes from downtown

FleurRating, 5 stars3 months ago
Absolutely loved our stay and would definitely stay longer if I ever return. Lovely host and a wonderful property with beautiful views and so many areas to relax in. Easy access to town for exploring and so much to see in the area.
Superhost

Home in Todi

4.91 out of 5 average rating, 11 reviews

Todi House private villa, large modern villa, airco

JulianeRating, 5 stars3 months ago
I've booked houses many times, I've never had hosts like this before. Upon our arrival, we found not only cheese and sausage, but also homemade bread and pastries. On the third day we were surprised with a cake and the day after they made lasagne and dessert for us. Samuele was by far the friendliest and most attentive host we have ever experienced. Its warm nature made the stunning house perfect. We were three families with children, each had their retreat. The kitchen was great for cooking together. The surroundings are fabulously beautiful, the view a dream. The pool and playground for the kids were perfect. We had a wonderful week and would come back anytime. Communication with Saskia in advance and with Samuele on site was excellent. I could rave for a long time, unfortunately the characters are not enough. 1000 thanks to Samuele for the great house and his hospitality. See you next time

Weekly house rentals

Superhost

Home in Contignano

4.77 out of 5 average rating, 31 reviews

Noi 2 Vacanze - Casina di Dario

LaurenceRating, 5 stars4 months ago
The views are beautiful. Peaceful neighborhood. However, the kitchen is missing several items for cooking.
Superhost

Home in Castellina in Chianti

4.75 out of 5 average rating, 60 reviews

Casa Belvedere with Pool

GeoffreyRating, 5 stars4 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 in Montefollonico

4.89 out of 5 average rating, 18 reviews

[15 min da Montepulciano] Villa Chiara

JoeRating, 5 stars4 months ago
Great location and the 2 full size bathrooms were nice!
Superhost

Home in Pietralunga

5 out of 5 average rating, 11 reviews

Il Monte

ConstanzeRating, 5 stars6 months ago
Great stay in beautiful house in beautiful house.
Guest favorite

Home in Castelfranco Piandiscò

4.96 out of 5 average rating, 82 reviews

Villa close to Florence amazing view private pool

Ane ElineRating, 5 stars4 months ago
Had a week here with good friends. Enjoyed the beautiful house and the area. Great for a slow, calm getaway!
Guest favorite

Home in Montebenichi

4.87 out of 5 average rating, 15 reviews

Colombaio di Montebenichi

AdamRating, 5 stars4 months ago
Beautiful house with amazing views, responsive host and property manager. Little village nearby had one restaurant open for dinner which was delicious. Great place to unwind highly recommend
Superhost

Home in Rietine

4.85 out of 5 average rating, 206 reviews

Gaiole in Chianti Poggio Casabianca

MonicaRating, 5 stars2 months ago
What a great getaway!! We hope to make it back soon!
Guest favorite

Home in Monte del Lago , Magione

4.97 out of 5 average rating, 29 reviews

Villa Profumo di Salvia. Lakefront

FrankRating, 5 stars3 months ago
By far one of the best places we have ever stayed. Almost surreal how beautiful this space is, and the surrounding property is almost too beautiful to describe. Silvia is certainly a top tier host, and her attention to detail is second to none. We are already planning a return trip. If you want to get away from it all, and never have to leave a property ( except to grab more wine), this is the place. But if you want venture out, many top attractions are less than hour drive away. The Lake views alone are worth the trip.

Private house rentals

Guest favorite

Home in Radda In Chianti

4.84 out of 5 average rating, 173 reviews

Tuscany House "La Querce Sola"

LeifRating, 5 stars4 months ago
Beautiful home with a gorgeous view of the Tuscan hills! Peaceful but still accessible to everything in area within an hour drive. We were definitely glad to have an SUV as our rental car, as the dirt road into the property is very bumpy. Rosanna was super friendly and accommodating - would definitely recommend staying here!
Superhost

Home in Monte San Savino

4.82 out of 5 average rating, 196 reviews

In Tuscany between Siena Arezzo, near Chianti

DonatellaRating, 5 stars4 weeks ago
I stayed in Lorenza's house with my family and a couple of friends, we had a great time, the kids had a really good time and there was ample space to move around and play. Rustic and clean house. Beautiful garden and cities around a convenient location! Recommended
Guest favorite

Home in Canneto

5 out of 5 average rating, 15 reviews

Three room apartment in a single house

Elisa ERating, 5 stars3 weeks ago
Federica is a friendly, pleasant and kind host. We had a really good time in her home, which is spacious, very clean and welcoming. Federica was available both for check-in and for info about the area and then being a pleasant person it is a fun chat with her, too bad we had a short time. central location for us since we visited Perugia, Assisi and Gubbio and nothing is missing in the apartment. thank you Federica!!!!
Superhost

Home in Ville

4.79 out of 5 average rating, 29 reviews

Independent Tuscan Villa Siena with Pool (7+1)

RonRating, 5 stars4 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 in Radda in Chianti SI

5 out of 5 average rating, 9 reviews

Le Bonatte by Interhome

CarlRating, 5 stars4 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!
Guest favorite

Home in Castiglion Fiorentino

5 out of 5 average rating, 17 reviews

Volpe by Interhome

MartinRating, 5 stars2 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.
Guest favorite

Home in Terranuova Bracciolini

4.91 out of 5 average rating, 23 reviews

VILLA MARINA, Large Private Villa w/ pool

MathiasRating, 5 stars18 months ago
Friendly host, and the villa looks better in reality than the pictures give impression of.
Superhost

Home in Arezzo

4.93 out of 5 average rating, 14 reviews

Dolce Casa 2 by Tiny Away

LorenzoRating, 5 stars4 weeks ago
First time in a Tiny House. Experience to try. Small space where nothing is missing and where everything is thought out accurately. Elena welcomed us with kindness and despite it being on 12/31 she waited for us until 8.15 pm and the next morning allowed us to stay until noon.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Arezzo
  5. Cortona
  6. House rentals