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House holiday rentals in Cortona

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Popular amenities for house rentals in Cortona

House rentals with a pool

Top guest favourite
Home in Castiglion Fiorentino
5 out of 5 average rating, 35 reviews

Hidden gem in Tuscany

MitchellRating, 5 stars3 weeks ago
Where to start? I truly can't say enough good things about this property. It exceeded expectations in every way. From start to finish, our time here was a delight. Amanda was responsive, helpful, and accommodating. The location is remote, and a bit of adventure to get to, but Amanda had communicated that and we were prepared with the proper rental car that made it a breeze. The house is beautifully appointed, has every amenity, and lots of perfect spaces for both quiet moments and areas to gather with your group. The outdoor spaces and pool area are lovely, beautifully landscaped, and the views are spectacular. Book this place; you won't be sorry.
Guest favourite
Home in Orvieto
4.99 out of 5 average rating, 211 reviews

Vineyards Paradise

KristineRating, 5 stars2 weeks ago
Our stay at Piero’s home was the highlight of our family’s three week Italy trip! It is one of the most beautiful homes we have stayed at and the spectacular vineyards, gardens, and pool really added something special. We plan to definitely return/stay again! Thank you Piero for sharing your special home!
Guest favourite
Home in Lecchi in Chianti
4.96 out of 5 average rating, 136 reviews

Casa di Lyndall - Entire house with exclusive pool

TerriRating, 5 stars7 months ago
This home is the epitome of a classic villa in the chianti region. Lecchi is very a small village that is walkable to a market, bar & cafe, and one of the best dinner spots we visited in our entire trip to Italy - the Malborghetto restaurant is a must! We rented a car for this week of our trip, and would highly recommend doing so. There are many nearby villages with great trattorias and shopping options - and gorgeous views everywhere you turn. Casa di Lyndall is a roomy, well appointed home with all the amenities you could need. Very clean, and very comfortable, and the view out the front windows is beyond compare. Lyndall was very responsive and provided us with excellent recommendations of things to do during our stay. Clementina greeted us when we arrived and was so sweet and helpful. There is nothing we would change about our stay!
Guest favourite
Home in Tavarnelle Val di Pesa
4.92 out of 5 average rating, 148 reviews

Nada Home

GuillermoRating, 5 stars1 week ago
The main thing is Nada' s attention to every communication you sent, she responds the same day. Anything you asks for within reason, you get from Nada. It was a new experience for us in Tuscany but her property is combiniently located within 40 minutes to an hour and 30 from all the Tuscany turistic places.
Guest favourite
Home in Cortona
4.91 out of 5 average rating, 43 reviews

Country charm walking distance from Cortona centre

MargaretRating, 5 stars5 days ago
Our group of ten absolutely loved staying at Nella's house this June. Nella was good at communicating and set us up in advance with a local driver and for the local chef to come up and cook for us one evening. When we arrived the house was in perfect condition and we quickly felt right at home. The house has a gorgeous view of the sunset in the evening and we were perfectly located to be able to walk into Cortona. Thank you Nella!
Guest favourite
Home in Lucignano
4.95 out of 5 average rating, 38 reviews

La Casetta

LauraRating, 5 stars3 weeks ago
Beautiful, peaceful stay. Amazing, secluded location. The hosts were very friendly and welcoming - made us feel right at home. Lots of great walks around, including the nearby winery. The only downside is it does get rather cold in the stone apartment but during warmer weather the coolness in the apartment would probably be perfect. They provided a portable heater & a hot water bottle though which was nice. Thank you Tebea for being such a lovely host!
Top guest favourite
Home in Subbiano
4.99 out of 5 average rating, 82 reviews

Romantic cosy flat - Toscana Italy

JoeRating, 5 stars5 days ago
Norma was an absolute treasure, and her home and family were lovely. The property sits overlooking a lovely castle and a beautiful church with great views on the other side. The property has a great pool with plenty of privacy or interaction with the family, I only wish I spoke more Italian to be able to sit and chat with her lovely in-laws! Norma offered great recommendations for day trips, and overall the local area was great to explore. My only advice would be the usual: rent a smaller car to make life easier! Sitting on the patio overlooking the castle, with a glass of wine, is a memory we will never forget, and is highly recommended. Whether during the day or after the sun has gone down and the fireflies comes out (weather permitting) it's a Tuscan treat you won't want to miss. We truly felt like a part of the family and would love to return to her home the next time we come back. Truly a wonderful experience!
Guest favourite
Home in Cortona
4.93 out of 5 average rating, 29 reviews

Beautifully restored villa with private pool

GaëlRating, 5 stars3 weeks ago
We had an awesome time at Lucy's and Tommy's, the house was spacious and beautifully decorated. The garden and surroundings are amazing, very peaceful and inspiring. Lucy and Tommy are great hosts who provided very helpful recommendations for off-the-beaten-track activities.

Weekly house rentals

Guest favourite
Home in Castelmuzio
4.98 out of 5 average rating, 40 reviews

Casa Ora d"Oro - Panoramic Views

Jason AllenRating, 5 stars2 weeks ago
first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!
Guest favourite
Home in Asciano
4.97 out of 5 average rating, 33 reviews

Family Forest - Pool in the Crete Senesi

SylviaRating, 5 stars5 days ago
The area is incredible, peaceful and the view spectacular. Asciano has the delightful charm of an Italian village. The people were friendly and welcoming. Even got greeted by their local police who offered up their number in case we needed anything. I felt safe, and it felt as if I lived there for years. I’d say this is a piece of heaven on earth. Bellezza maestosa! Non vedo l'ora di visitare di nuovo la Toscana e la città di Asciano! Grazie!
Guest favourite
Home in Castiglion Fiorentino
4.94 out of 5 average rating, 81 reviews

The small tower

LucaRating, 5 stars1 week ago
Franco is very welcoming, the apartment is a beautiful renovation equipped with every comfort. Highly recommended! Luca and Noélie
Top guest favourite
Home in Magione
5 out of 5 average rating, 19 reviews

Beach House, on the shores of Lake Trasimeno

Juan DiegoRating, 5 stars1 week ago
To assess this property, we must start with the HOST, a professional in every sense. From the minute 0 of the reservation, until the departure; always attentive, very kind and very professional. It is a pleasure to meet serious people and this gives value to the application. The beach house is a paradise in Italy. Easy access, attention to detail, peace, nature, comfort. Our trip was as a family with our two poodles and I think they were the ones who enjoyed the property the most, seeing them run and jump through the green areas of the property and live with many birds, rabbits is priceless. Our daughter enjoyed her stay studying and with the peace and tranquility of the place, it was not difficult for her to concentrate. We, on the other hand, did some sightseeing in the area, all very close and well connected by road. It is a very well-kept, safe property and above all, enjoying its sunset, sitting on a lounger, enjoying a good wine (from the area) is a unique experience. Thank you Maurizio.
Top guest favourite
Home in Cortona (Pierle)
4.98 out of 5 average rating, 51 reviews

"L'Antico Metato" house in the woods

FriederikeRating, 5 stars2 weeks ago
We were there for 4 days and it was simply fantastic. The arrival was smooth and Flavia welcomed us very warmly on site. After a short tour of the house and a short briefing, the holiday could begin. A note with restaurant recommendations and excursion destinations was ready on the table. After a short thunderstorm, we had a power outage, but Flavia was immediately available and within 5 minutes we had power again. Shopping and restaurants are easily accessible by car. I can recommend this accommodation to anyone who longs for peace and wants to enjoy nature. We will be happy to come back!
Top guest favourite
Home in Arezzo
5 out of 5 average rating, 12 reviews

Villa Medici Donnini Superior Apartment

RobertRating, 5 stars3 weeks ago
We had a wonderful week-long visit. I wish we had stayed longer. The villa is beautiful. It is spacious, clean, with modern amenities and appliances but also has some very nice antique furniture and decor. The outdoor patio is really amazing, with views of distant Tuscan hills and farms, olive and cypress trees - a great place to eat and relax outdoors. Nearby Arezzo is a great place to visit. There are many interested museums, churches and places to visit in the older section of the town (including the Basilica di San Francesco with frescoes by Piero della Francesca), but there are also more modern parts of town with shops and restaurants, and ample parking. The villa is also within easy driving distance of many other surrounding towns (such as Cortona) and places to visit. Our hosts were super helpful and friendly, and we especially enjoyed the olive oil that is provided and made from the trees growing on the property. We would definitely stay here again.
Top guest favourite
Home in Tuoro sul Trasimeno
5 out of 5 average rating, 51 reviews

the oasis of the foxes

AbbyRating, 5 stars6 days ago
Beautiful home in a more secluded area overlooking Lake Trasimeno. The trains and a highway are below but not invasive. The views are beautiful. The home was clean and tastefully updated but still clearly old and had a lot of character. We did not have a car and the train station is an hour walk away. There are a couple buses that pass through but not enough to be a reliable means of getting to and from the house. Even the taxi was busy and we had to be flexible on when we went to the train station but it worked out fine. We walked to and from Tuoro for groceries and visited La Puntabella for a great dinner with a view. It was an adventure and we enjoyed it despite our plan not being very good for this location. Sonia was patient and helpful in working out our means of travel and figuring out the bus schedule. Natolino reminded us of home and he is fun to watch and listen to.
Top guest favourite
Home in Monteroni d'Arbia
5 out of 5 average rating, 11 reviews

Golden View - Dream farmhouse in Tuscany

OliwiaRating, 5 stars1 week ago
The stay was like a fairytale – I highly recommend this place. We can’t wait to come back!

Private house rentals

Top guest favourite
Home in Città della Pieve
4.97 out of 5 average rating, 75 reviews

The Terrace of Victory

NickyRating, 5 stars1 month ago
Alessandro is a super nice guy. The place is just fantastically beautiful. The view is unique and the little house is very clean and nicely decorated. We'd come back any time. It was just a great vacation and we felt at home there
Guest favourite
Home in Arezzo
4.88 out of 5 average rating, 24 reviews

Colonial house immersed in a natural park.

MarieRating, 5 stars9 months ago
We spent two weeks at Rolando and Patrizia's with our two one-year-old and three-year-old children. The place is absolutely beautiful with a sublime view. They had a lot of little touches for our children throughout the stay. It was always a pleasure to chat with them. Accommodating, very considerate. The kids were always happy to see them. As for the house, it is very nice and easy to live in. The two terraces are a real plus. And again the views filled us throughout our stay.
Top guest favourite
Home in Monticchiello
5 out of 5 average rating, 39 reviews

Lovely home to dream

NadinRating, 5 stars1 week ago
Sarah was in touch with us before arrival, recommended restaurants and inform us about the parking place, as you can't park inside the old town. the apartment was as in the pictures, beautiful view
Top guest favourite
Home in Cortona
4.97 out of 5 average rating, 88 reviews

Traditional stone house in Tuscany

HannahRating, 5 stars1 week ago
What a wonderful stay. Perfect house for a family holiday with plenty of space for everyone. The house is beautiful and the beds all king size and comfy. The outdoor space and pool are perfect for relaxing after exploring the local area. Within easy reach of exploring the Tuscan gems of Siena and Montipluciano as well as lesser known villages such as spectacular Montone. Alessandro was so responsive and helpful providing recommendations for wine tours and a local chef. The local restaurant Mimmi is not to be missed - authentic home cooked food that was one of the best meals we ate - and the bar was set high. Thank you Alessandro for a wonderful and memorable stay.
Top guest favourite
Home in Montepulciano
4.95 out of 5 average rating, 19 reviews

Hortus Conclusus House

FionaRating, 5 stars2 weeks ago
Amazing place and would definitely be our number one place to stay when we return. Clean and spotless with luxuries like slippers are provided and some breakfast items too. Even a UK-Italy plug converter! Loved it! Thank you to Lucia, Luca and your mum! xx
Top guest favourite
Home in Montecchio
4.91 out of 5 average rating, 32 reviews

Private Tuscan country home with view near Cortona

RhodRating, 5 stars7 months ago
Suitable for those wanting a peaceful getaway in Tuscany which is close to Cortona and Castiglion Fiorentina. Great views over the valley to enjoy with public transport [ trains and buses] not far away to take you further afield. You do your own transport to get there as up a hill, which whilst walkable, but not with luggage. Modern kitchen, comfortable beds, good internet and a Smart TV ensure you don't miss your home comforts. But oh so peaceful!
Top guest favourite
Home in Cortona
4.97 out of 5 average rating, 74 reviews

Countryside house with garden

JulieRating, 5 stars6 months ago
Paola was a lovely, gracious and attentive host. The location was perfect, with in a short drive to everything Cortona has to offer.. We enjoyed exploring the area and found plenty of great dining options nearby. Overall, our experience was nothing short of amazing. We cannot recommend Paola and her property highly enough. Thank you for a wonderful stay.
Top guest favourite
Home in Arezzo
5 out of 5 average rating, 13 reviews

Santa Flora Home • Swimming pool • Gym

DanielRating, 5 stars1 month ago
Letizia and Virginia were absolutely great! The place is much bigger than we expected. Letizia takes great care of the garden and was prompt to respond. Virginia gave us great tips of places to visit. Would definitely recommend.

Destinations to explore

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