Holiday houses in Vallone Pip

4.99 out of 5 average rating, 155 reviews

Apartment in Cortona

Cortona’s Rooftop Nest

L’appartamento è sito in pieno centro storico proprio di fronte alla meravigliosa chiesa di San Francesco e a pochi passi dalla piazza principale.Arredato in stile country chic e dotato di tutti i comfort.Ospita 4 persone.Ventilatori nelle camer The apartment is located in the historic center right in front of the wonderful church of San Francesco and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It can host up to 4 people. Fan in the rooms.

4.96 out of 5 average rating, 164 reviews

Guesthouse in Macciano

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Home in Casorbica-Salcotto

4.93 out of 5 average rating, 28 reviews

Apt. Silvana-Tenuta VillaAugusto

La struttura è ubicata in un agglomerato distante 3/4 km dal centro di Cortona. Circondata dal verde, un vero paradiso di tranquillità. Alloggio indipendente e accogliente con ampi spazi arredati con mobili e oggetti d'epoca, cucina attrezzata, 2 camere (matrimoniale e 2 singoli), 1 bagno. Ambienti climatizzati. Spazio esterno attrezzato con tavolo, sedie e lettini. Ampio parco con molti spazi ombreggiati e grande piscina (14x7) immersa nel verde, condivisa con gli altri ospiti della tenuta.

4.95 out of 5 average rating, 218 reviews

Villa in Montepulciano

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Superhost

Place to stay in Terontola Alta

4.8 out of 5 average rating, 133 reviews

Villa Patrizia: Tuscany farmhouse apt 2

Villa Patrizia is the perfect place for a relaxing holiday with your family and for his unique position for someone who wants to enjoy art and historical cities like Cortona, Firenze, Perugia, is a typical Tuscan olive groves, with an amazing view of Trasimeno lake. The apartment offers you every kind of comfort you need. It has a portico, a great outdoors garden and even a big swimming pool where you and your children can spend time relaxing and having fun.The staff is always helpful.

4.94 out of 5 average rating, 16 reviews

Home in Camucia

Borgo La Fonte

❊ Private Outdoor Spaces: private garden with a gazebo adorned with fragrant jasmine, perfect for al fresco dining or relaxing moments ❊ Ease and Convenience: located between Camucia and Cortona, starting point for exploring the region and enjoying a relaxing vacation with all services close at hand ❊ Modern Comforts: fully equipped kitchen, two double bedrooms, and two bathrooms with showers ❊ Private Parking: a rarity in the area, for a more convenient stay

4.98 out of 5 average rating, 168 reviews

Condo in Cortona

Chicca: bright and panoramic in the historic center

Bright, delightful and welcoming apartment located right in the heart of the historic center of Cortona with an unforgettable view: the town hall on one side and Lake Trasimeno and the Valdichiana on the other. The apartment has been recently renovated and consists of a living room with sofa bed, a small kitchen, a double bedroom and two bathrooms. The apartment has WiFi, heating and air conditioning, a washing machine, oven, microwave, hairdryer and flat iron.

4.94 out of 5 average rating, 258 reviews

Holiday home in Cortona

La casina sulle Mura (with garden and spa jacuzzi)

La Casina è situata nella parte alta di Cortona, nella zona denominata "il Poggio". Si puo' giungere in auto fino al suo ingresso. Il Centro citta' e' raggiungibile a piedi in pochi minuti, percorrendo strade e vicoli caratteristici. Gode di una splendida vista su Cortona e la Valdichiana. E' facile parcheggiare nelle vicinanze. Gli ospiti che giungono in treno in una delle stazioni vicine, su richiesta, possono essere prelevati e accompagnati a destinazione.

5 out of 5 average rating, 13 reviews

Farm stay in Camucia

The Garden of Olives | Casa Ippocastano

Il Giardino degli Ulivi is a farmhouse in the heart of Tuscany, surrounded by olive groves and only 3 km away from the charming town of Cortona. The property features 6 restored farmhouse apartments, each offering authentic Tuscan character, modern comforts, and private outdoor spaces. Guests can enjoy peaceful garden, scenic views, and relax by the swimming pool, as well as easy access to Tuscany’s rich history and vibrant cultural offerings.

4.97 out of 5 average rating, 163 reviews

Apartment in Cortona

CasaNella: bright, central and panoramic

Cozy, elegant and delightful apartment in the center of Cortona, with an enchanting view that sweeps from Lake Trasimeno to Valdichiana. Carefully furnished, it is the ideal place to spend a few days in this wonderful town. A short walk from the main road, but in a quiet and panoramic location. Free parking is a short distance away. Equipped with heating and air conditioning. High speed WiFi available. Great for smart working.

4.94 out of 5 average rating, 202 reviews

Casa del Passerino

Apartment located inside a historic building in Cortona, dating back to the 1500s, overlooking the city's main square... Our property, while condemning the war, dissociates itself from all racist behavior towards the Russian and Belarusian population. At Casa del Passerino, people of these nationalities are welcome and will be treated the same as everyone else. We look forward to seeing you in Tuscany!

4.97 out of 5 average rating, 102 reviews

Home in Torreone

Tuscany House | View Breathtaking

Casa Belvedere is 10 minute drive from the center of Cortona. Is located along an old Roman road and enjoys a spectacular view of Cortona. Equipped cooking, 2 double room, 2 bathrooms, sofa bed, large garden with provides all the comforts to relax, sunbathe and have lunch under the pergola, enjoying the view of Cortona and the Val di Chiana.

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Other great holiday rentals in Vallone Pip

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.

5 out of 5 average rating, 7 reviews

Home in Monsigliolo

[5 minutes from Cortona]The farmhouse of Cortona

denizRating, 5 stars1 month ago

Antonella was a great host, very quick response to our questions, always had positive communication with us. Her house was an extraordinary house, this stone house and antique items from the 1800s were a very nice experience for us. The house was very nice and in a quiet location. Antonella had provided us with everything we needed, gave us a lot of activities and local advice, what we were able to do from what she recommended really pleased us very much, it was nice advice. We would recommend this house to anyone who wants to spend a quiet Tuscan holiday. If we go back here, Antonella's house will be our choice again.

Villa in Ossaia

4.79 out of 5 average rating, 14 reviews

Casa Lamate

MarcusRating, 5 stars9 months ago

Lovely house, great views over the plains, lovely for watching the sunset. Pool was good too. Only about 15 mins to Cortona, so very easy to go in for the day, or the evening to eat. We also visited Arezzo which is very historic - if you're staying in June or September then try to get tickets for the Giostra del Saracino in the main piazza. We shopped locally at the Conad in Camucia - opens until 9pm on Saturday which was useful when we were running late.

4.83 out of 5 average rating, 83 reviews

Nonna Nesti Vacation Home

DomenicoRating, 5 stars2 weeks ago

Sabrina is a very friendly and helpful person, the perfect accommodation to reach different places of interest and in a very quiet area.

5 out of 5 average rating, 6 reviews

Palazzo Passerini, Luxury Townhouse, Cortona

KarenRating, 5 stars1 month ago

Wow!! The home is beyond beautiful and extremely tasteful decorated. From the upstairs bedroom, the view is incredible. My family loved every aspect of the home and we enjoyed spending time together in the spacious living room. It is in the heart of Cortona, so we were able walk everywhere. Special thanks to Marialena, as she ensured we had everything we needed and helped us arrange rides from and to the train station. We can’t wait to return to stay here again!

4.78 out of 5 average rating, 72 reviews

The farmhouse of Leda, single family house

DanielRating, 5 stars8 months ago

Lorenzas villa is the perfect escape to Cortona. Set in the valley, its long, picturesque driveway leads you to a charming estate that is as fabulous as you’d imagine. Simplicity abounds in this Tuscan haven, complete with all you’d need for an extended stay such as mine. This is my second time renting the home for over a month and it will give you all the peaceful tranquility and zen vibes you may ever need. Close to Cortona for fantastic restaurant and sightseeing as well as local grocery stores to stock the home for your stay. To note: I his farmhouse has been in her family for generations and is delicate and simple, treat it with love as it holds so many special memories that exude from its walls. The farmhouse is located on the second story as the first story has not been renovated and remains locked. I hope to return again to finish my book. Thank you!

Farm stay in Cortona

4.88 out of 5 average rating, 40 reviews

Land of Cortona - Casa Smeraldo

HedwigRating, 5 stars10 months ago

We had a very nice stay. A beautiful separate private cottage on the property with a nice private terrace. Location is in a nice quiet place, but villages and towns are easily accessible by car. Also nice that a bakery comes by in the morning with fresh rolls.