Vacation rentals in Portole

4.99 out of 5 average rating, 187 reviews

A small balcony is featured with two black woven chairs flanking a round table. On the table, a bottle and two glasses are set against a backdrop of panoramic views of rolling hills and terracotta rooftops under a partly cloudy sky.

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.

ValueFamilyParking

4.95 out of 5 average rating, 108 reviews

The exterior of the house is depicted, featuring a two-story structure with a light yellow facade and brown shutters. Lush greenery surrounds the building, including tall trees and flowering plants. A pathway leads to the home against a backdrop of a blue sky with scattered clouds.

Home in Cortona

Casa Lucy

Casa situata sulla collina cortonese, completamente ristrutturata, costituita da 3 camere matrimoniali, 2 bagni e openspace cucina e sala da pranzo. Si trova a 5 minuti dal centro storico di Cortona e in ottima posizione per raggiungere le più belle e caratteristiche località della Toscana e Umbria come Pienza, Montepulciano, Castiglione del Lago fino a città culle dell'arte come Firenze, Arezzo,Siena e Perugia. Obbligatoria tassa di soggiorno da pagare in loco (2,50 euro a persona per 4 giorni)

LocationValueWalkability

Superhost

A saltwater swimming pool is framed by lush greenery, with sunbeds positioned on the grass nearby. A natural fence enhances the privacy of the outdoor area, which is surrounded by trees that provide shade and a serene environment.

Villa in Pierle

Historic Villa Getaway with 6BR/9BA, Pool, Views

This six-bedroom villa complex, set in atop a hill, overlooks a panorama of surrounding hills, fully immersed in nature. Villa was estored in 2020, with the rustic flair preserved to maintain its unique charm. The authentic stonework, the open fireplace in the entrance hall, and the exposed beams are in harmony with wooden floors. The villa is within 30min drive of Cortona. Also near Siena, Gubbio, Assisi, Lake Trasimeno, Arezzo, Montepulciano, Spoleto, and Perugia. (Read other details to note)

ValueFamilyGrill

4.89 out of 5 average rating, 46 reviews

A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.

4.9 out of 5 average rating, 240 reviews

Tuscan charm of villa - countryside - Villa Senaia

Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

ValueFamilyIndoor spaces

Farm stay in Montepulciano

Aerial view of a scenic agriturismo surrounded by vineyards and rolling hills. The property features a pool and is framed by tall cypress trees, enhancing the natural landscape of lush green and golden fields under a partly cloudy sky.

Rural Tuscany | Family farmstay with restaurant

Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

LocationFamilyWalkability

4.96 out of 5 average rating, 115 reviews

5.0 out of 5 average rating, 25 reviews

Home in Cortona

Breathtaking views: Historic House w/Terrace & BBQ

Welcome to our longtime family home — an elegant, light-filled space in the heart of Cortona. Set in a quiet historical square just steps from the main piazza. Enjoy spectacular views of the valley, lake and city. This elegant house blends the character of Tuscany with warmth and comfort. Antique terracotta beamed ceilings floors, a terrace with panoramic views, a house that tells a story. It's a space for travelers who appreciate beauty, quiet, and the atmosphere of an authentic home.

LocationFamilyQuiet

A private pool area is surrounded by lush greenery and offers stunning views of the landscape below. Several sun loungers are positioned on the pool deck, with large umbrellas providing shade. The serene ambiance invites relaxation amid nature.

4.99 out of 5 average rating, 89 reviews

Tuscany Villa Mammi

Grande villa in pietra ristrutturata tra i boschi di Castiglion Fiorentino, vicono a Cortona, Arezzo e Siena. Un paradiso di privacy con piscina, idromassaggio panoramico con vista mozzafiato sulla valle e ping pong. Godetevi serate magiche sotto le stelle grazie all'autentico barbecue in pietra e al forno a legna per la pizza. Il rifugio ideale per chi cerca relax, natura e comfort nel cuore della Toscana, perfetto per famiglie o gruppi che sognano una vacanza davvero indimenticabile.

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The traditional stone house is surrounded by a well-maintained lawn, showcasing a multi-level structure with a picturesque roofline. Large arched windows accentuate the façade, providing ample natural light. A clear blue sky serves as a backdrop, highlighting the tranquil rural setting.

4.95 out of 5 average rating, 19 reviews

Podere Ortaglia di Sotto

Located in the Tuscan countryside, a 10-minute drive from Castiglion Fiorentino, Podere Ortaglia di Sotto offers a private pool with enclosed garden, WiFi and free private parking. The holiday home features 5 bedrooms, 6 bathrooms, a flat-screen TV, a dining area, a fully equipped kitchen and a terrace with mountain and valley views.(The swimming pool is available from 23 May to 17 October, closing and opening dates may vary depending on the weather)

LocationFamilyGrill

5.0 out of 5 average rating, 17 reviews

The villa is shown from an angled view, featuring a well-maintained exterior with decorative lighting illuminating the grounds at twilight. Neatly arranged flower beds enhance the entrance, while a spacious porch with multiple windows reflects a classic architectural style.

Home in Cortona

Villa Lucia

Nel cuore della Toscana, a pochi chilometri da Cortona si trova questa incredibile villa moderna. La villa è il circondata da un lussureggiante giardino, una suggestiva fontana, una vasca per pesci e dalla meravigliosa piscina. Per allietare le giornate fredde e nebbiose, senza rinunciare al benessere, la villa mette a disposizione un angolo con Jacuzzi, ideale in ogni momento dell'anno. Per i più piccoli uno spazio con giochi all'aperto.

ValueFamilyAccuracy

5.0 out of 5 average rating, 65 reviews

An aerial view showcases the expansive grounds of Villa Pergo, surrounded by lush greenery and fields. The infinity pool is highlighted, surrounded by sunbeds and shaded by cypress and ancient trees. The countryside landscape stretches into the distance, enhancing the villa's serene setting.

Villa in Pergaccio

Villa Pergo is an ancient charming country villa

Stay in a piece of Tuscan history at Villa Pergo, a charming countryside estate dating back to 1640. Surrounded by olive groves and rolling hills near Cortona, the villa offers authentic character, panoramic views, and a beautiful infinity pool. With space for up to 11+1 guests in 6 bedrooms, large gardens and peaceful surroundings, it is the perfect retreat for families or groups looking to experience the true charm of Tuscany.

FamilyLocationOutdoor spaces

4.96 out of 5 average rating, 419 reviews

The bedroom features a spacious double bed adorned with soft linens and cushions, complemented by subtle bedside lamps. Exposed wooden beams highlight the ceiling, while natural light filters through a window, adding warmth to the serene, neutral color palette.

Apartment in Cortona

Cortona Shabby Chic House - independent & balcony-

Questo è un appartamento curato da una Superhost che vive Cortona ogni giorno. Il mio alloggio è situato in pieno centro storico a soli pochi passi dalle piazze e vie principali. Questo grazioso appartamento è di recente ristrutturazione e può ospitare fino a 3 persone. Appartamento indipendente con entrata singola tutto in un solo piano, con balcone. Arredato con cura, dotato di tutti i comfort per un totale relax

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The property features a charming rustic stone house and a secondary building set against a backdrop of bright blue skies and scattered clouds. Lush green grass surrounds the structures, enhancing the natural beauty of this tranquil countryside setting.