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Holiday houses in Montecchio

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Top-rated holiday rentals in Montecchio

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
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.
Villa in Castiglion Fiorentino
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

LocationValueOutdoor spaces

Guest favourite
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.
Farm stay in Montepulciano
4.96 out of 5 average rating, 115 reviews

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.

LocationValueOutdoor spaces

Guest favourite
An aerial view captures a spacious garden with a private pool surrounded by sun loungers and umbrellas. Tall cypress trees line the area, while lush greenery and an expansive landscape extend into the distance, revealing rolling hills and farmland.
Villa in Chianacce
4.87 out of 5 average rating, 54 reviews

Podere Biagio | Rural Tuscan farmhouse with pool

Podere Biagio is the typical Tuscan farmhouse. It has a large panoramic garden with a beautiful landscape and a private pool. The garden has numerous shade areas to relax and a large pergola with a dining table. This is an excellent place for having lunch or dinner with a view over the Montepulciano valley. The farmhouse is located in Valdichiana, the south of Tuscany, between the towns of Cortona and Montepulciano. In this particular part of Tuscany there are some famous winemakers.

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Top Guest favourite
An infinity pool is framed by stone decking and wooden lounge chairs, inviting relaxation. Umbrellas provide shade, while terraced gardens with olive trees rise in the background. The surrounding landscape features gently rolling hills and clear blue skies, enhancing the serene outdoor setting.
Villa in Cortona
5.0 out of 5 average rating, 96 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

FamilyLocationBarbecue

Guest favourite
A ceramic pot holds fresh flowers, including daffodils and delicate blossoms, resting on a lace tablecloth. Natural light streams in from a nearby window, illuminating the arrangement. Wooden furniture is visible in the background, adding to the inviting indoor setting.
Home in Cortona
4.84 out of 5 average rating, 166 reviews

Casa vacanze Nonna Nesti

La nostra casa vacanze si trova a Cortona m a pochi km da Arezzo Siena Perugia Assisi Montepulciano e il lago Trasimeno Ideale per tour enogastronomici e culturali Oltre al grande terrazzo panoramico dove rilassarsi e ammirare le stelle ma anche cenare all'aperto vi accoglierà un grande soggiorno, sala da pranzo con camino e cucina nonché due grandi camere da letto . Sarà piacevole rilassarsi anche nel grande giardino dove poter trascorrere momenti di serenità e tranquillità.

ValueFamilyWalkability

Guest favourite
The pool area features a rectangular swimming pool surrounded by meticulously landscaped gardens. Olive trees, rosemary, and rose bushes complement the scenic views of rolling hills and distant mountains under a clear blue sky.
Villa in Pozzuolo
4.92 out of 5 average rating, 59 reviews

Fabulous Farmhouse with Pool & 360 Panoramic View

In the very centre of Italy, straddling the border of Umbria and Tuscany, this carefully restored farmhouse makes a great base for a memorable Italian holiday. Situated in an idyllic hillside position overlooking Montepulciano, ‘La Colomba’ is blessed with 360-degree views of iconic Italian landscape and fully equipped with all child amenities. Within easy reach of many of the world’s most important historical and cultural attractions, this house really is The Italian Dream.

LocationFamilyBarbecue

Top Guest favourite
The pool is illuminated with soft lighting, creating a calming ambiance during the evening. Surrounding greenery provides privacy, and seating areas are visible. The smooth water surface reflects the gentle glow, inviting relaxation in a serene outdoor setting.
Villa in Monte San Savino
4.99 out of 5 average rating, 107 reviews

Villa Tonacato - Charming Villa with private pool

Antico casale rurale, situato sulle colline Toscane con vista sulla campagna circostante . Isolato e ideale per chi desidera rilassarsi ma vicino alle principali città turistiche italiane. Ogni camera è dotata di condizionatori con tecnologia windfree, nel salotto è presente una TV 82" ULTRA HD con SKY e canali internazionali. La piscina è dotata di illuminazione Philips Hue per creare l'atmosfera giusta in ogni momento e di impianto audio Bose Soundtouch bluetooth

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Top Guest favourite
Home in Castiglion Fiorentino
5.0 out of 5 average rating, 23 reviews

Villa with Private Pool in the Tuscan Countryside

Modern villa with private pool, waterfall, large garden and relaxation area. Divided into: Suite with hydromassage bathtub, private bathroom and small refreshment corner; Apartment with 2 bedrooms, equipped kitchen and a second bathroom in elegant white faux marble. Perfect for families and groups up to 7. Features American BBQ, panoramic gazebo, ping pong, outdoor dining area and poolside shower. Close to Cortona, Arezzo, Montepulciano, Siena and the Crete Senesi.

LocationFamilyHospitality

Top Guest favourite
An aerial view captures a sprawling property surrounded by greenery, featuring a refreshing pool bordered by sun loungers. Two rustic buildings are visible, along with shaded outdoor seating areas and a playground, all set against the backdrop of the Tuscan landscape.
Farm stay in Camucia
5.0 out of 5 average rating, 26 reviews

Il Giardino degli Ulivi | 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.

ValueLocationNearby

Guest favourite
Home in Cortona
4.91 out of 5 average rating, 35 reviews

Villa Bellora | Pool & Panoramic Views | Cortona

Villa Bellora: Your Tuscan Summer Escape Perched among Tuscany's rolling hills and vineyards, Villa Bellora sits 20 minutes from both Cortona and Montepulciano. Spend your days by the private pool, with a sun deck overlooking the views. Three bedrooms, two bathrooms — ideal for families, couples, or friends. Tuscany's best wine estates, hilltowns, and thermal spas are all within reach. We're happy to share our favorite local spots.

LocationFamilyHospitality

Superhost
Villa in Lombriciano
4.85 out of 5 average rating, 67 reviews

Tuscan Villa with Pool & Views in Cortona

Set in the peaceful countryside near Cortona, Villa Il Forno offers bright, relaxed Tuscan living with private pool and fenced garden. The 3-bedroom villa hosts up to 6+2 guests and features air conditioning, Wi-Fi, outdoor kitchen, pizza oven and BBQ. Perfect for families and pet-friendly stays, it combines comfort, privacy and authentic charm just minutes from historic villages.

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Guest favourite
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.
Villa in Castiglion Fiorentino
4.96 out of 5 average rating, 55 reviews

Villa il Laghetto with Infinity Pool in Tuscany

PERFECT LOCATION FOR YOUR WEDDING, SPECIAL EVENTS & PRIVATE PARTY! PAY ATTENTION: You can book Food&Wine services such as Chef in Villa, Cooking Class and delivery shopping. The ideal location to spend days in the tranquillity of a natural oasis with breathtaking views. It's divided in a main building and a dependance, it offers pool and Jacuzzi (not hot)

LocationFamilyLaundry

Popular amenities for Montecchio holiday rentals