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Holiday houses in Monsigliolo

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Top-rated holiday rentals in Monsigliolo

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Top Guest favourite
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.

4.99 out of 5 average rating, 189 reviews
Top Guest favourite
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)

4.95 out of 5 average rating, 109 reviews
Top Guest favourite
A light-filled living space features a comfortable sofa and a dining table set for four. A large TV is mounted on a white cabinet, while a door leads to the bedroom area, which appears partially visible in the background. Wooden beams enhance the ceiling's charm.
Condo in Cortona

Chicca: centro storico di Cortona

Luminoso, delizioso e accogliente appartamento situato proprio nel cuore del centro storico di Cortona con un panorama indimenticabile: il palazzo comunale da una parte ed il lago Trasimeno e la Valdichiana dall'altra. L'appartamento è stato recentemente ristrutturato ed è composto da una sala con divano letto, una piccola cucina, una camera matrimoniale e due bagni. Nell'appartamento è disponibile WiFi, riscaldamento ed aria condizionata, lavatrice, forno, microonde, asciugacapelli e piastra.

4.98 out of 5 average rating, 223 reviews
Superhost
Villa in Cortona

Casa I Pini

Casa I Pini has spacious and comfortable interiors. The main building, the Leopoldina, has two entrances on the ground floor. The first access takes you directly to the spacious kitchen, equipped with everything needed for cooking and complete with dining table; the kitchens location is very convenient in order to reach the gazebo and the outdoor barbecue. On the left side of the kitchen there is a small living room with sofa, satellite TV and DVD; on the right side instead you will access ...

5.0 out of 5 average rating, 9 reviews
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

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

4.9 out of 5 average rating, 241 reviews
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

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.

4.96 out of 5 average rating, 116 reviews
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

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.

4.92 out of 5 average rating, 61 reviews
Guest favourite
Home in Cortona

[Antico Casale]Tuscan Views & Private Pool Cortona

Entire farmhouse finely restored to bring back the authentic spirit of a historic stone farmhouse in Cortona. ✔ Suitable for up to 12 guests ✔ Private swimming pool ✔ 1 km from the center of Cortona ✔ Property composed of the main farmhouse on two levels (ground floor and first floor) plus a separate dependance ✔ 3 double bedrooms, 2 twin bedrooms, 1 sofa bed ✔ 3 fully equipped kitchens, 3 full bathrooms, private parking ✔ Outdoor space with a unique view and dining tables

4.94 out of 5 average rating, 34 reviews
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

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.

5.0 out of 5 average rating, 26 reviews
Top Guest favourite
The image captures a vibrant town square in Cortona, featuring a historic clock tower and a series of stone steps leading to a large building. Outdoor seating is visible, with visitors enjoying the sunny day, and nearby buildings display a range of architectural styles.
Home in Cortona

Casa del Passerino

Appartamento inserito all'interno di un palazzo storico di Cortona, collocabile nel 1500, con vista sulla piazza principale della città... La nostra struttura, pur condannando la guerra, si dissocia da tutti i comportamenti razzisti verso la popolazione russa e bielorussa. A Casa del Passerino le persone di queste nazionalità sono ben accette e saranno considerate alla stregua di tutte le altre. Vi aspettiamo in Toscana!

4.94 out of 5 average rating, 225 reviews
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

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)

4.96 out of 5 average rating, 56 reviews
Guest favourite
Home in Monsigliolo

Casale del '700 a Cortona, giardino e 4 bagni

A 5 minuti da Cortona, un casale in pietra del '700 restaurato con gusto: affreschi, travi e cotto originale, immerso tra girasoli e cipressi. Giardino privato e grande silenzio, con tutto il comfort moderno. Fino a 7 ospiti, 4 bagni, aria condizionata in ogni stanza e utenze sempre incluse. La base ideale per vivere la Toscana con calma, in totale privacy.

4.87 out of 5 average rating, 31 reviews

Popular amenities for Monsigliolo holiday rentals