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Holiday houses in Calzolaro

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Top-rated holiday rentals in Calzolaro

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

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Guest favourite
A large heated swimming pool is surrounded by a stone patio, featuring a wooden gazebo with seating and sun loungers. Lush greenery and trees frame the pool area, providing natural shade, while expansive views of rolling hills and valleys stretch out in the background.
Home in Umbertide

Casa Maestra, Umbria hills, AC, large heated pool

High above the beautiful Niccone Valley, with extensive views over the green hills and valleys of Umbria and Tuscany. In a secluded and quiet position and not over-looked. 10 minutes drive down to the valley where there is a small village with grocery store, good restaurants and a vineyard. The historic and stunning towns of Umbria and Tuscany, including Cortona, Assisi, Siena, Todi, Gubbio, and Perugia are within easy driving distance. Air conditioning in bedrooms and a large scenic heated pool

FamilyLocationBarbecue

4.96 out of 5 average rating, 25 reviews
Guest favourite
An aerial view captures a large hilltop property surrounded by lush greenery, with a spacious pool at its center. Two rustic buildings, with traditional tiled roofs, sit amidst olive trees, and expansive hills stretch into the distance under a clear blue sky.
Villa in Umbertide

Il Posto Umbria - full property with large pool

Il POSTO UMBRIA is large hilltop property with an olive grove in the middle of the Umbrian nature. It's quiet and peaceful yet not isolated. It has a large pool (10x15m) and lots of sunny areas as well as shaded spots under the trees. There are options to book culinary experiences and activities: truffle hunting, wine tastings and cooking classes. Il Posto is the perfect place to stay with a large family, multiple families or a group of friends. Come and live ‘la dolce vita’ at IL POSTO

FamilyLocationOutdoor spaces

5.0 out of 5 average rating, 9 reviews
Top Guest favourite
A spacious exterior view reveals a charming stone house complemented by vibrant sunset lighting. The image showcases an inviting outdoor seating area with two chairs, set against a backdrop of lush hills and the distant glimmer of the lake.
Home in Perugia

La Perla del Lago Casa vacanze al Lago Trasimeno

La Perla del Lago:il tuo rifugio al Trasimeno ​Ritrova la tua armonia in questa oasi di pace assoluta. Lasciati incantare dalla nostra vista magica e dai tramonti che il Lago regala ogni sera. La Casa Vacanze La Perla del Lago domina lo specchio del Trasimeno. A 8 minuti trovi la superstrada per visitare borghi come Firenze, Perugia, Gubbio, Spoleto, Norcia e molti altri. Nel borgo avrai bar,ristoranti,market, farmacia, bancomat e aree bimbi;a 3 km sorge un'azzurra piscina per il relax estivo.

ValueLocationTV

4.98 out of 5 average rating, 208 reviews
Guest favourite
The image captures a tranquil outdoor area featuring a private swimming pool with clear blue water. Surrounding the pool are several lounge chairs and umbrellas, providing shaded seating. In the background, a rustic stone villa is framed by lush greenery, enhancing the serene atmosphere.
Villa in San Pietro A Monte

Villa Casanova - Private Pool & Garden in Umbria

Countryhouse Casanova is a typical Umbrian farmhouse framed in the peaceful environment of its surrounding olive grove and centuries-old trees and the breathtaking view of the valley below. The villa features 3 independent apartments and, on the ground floor, a common lounge perfect for pleasant convivial moments. The villa is 15 km from Città Castello and 30 km from Cortona. The entire villa is fenced and the large park with private swimming pool is perfect for an holiday in total relaxation.

LocationFamilyAir conditioning

4.95 out of 5 average rating, 20 reviews
Top Guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
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.

FamilyValueDecor

4.97 out of 5 average rating, 251 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

ValueLocationPets

4.9 out of 5 average rating, 240 reviews
Guest favourite
The villa is surrounded by lush greenery, showcasing an inviting infinity pool that reflects the sky. The stone exterior of the house features warm wooden shutters, with outdoor seating visible on the terrace. Nearby, lavender plants create a serene ambiance against the landscape.
Villa in Lisciano Niccone

Villa San Martino, on the Tuscany/ Umbria border

Villa San Martino is not just another holiday in Tuscany or Umbria - this is a really special place. With spectacular views across the world famous Niccone Valley towards Mercatale di Cortona, relax in the infinity pool, or dine alfresco on the terrace. From the villa you can easily access the enchanting towns of Cortona, Pienza, Montepulciano, Siena, Perugia, Assisi and Florence. The Niccone valley is home to delightful restaurants and you can sample great local Tuscan & Umbrian cuisine.

FamilyLocationDecor

4.9 out of 5 average rating, 59 reviews
Top Guest favourite
The rustic stone building is set amidst lush gardens, framed by tall cypress trees. A winding pathway leads through the greenery, guiding towards the entrance. The structure showcases rustic charm with climbing vines and an inviting, well-maintained outdoor space. A small dog is seen wandering nearby.
Home in Città di Castello

Due Torri, Umbrian elegance

Due Torri oozes rustic Italian elegance and charm amongst the rolling hills of the Umbrian/Tuscan border. A private estate with vineyard, immersed in nature, Due Torri is the perfect place to relax and unwind. Comprising two original watch towers dating back to the 13th century, the property has been painstakingly renovated in a way which preserves the character and features of this historic building, whilst providing a modern level of comfort, style and convenience (air-con throughout).

FamilyLocationGetting around

5.0 out of 5 average rating, 27 reviews
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

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.

LocationValueCondition

5.0 out of 5 average rating, 96 reviews
Top Guest favourite
The farmhouse entrance is framed by two potted plants and orange pumpkins. A stone facade features a wooden door with gray shutters, complemented by a tiled roof. Natural surroundings are visible in the background, emphasizing the peaceful rural setting.
Home in Prato

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.

LocationFamilyBarbecue

4.98 out of 5 average rating, 145 reviews
Top Guest favourite
Apartment in Umbertide

B&B Lavinia

Nel cuore del centro storico di Umbertide, B&B Lavinia, offre un accogliente appartamento, con comodo accesso a piano terra, ristrutturato e curato nei minimi dettagli composto da una spaziosa camera matrimoniale, bagno con doccia e bidet, ampia zona living con divano letto e cucina. La location è strategica oltre che per visitare la caratteristica cittadina, anche per raggiungere facilmente i luoghi più famosi della regione come Perugia, Assisi e Gubbio.

FamilyLocationQuiet

5.0 out of 5 average rating, 26 reviews
Top Guest favourite
A rustic living area features a wooden table surrounded by two elegant armchairs and a beige sofa. A stone fireplace, stocked with logs, stands as a focal point, while wooden beams adorn the ceiling. An inviting atmosphere is created by warm, natural colors and soft furnishings.
Home in Anghiari

Casa Rosmarino Eco-Wellness Country Home

Price includes: - Infrared Sauna - Wood for Fireplace - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Treats during your stay The house is located inside a Borgo (small group of houses) Pool & parking lot are shared areas. We have 6 units for rent Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.

ValueLocationPool

4.99 out of 5 average rating, 274 reviews

Popular amenities for Calzolaro holiday rentals