Vacation rentals in Olevole

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Top-rated vacation rentals in Olevole

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Top guest favorite

Guesthouse in Macciano

4.96 out of 5 average rating, 165 reviews

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.

Guest favorite

A private pool is surrounded by well-maintained grass and lined with sun beds, offering views of cypress trees and the countryside. The rustic house in the background is complemented by a serene landscape under a wide sky, providing a tranquil atmosphere.

Home in Orvieto

4.99 out of 5 average rating, 212 reviews

Vineyards Paradise

Amazing country house immersed in the vineyard of Cantina Lapone, viewing Orvieto. Recently restored, over 100 sm, organised on two floors. Ground floor is a single space with a big living room (with fireplace) and a spacious open kitchen. First floor with two bedrooms and two bathrooms: the main bedroom (looking at Orvieto) with a double bed and internal bathroom and a second one with a double bed and a bed sofa. Private garden and parking. Private pool (shared with another 4 guests house).

Guest favorite

A spacious terrace features natural wooden beams and panoramic views of the surrounding landscape. Comfortable wooden seating arrangements are placed across the area, creating a welcoming environment. Potted plants add a touch of greenery, enhancing the overall ambiance of the outdoor space.

Villa in Montepulciano

4.95 out of 5 average rating, 221 reviews

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

Top guest favorite

The rustic stone facade of the home is seen alongside the ancient church of San Giovenale, featuring a tall bell tower. A wooden door invites entry, while the church's distinctive architecture showcases historic details. Clear blue skies create a bright backdrop.

Home in Orvieto

4.95 out of 5 average rating, 236 reviews

The Loggia of San Giovenale

The house is in the oldest square of Orvieto, San Giovenale with the beautiful Romanesque church of the 11th century. A Loggia with stunning views of the Paglia Valley from where you can discover Mount Amiata, Mount Cetona and Mount Peglia. Furnished with custom-made furniture by Orvieto master carpenters, the wooden ceilings on the first floor and the handmade terracotta floor make it a charming accommodation in which to spend a wonderful stay in Orvieto. CIR 055023CASAP19060

Guest favorite

The exterior of the house is constructed from local stone, showcasing a rustic charm. A covered porch extends over the front entrance, providing shaded seating areas. Surrounding the house, a spacious grassy area features trees and landscaping, enhancing the serene natural environment.

Home in Parrano

4.82 out of 5 average rating, 110 reviews

The Wood's House between Umbria and Tuscany

The house is surrounded by dense Mediterranean vegetation and a 1,000 m² garden. The house is equipped with 2 rooms mezzanine ( the ceilings are high about 5 meters ) and was restored preserving the characteristic local stone . Within a radius of about 25-30 km you will find: Citta' della Pieve, Orvieto, Cetona, San Casciano de' Bagni and many more ... In an hour by car you can reach cities such as Florence, Siena, Perugia, Assisi, in addition to Val D'Orcia and Val di Chiana.

Top guest favorite

The kitchen area features wooden cabinets and modern appliances, including a gas stove and oven. A round table with a colorful design is surrounded by black wire chairs. Large windows provide natural light and views of the surrounding landscape.

Cottage in Castell'Azzara

4.99 out of 5 average rating, 139 reviews

Your Private Tuscan Retreat

This beautiful sheepherder’s stone cottage is equipped with modern comforts and spa facilities free of charge. The large grounds of forest and meadow span a ridge and provide panoramic views of the valley toward Val d’Orcia to the north, the expansive Maremema to the south, and the ancient volcano of Amiata to the west. This is the perfect getaway for those wanting a private retreat from which to explore the rich wine, food, culture, history, and landscape of southern Tuscany.

Top guest favorite

A view from the window reveals a serene landscape of rolling hills and valleys bathed in soft morning light. The garden below is adorned with colorful flowers and greenery, enhancing the tranquil atmosphere of the Tuscan countryside.

Home in San Quirico d'Orcia

4.99 out of 5 average rating, 209 reviews

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni

Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

Top guest favorite

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

4.98 out of 5 average rating, 134 reviews

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.

Top guest favorite

A view from the apartment window shows terracotta rooftops and stone buildings of Assisi. The landscape is dotted with greenery, and a sky filled with soft clouds reflects the historical charm of the neighborhood.

Apartment in Assisi

4.96 out of 5 average rating, 135 reviews

[Breakfast included] Vacation under the Paintings

Prestigious apartment in a historic building from the early 19th century in the center of Assisi overlooking the central Piazza del Comune, therefore not completely silent. BREAKFAST includes a typical Italian breakfast at the BAR TROVELLESI under the house. The ZTL times may vary, so we advise all guests to pay attention and look at the times on the displays before entering the gates with the cameras. CHECK-IN at 4:00 PM CHECK-OUT at 10:00 AM

Top guest favorite

A charming stone cottage is surrounded by lush greenery and blooming flowers. A small outdoor seating area with green metal chairs and a table is positioned in the garden, inviting guests to enjoy the peaceful surroundings. The cottage features a sloped roof and a chimney.

Cabin in Massa Martana

4.94 out of 5 average rating, 162 reviews

Country Chalet and mini spa

A welcoming and comfortable nest, immersed in the bright colors of the Umbrian countryside, among roses and lavender, in the silent garden that frames it... Live a romantic dream: let yourself be enveloped by the warmth of the hot tub, under a starry sky and in the heart of the magic of our chalet. An oasis of tranquility, but well connected to all the major attractions of the region...

Guest favorite

A spacious green garden is visible, dotted with trees offering natural shade. A wooden dining table with chairs is positioned under the trees, providing an inviting setting for outdoor meals. The rustic brick building stands in the background, complementing the serene surroundings.

Farm stay in Simignano

4.89 out of 5 average rating, 198 reviews

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Top guest favorite

A bright kitchen features a glass ceiling with arched windows, allowing ample natural light. A wooden dining table is adorned with a bowl of fresh fruit, surrounded by chairs. Shelves display various kitchen items, while the overall space is enhanced by potted plants.

Apartment in Orvieto

5 out of 5 average rating, 104 reviews

Casa Teatro

Casa teatro is an elegant apartment located inside a prestigious building in the heart of Orvieto's historic center, a few steps from Piazza del Popolo and the city's most important tourist sites. The apartment is stylishly furnished, bright, characterized by ceilings and walls with frescoes attributed to the famous 19th-century painter Andrea Galeotti.