Holiday rentals in Oliveto

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Oliveto

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

1 of 1 pages1 / 1

Top guest favourite

An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.

Home in Simignano

4.97 out of 5 average rating, 195 reviews

Casa al Gianni - The Simignano Barn

Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

FamilyLocationView

Top guest favourite

A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.

Farm stay in Ruscello

4.99 out of 5 average rating, 527 reviews

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

FamilyLocationTV

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

In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas

LocationFamilyKitchen

Guest favourite

Home in Montagnano

5.0 out of 5 average rating, 10 reviews

Il Podere - Rustic charm in Tuscany

Imagine a Tuscan farmhouse, rustic but furnished with modern and functional taste, where you immediately feel at home. It is located between Arezzo, in Valdichiana, in a quiet area but close to all amenities, among the most beautiful villages such as Cortona, Montepulciano, and Lake Trasimeno, a short distance from Umbria. Three double bedrooms, two bathrooms, living room with sofas, kitchen, dining room, enclosed garden, furnished porch, patio with table tennis and heated swimming pool. Wi-Fi.

LocationFamilyTV

Guest favourite

Holiday home in Albergo

4.95 out of 5 average rating, 39 reviews

Charming Tuscan Stone House • Private Pool & View

CITY TAX FREE! Hello!I bought this house because I had the dream to have a tipical house made of stones in the Tuscan country. I enjoy having guests to share my love for this place. It is very quiet and it has all comforts, all the furniture is pretty new and modern. The interiors are tipical of the area, with the red "cotto" floor and the exposed wooden ceilings. It is my paradise because I love the big garden (300 mts) and the view that it has on the tuscan hills, with breathtaking sunsets.

FamilyLocationKitchen

Top guest favourite

A serene pool area is showcased with two sun loungers positioned beside a tranquil salt-water pool. The expansive view of the valley and distant cityscape adds to the peaceful ambiance, while greenery surrounds the space, enhancing the sense of privacy and relaxation.

Farm stay in Monte San Savino

4.99 out of 5 average rating, 114 reviews

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.

FamilyValueQuiet

Top guest favourite

A spacious piazza is surrounded by elegant medieval architecture, featuring a central hexagonal area with open-air seating. Stone pathways lead to various shaded spots, while umbrellas provide shelter for patrons. Beautiful clouds drift overhead, enhancing the vibrant scene of daily life in the historical center.

Flat in Arezzo

5.0 out of 5 average rating, 155 reviews

Piazza Grande Boutique Apartment

Overlooking the most beautiful square in the historic center of Arezzo, where the re-enactment of the Giostra del Saracino takes place, the Piazza Grande Boutique Apartment is located on the second floor of a medieval building, overlooking the beautiful palaces and the Vasari Loggias and is a unique location of its kind. The decor, the work of Countess Cesaroni Venanzi, was created with beautiful antique furniture reinterpreted in a modern way and enriched with contemporary influences.

ValueFamilyBiking

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.

LocationFamilyNearby

Guest favourite

Aerial view of the estate displaying lush vineyards surrounding an inviting shared pool. The landscaped garden features numerous trees and red sun loungers. Two rustic buildings, one with a tiled roof, are visible, enhancing the serene rural atmosphere.

Apartment in Monte San Savino

4.93 out of 5 average rating, 58 reviews

Casa Bianchini | Duplex 6-bedroom apartment (12 +1

La Foresteria is a historical rural estate located near Arezzo in southeast Tuscany. Surrounded by lush countryside and fruit orchards, it offers guests serenity and peace. The property features ten carefully restored apartments, a private swimming pool, and an on-site restaurant where guests can enjoy breakfast and dinner. Its location is perfect for relaxing or exploring Tuscany’s art, culture, and nearby cities like Cortona, Florence, Siena, and Montepulciano.

FamilyLocationView

Guest favourite

A bright and airy bedroom features a spacious bed dressed in crisp white linens. A colorful abstract painting adorns the wall above the bed. A full-length mirror reflects light, and an ensuite bathroom can be seen through an open door.

Apartment in Albergo

5.0 out of 5 average rating, 60 reviews

[Tuscany Hills] Relax e Charging Station

Elegant apartment, nestled in the Tuscan countryside, functionally furnished for travelers from around the world looking for an exclusive and relaxing stay. Located in a strategic position to admire the beauty of the Tuscan countryside and reach characteristic villages and cities such as Arezzo and Siena. You can also go horseback riding or rent a bike and e-bike to enjoy unforgettable landscapes or ride the famous white roads.

ValueFamilyLaundry

Guest favourite

A serene saltwater infinity pool showcases a stunning view of rolling hills blanketed in lush greenery. The expansive sky transitions into soft hues, reflecting the natural tranquility of the surrounding landscape. The scene encapsulates the peaceful atmosphere of the Tuscan countryside.

Home in Civitella in Val di Chiana

4.95 out of 5 average rating, 42 reviews

Tuscan house with private infinity pool

Gello is an ancient house originally built as a watchtower, meticulously restored using original materials. Its interior features predominantly antique furnishings, complemented by all the amenities necessary for a pleasant and comfortable stay. Outside, numerous spaces are available for relaxation and outdoor dining, providing ample opportunities to enjoy the surroundings in natural tranquility.

LocationFamilyHospitality

Top guest favourite

A panoramic view reveals rolling hills adorned with vineyards and olive groves, stretching under a dramatic sky. The tan-coloured buildings of the property are nestled among lush greenery, while a serene pool reflects the surrounding landscape.

Flat in Quercegrossa

4.98 out of 5 average rating, 85 reviews

Tuscany jem: The Chianti Farmer's House

This wonderful newly renovated apartment retains the charm of the Chianti farmhouses and the comforts of a modern apartment. The house is located within the complex of the Fattoria di Petroio, a Chianti Classico winery. You can enjoy the beauty and tranquility of the Chianti hills, while immersing yourself in the dynamic life of a company dedicated to the production of quality wines.

LocationFamilyOutdoor spaces