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Vacation rentals in San Sisto

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Top-rated vacation rentals in San Sisto

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

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Top guest favorite
Villa in Chianciano Terme
4.97 out of 5 average rating, 126 reviews

Charming Tuscan Villa with View forFamily&Friends

Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visits & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Top guest favorite
A shaded pergola stands by a large swimming pool, draped with light curtains. Comfortable outdoor seating surrounds a circular table. Lush greenery and flowering plants create a serene backdrop, enhancing the tranquil atmosphere of the estate.
Villa in Guardea
4.99 out of 5 average rating, 101 reviews

Exclusive 10 Acre Estate w/ Pool & Olive Grove!

Enchanting, exclusive 10acres estate on a hill, memorable sunsets; large pool framed by lavender&rosemary, open year-round. New air conditioning, Starlink internet. Very private&peaceful 2 floors, 4bedrooms, 4baths, jacuzzibathtub, 55inch smartTV, well-equipped kitchen, porch & pergola for alfresco dining, Weber barbecue, pizza oven, olive grove, fireplace; 20 min. to Orvieto,Todi,Amelia; 10 minutes drive to train station to Rome/Florence, 5min drive to shops in town. Grounds/pool caretaker

Guest favorite
The rustic farmhouse, crafted from natural stone, features a welcoming facade with light green shutters. A tiled roof is complemented by a traditional chimney. Steps lead to the entrance, surrounded by lush greenery and unobstructed views of the rolling hills beyond.
Villa in Porzone
4.92 out of 5 average rating, 105 reviews

Stylish Umbrian farmhouse in stunning countryside

Welcome to Casale Amerina, an idyllic place to rest, rebalance and revitalise. This is a much-loved Umbrian farmhouse, with stylish contemporary interior, set in wonderful Umbrian countryside. There are two bedrooms with king size beds, a comfy sitting room with a balcony, and a gorgeous kitchen-dining room with Tuscan oak beams and a fireplace. Soak up the sun on our grass lawn, relax in the shade of our olive, walnut and fig trees, or explore the local area with its wonderful hilltop towns.

Top guest favorite
The villa is showcased from an elevated perspective, revealing its traditional stone facade. A well-maintained garden surrounds a clear swimming pool, adding to the serene landscape of rolling hills. The evening light enhances the inviting atmosphere of the outdoor and indoor spaces.
Villa in Todi
5 out of 5 average rating, 31 reviews

Exclusive panoramic villa with private pool

Villa Giorgia is a farmhouse located on the hills of Todi that offers a breathtaking view in a context of complete privacy, just 10 minutes from the city center. The villa accommodates up to 7+1 people in 4 bedrooms, 2 of which have a private bathroom. The refined yet traditional interiors, the living room with fireplace and the equipped kitchen overlook a garden with swimming pool and relaxation areas. A perfect retreat for those seeking relaxation and privacy with all the necessary comforts.

Top guest favorite
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
4.97 out of 5 average rating, 231 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.

Top guest favorite
A serene landscape features rolling green hills under a vibrant sunset sky, casting soft colors across the horizon. A stone wall is adorned with lush greenery and flowers, providing a tranquil viewpoint for someone contemplating the picturesque view of the valley and distant hills.
Home in Cetona
4.99 out of 5 average rating, 167 reviews

Casa Dolce Toscana | Panoramic Suite with a View

CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.

Top guest favorite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.93 out of 5 average rating, 313 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

Guest favorite
A natural stone path leads from a vibrant garden to a sparkling swimming pool, surrounded by lush greenery. The pool is visible in a sunlit area, with scenic mountains serving as a backdrop. Flowering plants add color and texture to the outdoor space.
Villa in Todi
4.95 out of 5 average rating, 38 reviews

Tiber Valley’s spectacular view - jacuzzi & pool

A stone farmhouse with pool and jacuzzi, nestled in the woods and in the Umbrian countryside, overlooking a breathtaking view from which you can see a bend of the Tiber river. Suitable for those seeking a relaxing stay in a context of peace and nature. With its hill-top towns and ancient castles, sunflower fields and olive groves, Umbria is a region steeped in history, art and culture. Its cuisine and wines rival those of its neighbours Tuscany and Lazio. CIN: IT054052C21J031410

Top guest favorite
A spacious bedroom features a large, inviting bed adorned with a light blanket. Natural light floods through sheer curtains draped over a large window, revealing views of the lush valley outside. The rustic walls, made of tufo, add a unique character to the room.
Apartment in Civita
4.94 out of 5 average rating, 286 reviews

The Cellar (Palazzo Pallotti)

The apartment is two floors below the square, entirely dug into the tuff. Overlooking the valley, it is isolated from the noises of the street, quiet, private, and very welcoming. The tuff walls give it an ancient vibe to transport you to another time. It can be reached on foot, via a footbridge that takes you directly to the square where the property is located. It is perfect for short stays of complete relaxation, but with the fully equipped kitchen you can make the most of it.

Guest favorite
An infinity pool stretches across the foreground, reflecting the blue sky and surrounding landscape. A single turquoise umbrella provides shade beside a lounge chair, while lush greenery and distant hills create a serene backdrop.
Home in Todi
4.83 out of 5 average rating, 165 reviews

"Palazzaccio Todi Estate" hideaway

from 15th JULY to 31st AUGUST - Bookings should start on a Saturday and be a minimum of 7 nights or multiples. Nestled in the hills opposite Todi lies our centuries old estate. A 3 bedrooms stone house with fireplace, 18 mt infinity pool, kids' pool and playground, surrounded by 40 hectares of private oak wood and olive orchard. Perfect place for a family holiday, friends get together or couple getaway. We have put our love and sweat to make this place like no other.

Top guest favorite
A rustic stone farmhouse is embraced by mature olive trees and lush greenery. The building features traditional window shutters and is set against a clear blue sky, with a gravel pathway leading up to the entrance, enhancing the tranquil countryside ambiance.
Farm stay in San Quirico d'Orcia
4.98 out of 5 average rating, 115 reviews

Podere Pereti Nuovi – Modern Tuscan Villa

Podere I Pereti was entirely build by our grandfather Remo in the 1970's. My siblings and I spent most of our summers on the porch with our grandparents watching sunsets and admiring the view of the Val d'Orcia. Entirely surrounded by vineyards and olive groves. Nonno Remo, besides having a building company, proudly produced Orcia red wine that was consumed by the family. From the 150 olive trees, every November we filled our tanks with green gold olive oil.

Top guest favorite
The outdoor scene showcases a renovated stone farmhouse surrounded by lush greenery. An inviting pool reflects the sky, while the covered porch is framed by a combination of shrubs and trees, enhancing the tranquil setting. A wooden pergola is visible beside the pool area.
Villa in Todi
4.97 out of 5 average rating, 64 reviews

Casa Roscetta, Todi Home with a view

Casa Roscetta, situated in the Hills of Umbria, with breathtaking views of the Italian countryside, especially the medieval town of Todi, only a 10 minute drive away. The outdoor pool and Wifi are part of the various high-end amenities available to our guests. The house was first renovated in the 1980's from a stone farm house. The pool was built in the 1990's and the entire house has just been completely renovated in 2020 to a high standard.

Popular amenities for San Sisto vacation rentals

  1. Airbnb
  2. Italy
  3. Umbria
  4. Perugia
  5. San Sisto