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Vacation rentals in San Rocco a Pilli

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Top-rated vacation rentals in San Rocco a Pilli

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

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Guest favorite
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home in Asciano
4.96 out of 5 average rating, 130 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favorite
Cottage in Geggiano
4.99 out of 5 average rating, 151 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Top guest favorite
Guesthouse in Macciano
4.97 out of 5 average rating, 221 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 tranquil scene captures a stone building featuring a tall chimney, nestled among lush greenery. The image also showcases a swimming pool area with a shallow edge, inviting relaxation within a private garden surrounded by flourishing plants.
Home in Sovicille
5 out of 5 average rating, 33 reviews

Boutique house with pool reserved for 2 guests

Casina Boutique is the only property on the estate dedicated to hospitality, and from May to September the only couple of guests is reserved the splendid swimming pool set in an ancient stone basin: an almost unique and unparalleled privilege! Casina Boutique is a typical Tuscan independent building, with terracotta floors and a beamed ceiling, part of the ancient Canonica di Trecciano. Absolute privacy and a beautiful garden, just 15 km from Siena in the quiet of the Montagnola Senese.

Top guest favorite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.92 out of 5 average rating, 267 reviews

Casa al Gianni - Hut

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Guest favorite
A swimming pool surrounded by wooden deck is visible, with sun loungers positioned nearby. The clear blue water reflects the bright sky. In the background, rustic buildings blend into a lush green landscape, creating a serene outdoor setting.
Apartment in San Rocco a Pilli
4.95 out of 5 average rating, 44 reviews

Authentic Italian Apartment in Historic Farmhouse

Set in the heart of an old hamlet, 10 minutes away from the town of Siena, this rustic apartment in a farmhouse offers charming views of the Tuscany surroundings. Enjoy the tranquillity and beauty of this stunning location right from your apartment with direct access to the gardens! Immerse into Italian culture and give yourselves the time to enjoy all the wonderful activities that the Tuscan region has to offer. The maximum occupancy is 6 people.

Top guest favorite
A field of sunflowers fills the foreground, with vibrant yellow blooms facing the sun. In the background, a rustic stone building with a bell tower is visible, surrounded by lush greenery and rolling hills under a clear blue sky with a few scattered clouds.
Apartment in San Rocco a Pilli
4.93 out of 5 average rating, 98 reviews

House of Frescoes in Siena, Tuscany

10 minutes from Siena, a recently renovated ground floor apartment with a private square ideal for relaxing. Located in a quiet area, with the convenience of walking to all the services available: supermarket, pizzerias, restaurants, bank, pharmacy, etc. Bus stop for Siena 50 m away. Great for visiting Chianti, Val d'Orcia, Crete Senesi. Marked hiking trails, both on foot and by bicycle (Strade Bianche, Via Francigena, Tuscany Camp).

Top guest favorite
An elegant medieval castle is surrounded by lush olive trees, showcasing its stone façade and characteristic towers. Soft lighting emanates from the windows, creating a warm ambiance as dusk approaches. The castle is set against a backdrop of gently rolling hills, enhancing its historic charm.
Castle in Barberino Tavarnelle
4.89 out of 5 average rating, 123 reviews

Suite in Castello di Valle

A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.

Top guest favorite
A view from the interior showcases a private terrace with a small table and chairs. The scenery includes rolling hills and distinctive Tuscan landscapes, framed by the open window and rustic brick walls.
Vacation home in Monteroni d'Arbia
4.93 out of 5 average rating, 101 reviews

White lily with a view of Siena

Caggiolo is a completely renovated farm consisting of several apartments, with a panoramic view of Siena. Located 1 km from Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Guest favorite
A wide arched window frames a panoramic view of the historic cityscape at dusk. Illuminated buildings, including two prominent towers and a cathedral, are visible amidst the gently rolling rooftops. A wrought iron railing adds a touch of elegance to the architectural detail.
Apartment in Siena
4.89 out of 5 average rating, 180 reviews

Terrace with a view of Siena

A fianco della Basilica di San Domenico, a pochissimi passi dal Duomo e da Piazza del Campo, in questo splendido ed elegante attico potrete godere della splendida vista e della comodità di raggiungere a piedi in pochi minuti tutti i maggiori punti di interesse della città.

Top guest favorite
Home in Pievescola
4.95 out of 5 average rating, 195 reviews

Borgo Ripostena – No. 8 Casa Vecchia

Charming cottage in the heart of Tuscany on a peaceful property surrounded by 5 hectares of private gardens and forest. The apartment has stunning views over San Gimignano and the Chianti Hills. One of the two bedrooms has air conditioning.

Top guest favorite
A shaded outdoor terrace features a wooden pergola draped with green vines. A round table is set with a potted plant at its center, surrounded by several chairs. Stone paths lead to the entrance of the house, framed by blooming flowerbeds.
Home in Siena
4.98 out of 5 average rating, 210 reviews

Secret Garden Siena

A beautiful house located inside the city walls of Siena. The house develops on two floors has three bedrooms and two toilets. The real strong point of this location is the private garden. Walking distance to all the main attractions.

Popular amenities for San Rocco a Pilli vacation rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. San Rocco a Pilli