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Holiday houses in San Rocco-Lischeto

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Top-rated holiday rentals in San Rocco-Lischeto

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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
4.98 out of 5 average rating, 176 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, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!

Top Guest favourite
A balcony is shown with a small table set for dining, accompanied by two red chairs. A kettle is visible on the table, and greenery from nearby trees enhances the natural setting. The view includes open fields and a clear sky.
Condo in San Rocco a Pilli
4.9 out of 5 average rating, 30 reviews

La Casina di Coco

Welcome to Casina di Coco, where you can enjoy the comfort and tranquility of a small town just a few kilometers from the center of Siena! Located on the ground floor with a separate entrance, living room, kitchen, two bedrooms, bathroom, large terrace overlooking the countryside and parking space, the apartment is in a strategic position to visit Siena and less than an hour from the main tourist and food and wine destinations of the province such as Montalcino, Pienza, San Gimignano and the Crete Senesi.

Guest favourite
A bright and spacious living room features a large marble coffee table and a pair of elegant chaise lounges. A striking painting hangs above a contemporary white sofa adorned with colorful cushions. Antique furnishings and a patterned rug enhance the room's sophisticated ambiance.
Apartment in Centro
4.94 out of 5 average rating, 363 reviews

Museum Suite - Luxurious unit with a River View -

After 13 wonderful years of hosting on Airbnb, the time has come to close this incredible chapter and embrace the next. These upcoming 7 months will be the final season for MuseumSuite, in Jan 2027, the property will be sold and transformed into a private family residence. It has been an absolute honor and a privilege to welcome guests from all walks of life. Each of you has deeply enriched my journey, and I hope that MuseumSuite has left a beautiful, lasting impression on your lives as well.

Guest favourite
The image captures a tranquil outdoor area featuring a swimming pool surrounded by well-maintained grass and foliage. A shaded structure offers seating beside the pool, with steps leading into the water visible. Rolling hills and clear blue skies are seen in the background.
Home in Sovicille
4.94 out of 5 average rating, 128 reviews

Podere Scorno country house with swimming pool

Piccola e accogliente casa di campagna ideale per coppie, su una collina della campagna senese. Edificio in stile toscano in pietra, con una storia secolare. La proprietà è stata comprata e ristrutturata a fine anni '90. Con un ampio giardino con piscina, frutteto, oliveto, vigna e orto, per gli amanti del verde. La piscina è aperta da metà maggio a fine settembre. Non accettiamo animali domestici. Informiamo i nostri ospiti che come host privati non siamo abilitati a fornire colazione.

Top Guest favourite
A medieval stone tower stands tall against a clear blue sky, showcasing its historic architecture. The narrow road lined with greenery leads to the entrance, with the texture of the stonework and windows highlighted, inviting guests to explore its unique charm.
Tower in San Quirico d'Orcia
5 out of 5 average rating, 111 reviews

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Top Guest favourite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.98 out of 5 average rating, 131 reviews

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Top Guest favourite
A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.
Apartment in Castelnuovo Berardenga
4.94 out of 5 average rating, 179 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Top Guest favourite
Cottage in Sovicille
4.94 out of 5 average rating, 236 reviews

From Simone, podere santi Lucia and Pietro

Recently opened, the property is part of a Tuscan farmhouse with a separate entrance, located in the Sienese countryside just 10 minutes from Siena's historic center. The apartment features two double bedrooms, a bathroom with a shower and a bathtub, a living room, and a kitchen. A 60*120 cm baby crib with safety rails is available upon request. A shared farmyard is available outside. The price is for the entire apartment. Tourist tax €1.50/person

Top Guest favourite
A natural swimming pool features a sandy beach area, surrounded by lush greenery and plants. Soft, clear water reflects the blue sky, creating a serene environment for relaxation.
Villa in Tavarnelle Val di Pesa
5 out of 5 average rating, 25 reviews

Tuscan Luxury Villa • Natural Pool & Privacy

Immagina di svegliarti in totale privacy, circondato dalle colline del Chianti, con la tua piscina naturale, la spiaggia e il chiringuito. Non è solo un soggiorno, ma una vera “private luxury experience” toscana. Tenuta Virgilio nel Chianti è una villa immersa nella natura, perfetta per chi cerca relax, silenzio ed esclusività in Toscana. Oltre 3 ettari di uliveto e totale privacy: nessuno spazio condiviso, solo la tua esperienza in Toscana.

Guest favourite
A bright kitchen features modern amenities including a stove, refrigerator, and microwave. Natural light floods through the open window, offering views of the Tuscan herb garden. A wooden dining table is surrounded by six white chairs, complemented by soft earth-toned cabinetry.
Apartment in SAN ROCCO A PILLI - SOVICILLE
5 out of 5 average rating, 9 reviews

Nero 3 bedroom 2 bathroom semi detached apartment

Rinidia Bio offers self-catering apartments set in an organic fruit and vegetable farm. The Tuscan herb garden, features an infinity pool with views of the countryside. Parking is free. Each apartment comes with a fully equipped kitchen, independent air conditioning, heating, and free Wi-Fi. The furniture and the linens follow the Tuscan tradition with a twist of shabby chic. The bathrooms feature a shower excavated in travertine stone.

Top Guest favourite
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, 100 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).

Guest favourite
Home in Monteroni d'Arbia
4.98 out of 5 average rating, 55 reviews

Golden View - Dream Farmhouse in Tuscany

A peaceful corner among beautiful cypress trees, where silence and tranquility reign. Relax in the hydromassage waterfall in the garden, light the fireplace on cooler evenings, or enjoy a barbecue. The master bedroom pampers you with a hot tub and private sauna. The outdoor tub will be usable from May 1 to November 1 of each year, then it can be used on request but the internal water will not be able to exceed 25 degrees.

Popular amenities for San Rocco-Lischeto holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. San Rocco-Lischeto