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Apartment holiday rentals in Roccastrada

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Top-rated apartment rentals in Roccastrada

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Top guest favourite
Flat in Caminino
4.91 out of 5 average rating, 184 reviews

Pieve di Caminino Historic Farm

Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Top guest favourite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Flat in Montepulciano
4.97 out of 5 average rating, 131 reviews

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

Top guest favourite
The elegantly structured Villa di Geggiano is set amidst lush vineyards and well-maintained gardens. Its classic stone facade and terracotta roof harmonize with the surrounding greenery, while neatly manicured pathways and symmetrical garden beds create a picturesque landscape under a partly cloudy sky.
Flat in Siena
4.99 out of 5 average rating, 164 reviews

Villa di Geggiano – Alfieri Suite

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 idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. 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.

Top guest favourite
Aerial view of the agriturismo Santa Lucia, showcasing well-maintained grounds surrounded by lush greenery and neatly lined cypress trees. A shared swimming pool is visible at the center, complementing the rustic charm of the old farmhouse and the rolling hills in the background.
Flat in Asciano
4.94 out of 5 average rating, 141 reviews

Loggiato 2 Apartment in Tuscany with pool

The Loggiato 2 apartment for 2 people is located in the Santa Lucia farmhouse (THE FARMHOUSE IS DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is a two-room apartment located on the first floor with a private table in front of the windows of the entrance loggia. There is a double bedroom (two single beds joined to form a double bed), a bathroom with shower and a living room with functional kitchen and television. The apartment has air conditioning in the room (for a fee).

Guest favourite
A spacious bedroom features a double bed adorned with a yellow bedspread. Natural light floods in from wide glass doors leading to a balcony with views of the valley. A cozy seating area includes two armchairs and a small table, complemented by decorative curtains.
Flat in Montepulciano
4.97 out of 5 average rating, 142 reviews

Stuart White Tea Central Panoramic & Garden

Offering ample space, the apartment features two double bedrooms, two full bathrooms, and a living room with a kitchen. The bedroom balconies offer stunning views of the valley and natural light. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. It has also access to a secluded, terraced backyard garden. It provides a comfortable retreat perfect for long term stays. A public parking is available nearby.

Top guest favourite
A scenic view features a gentle hillside dotted with wildflowers, leading to the ancient Montemassi Castle perched atop. Olive trees are visible in the background, with a sky presenting a soft blend of clouds and blue hues.
Flat in Montemassi
4.97 out of 5 average rating, 116 reviews

Casa Sabina

The apartment, which provides your own private entrance, has been recently renovated and furnished with care. It is located at the foot of the ancient Castle of Montemassi in a historic square in the characteristic medieval village. With only pedestrian access allowed in this square, you can be assured to have a tranquil and peaceful stay. A 5 minute walk from the apartment, the Castle of Montemass provides visitors with a cultural activity during their stay.

Top guest favourite
A scenic view captures a quaint village nestled in the greenery, with terracotta rooftops visible among the landscape. The paved road leads to parked cars, while the distant rolling hills are dotted with trees, creating a serene backdrop.
Flat in Montemassi
4.96 out of 5 average rating, 115 reviews

"DA OSCA" in the heart of Maremma

The "DA OSCA" apartment is located on the first floor (the owners live on the ground floor) of a building located at the foot of the famous Montemassi Castle. The apartment consists of an equipped kitchen, a living room (with sofa, fireplace and dining table), 2 double bedrooms, a bedroom with a double sofa bed, 1 bathroom with shower and tub and 2 balconies. The garden is available to guests for breakfast, lunch, dinner and relaxation (use of barbecue).

Top guest favourite
Two comfortable chairs are positioned on a lush green lawn, complemented by a small wooden table. A basket of vibrant yellow flowers is nearby, set against a backdrop of rolling hills and cypress trees under a clear blue sky.
Flat in Monticchiello
4.97 out of 5 average rating, 173 reviews

Casa Bonari - a paradise for the eyes

Casa Bonari is a single-level independent apartment inside a villa at the foot of Monticchiello. It consists of 3 bedrooms, 2 bathrooms, an equipped kitchen and a living room. The rooms are bright and furnished in Tuscan style, with old restored family furniture combined with contemporary elements. The kitchen is fully equipped and the apartment is surrounded on all sides by a large garden, so that all rooms boast a beautiful view of the countryside.

Top guest favourite
A terrace table is set with two glasses of sparkling wine and a plate of cookies, overlooking the rooftops of the city. The distant bell tower is visible against a clear blue sky, framed by the balcony's railing.
Flat in Siena
4.96 out of 5 average rating, 386 reviews

The rooftop terrace

Bright and cozy 95 sqm apartment located on the 4th floor without elevator of a notified building in the heart of the city a few steps from Piazza del Campo, the Duomo and the major attractions of the city. A splendid view overlooking the rooftops will frame your apartment from which you can see the Torre del Mangia, the Basilica dei Servi and the wonderful Val d'Orcia.

Top guest favourite
The outdoor pool area features a light blue water surface complemented by three tiered fountains. A small white table with a glass is placed on the wooden deck, surrounded by two white chairs. The rustic stone buildings create a charming backdrop, adorned with greenery.
Flat in Montalcino
4.99 out of 5 average rating, 114 reviews

Castel Brunello - 2 doublebed rooms + terrace

Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.

Guest favourite
An outdoor dining area is surrounded by lush greenery and flowering plants, featuring a circular table with four elegant wrought iron chairs. A cozy blanket is draped over one chair, and a scenic view of rolling hills extends in the background under a muted sky.
Flat in Monteroni d'Arbia
4.95 out of 5 average rating, 269 reviews

"Red Rose" apartment with view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, each with an independent entrance and private garden, with a panoramic view of Siena. Located in 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).

Top guest favourite
A scenic rural landscape captures rolling hills and expansive fields bathed in warm sunset hues. The silhouette of a rustic villa, surrounded by trees and olive groves, is positioned in the foreground, while distant mountain outlines are visible on the horizon.
Flat in Pienza
4.99 out of 5 average rating, 101 reviews

Unplug at a 17th-Century Farmhouse Enveloped by Olive Groves

Pick figs and rosemary in secluded, extensive gardens and soak up the peace and quiet of this beautiful rural setting with spectacular panoramic views. Whitewashed walls, terracotta-tiled floors, and ceiling beams reflect the space's rich history.

Popular amenities for Roccastrada apartment rentals

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