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Holiday rentals in Armaiolo

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Top-rated holiday rentals in Armaiolo

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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
4.97 out of 5 average rating, 192 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!

Top guest favourite
Flat in Rapolano Terme
5.0 out of 5 average rating, 36 reviews

The Nest Il Giglio | Rapolano Terme

Il Giglio is one of the 6 housing units within the Podere Barottoli, an ancient commune of the Baroti counts whose construction dates back to the year 1000. It is located in the heart of the Crete Senesi and its location makes it an ideal destination to visit the most famous villages and cities between Tuscany and Umbria, combining history and nature without forgetting the comfort you are looking for on vacation. The beautiful swimming pool overlooking the hills and the green areas around the Podere are shared with other guests.

Top guest favourite
An aerial view reveals a charming country house nestled among rolling hills. Olive trees and vineyards extend across the landscape, while a winding road leads to the property, which is framed by tall cypress trees and lush greenery.
Apartment in Asciano
4.99 out of 5 average rating, 233 reviews

Pink like the sunset sky

The apartment is located on the 2nd floor, consisting of 2 bedrooms (possibility of making double or single beds depending on the needs of the customer), a bathroom, large living room and kitchen equipped for cooking. TV, (for those who request it, a washing machine is available from 9 a.m. to 8 p.m. in our laundry room). To come to us, a car is recommended, to be independent, and to visit the Tuscan countryside. Convenient location for visiting Tuscany I look forward to showing you the real Tuscany!

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 138 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 favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 155 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 favourite
The exterior of a charming farmhouse is visible, featuring stone walls adorned with climbing greenery. Large windows reflect natural light and overlook the landscaped garden. A gravel path leads to the entrance, surrounded by greenery and trees under a clear blue sky.
Home in Rigomagno
4.96 out of 5 average rating, 122 reviews

House Rigomagno Siena

Apartment with beamed ceilings and terracotta floors, this apartment is set in a 19th-century farmhouse located in the hills of Siena in Rigomagno Toscana. From the solarium next to the swimming pool in the middle of the olive trees, you can admire the panorama of the Sienese hills and the medieval village of Rigomagno ... all this characterizes the ideal holiday for couples or families who want to relax. Solarium, garden, terrace, swimming pool are exclusively for guests of the apartment.

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, 113 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.

Guest favourite
A green metal table is set with a bouquet of fresh flowers, surrounded by two matching chairs. In the background, a rustic brick building with barred windows is partially concealed by lush greenery, creating a serene, natural setting.
Farm stay in Rapolano Terme
4.8 out of 5 average rating, 163 reviews

Capannacce more than a Farmhouse: La Casetta

Capannacce is a special place for us. Farm, but not only. It is home. For us and for the animals that live here, horses, chickens, cows, felines and canids. Indeed, the heart of the farm is the breeding of racehorses, English thoroughbreds. And of the Pontremolese cow, a native heritage breed. We are immersed in the Crete Senesi, where every summer sunset is a delight. The countryside made of quietness that soothes, but not far from the town of Rapolano Terme and all related comforts.

Top guest favourite
The pool is illuminated with soft lighting, creating a calming ambiance during the evening. Surrounding greenery provides privacy, and seating areas are visible. The smooth water surface reflects the gentle glow, inviting relaxation in a serene outdoor setting.
Villa in Monte San Savino
4.99 out of 5 average rating, 105 reviews

Villa Tonacato - Charming Villa with private pool

Ancient rural farmhouse, located on the Tuscan hills with views of the surrounding countryside. Isolated and ideal for those who want to relax but close to the main Italian tourist cities. Each room is equipped with air conditioners with windfree technology, in the living room there is an 82" ULTRA HD TV with SKY and international channels. The pool is equipped with Philips Hue lighting to create the right atmosphere at all times and a Bose Soundtouch bluetooth sound system

Top guest favourite
A yurt is shown at night, illuminated warmly from within. The starry sky features the Milky Way, providing a stunning backdrop. An outdoor seating area with a thatched roof is visible, showcasing a tranquil atmosphere amidst a natural landscape.
Yurt in Asciano
4.98 out of 5 average rating, 196 reviews

2 ❤️ and 1 Yurt Glamping in Tuscany for adults only

Romantic glamping for adults, in the heart of the Tuscan countryside. Silver 35 m² yurt tent + 7 m² private en-suite bathroom + private outdoor wood-fired hot tub* (*EXTRA CHARGE), private relaxation veranda. Heating in the winter and air conditioning in the summer. Dinners with delivery directly to the Yurt, available for an even tastier experience (*SURCHARGE*). - Private parking, WiFi - Kitchen with refrigerator, microwave, (NO STOVE) + private outdoor barbecue.

Top guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 105 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Guest favourite
Flat in Rapolano Terme
5.0 out of 5 average rating, 20 reviews

Dimora Senea - Stunning Panoramic Pool

❤Dimora Senea❤ ✔ Luxury apartment (100 m²) in the context of a farm overlooking the Crete Senesi ✔ Comfortable and relaxing environment ✔ Panoramic swimming pool shared with other guests of the Podere ✔ Free and reserved parking on site ✔ About 10 minutes to reach the Baths of Rapolano ✔ Ideal location to reach several characteristic villages ✔ Routes for nature lovers on foot and by bicycle ✔ Fast and FREE Wi-Fi ✔ Suitable for remote working

Popular amenities for Armaiolo holiday rentals