
Vacation rentals in Armaiolo
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Top-rated vacation rentals in Armaiolo
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Casa al Gianni - Hut
Hi, we’re Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism property nestled in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a vacation; it’s a return to our roots. This peaceful haven will stay in your heart. We look forward to welcoming you!
4.93 out of 5 average rating, 294 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.
4.96 out of 5 average rating, 142 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.
4.99 out of 5 average rating, 155 reviews
Capannacce more than a Farm House: La Casella
Capannacce is a special place for us. Farm, but not only. It is home. For us and for the animals that live there, horses, chickens, cows, felines and canids. The heart of the farm is the breeding of racehorses, thoroughbreds. And of the Pontremolese cow, a native breed and a world heritage site. We are immersed in the Crete Senesi, where every summer sunset is a delight. A countryside made of quietness that soothes, but not far from the town of Rapolano Terme and all the related conveniences.
4.79 out of 5 average rating, 118 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.
4.97 out of 5 average rating, 251 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.
4.96 out of 5 average rating, 125 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.
4.99 out of 5 average rating, 116 reviews
Your Tuscan oak tree house, enchanting Val d'Orcia
The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.
5.0 out of 5 average rating, 116 reviews
2 ❤️ and 1 Yurt Glamping in Tuscany for adults only
Romantic glamping for adults, in the heart of the Tuscan countryside. Silver Yurt tent, 35 sq m + private en-suite bathroom, 7 sq m + private outdoor wood-fired hot tub* (*EXTRA CHARGE), private relaxation veranda. Heated in winter and air-conditioned in 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.
4.98 out of 5 average rating, 196 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.
4.98 out of 5 average rating, 107 reviews
The Chianti window
A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.
4.9 out of 5 average rating, 136 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
4.95 out of 5 average rating, 22 reviewsPopular amenities for Armaiolo vacation rentals
Other great vacation rentals in Armaiolo

The Nest Il Giglio | Rapolano Terme
5.0 out of 5 average rating, 39 reviews
The Golden Stone
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Acqua Apartment - Water and Stone
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Charming Residence Castello di Orgiale near Siena
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XIII Century Tower with Private Panoramic Pool
4.8 out of 5 average rating, 296 reviews
[The Tower] Pool - WiFi - Air Conditioning
4.84 out of 5 average rating, 19 reviews
house with pool between Siena and Valdorcia
4.91 out of 5 average rating, 33 reviews
Luxury penthouse with a view of Piazza del Campo
5.0 out of 5 average rating, 23 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Mercato Centrale
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Parco delle Cascine
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino
- Stadio Artemio Franchi





