
Holiday Homes in Siena
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Top-rated Holiday Homes in Siena
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"Lisa" apartment with fireplace
Lisa apartment is very romantic, the most peculiar of our farm.... You enter directly into a large living room with fireplace, dining table, two sofas and television. In this room there is a charming loft where the bed is located. Bathroom with bath, dressing room with closet and washing machine. Large kitchen with dining table and a view over the Chianti hills. This apartment has a private solarium with deck chairs and table.“Il Poderaccio” dates back to 13th century when its ancient building served as an outpost of Siena against the “League”. Dominating “Chiantishire” , this charming country house offers all recently refurbished, independent flats just a few minutes from Siena city centre. Perfectly integrated in the surrounding environment, the flats can host from 2 to 5 people and come complete with bed and bath linen, dishes and pottery and traditionally furnished with country furniture. Guests can swim in the 18x6-mt swimming-pool, sunbathe in the cotto sundeck surrounded by an orchard and flowers, play bowls and table tennis while children enjoy the playground in the garden or play in the beautiful park spotted with trees and flowers coming from all over the world. Garden areas are reserved for each flat together with sun chairs, garden table and chairs for a perfectly relaxing stay. Furthermore, two wooden desks are available in the shadow and perfect silence of a fenced-in grove where you can hear the birds singing … “Il Poderaccio” stretches for 32 hectares, all cultivated. This ICEA -controlled farm offers totally organic products such as wine, extra vergin olive oil and Grappa. On sale at the farm are: Chianti Colli Senesi DOCG, the “Brunaccio” a special IGT Tuscan red wine, extra virgin olive oil, and a grappa These organic products are the result of an environment- and consumer-friendly growing. “Il Poderaccio” hosts a lot of animals: horses, dogs, cats, a cow, a donkey, a kid as well as the geese, ducks and mallards swimming together in the farm pond. Horse trekking and riding can be organized upon request at a riding school renowned for its highly-qualified trainers situated near the farm. Mountain bikes rental is also available. All the flats are equipped with independent central heating thus being available all year round. NB: FOR WEEKLY STAYS THE AMOUNT OF THE HEATING WILL BE CALCULATED ON CONSUME
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Casa al Gianni - Oak
Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located 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 with you in your heart. We look forward to welcoming you!
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[Florence Hills] Tuscan house with parking space
Our B&B offers a peaceful and quiet corner, quick and easy to reach, in a renovated, characteristic Tuscan house just 7 km (25 minutes) from the parking lot in the historic center of Florence. At Borgo Le Palaie, you can immerse yourself in the landscape of the Florentine hills among cypresses and olive trees, enjoy the view, and visit important vineyards and wineries just a short distance away. You can easily get there by car (including a reserved parking space for guests) or by bus, which is 300 meters away.
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[Traditional Cozy House] Garden & Viewpool Apt
In the heart of the Chianti countryside, this charming two-bedroom home stands within a medieval hamlet surrounded by vineyards. From the garden’s top terrace, a panoramic pool overlooks the rolling hills, offering an idyllic view of Tuscany’s timeless beauty. Just a few Km from Greve in Chianti and around 30 minutes from Florence and Arezzo, the property is ideally located for exploring the region’s art, wine, and gastronomy. Authentic trattorias and family-run wineries are a short drive away.
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Vittoria Chianti Vacations 🍇🍷
Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.
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Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.
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Chianti Craft House Badia a Passignano
Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area
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Breathe in Tuscany: 180° view of the hills
Please note that the second bedroom is divided from the hallway by a curtain and not by a door. Experience San Gimignano with a splendid view of the Tuscan hills! In the heart of San Gimignano, experience the city with a separate entrance, second floor and breathtaking views of the Tuscan hills. Private parking is available upon request. Entrance, living room, 2 double bedrooms, kitchen and large bathroom. city tax to be added to the price, €2.50 per person per night.
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In Tuscany Rooms
**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.
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La Loggia. House with pool and stunning view
LA LOGGIA House, renovated in 2015, is a large independent apartment, ideal to be rented by those who love nature, tranquility and peace of these uncontaminated places immersed in nature. The apartment is characterized by a huge window overlooking the valley where you can enjoy one of the most spectacular views in the region. The view that can be admired from LA LOGGIA spans more than 60 km on the Chianti and the Crete Senesi.
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AM Apartment
The apartment is 10 km from the center of Siena in a very relaxing and quiet place in Chianti where you can enjoy a beautiful view, take long walks on foot and by bike or taste good wine in local companies. The house includes two bedrooms, two bathrooms, a living room with fireplace, sofa and smart TV and a large equipped kitchen. In addition, there are sheets, towels, hairdryer and free wifi
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PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property
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Popular amenities for Siena holiday homes
Family-Friendly holiday homes

Experience rustic off-grid life in the wilderness
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Fienile Santa Teresa
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Charming farmhouse with garden, views & pool
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Fontarcella, H&R- mediterranean home with jacuzzi
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Barrel Suite Tuscany • Hot Tub • Vineyard View
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San Gimignano, Montagongolfi SIX
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Tuja
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Apartment in historic Villa in Siena_"LE CONTRADE"
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Holiday home rentals with a patio

The Eagle and the Olive Tree
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Pienzalettings
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I Rosai apartment on the Florentine hills
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Il Toscano - New with terrace in downtown Greve
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Tuscany Country House, Central Chianti, Pano Views
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The Piccola Villa of Borgo Argenina
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Tuscany Breath - Panoramic Pool & Tennis Court
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Unique & Historic Getaway: Dreamy Garden
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Holiday home rentals with a washing machine and dryer

Chianti Panorama | House with 3 En-Suite Bathrooms
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4BR • Luxury Palazzo • Iconic Views • Pitti Palace
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Zen Island downtown Florence, new apartment for 6
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Melarancio Residence
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Duomo Charme – A few steps from the Duomo
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SMN Luxury Secret Garden View
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TOSCANELLA APARTMENT
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Verde, space and relax in historic Florence
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When is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $200 NZD | $208 NZD | $265 NZD | $292 NZD | $289 NZD | $287 NZD | $280 NZD | $251 NZD | $287 NZD | $299 NZD | $256 NZD | $244 NZD |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
Destinations to explore
- Cottage rentals Siena
- Rentals with breakfast Siena
- Boutique hotels Siena
- Serviced apartment rentals Siena
- Family-friendly rentals Siena
- Pet-friendly rentals Siena
- Rentals with pools Siena
- Bed and breakfasts Siena
- House rentals Siena
- Villa rentals Siena
- Condo rentals Siena
- Apartment rentals Siena
- Rentals with a hot tub Siena
- Hotel rooms Siena
- Holiday home rentals Siena
- Holiday home rentals Tuscany
- Holiday home rentals Italy
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Cala Violina
- Stazione Santa Maria Novella
- Mugello Circuit
- Parco Regionale Della Maremma
- Mercato Centrale
- Spiagge Bianche
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Gulf of Baratti
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Del Chianti
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Things to do Siena
- Food tours Siena
- Cultural tours Siena
- Tastings Siena
- Cooking Siena
- Things to do Siena
- Art workshops Siena
- Tastings Siena
- Museums Siena
- Food tours Siena
- Dining Siena
- Cultural tours Siena
- Outdoors Siena
- Landmarks Siena
- Wildlife Siena
- Cooking Siena
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
- Cooking Tuscany
- Wildlife Tuscany
- Landmarks Tuscany
- Workouts Tuscany
- Tastings Tuscany
- Galleries Tuscany
- Outdoors Tuscany
- Food tours Tuscany
- Dining Tuscany
- Museums Tuscany
- Performances Tuscany
- Shopping and fashion Tuscany
- Art workshops Tuscany
- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Food tours Italy
- Cooking Italy
- Flying Italy
- Cultural tours Italy
- Wellness Italy
- Tastings Italy
- Wildlife Italy
- Landmarks Italy
- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Outdoors Italy
- Architecture Italy
- Water sports Italy







