
Holiday home rentals in Siena
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Top-rated holiday home rentals 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
4.83 out of 5 average rating, 103 reviews
Casa al Gianni - Oak
Hello, we’re Cristina and Carmelo! We look forward to welcoming you to ‘Casa al Gianni’, our farmhouse 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 holiday; it’s a return to our roots. This peaceful haven will stay with you forever. We look forward to welcoming you!
4.93 out of 5 average rating, 244 reviews
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.
4.94 out of 5 average rating, 205 reviews
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.
4.97 out of 5 average rating, 160 reviews
Stuart Jasmine central, panoramic top location
This abode boasts 1 double and 1 single bedroom, a spacious living room with a fully equipped kitchen, and 1 bathroom with shower. Every window frames a breathtaking view, filling the space with natural light. High-speed Wi-Fi ensures comfort for both work and leisure. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. Here, you can unwind and relax, study and learn, discover and explore, or create and dream.
4.92 out of 5 average rating, 206 reviews
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.
4.98 out of 5 average rating, 163 reviews
Fontarcella, H&R- mediterranean home with jacuzzi
Located in the hills between Montepulciano, Castiglione del Lago, and Cortona, Fontarcella is a detached villa surrounded by greenery, offering a private jacuzzi and parking. You'll discover a timeless place to share precious moments. The property, furnished in Mediterranean style, features air conditioning and free Wi-Fi. The fully fenced garden offers a variety of amenities. Just minutes from the highways, Fontarcella is easily accessible for travelers.
4.98 out of 5 average rating, 166 reviews
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.
4.96 out of 5 average rating, 137 reviews
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.
4.99 out of 5 average rating, 102 reviews
La Casa dei Ricordi - car/motorcycle garage at 650m
Welcome to La Casa dei Ricordi, a 17th-century home full of soul: this is where I was born and raised. Today, it opens its doors to offer you an authentic experience. Located in an incredibly quiet and peaceful area, it’s the perfect place to relax just steps away from Piazza del Duomo and Piazza della Cisterna. A charming retreat in the heart of the historic center, where history meets the peace of a true family home.
4.96 out of 5 average rating, 139 reviews
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
4.89 out of 5 average rating, 200 reviews
White lily with a view of Siena
Caggiolo is a completely renovated farm consisting of several apartments, with a panoramic view of Siena. Located 1 km from 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).
4.92 out of 5 average rating, 112 reviewsPopular amenities for holiday home rentals in Siena
Family-friendly holiday home rentals

PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
4.91 out of 5 average rating, 99 reviews
Tuja
5.0 out of 5 average rating, 35 reviews
Elegant farmhouse overlooking Pienza
5.0 out of 5 average rating, 36 reviews
Siena house with private garden 300m from the center
4.89 out of 5 average rating, 96 reviews
Apartment in the historic center of Siena
5.0 out of 5 average rating, 25 reviews
Tuscan House with Private Jacuzzi in Chianti
4.95 out of 5 average rating, 92 reviews
1 bedroom apartment in Tuscan farmhouse
5.0 out of 5 average rating, 51 reviews
La Campanina-in the heart of Siena and the district
4.93 out of 5 average rating, 71 reviewsHoliday home rentals with a patio

Pienzalettings
4.92 out of 5 average rating, 114 reviews
Pian'D'olmo, an ancient farmhouse in the heart of Tuscany
4.9 out of 5 average rating, 30 reviews
Tuscany Breath - Panoramic Pool & Tennis Court
5.0 out of 5 average rating, 8 reviews
Prachtig huisje in Tuscany, Luca's House
4.86 out of 5 average rating, 51 reviews
cenerentola chianti 2 apartment - near Panzano
5.0 out of 5 average rating, 12 reviews
Orchid apartment with terrace
5.0 out of 5 average rating, 10 reviews
Flat, terrace, pool, Spa resort,restaurant, A/C,S1
5.0 out of 5 average rating, 4 reviews
Villetta la Fortezza · Tuscan Green Oasis & Relaxation
5.0 out of 5 average rating, 13 reviewsHoliday home rentals with a washing machine and dryer

The Eagle and the Olive Tree
5.0 out of 5 average rating, 127 reviews
Apartment in historic Villa in Siena_"LE CONTRADE"
4.96 out of 5 average rating, 91 reviews
Unique & Historic Getaway: Dreamy Garden
4.97 out of 5 average rating, 30 reviews
My cozy home in Chianti
4.98 out of 5 average rating, 94 reviews
Summer in Tuscany MAE
4.87 out of 5 average rating, 98 reviews
Vicolo delle Rose Apartment
5.0 out of 5 average rating, 11 reviews
The Piccola Villa of Borgo Argenina
4.97 out of 5 average rating, 38 reviews
Montalcino Vacation Home Idolina Guest House
4.96 out of 5 average rating, 28 reviewsDestinations to explore
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- 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
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Mount Amiata
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- Things to do Italy
- Workouts Italy
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- Cooking Italy
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- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
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- Architecture Italy
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