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Holiday home rentals in Siena

Find and book unique holiday home rentals on Airbnb

Top-rated holiday home rentals in Siena

Guests agree: these holiday home rentals are highly rated for location, cleanliness and more.

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Guest favourite
An open living area features two red sofas and a round dining table surrounded by chairs. The space is illuminated by ceiling lights and natural light from windows. A wooden staircase leads to a loft area above, which includes a sleeping space.
Holiday home
4.83 out of 5 average rating, 101 reviews

"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

Top guest favourite
A charming rustic farmhouse is set against a dramatic sky, framed by lush green trees. The exterior features warm-toned walls and a tiled roof, while a spacious yard includes seating arrangements for outdoor relaxation, inviting guests to enjoy the serene countryside.
Holiday home
4.92 out of 5 average rating, 239 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!

Guest favourite
An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.
Holiday home
4.97 out of 5 average rating, 160 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.

Guest favourite
An aerial view captures a charming Tuscan farmhouse nestled within lush green vineyards and rolling hills. The property features a rustic stone exterior and a terracotta roof, complemented by surrounding greenery and a clear blue sky.
Holiday home
4.94 out of 5 average rating, 203 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.

Top guest favourite
A bright double bedroom is presented with a spacious bed featuring crisp white linens. Natural light floods the room through an open window, framing a view of the surrounding valley. Wooden beams add character to the ceiling, and bedside tables with lamps are positioned beside the bed.
Holiday home
4.92 out of 5 average rating, 206 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.

Top guest favourite
A bright bedroom features a spacious bed with crisp white linens and a decorative pillow. A vivid landscape painting hangs above, while a window with wooden frames reveals a scenic view of the Tuscan hills, complemented by soft natural light filtering through sheer curtains.
Holiday home
4.98 out of 5 average rating, 161 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.

Top guest favourite
Holiday home
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.

Top guest favourite
An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.
Holiday home
4.96 out of 5 average rating, 135 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.

Top guest favourite
An expansive window offers a breathtaking view of rolling hills and valleys, extending into the distant horizon. A small table with a laptop is positioned in front, accompanied by a white chair. Soft light fills the inviting space, emphasizing the serene landscape outside.
Holiday home
4.99 out of 5 average rating, 101 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.

Top guest favourite
Holiday home
4.96 out of 5 average rating, 137 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.

Guest favourite
The image depicts a historic church from the XVI century, characterized by its brick façade and charming architecture. Nestled among greenery, it stands against a serene sky during twilight, highlighting the surrounding hills and countryside.
Holiday home
4.92 out of 5 average rating, 103 reviews

Villa Madonna of the Rose

Villa a few steps from the historic center but facing the countryside and the famous 16th century Madonna della Rosa church, there is a private parking for guests inside the property, the structure is surrounded by a garden and in front of an olive grove. there is a gazebo in the garden surrounded by Tiglio trees, a solarium on the top floor. The villa has all the comforts and large outdoor green spaces.

Top guest favourite
A bright bedroom features a spacious bed with light linens and a decorative throw. Natural light enters through open double windows, revealing a private terrace. A television and a small desk with a chair are present, while two bedside tables with lamps offer soft lighting.
Holiday home
4.93 out of 5 average rating, 109 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).

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