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Holiday rentals in Siena

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Top-rated holiday rentals in Siena

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Guest favourite
A cozy living area is adorned with soft natural light from a large window, offering views of the countryside. A light gray sofa and a wooden side table with a lamp create a welcoming space. A decorative planter filled with white flowers adds a touch of greenery.
Flat in Siena
4.86 out of 5 average rating, 102 reviews

Le Camelie Suite. Belle Époque Rural Retreat in Siena

Decorated with vintage furniture and offering breath-taking views of the Tuscan Countryside, Suite Le Camelie offers a truly relaxing retreat. Lounge outside in the beautiful gardens and end the day with a bath in the tiled bathroom. Villa Caprera is part of a little village located at the end of a local road. Gardens, yards, olive orchards and fields surround the place where old ladies sit outside the door for chatting and knitting. Suite Le Camelie occupies part of the first floor; thank to the difference in level between the two sides of the villa, the entrance to Suite Le Camelie is comfortably located on the ground floor. Decorated with vintage furniture and modern linens and accessories, feels sophisticated and elegant. Very quiet and with an amazing view. Ideal for a romantic trip. The gardens and yards surrounding the villa are free to access for our guests with the exception of a small private family area reserved for ourselves. Outdoor spaces are not gated or fenced and are shared with other two accommodations; private dining zones are dedicated to each property. My family loves holding conversation with our guests and we are available for any need but we also leave them space to enjoy their time with no interference. The home is in a very traditional area full of family-owned bistros and exquisite boutique shops. Walk through the stunning scenery to visit the church and explore the history of the ancient monastery nearby. Bus stop ten minutes on foot; the bus take you to the city centre. You can get anywhere from there by bus or train. Busses run according to a time table - average every hour. Last run approx 20.00. The road to Siena is not safe to walk. Taxis available to and from the city; very short ride so it is affordable. I recommend a car if you like to get lost in the countryside, but get a driver when you go for winery tours. Private free car park on premises approx 80m from door. The car park is not supervised or gated. Private free car park on premises approx 80m from door so you can enjoy the yards with no parked cars around. The car park is part of our premises but is not supervised or gated; garage available for a fee. We can arrange extra cleaning, cooking lessons or a cook at the house if requested. Cot available on request.

Top guest favourite
An open dining area features a wooden table surrounded by white upholstered chairs. A large window allows natural light to fill the space, highlighting plants in decorative pots. The room is adorned with artwork and has a comfortable seating area in the background.
Apartment in Siena
4.96 out of 5 average rating, 180 reviews

Elegant fine home 400 m away from Piazza del Campo

Apartment with independent heating and entrance, renovated , furnished with great care, located in the old part of the city. It features 2 computer friendly zones and allows you to stay with every kind of comfort, including a fitness area. Immersed in the enchantment of the traditional but silent atmosphere of a district of the historic center, it is 50 meters from the Main Street, and from all kinds of shops: restaurants, supermarkets, laundries, newspapers and tobacconists, pastry shops, etc.

Guest favourite
Farm stay in Castelnuovo Berardenga
4.92 out of 5 average rating, 313 reviews

Apartment in Tuscan farm house.

Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.

Top guest favourite
The elegantly structured Villa di Geggiano is set amidst lush vineyards and well-maintained gardens. Its classic stone facade and terracotta roof harmonize with the surrounding greenery, while neatly manicured pathways and symmetrical garden beds create a picturesque landscape under a partly cloudy sky.
Flat in Siena
4.99 out of 5 average rating, 164 reviews

Villa di Geggiano – Alfieri Suite

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 idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. 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.

Top guest favourite
A modern villa with a stone exterior features strategically placed windows and a prominent porch area. The surrounding greenery includes an olive tree, while steps lead to a well-maintained garden. An ornamental planter sits at the forefront, adding a decorative touch to the entrance.
Villa in Siena
4.98 out of 5 average rating, 200 reviews

Virgi House

Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

Top guest favourite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.98 out of 5 average rating, 127 reviews

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Guest favourite
The living space features high ceilings with decorative beams and elegant pendant lighting. A modern kitchen is visible, complemented by a dining table and white chairs. Two plush white sofas are arranged for comfort, with a decorative plant adding a touch of greenery.
Flat in Siena
4.91 out of 5 average rating, 252 reviews

Palazzo Casini Piccolomini Apartment

Newly renovated apartment, located on the 2nd floor of the historic Palazzo Casini Piccolomini, in the heart of downtown Siena, 30 meters from the famous Piazza del Campo, equipped with every comfort to offer our guests an unforgettable stay. Renewed apartment, located on the 2nd floor in the historic Casini Piccolomini building, in the heart of downtown Siena, 30 meters from the famous Piazza Del Campo, fully equipped to offer our guests a great stay in our city.

Top guest favourite
The lounge features elegant walls adorned with intricate frescoes and moldings. A large mirror reflects the refined decor. Two white armchairs and a colorful sofa provide seating, while a coffee table rests on a patterned rug before a decorative fireplace.
Flat in Siena
4.98 out of 5 average rating, 103 reviews

Luxury frescoed apartment in the historical center

The Palazzo Pannilini Superior apartment is composed of a bright entrance enriched by an elegant coffered ceiling, a large fully frescoed lounge, a large foyer, a kitchen equipped with a terrace, a dining room topped with a frescoed vault, four bedrooms, three bathrooms, a wardrobe room, and a panoramic terrace where you can sunbathe and relax. The apartment is located at the second floor with no elevator. The apartment has air conditioning.

Top guest favourite
A bright living area features a modern white sectional sofa and a white entertainment unit with a flat-screen TV. Stylish decor includes a potted plant and black accents against light walls and exposed wooden beams, creating a spacious and uncluttered environment.
Apartment in Siena
4.96 out of 5 average rating, 131 reviews

Olympia's House

A few steps from the wonders of Siena, this apartment combines comfort and refinement. Two bedrooms, two bathrooms, studied lights, careful design and tastefully chosen materials. Outside the ZTL but close to the center, with convenient parking and escalators 500 meters away. A contemporary retreat where you can feel at home and live the authentic soul of the city, between history, beauty and harmony.

Top guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.91 out of 5 average rating, 243 reviews

Casa al Gianni - Hut

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Guest favourite
An outdoor terrace offers seating for four, featuring a table and chairs. The view captures the skyline illuminated against a twilight backdrop, showcasing notable landmarks such as the Torre del Mangia and the Duomo in the distance.
Flat in Siena
4.88 out of 5 average rating, 162 reviews

Penthouse with a view of Siena

Next to the Basilica of San Domenico, a few steps from the Duomo and Piazza del Campo, in this splendid and elegant penthouse you can enjoy the splendid view and the convenience of walking to all the major points of interest in the city in just a few minutes.

Top guest favourite
A warm living area is presented, featuring a comfortable sofa adorned with soft pillows and a round dining table. The space is illuminated by wall sconces, while an arched entryway leads to another room. Large windows allow natural light to fill the area.
Farm stay in Gaiole in Chianti
4.96 out of 5 average rating, 103 reviews

La Pieve - the house next to the church

To the right of the Argenina church, after which it is named, it has the persuasive look of its 2 small arches facing west. Perhaps it was once the parish priest's house, or the one where cooking was done in the large wood-burning oven, who knows?

Popular amenities for Siena holiday rentals

When is the best time to visit Siena?

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Avg. price$132 SGD$123 SGD$141 SGD$157 SGD$167 SGD$174 SGD$169 SGD$171 SGD$164 SGD$160 SGD$146 SGD$157 SGD
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Frequently Asked Questions

  • What are the best places to stay in Siena?

    Siena has a variety of stays in the historic center, known for medieval streets and easy access to local cafes. Neighborhoods around Piazza del Campo and near the Duomo di Siena are frequently suggested for both charm and convenience.

  • What are the best things to do in Siena with kids?

    Families often explore the interactive exhibits at local museums, stroll the car-free historic center, and enjoy gelato in public squares. Parks and gardens around Siena provide space for outdoor play and picnics.

  • What are some of the best things to do in Siena?

    Siena has renowned sites like Piazza del Campo, the Duomo di Siena, and Torre del Mangia, as well as lively markets and guided walks through medieval streets. Many visitors also explore local art galleries and enjoy Tuscan cuisine in trattorias.

  • How is the weather in Siena?

    Siena experiences cool winters with temperatures from 33–49°F (0–9°C), and warm, dry summers reaching up to 89°F (31°C). Spring and autumn are mild, with occasional rainfall.

  • What are the best places to visit in Siena?

    Explore Piazza del Campo, climb Torre del Mangia for wide city views, and visit the Duomo di Siena with its striking facades. Many also enjoy time at the Pinacoteca Nazionale for regional art collections.

  • What are some hiking trails in Siena?

    Siena has gentle nature trails around the city’s hills, as well as paths passing vineyards and olive groves just outside town. Locals also suggest exploring the parks and green areas for a relaxed outdoor walk.

  • What are some family activities we can do in Siena?

    Families can join hands-on workshops in art or cooking, watch lively street performances in main squares, and wander through gardens and interactive museums. Exploring Siena’s pedestrian-friendly center is a favorite for many.

  • What are some of the best day trip ideas from Siena?

    Popular day trips include visiting nearby hill towns, exploring Tuscan vineyards, and discovering historic abbeys tucked into the landscape. Local guides frequently suggest nature reserves and traditional villages just outside the city.

  • Are there any pet friendly accommodations available in Siena?

    Many accommodations around the city center and in quieter neighborhoods welcome pets. Parks and walking trails make it convenient for travelers exploring Siena with dogs or other companions.

  • What are some local tips for visiting Siena?

    Wear comfortable shoes for cobbled streets, and consider arriving early at popular sites to enjoy calmer mornings. Locals often recommend tasting seasonal dishes at small trattorias and checking neighborhood markets for fresh ingredients.

  • What is Siena known for?

    Siena is known for its medieval architecture, vibrant traditions, and the Piazza del Campo, a unique shell-shaped square. The city’s cuisine, local art, and recurring historic festivals draw visitors from around the world.

  • What are the best hidden gems to explore in Siena?

    Exploring narrow alleys near Piazza del Campo may reveal small artisan shops and tucked-away cafes. Many seek out the Orto dei Pecci, a quiet garden just behind the city’s old walls.

  • What are the best foods to try in Siena?

    Siena has classic Tuscan flavors, including pici pasta, panforte, and ricciarelli cookies. Wild boar stew and pecorino cheese are often recommended specialty dishes in local trattorias.

  • What should I bring for a trip to Siena?

    Pack sturdy walking shoes for uneven streets, a light jacket for changing weather, and sun protection in warmer months. A refillable water bottle and a camera for city views are frequently suggested.

  • What is the nightlife in Siena like?

    Siena has a relaxed nightlife, with wine bars, small music venues, and cafes around the historic center. Evening strolls in lively squares and university hubs are popular for gathering with friends.

  • What are the most popular events or festivals in Siena?

    The Palio di Siena is a renowned horse race held in Piazza del Campo during summer months, celebrating centuries-old traditions. The city also hosts food festivals and cultural events, especially around late spring and autumn.

  • Are there family friendly vacation rentals in Siena?

    Siena has many family-friendly rentals in central neighborhoods and near public gardens. These stays often provide flexible layouts and easy access to parks, shops, and local events.

  • When is the best time to visit Siena?

    Late spring through early autumn is often recommended for pleasant weather and outdoor events. Winter has a quieter atmosphere and cooler temperatures, while fall brings colorful landscapes and cultural festivities.

Quick stats about holiday rentals in Siena

  • Total holiday rentals

    Explore 1,390 holiday rentals in Siena

  • Nightly prices starting at

    Siena holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 79,040 verified reviews to help you choose

  • Family-friendly holiday rentals

    550 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 520 rentals that welcome pets

  • Holiday rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    650 properties have a dedicated workspace

  • Wifi availability

    1,310 of Siena holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Siena rentals

  • 4.8 Average rating

    Siena stays are highly rated by guests – averaging 4.8 out of 5!

Destinations to explore

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