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House holiday rentals in Siena

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Top-rated house rentals in Siena

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Top Guest favourite
A bright living area is highlighted by a white sectional sofa, complemented by red throw pillows. An elegant area rug sits on terracotta tiles, with wooden beams and a staircase leading to the upper level visible. Light streams through a window, enhancing the warm atmosphere.
Home in Tavarnelle Val di Pesa
4.95 out of 5 average rating, 111 reviews

Casa Luigi Suite with exclusive pool

Come to this apartment: you will be welcomed by centuries of tranquility, and appreciate nature and relaxation. Carefully modernized (and with a swimming pool), this space embodies the roots of good Tuscan living – an equipped olive grove consisting of a pergola with a table and bathroom, a garden with a hammock and in the shade of pine and cypress trees, with chairs, deck chairs and a rocking chair, you can admire the rolling Chianti hills. Courtyard equipped with table and chairs. There is a beautiful elevated swimming pool with some games and a barbecue In addition to the farmhouse, the property includes an olive grove of about 1 hectare, in which equipped spaces have been created for complete relaxation. The Suite has a private entrance that leads directly to the upper floor of the farmhouse, allowing maximum privacy for guests. The farmhouse is part of a small old village inhabited by 4 very discreet and friendly family units. The suite's surface area is 90 square meters and consists of a dining room with kitchenette, large living room, double bedroom, bathroom with shower and a large attic (the door is 1.2 meters wide) with 3 single beds. A very bright environment and immersed in the complete tranquility of the countryside, it is equipped with air conditioning, satellite TV, and free 24-hour Wi-Fi. The owners provide the laundry area. Uncovered private parking. The owners are happy to welcome their guests and are available to resolve any issues. The small village is inhabited by three other very kind and discreet families, ready to help the guest. Tavarnelle is 25 km from Florence, 15 km from San Gimignano, 35 km from Siena. - Images of the exterior, swimming pool, garden and equipped olive grove will be visible soon. We kindly ask you to wait. The accommodation is about 5 km from the center of Tavarnelle. The historic center is equipped with all the services for the citizen and tourist: post office, police, municipality, emergency room, supermarket, trattorias, pizzerias, banks, etc. In addition, in the summer there are various musical events, small craft markets, and finally, every Thursday morning, the classic municipal market takes place. Places of interest (medieval villages) around Tavarnelle: San Donato in Poggio about 12 km. Barberino Val d'Elsa 6 km. Distances from art cities: Tavarnelle - Florence about 25 km Tavarnelle - San Gimignano/Monteriggioni about 20 km Tavarnelle - Siena about 35 km. In the organized outdoor spaces there is an ABOVE GROUND pool, the dimensions are: 10 meters X 5 meters, with a depth of 1.20 meters. A bathroom with shower completes the pool area. In the courtyard, guests have a nice table with barbecue. The entire olive grove area is at their disposal with maximum privacy. The owners, at the guest's request, can book hiking tours or wine-testing tours with the help of professionals. The price of any tour booking is not included in the price of the stay. The small village was once a military fortress, then a parish church or place of worship and from the beginning of the 20th century inhabited by farmers. Today it is inhabited by four very nice and discreet families ready to help the guest. Florence is 15.5 miles away and Siena is 21.7 miles away

Top Guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.98 out of 5 average rating, 174 reviews

Casa al Gianni - The Simignano Barn

Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 131 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.

Top Guest favourite
A serene landscape features rolling green hills under a vibrant sunset sky, casting soft colors across the horizon. A stone wall is adorned with lush greenery and flowers, providing a tranquil viewpoint for someone contemplating the picturesque view of the valley and distant hills.
Home in Cetona
4.99 out of 5 average rating, 159 reviews

Casa Dolce Toscana | Panoramic Suites & Views

CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.

Top Guest favourite
Home in Siena
4.97 out of 5 average rating, 195 reviews

Podere Piazza house with panoramic view

Podere Piazza ist ein Landgut, hat seinen Ursprung im 15. Jahrhundert, das Ferienhaus wurde Anfang 17. Jahrhundert erbaut. Podere Piazza war der Wohnsitz von Alessandro Cervini degli Spannocchi, der am 29 Mai 1747 zum Erzbischof von Siena ernannt wurde, er war ein Nobile di Montepulciano und Patrizier von Siena. Die Gebäude von Podere Piazza tragen noch heute sein Wappen. Somit erklärt sich auch unser Kirchlein, am Straßenabzweig, davor rechts zur Pinienallee und links in die Einfahrt.

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, 130 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
A serene bedroom features a spacious bed with a simple white coverlet. A wooden chair with a striped cushion is placed beside a bench. Natural light filters through the two wooden windows, revealing views of the lush vineyards outside.
Home in Castelnuovo Berardenga
4.9 out of 5 average rating, 122 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.

Superhost
A spacious bedroom is presented with a large bed featuring neatly arranged pillows and rolled towels. Soft lighting accentuates the room's decor, including a distinctive wall art piece. Exposed beams add character to the inviting space, creating a comfortable atmosphere.
Home in Siena
4.88 out of 5 average rating, 349 reviews

[Duomo 8 min. walk] Luxury Home • Self Check-in

Gorgeous private house, located in the heart of Siena, with spacious and luxurious spaces. Finely renovated with use of fine materials, up to 8 guests can stay in this luxurious property. Its very central location, just 8 minutes' walk from Siena Cathedral and 8 minutes' walk from Piazza del Campo, with its luxury boutiques and the many amenities around, make it the ideal location for a pleasant stay in Siena.

Guest favourite
A charming stone exterior reveals a rustic villa surrounded by greenery. The entrance features a wooden door and terracotta roof tiles. Potted plants add color, while seating areas are positioned on a patio, inviting relaxation in the scenic surroundings under a clear blue sky.
Home in Radda in Chianti
4.92 out of 5 average rating, 166 reviews

Casa Dante – Authentic Chianti Stay | Views & Relaxation

Wake up to breathtaking views over the rolling hills of Chianti and enjoy a glass of wine at sunset from your private terrace. This peaceful home offers the perfect mix of privacy, comfort, and authentic Tuscan charm. Located just minutes from the center of Radda in Chianti, the house is ideally positioned to explore wineries, charming villages, and the surrounding countryside—while still feeling quiet.

Top Guest favourite
A spacious outdoor area features a well-maintained garden with a grassy lawn, an olive tree, and a stone patio. A white lounge chair is positioned on the lawn, and a shaded seating area is visible against the house's exterior, which showcases traditional architecture and wooden window shutters.
Home in Siena
4.95 out of 5 average rating, 756 reviews

A green oasis in the historic center.

Right in the heart of the historic center while simultaneously surrounded by the tranquility of nature. Just a 2-minute walk from PIAZZA DEL CAMPO, the heart of city tourism, but in a secluded, quiet location with a private garden. Maximum security is ensured with access via 2 electric gates. Regional Code 052032LTN0236 CIN IT052032C2IV4RLNUV

Guest favourite
A spacious sleeping area is featured, with a plush bed covered in crisp white linens and multiple decorative pillows. Natural light streams through a large window, framed by soft curtains. A stylish round table stands beside the bed, offering a modern touch to the room.
Home in Siena
4.94 out of 5 average rating, 103 reviews

Domus Nannini - Crossed Loggia Spa

Appartamento appena ristrutturato composto da un salotto, moderna cucina open space completamente attrezzata con sala da pranzo, due camere e due bagni.  Interamente rivestito con un pregiato pavimento in parquet di Olmo, originale e restaurato, che conferisce un'atmosfera calda e accogliente.

Guest favourite
A spacious living room is presented with terracotta flooring and wooden beams overhead. A comfortable sofa arrangement surrounds a wooden coffee table, with a flat-screen TV positioned nearby. Natural light filters through the windows, enhancing the inviting ambiance.
Home in Monteriggioni
4.9 out of 5 average rating, 213 reviews

Siena Countryside Colle Ciupi

Countryside Villa apartment. Located in the nearby of Siena (Colle Ciupi, 10 kms away) Ground floor: Kitchen, living room with fireplace, bathroom with shower. First Floor: 3 Double Bedrooms and 2 bathrooms, outdoor with courtyard and huge garden

Popular amenities for Siena house rentals

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Avg. price$206 NZD$182 NZD$237 NZD$211 NZD$201 NZD$216 NZD$220 NZD$232 NZD$213 NZD$218 NZD$210 NZD$213 NZD
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Quick stats about house rentals in Siena

  • Total holiday rentals

    Explore 100 holiday rentals in Siena

  • Nightly prices starting at

    Siena holiday rentals start at $51 NZD per night before taxes and fees

  • Verified guest reviews

    Over 8,680 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Siena holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Siena rentals

  • 4.8 Average rating

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

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