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Holiday rentals in Siena

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Top-rated holiday rentals in Siena

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Top guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Apartment in Noce
5 out of 5 average rating, 309 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Top guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 145 reviews

Villa di Geggiano – Guesthouse

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

Top guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guest house in Macciano
4.97 out of 5 average rating, 207 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

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, 199 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.

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 modern living space features a bright red sectional sofa positioned against a textured stone wall. A stylish kitchen island with seating is visible, along with minimalistic lighting fixtures and decorative plants, creating a blend of comfort and contemporary design.
Apartment in Siena
4.99 out of 5 average rating, 234 reviews

Palazzo del Taja - in the center with whirlpool

Brand new apartment just renovated, located inside the historic Palazzo del Taja in the heart of Siena's historic center, a few meters from Piazza del Campo and the city's main attractions. Subjected to a renovation attentive to details, the apartment is elegant, bright, welcoming and quiet. Complete with every comfort, including a beautiful bathroom with a whirlpool tub, to offer an unforgettable stay to our customers.

Top guest favourite
A spacious terrace features a large dining table with ample seating, complemented by an umbrella for shade. A scenic view of the distant church and surrounding architecture is visible, framed by lush greenery and a picturesque sky.
Flat in Siena
4.98 out of 5 average rating, 101 reviews

CASA WOW panoramic terrace * . *

Nel cuore di Siena con una terrazza panoramica. La casa offre un sapore sincero, realmente vissuto da una famiglia italiana: con arredi di pregevole antiquariato e moderni confort, cimeli di viaggi, libri e riviste. Ideale per due coppie di amici o una famiglia con bambini. Ammessi gli animali non molesti. Wifi gratuito 24 h. LGBTQ friendly. Viene rispettato il Protocollo Covid-19 CIN: IT052032C2EQVX5ICB

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, 130 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.

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.

Guest favourite
A tranquil garden space is visible, featuring a large, white umbrella providing shade over two reclining chairs. Lush green grass surrounds the area, complemented by potted greenery and flowering plants, creating a serene outdoor escape.
Flat in Siena
4.93 out of 5 average rating, 113 reviews

Casa Borgianni in Villa Caprera

Distinguish historic family villa with a bucolic charm for a true Tuscan holiday in a set of olive trees, gardens, vineyards, old churches. Just five minutes from Siena centre with an amazing view of the city. A relaxing place with all comforts

Top guest favourite
A shaded outdoor terrace features a wooden pergola draped with green vines. A round table is set with a potted plant at its center, surrounded by several chairs. Stone paths lead to the entrance of the house, framed by blooming flowerbeds.
Home in Siena
4.97 out of 5 average rating, 196 reviews

Secret Garden Siena

A beautiful house located inside the city walls of Siena. The house develops on two floors has three bedrooms and two toilets. The real strong point of this location is the private garden. Walking distance to all the main attractions.

Popular amenities for Siena holiday rentals

When is the best time to visit Siena?

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Avg. price$131 SGD$122 SGD$140 SGD$157 SGD$167 SGD$173 SGD$168 SGD$171 SGD$163 SGD$159 SGD$145 SGD$157 SGD
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°C

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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  3. Tuscany
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