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Holiday rentals in Siena

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Top-rated holiday rentals in Siena

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A spacious courtyard bordered by terracotta tiles features several potted plants, including palm trees and shrubs. The walls are painted in warm yellow tones, with green shutters framing the windows. A historic building can be seen in the background, adding to the serene ambiance.
Flat in Siena
4.87 out of 5 average rating, 466 reviews

Two-room apartment in a former convent within walking distance of the center

CHECK-IN NO EARLIER THAN 4:00 PM NOT SUITABLE FOR CHILDREN UNDER 12 YEARS OF AGE IT IS NOT POSSIBLE TO LEAVE YOUR LUGGAGE BEFORE CHECK-IN THE PARKING LOT IS NOT SUITABLE FOR CARAVANS OR VAN-TYPE VEHICLES My little apartment is located in a condominium that for centuries was a convent built around a medieval courtyard: very close to the historic center, it is ideal for discovering Siena. In 10-15 minutes, you'll be in Piazza del Campo, the heart of the city. The countryside is also easy to reach.

Top guest favourite
A bright living area features comfortable seating arranged around a glass coffee table. Light wood flooring complements the soft neutral tones of the furniture. Decorative shelves display various items, and artwork adorns the walls, enhancing the welcoming ambiance.
Flat in Siena
4.95 out of 5 average rating, 273 reviews

SAN DOMENICO LUXURY APARTMENT

Un appartamento luminoso ed accogliente nel cuore di Siena al primo piano di un palazzo storico e curato nei minimi dettagli. Dotato di una cucina, di due camere da letto e di 2 bagni. E' ideale per 4 persone. La zona è ricca di locali, ristoranti e negozi. La casa è vicina al parcheggio dello stadio ed alle stazioni degli autobus di piazza Gramsci e dei taxi di piazza Matteotti Costo per neonati a notte 20€ Check in 15-20 Check-out entro le 10.00 Codice CIN IT052032C2DTDZF9NA

Top guest favourite
A doorway opens to a warm, inviting space featuring a cozy bedroom with a spacious bed dressed in light linens. The room includes wooden ceiling beams and a small table with chairs in the background, complemented by natural light filtering through the window.
Flat in Siena
4.94 out of 5 average rating, 202 reviews

Casa Fusari - Apartment next to the Duomo

! Please check the house rules before booking ! Completely renovated apartment with fine finishes located in a building of 1746, one minute walk from Piazza del Duomo and two minutes from Piazza del Campo. Strategic position in the heart of the historic center, very convenient raised ground floor from which you can see part of the Duomo, next to the apartment you will find two great restaurants. A few steps away you will also find the escalator to the parking lot Santa Caterina.

Guest favourite
A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.
Flat in Castelnuovo Berardenga
4.93 out of 5 average rating, 169 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Top guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 446 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

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, 232 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.

Guest favourite
A charming rooftop terrace featuring woven seating arrangements, highlighted by a coffee table and a decorative lamp. Sunlight fills the space, illuminating the brick walls and rooftops of Siena, with a distant view of the tower visible against a clear blue sky.
Flat in Siena
4.9 out of 5 average rating, 141 reviews

Secret Terrace in the Heart of Siena

Appartamento elegante, dal design moderno, arredato in maniera funzionale per soddisfare i viaggiatori provenienti da tutto il mondo. Situato in una posizione centralissima e strategica, a pochi minuti a piedi dal Duomo e a soli 150 metri da Piazza del Campo, . Troverete inoltre numerosi supermercati, ristoranti, luoghi storici e bar. Un punto di partenza perfetto sia per viaggi d'affari che per puro svago a Siena!

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, 242 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!

Top guest favourite
A terrace table is set with two glasses of sparkling wine and a plate of cookies, overlooking the rooftops of the city. The distant bell tower is visible against a clear blue sky, framed by the balcony's railing.
Flat in Siena
4.96 out of 5 average rating, 386 reviews

The rooftop terrace

Bright and cozy 95 sqm apartment located on the 4th floor without elevator of a notified building in the heart of the city a few steps from Piazza del Campo, the Duomo and the major attractions of the city. A splendid view overlooking the rooftops will frame your apartment from which you can see the Torre del Mangia, the Basilica dei Servi and the wonderful Val d'Orcia.

Top guest favourite
Flat in Siena
4.91 out of 5 average rating, 229 reviews

Building 1632 with terrace in the Campo and Duomo area

Entire bright and cozy accommodation just 200 meters from Piazza del Campo, 400 meters from the Duomo, with convenient car parking just 150 meters away. The beauty and tranquility of the countryside in the historic center, which can be enjoyed from the terrace. All services are within walking distance. Only 5 steps to the entrance.

Guest favourite
An open-plan living and dining area features a comfortable red couch and a wooden dining table surrounded by chairs. Natural light enters through large windows adorned with green curtains, illuminating the space. A piano and a wooden cabinet are positioned along the walls, complemented by wooden beams on the ceiling.
Apartment in Siena
4.92 out of 5 average rating, 135 reviews

The most ancient part of the city

Inside the medieval walls of Siena, in the most ancient part of the city you will find your home away from home at Buonsignori Apart built in the 1300s. Your opportunity to enjoy living like a native as you experience life in a small Tuscan city.

Top guest favourite
A spacious living area features high ceilings with decorative beams. Comfortable sofas are arranged near a television. Natural light floods through large windows, illuminating the hardwood floor. A small plant adds a touch of greenery, while artwork adorns the walls, contributing to the refined atmosphere.
Apartment in Siena
4.96 out of 5 average rating, 394 reviews

Palazzo Bichi Ruspoli-Historical Home-Very Central

Historical Home Palazzo Bichi Ruspoli is situated on the elegant main street, in the heart of Siena. Located in a beautiful and ancient medieval building, the house is on the third floor with elevator and has a stunning view on the city.

Popular amenities for Siena holiday rentals

When is the best time to visit Siena?

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Avg. price$130 SGD$121 SGD$139 SGD$155 SGD$166 SGD$172 SGD$167 SGD$169 SGD$162 SGD$158 SGD$144 SGD$155 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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  3. Tuscany
  4. Siena
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