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Holiday houses 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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Guest favourite
Home in Asciano
4.96 out of 5 average rating, 119 reviews

Palazzo Monaci - Piscina nelle crete Senesi

Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

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, 149 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
An open living area features a round dining table surrounded by wooden chairs, and a cozy sofa adorned with decorative cushions. Exposed wooden beams run overhead, adding character to the space. A soft rug enhances the warmth of the wooden flooring, creating a welcoming atmosphere.
Condo in Siena
4.97 out of 5 average rating, 153 reviews

APPARTAMENTO ROMANTICO NEL CENTRO STORICO DI SIENA

A 150 METRI DA PIAZZA DEL CAMPO, INGRESSO INDIPENDENTE, ARREDAMENTO ROMANTICO E SIGNORILE, A PIANO TERRA. SITUATA VICINO AI LUOGHI DI INTERESSE ARTISTICO E TURISTICO. DISPONIBILE A DARE TUTTE LE INFORMAZIONI UTILI PER FAR VIVERE AL MEGLIO LA CITTA' FAMOSA ANCHE PER LE SUE CONTRADE E TRADIZIONI SECOLARI. ESSENDOIN PIENA ZONA BLU NON E POSSIBILE PARCHEGGIARE AUTO, MA ESISTE UN PARCHGGIO COPERTO ALLA STAZIONE FERROVIARIA A 2 EURO PER GIORNO, SITUATO A 2 KM DALLA CASA, RAGGIUNGIBILE CON TAXI O BUS

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.
Apartment in Siena
4.91 out of 5 average rating, 253 reviews

Appartamento Palazzo Casini Piccolomini

Appartamento nuovo appena ristrutturato, situato al piano 2 dello storico Palazzo Casini Piccolomini, nel cuore del centro di Siena, a 30 metri dalla celebre Piazza del Campo, dotato di ogni confort per offrire ai nostri ospiti un soggiorno indimenticabile. Renewed apartment, located on the 2nd floor in the historic Casini Piccolomini building, in the heart of Siena downtown, at 30 metres from the famous Piazza Del Campo, fully equipped for offering to our guests a great staying in our city .

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.
Condo in Siena
4.99 out of 5 average rating, 235 reviews

Palazzo del Taja-in pieno centro con idromassaggio

Appartamento nuovissimo appena ristrutturato, situato all'interno dello storico Palazzo del Taja nel cuore del centro storico di Siena, a pochissimi metri da Piazza del Campo e dalle principali attrazioni della città. Sottoposto ad una ristrutturazione attenta ai dettagli, l'appartamento risulta essere elegante, luminoso, accogliente e silenzioso. Completo di ogni comfort, tra cui una stupenda sala da bagno con vasca idromassaggio, per offrire un soggiorno indimenticabile ai nostri clienti.

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.
Condo in Noce
5 out of 5 average rating, 315 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica e autentica casa colonica risalente al 1600 situata nelle splendide colline del Chianti in Toscana . L'appartamento è arredato in perfetto stile tradizionale locale dell'antica Toscana : antiche travi in legno, pavimenti in cotto e arredamenti unici. Nel grande cortile esterno troverete a vostra disposizione una grande piscina con terrazza panoramica che si affaccia su una valle con vista mozzafiato su vigneti e oliveti dove godersi tramonti spettacolari.

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.
Apartment in Siena
4.94 out of 5 average rating, 207 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.

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, 162 reviews

Casa al Gianni - Il Fienile di Simignano

Trasformato da un antico fienile, questo rifugio lussuoso offre 5 camere, 4 bagni, grande cucina attrezzata, ampio living, un ampio giardino privato con parcheggio, hot tub, patio con divani, BBQ, fire pit e cucina esterna. Ideale per chi cerca un'esperienza unica, unisce fascino rustico a comfort moderni. Perfetto per famiglie o gruppi, promette serate magiche sotto le stelle, tra relax nell'hot tub e cene all'aperto. Una fuga memorabile vi aspetta in questo angolo di paradiso!

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.

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.
Apartment 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.

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.
Apartment in Siena
4.88 out of 5 average rating, 164 reviews

Attico con vista su Siena

A fianco della Basilica di San Domenico, a pochissimi passi dal Duomo e da Piazza del Campo, in questo splendido ed elegante attico potrete godere della splendida vista e della comodità di raggiungere a piedi in pochi minuti tutti i maggiori punti di interesse della città.

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.
Condo in Siena
4.96 out of 5 average rating, 395 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$149 AUD$139 AUD$159 AUD$178 AUD$189 AUD$197 AUD$191 AUD$194 AUD$185 AUD$181 AUD$165 AUD$178 AUD
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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 $14 AUD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    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

  • Wi-Fi availability

    1,310 of Siena holiday rentals include Wi-Fi 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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