Siena vacation rentals
Vacation rentals in Siena by owner — compare homes, condos and cabins, message verified hosts, and book direct with no service fees.
Siena, in the heart of Tuscany, is renowned for its medieval streets and landmarks like Piazza del Campo, the Gothic Siena Cathedral, and the Torre del Mangia. Visitors come to experience the historic Siena Palio horse race held twice yearly, explore the rich Tuscan food and wine scene, and admire the art at Pinacoteca Nazionale. Houfy connects you directly with hosts in Siena, ensuring bookings are straightforward. Discover vacation rentals throughout Siena's historic center as well as nearby areas like Chianti and Monteriggioni, offering everything from Renaissance-style apartments to countryside villas. The region is especially picturesque in fall, when the vineyards are full and the air is crisp.
Top-Rated Vacation Homes in Siena
Browse the highest rated vacation properties in Siena.
We had the most unforgettable stay! From the moment we arrived, the breathtaking views of the vineyards made us feel like we were in a dream. The villa itself was incredibly cozy, smart, and spotless, blending rustic charm with modern comfort, truly a home away from home ❤️ What really made this experience special was the warmth and kindness of our hosts. They went above and beyond, from the delicious local treats they left for us to their thoughtful recommendations for exploring the area. Their hospitality made us feel so welcome and cared for 😊 Traveling with young children can be a challenge, but this villa was perfect for them. The kids had an absolute blast with the trampoline, playhouse, pool, and plenty of toys. We shared countless laughs and created so many happy memories here with our friends and family. If you're looking for a place to unwind, reconnect with loved ones, and soak in the beauty of Tuscany, I can't recommend this villa enough. We hope to return someday! 🙌🌄✨
€5,600.00 EUR total for 7 nights
Oct 24 – 31, 2026
Liebe Paola, lieber Valerio Wir durften Ende Juni 2018 eine Woche in der Villa «Le Ginepraie» in Pignano von Paola & Valerio verbringen. Die Villa liegt zwischen San Gimignano und Volterra, die beide in einer 20-minütigen Autofahrt erreichbar sind. Das Anwesen ist platziert auf einem wunderschönen toskanischen Hügel und ist rundum von zeichnerischen Weizenfeldern umgeben. Es besteht aus dem Haus für die Gäste, einem separaten Gastrohaus, einem Pool-Areal (wird täglich gereinigt), einem freistehenden Pizzaofen und dem Haus, in dem Paola & Valerio wohnen. Die zweigeschossige Gäste-Villa verfügt im Erdgeschoss über drei Schlafzimmer und einer grossen Hauptküche mit Zugang zur Pergola. Im Obergeschoss sind zwei baugleiche und sehr grosszügige Wohnungen zu finden. Alle fünf Doppelschlafzimmer verfügen über ein gepflegtes, sauberes und voll ausgestattetes Bad (Dusche, Waschbecken, Fusswaschbecken und Toilette) und über ein Fernsehgerät. Die beiden Küchen im Obergeschoss wie auch die Küche im Erdgeschoss verfügen über alle nötigen Utensilien. Im hinteren Bereich des Hauses, hat es eine grosse Pergola (Unterstand), in welcher eine Lounge und ein grosser Tisch für ca. 12 Personen eingerichtet sind. Während des Abendessens kann man von hier aus wunderbar den Sonnenuntergang geniessen. Gerne möchten wir uns nochmals für die herzliche Gastfreundschaft bei Paola & Valerio bedanken, die uns bei allen Belangen behilflich waren - Grazie per i ricordi meravigliosi -. Kevin, Miro, Gian, Andrew, Marcial e Valentino
$432.00 USD total for 3 nights
Sep 21 – 24, 2026
Alles war perfekt. Wir hatten einen wunderbaren Aufenthalt in Sarteano. Das Apartment hat den typischen italienischen Stil und ist gleichzeitig super modern und makellos. Sarteano ist ein traumhafter Ort mit schönen kleinen Restaurants und Ateliers. Gleichzeitig ist es ein perfekter Ausgangspunkt um die Toskana von dort erkunden zu gehen. Stefano hat uns wertvolle Tipps gegeben für Sarteano und die Umgebung, sodass wir perfekt aufgehoben waren. Die Kommunikation lief super und alles Organisatorische lief reibungslos. Wir würden jederzeit wiederkommen und können die Unterkunft nur wärmstens empfehlen!
€258.00 EUR total for 3 nights
Sep 16 – 19, 2026
Traveling by myself I spent three nights in Riccardo's apartment in Arezzo. Spotlessly clean and warm, it has arched brick ceilings over the passage ways from one room to another which add character to the place. By Italian standards the bathroom and its shower are modern and spacious. The big bed was very comfortable. The kitchen is fully equipped. The only thing that makes it somewhat less than perfect is that the apartment is located on a very busy street. This street has rather narrow sidewalks. Cars, trucks and buses constantly roar by, as there are very few stop signs or traffic lights to slow them down. The good news is that after a very short walk, 5 to 7 minutes, you reach the Porta San Lorentina and enter the historic center, into which only residents, taxis and public service vehicles are allowed. Then you are saved from the noise and chaos of the modern world and in a totally different world you can start to appreciate the charm and beauty of Arezzo. Riccardo is a very friendly and I considerate fellow. He even offered to pick me up at the train station and arranged for his Mom to drive me to the train station on my departure, as he was at work. If and when I will return to Arezzo I will most definitely try to stay again at Riccardo's apartment unless I win the lottery and obtain the means to book a hotel and eat out all the time in the historic center.
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Vacation houses with pools in Siena
Cool off in style with these amazing pool homes in Siena.
€1,998.50 EUR €1,908.65 EUR total for 3 nights
Sep 16 – 19, 2026
€1,194.00 EUR total for 3 nights
Sep 25 – 28, 2026
€892.00 EUR total for 3 nights
Sep 30 – Oct 3, 2026
€9,926.00 EUR total for 4 nights
Oct 19 – 23, 2026
€1,003.00 EUR total for 3 nights
Sep 28 – Oct 1, 2026
€1,076.00 EUR total for 4 nights
Oct 8 – 12, 2026
Pet friendly vacation rentals in Siena
Bring your furry friend along! Browse pet-welcoming homes in Siena.
€384.00 EUR total for 5 nights
Oct 5 – 10, 2026
€1,624.00 EUR total for 7 nights
May 22 – 29, 2027
€586.00 EUR total for 5 nights
Oct 4 – 9, 2026
Why visit Siena
Discover what makes Siena a perfect vacation rental destination.
Explore Historic Siena
Visit the famous Piazza del Campo.
Siena's Piazza del Campo, just 1.5 miles from city center, is renowned for its stunning medieval architecture and hosts the Palio di Siena horse race.
Taste Tuscan Delights
Indulge in local specialties like pici pasta.
Try traditional Tuscan dishes at Osteria Le Logge, located 0.3 miles from the city center, for authentic flavors and a superb wine selection.
Admire Frescoes at Duomo
Discover masterpieces within the Siena Cathedral.
The Siena Cathedral features intricate frescoes and is a short 0.4 miles from the heart of the city, showcasing works by Pinturicchio.
Boutique Shopping
Discover artisanal shops in the city center.
Walk along Via di Città, just 0.2 miles from Piazza del Campo, known for its high-quality leather goods, ceramics, and Italian fashion.
Where to stay in Siena
The best areas and neighborhoods for your vacation rental in Siena.
Il Campo
Centered around the Piazza del Campo, this area is vibrant with cafes, restaurants, and events like the Palio horse race.
San Prospero
A quiet residential area just north of the city center, offering lush parks and local markets for an authentic experience.
Porta Romana
Famed for its artistic flair, this neighborhood boasts galleries and easy access to Siena's southern gate.
Sant'Agostino
Known for its historic churches and traditional eateries, it's a laid-back area perfect for leisurely exploration.
Siena vacation rentals with free WiFi, air conditioning or kids friendly
Free WiFi, air conditioning, kids friendly and more — every Siena vacation rental here is listed by a verified host and bookable direct, with the price the host set.
Top attractions in Siena
All within driving distance of Siena vacation rentals.
Piazza del Campo
Home to the famous Palio horse race held twice a year. · 0 miles
Siena Cathedral
Stunning Gothic cathedral known for its intricate facade. · 0.4 miles
Santa Maria della Scala
A complex housing museums and exhibitions, once a hospital. · 0.5 miles
Orto Botanico dell'Università di Siena
Botanical gardens featuring native and exotic plant species. · 0.7 miles
Palazzo Pubblico
Historic town hall with spectacular frescoes. · 0.1 miles
Via di Città
Famous for cafes and artisanal food stores. · 0.2 miles
Getting to and around Siena
Siena is accessible by train, bus, or car, with local buses connecting neighborhoods.
- SIENA RAILWAY STATION
- Located 1.5 miles from the city center, provides regional connections to Florence and beyond.
- CAR RENTALS
- Available at Siena's city center for convenient exploration of the Tuscan countryside.
- SIENA URBAN BUSES
- Frequent routes connect key areas like Piazza del Campo and residential neighborhoods.
- FLORENCE AIRPORT
- About 50 miles north, connects Siena to major European cities.
Similar vacation rentals near Siena
Homes within 60 miles of Siena, from verified hosts.
€680.00 EUR total for 3 nights
Jan 2 – 5, 2027
Explore near Siena
Cities and towns within driving distance of Siena, each bookable direct with the host.
Direct with the host
Message the host before you book. Ask questions, confirm details, and deal with the person who owns the property.
Verified hosts
Every host completes identity verification before a listing goes live.
Itemised pricing
Every charge is shown before you pay — including the API connection fee, where one applies.
More vacation rental destinations around Siena
Frequently asked questions
Quick answers about booking vacation rentals in Siena and what direct booking on Houfy actually means.
On Houfy, rental prices typically range from €100 to €250 per night depending on the property location and season.
Yes, several rentals on Houfy in Siena are pet-friendly. Always check the listing details for specific pet policies.
Il Campo for historic attractions, San Prospero for parks, and Camollia for shops and nightlife offer great options.
Visit in May or September for pleasant weather and to experience the Palio horse race in July or August.
Siena offers a range of rentals from historic apartments in the city center to charming villas in the countryside.
Rentals provide spacious living and kitchen facilities ideal for families, while hotels offer full-service amenities.
Siena is renowned for its medieval architecture, the Palio di Siena horse race, and its status as a UNESCO World Heritage Site.
Houfy is a platform for vacation rentals; guests pay the listed price directly to the host.
Yes, Houfy ensures secure transactions and direct communication between guests and hosts for a trustworthy booking process.






















































































































































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