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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.

Luxury Serviced Family Villa - Pool/Hot Tub *A/C*

6 bd·3 ba
5· 23
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! 🙌🌄✨
D. · Stay August 2024

Luxury villa, chef, massage, yoga, home shopping

5 bd·5 ba
5· 18

€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
V. · Stay June 2018

The Corte del Podestà

1 bd·1 ba
5· 12

$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!
F. · Stay October 2024

Your oasis in the heart of Tuscany

1 bd·1 ba
4.85· 65

€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.
A. · Stay November 2017

Recommended Homes in Siena

Handpicked properties we think you'll love in Siena.

Apartment in the historic center | Campagnatico

1 bd·1 ba
4.7· 23

La Smarrita

5 bd·7 ba

€1,324.00 EUR total for 4 nights

Oct 18 – 22, 2026

Casa Frati

4 bd·4 ba

€1,182.00 EUR total for 3 nights

Sep 16 – 19, 2026

Il Feudo

5 bd·3 ba

€538.00 EUR total for 3 nights

Sep 21 – 24, 2026

Nido del Sorbino

1 bd·1 ba

€768.00 EUR total for 7 nights

Oct 17 – 24, 2026

Sissi

3 bd·3 ba

€1,681.00 EUR total for 7 nights

Sep 20 – 27, 2026

Podere dei Venti

6 bd·6 ba

€1,731.00 EUR total for 5 nights

Sep 19 – 24, 2026

Val d'Orcia

5 bd·5 ba

€1,299.00 EUR total for 3 nights

Sep 27 – 30, 2026

Vacation houses with pools in Siena

Cool off in style with these amazing pool homes in Siena.

Il Lamone

2 bd·1 ba

€884.00 EUR total for 5 nights

Oct 3 – 8, 2026

€1,998.50 EUR €1,908.65 EUR total for 3 nights

Sep 16 – 19, 2026

Podere Vignali

4 bd·4 ba

€1,194.00 EUR total for 3 nights

Sep 25 – 28, 2026

Poggio all'Aia

4 bd·4 ba

€892.00 EUR total for 3 nights

Sep 30 – Oct 3, 2026

Antico Borgo San Lorenzo

18 bd·13 ba

€9,926.00 EUR total for 4 nights

Oct 19 – 23, 2026

Il Mulinaccio

6 bd·5 ba

€1,003.00 EUR total for 3 nights

Sep 28 – Oct 1, 2026

Tegliaia

5 bd·5 ba

€1,076.00 EUR total for 4 nights

Oct 8 – 12, 2026

Reggine

6 bd·3 ba

€1,151.00 EUR total for 4 nights

Oct 12 – 16, 2026

Pet friendly vacation rentals in Siena

Bring your furry friend along! Browse pet-welcoming homes in Siena.

Dilia

2 bd·1 ba

€384.00 EUR total for 5 nights

Oct 5 – 10, 2026

Le Sodole - Petunia

4 bd·4 ba

Allerona

3 bd·3 ba

€382.00 EUR total for 3 nights

Oct 13 – 16, 2026

Podere Agnese

3 bd·2 ba

€1,624.00 EUR total for 7 nights

May 22 – 29, 2027

Pergola

3 bd·1 ba

Casale Ulisse

3 bd·3 ba

€586.00 EUR total for 5 nights

Oct 4 – 9, 2026

Allerona

2 bd·2 ba

€296.00 EUR total for 3 nights

Oct 25 – 28, 2026

Allerona

3 bd·3 ba

€399.00 EUR total for 3 nights

Oct 5 – 8, 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.

Best for: history enthusiasts, foodies, event seekers

San Prospero

A quiet residential area just north of the city center, offering lush parks and local markets for an authentic experience.

Best for: families, local living lovers, park enthusiasts

Porta Romana

Famed for its artistic flair, this neighborhood boasts galleries and easy access to Siena's southern gate.

Best for: art lovers, photographers, explorers

Sant'Agostino

Known for its historic churches and traditional eateries, it's a laid-back area perfect for leisurely exploration.

Best for: history buffs, leisure travelers, food lovers

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.

Trains
SIENA RAILWAY STATION
Located 1.5 miles from the city center, provides regional connections to Florence and beyond.
Driving
CAR RENTALS
Available at Siena's city center for convenient exploration of the Tuscan countryside.
Buses
SIENA URBAN BUSES
Frequent routes connect key areas like Piazza del Campo and residential neighborhoods.
Airports
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.

La Chiave di Sol

1 bd·1 ba
4.88· 43

Casa Ettore - Historic Palazzo

3 bd·3 ba
5· 19

Villetta La Poderosa [Saturnia Hotsprings]

4 bd·2 ba
4.9· 10

Bettini House – House with terrace near Florence

2 bd·1 ba
5· 4

La Chiave di Sol 2

2 bd·1 ba
5· 21

Fronte Mare, Altaluna

2 bd·1 ba
4.75· 4

Casina di Andrea with an above-ground pool

2 bd·2 ba
5· 12

€680.00 EUR total for 3 nights

Jan 2 – 5, 2027

Superior Suites 5

1 bd·1 ba

Comfort - Green

2 bd·1 ba
5· 3

Premium - Orange

1 bd·1 ba
4.5· 2
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