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Vacation rentals in Siena

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Top-rated vacation rentals in Siena

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

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Top guest favorite
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, 290 reviews

Podere Vergianoni immerso nelChianti con piscina

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 favorite
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, 142 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 favorite
A cozy table set for two holds two glasses of red wine alongside a stack of books. A view of the dramatic Mangia Tower can be seen through the window, illuminated by the evening sky. A green plant adds a touch of nature to the scene.
Apartment in Siena
4.99 out of 5 average rating, 132 reviews

Piazza del Campo Honeymoon Suite: romantic gateway

The 800-year-old Palazzo Accarigi, a Palazzo-Tower overlooking Piazza del Campo, offers a dreamy suite for Honeymoons and Anniversaries. As inside a fairy-tale, you will sleep in a princely baldaquin with a magnificent view of Piazza del Campo, while the highest quality noise-reducing windows will ensure you the quietest stay. This suite offers a private and safe place to live the most authentic Tuscan lifestyle: plan to stay more days, use this flat as a base to explore Siena province

Top guest favorite
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, 193 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 favorite
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, 433 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 favorite
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, 228 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 favorite
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.
Apartment in Siena
4.98 out of 5 average rating, 100 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 favorite
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, 235 reviews

Casa al Gianni - Capanna

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 favorite
A panoramic view showcases the charming rooftops of the city, with terracotta tiles and historic buildings. The Torre del Mangia stands prominently in the background, alongside lush greenery and the distant valley. The cloudy sky adds depth to this serene urban landscape.
Apartment in Siena
4.96 out of 5 average rating, 379 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.

Guest favorite
An outdoor dining area is surrounded by lush greenery and flowering plants, featuring a circular table with four elegant wrought iron chairs. A cozy blanket is draped over one chair, and a scenic view of rolling hills extends in the background under a muted sky.
Apartment in Monteroni d'Arbia
4.95 out of 5 average rating, 265 reviews

"Red Rose" apartment with view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, each with an independent entrance and private garden, with a panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Top guest favorite
Farm stay in Campiglia D'orcia
4.94 out of 5 average rating, 467 reviews

Poggio Bicchieri Holiday Farm - Poesia apartment

Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.

Top guest favorite
The aerial view captures the historic structure nestled among rolling green hills, framed by tall trees. The stone walls reflect medieval architecture, while a terrace offers an inviting space below. The surrounding landscape showcases farms and cypress trees against a clear blue sky.
Home in Monticchiello
4.98 out of 5 average rating, 195 reviews

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

Popular amenities for Siena vacation rentals

When is the best time to visit Siena?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR1,759 ZARR1,640 ZARR1,879 ZARR2,101 ZARR2,238 ZARR2,323 ZARR2,255 ZARR2,289 ZARR2,186 ZARR2,101 ZARR1,845 ZARR1,896 ZAR
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°C

Frequently Asked Questions

  • What types of vacation rentals are available in Siena?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Siena. From over 100 house rentals to over 730 apartment rentals, we've got you covered.

  • Are there pet-friendly bed and breakfast rentals in Siena?

    Four-legged friends are welcome in Siena. Choose from more than 30 bed and breakfast rentals for guests traveling with pets.

  • Do hotel rentals in Siena have self check-in?

    Absolutely! We offer over 10 hotel rentals with self check-in in Siena. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly villa rentals in Siena?

    Siena has more than 20 family-friendly villa rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there condo rentals with a dedicated workspace in Siena?

    Yes! Work meets play with ease at over 150 condo rentals in Siena featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do villa rentals in Siena have a bbq area?

    Absolutely! We offer over 10 villa rentals with a bbq area in Siena. Enjoy a tailored experience with all the comforts you desire.

  • Do bed and breakfast rentals in Siena have wifi?

    Absolutely! We offer over 70 bed and breakfast rentals with wifi in Siena. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in boutique hotel rentals in Siena?

    Experience the best of Siena with our boutique hotel rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Siena villa rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 villa rentals with pools in Siena, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in Siena have a gym?

    Absolutely! We offer over 10 apartment rentals with a gym in Siena. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Siena

  • Total vacation rentals

    Explore 1,390 vacation rentals in Siena

  • Nightly prices starting at

    Siena vacation rentals start at R171 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 76,560 verified reviews to help you choose

  • Family-friendly vacation rentals

    560 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 510 rentals that welcome pets

  • Vacation rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    630 properties have a dedicated workspace

  • Wi-Fi availability

    1,310 of Siena vacation 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

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Siena