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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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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, 292 reviews

Podere Vergianoni nestled in Chianti with a pool

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 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, 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 favourite
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 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, 194 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 aerial view captures the property nestled in a scenic landscape, surrounded by rolling hills and cultivated fields. Olive groves line the winding road, with cypress trees dotting the surroundings, showcasing the natural beauty of the Tuscan countryside.
Condo in Asciano
4.97 out of 5 average rating, 319 reviews

Green – The meadows in Tuscany

Apartment consisting of 1 double bedroom, equipped kitchen, large living room and bathroom TV, BBQ, (we provide the washing machine from 9 a.m. to 8 p.m. which is in our laundry room for those who request it). We recommend the car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and wifi Strategic location for visiting Tuscany and Umbria.

Top Guest favourite
An open living area is shown with a dining table surrounded by black and white chairs. The ceiling displays decorative beams, and light enters through a window, illuminating the space. A fireplace is positioned against one wall, with artwork adorning the surrounding walls.
Apartment in Siena
4.95 out of 5 average rating, 287 reviews

Renovated flat 50 meters from Piazza del Campo

Apartment in the historic center of Siena, just 50 meters from Piazza del Campo. The accommodation was completely renovated in 2019. The restoration was carried out trying to keep its main features intact, but adding all the necessary equipment to today's way of life. The apartment is an ideal place for those who want to visit and experience the city; In fact, all the monuments and attractions of the historic center can be reached on foot in a few minutes.

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, 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 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, 229 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 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, 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 favourite
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.

Top Guest favourite
Farm stay in Campiglia D'orcia
4.94 out of 5 average rating, 469 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 favourite
A terrace view reveals the vibrant Piazza del Campo, framed by historic buildings. The distant Torre del Mangia stands tall against a backdrop of clouds. A rustic wooden table is placed on the terrace, inviting relaxation while overlooking the lively square.
Apartment in Siena
4.9 out of 5 average rating, 496 reviews

Apartment in Piazza del Campo-Balcone delle Aquile

A cozy apartment with a terrace with unparalleled views of the Torre del Mangia tower and Piazza del Campo. The apartment has three comfortable bedrooms, a living room, a large bathroom and a fully equipped kitchen. A perfect terrace from which to see the Palio, as indicated in the reviews.

Popular amenities for Siena holiday rentals

When is the best time to visit Siena?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$181 NZD$169 NZD$194 NZD$217 NZD$231 NZD$240 NZD$233 NZD$236 NZD$226 NZD$217 NZD$190 NZD$196 NZD
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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 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.

  • 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 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.

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 $18 NZD per night before taxes and fees

  • Verified guest reviews

    Over 76,560 verified reviews to help you choose

  • Family-friendly holiday rentals

    560 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 510 rentals that welcome pets

  • Holiday 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 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

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