
Holiday houses in Siena
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Top-rated holiday rentals in Siena
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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.

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.

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.

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 to 20 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 Wi-Fi Strategic location for visiting Tuscany and Umbria.

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.

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.

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

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!

"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).

Central with a view of the green house with terrace
Entire bright and welcoming accommodation just 200 MT from Piazza del Campo, 400 MT from the Duomo, with convenient car parking just 150 MT away. The beauty and quiet of the countryside in the historic center, enjoyable from the terrace. All amenities within walking distance. Only 5 steps to the entrance.

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.

Amazing Cott. in the heart of Siena
Fantastic apartment recently renovated by a famous architect from Siena. It is sited in the garden of the manor house in the heart of the city. A corner of paradise where you can relax few steps from the main tourist attractions.
Popular amenities for Siena holiday rentals
Other great holiday rentals in Siena

AnticaVista, Luxury Apartment with Tower Views

Tuscan cottage with an heavenly view

The Arches of Corsanello | Apt "Siena" x 3

Poggio Bicchieri Holiday Farm - Poesia apartment

Casa Duprè - Cozy Apartment near Piazza del Campo

Enjoy Amazing View in Tuscany in Our Country House

The twigs

Cipressini 2 - pool and amazing views
When is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $159 AUD | $148 AUD | $169 AUD | $190 AUD | $202 AUD | $210 AUD | $203 AUD | $206 AUD | $197 AUD | $190 AUD | $166 AUD | $171 AUD |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°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 holiday rentals in Siena

Total holiday rentals
Explore 1,390 holiday rentals in Siena

Nightly prices starting at
Siena holiday rentals start at $15 AUD 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!
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- Santa Maria Novella
- Piazzale Michelangelo
- Lake Trasimeno
- Duomo di Firenze
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Cala Violina
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- Kite Beach Fiumara
- The Boboli Gardens
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Spiagge bianche
- Medici Chapels
- Spiaggia Marina di Cecina
- Mugello Circuit
- Palazzo Vecchio
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