
Villa holiday rentals in Siena
Find and book unique villas on Airbnb
Quick stats about villa rentals in Siena

Total holiday rentals
Explore 40 holiday rentals in Siena

Nightly prices starting at
Siena holiday rentals start at $102 NZD per night before taxes and fees

Verified guest reviews
Over 1,410 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Siena holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Siena rentals

4.7 Average rating
Siena stays receive an average rating of 4.7 out of 5 from guests
Top-rated villa rentals in Siena
Guests agree: These villas are highly rated for location, cleanliness and more.

Manor House - IlVillinoFarmhouse
Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Charming Tuscan Villa with View forFamily&Friends
The house is a typical podere of the late 1800, stone walls, chestnut beams, and hand-made tiles have all been kept; what has changed is the comfort behind them. The Host Fulvia lives in the ground-floor apt. and she's on hand throughout your stay without ever intruding — a rhythm that guests consistently single out. Total accommodation is 8 guests across 2 bdr and 2 bathrooms. Visit Montepulciano, Pienza, Bagni Vignoni and iconic Unesco sites in Val d'Orcia within short and easy driving away

Villa La Doccia, Greve in Chianti
Villa La Doccia si trova a circa 8 minuti di auto dal centro di Greve in Chianti, in Località Casole, nel cuore della splendida campagna del Chianti. La villa è situata in una zona tranquilla e silenziosa, all’interno di una piccola azienda agricola circondata da vigneti e uliveti, dove gli ospiti possono godere della natura e dei tipici paesaggi toscani. La posizione è ideale per chi desidera rilassarsi immerso nella campagna ma allo stesso tempo essere vicino al centro di Greve in Chianti

Tuscan charm of villa - countryside - Villa Senaia
Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Villa of the 2 Olive Trees (Abbadia Isola)
FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)

Virgi House
Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

Il Vichiaccio: Accessible Chianti Villa & Jacuzzi
Cozy Chianti getaway near Florence. This 135sqm stone house has a rustic kitchen with a fireplace. It sleeps 9 guests in 3 rooms, but for groups of 11, a 4th bedroom is included. Smaller groups can add it for extra comfort (extra fee). Enjoy the private garden with a covered dining area, a patio with armchairs and parking. The ground floor is fully wheelchair-friendly (kitchen, bedroom, bath). Plus, A/C and a private Jacuzzi (extra fee) for relaxing under the stars!

Stone farmhouse in Val D'Orcia
19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.

Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Luxury Villa in the very heart of Chianti
The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.

Villa unesco heritage, Jacuzzi & garden. BB Daria
Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant
Popular amenities for Siena villa rentals
Private villa rentals

Tuscan Villa with Private Jacuzzi & River

Villa Holm stunning view 10 mn walk to city centre

Podere Scaluccia Chianti Agritourism, Florence

Elf's Hut - Elf's Hut

Villa Montemaggio

Villa Tonacato - Charming Villa with private pool

The Villa of the Spendthrift Brigade!

Charming Cottage in the Heart of Tuscany
Luxury villa rentals

Pasqui Villas : Tribbio private house pool WiFi

Villa in Montepulciano with a Pool

Luxury Villa in Chianti • Private Natural Pool

La Vignaccia (Farmhouse) - villa w/private pool

Beautiful tuscan country house

Villa with garden. The Cardinal's Garden.

Villa Isabella

Villa Poggio in Mandria in Chianti
Villa rentals with a pool

Tuscany Villa Mammi

Villa with pool in Chianti Area

Luxury Villa on Chianti Wine Estate

Poggelleri the postcard on Poppi and Tuscan hills

Podere Biagio | Rural Tuscan farmhouse with pool

Montemarcoli

[Le rondini in Tuscany] Exclusive View Pool Villa

Villa il Balocco
When is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $993 NZD | $410 NZD | $228 NZD | $364 NZD | $555 NZD | $320 NZD | $504 NZD | $507 NZD | $378 NZD | $535 NZD | $984 NZD | $598 NZD |
| 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 |
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- Wildlife Italy
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- Museums Italy
- Performances Italy
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- Dining Italy
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- Galleries Italy
- Tours Italy
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