
Villa vacation rentals in Siena
Find and book unique villas on Airbnb
Top-rated villa rentals in Siena
Guests agree: these villas are highly rated for location, cleanliness, and more.

The Farmhouse Cottage
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

Poggio del Fattore-Villa with pool, hilltop, Chianti
Poggio del Fattore is situated at the eastern edge of the Chianti region in Valdambra, a green valley that joins the lands of Florence, Siena and Arezzo. The farmstead is on the top of an hill and lies at the end of a long private road through a large olive growing estate; therefore you absolutely need a car. The breathtaking landscapes and the location of the villa offer the privacy needed for a peaceful and relaxing holiday and a perfect departure point from which to explore central Tuscany.

Wine Experience Villa in Montepulciano
🏡 Villa Talosa è immersa nei vigneti della Fattoria della Talosa, storica azienda vitivinicola di Montepulciano produttrice di Vino Nobile. Un luogo autentico, ideale per rilassarsi con la magia della campagna toscana e una vista incantevole da ogni finestra. A soli 1,5 km dal centro storico, raggiungibile anche a piedi, potrete visitare la nostra Cantina Storica del 1500 sotto Piazza Grande: un’esperienza unica tra storia, passione per il vino. Riscaldamento e aria condizionata sono inclusi.

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

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.

San Giovanni in Poggio, villa Meriggio 95mq
Detached house, two double bedrooms, two bathrooms with shower, living room with fully equipped kitchen (dishwasher, washing machine, oven, microwave), double sofa bed, private garden with equipped pergola. Satellite TV and free Wi-Fi. Additional services at the property, upon reservation, include Focus brand Jarifa2 6.7 pedal-assisted bicycles and a wellness area with a Forest outdoor Finnish sauna and a heated mini-pool with hydromassage and chromotherapy with panoramic views.

Stone farmhouse in the 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.

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 Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

Villa Isabella
Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

Villa La Doccia, Greve in Chianti
Villa la Doccia is an 8-minute drive from the center of Greve in Chianti, Località Casole, The Villa in a quiet and quiet area is located inside a small farm surrounded by vineyards and olive groves. ➡️ We want you to know that we're doing everything we can to help and protect our guests by adopting a thorough and strict cleaning approach to this emergency. We disinfect and sanitize all parts of the house.

"Villa Daisy" overlooking Siena
Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful 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).
Popular amenities for Siena villa rentals
Private villa rentals

Charming villa 15' walk to center stunning view

Casale La Querce-Tuscan Farmhouse with pool & view

Sestuccina

Podere San Carlo

Poggio Novoli 6, Emma Villas

Terra Antica Suites & Villas – Cervognano

The Lazy Oak

The Villa of the Spendereccia Brigade!
Luxury villa rentals

Valluccia 51

Villa of the 2 Olive Trees (Abbadia Isola)

Podere on the Crete Senesi

Villa "The memory of time"

Villa with garden. The Cardinal's Garden.

Beautiful tuscan country house

Villa unesco heritage, Jacuzzi & garden. BB Daria

Villetta dei Fagiani - pools, Jacuzzi in Florence
Villa rentals with a pool

Pasqui Villas : Tribbio private house pool WiFi

La Cipresseta Estate | Cipresso House

Villa with pool in Siena

Romantic Villa with private pool and fabulous view

Romantic Villa with private pool - "Il Pollaio"

Casa al Fiume - Villa with exclusive pool

Villa La Poggerina, private pool and amazing view

Put down your luggage, this is just the beggining!
When is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R2,743 ZAR | R2,300 ZAR | R3,033 ZAR | R2,045 ZAR | R3,084 ZAR | R5,862 ZAR | R5,044 ZAR | R5,078 ZAR | R3,783 ZAR | R3,510 ZAR | R4,056 ZAR | R4,499 ZAR |
| 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 |
Quick stats about villa rentals in Siena

Total vacation rentals
Explore 30 vacation rentals in Siena

Nightly prices starting at
Siena vacation rentals start at R1,193 ZAR per night before taxes and fees

Verified guest reviews
Over 1,320 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Siena vacation 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
Destinations to explore
- Boutique hotels Siena
- Rentals with a fireplace Siena
- Family-friendly rentals Siena
- Hotel rooms Siena
- Vacation home rentals Siena
- Fitness-friendly rentals Siena
- Cottage rentals Siena
- Serviced apartment rentals Siena
- Apartment rentals Siena
- House rentals Siena
- Pet-friendly rentals Siena
- Rentals with breakfast Siena
- Rentals with outdoor seating Siena
- Rentals with a fire pit Siena
- Condo rentals Siena
- Rentals with a patio Siena
- Rentals with a hot tub Siena
- Rentals with pools Siena
- Rentals with a washer and dryer Siena
- Bed and breakfasts Siena
- Smoking-friendly rentals Siena
- Rentals with an EV charger Siena
- Villa rentals Siena
- Villa rentals Tuscany
- Villa rentals Italy
- Santa Maria Novella
- Piazzale Michelangelo
- Lake Trasimeno
- Duomo di Firenze
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Cala Violina
- Spiagge bianche
- Mercato Centrale
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Uffizi Gallery
- Fortezza da Basso
- Gulf of Baratti
- 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
- Medici Chapels
- Stadio Artemio Franchi
- Mugello Circuit
- Spiaggia Marina di Cecina
- Things to do Siena
- Art and culture Siena
- Food and drink Siena
- Sightseeing Siena
- Nature and outdoors Siena
- Tours Siena
- Things to do Siena
- Food and drink Siena
- Art and culture Siena
- Nature and outdoors Siena
- Sightseeing Siena
- Sports activities Siena
- Tours Siena
- Things to do Tuscany
- Tours Tuscany
- Sports activities Tuscany
- Entertainment Tuscany
- Nature and outdoors Tuscany
- Sightseeing Tuscany
- Art and culture Tuscany
- Food and drink Tuscany
- Things to do Italy
- Sightseeing Italy
- Wellness Italy
- Food and drink Italy
- Tours Italy
- Art and culture Italy
- Entertainment Italy
- Sports activities Italy
- Nature and outdoors Italy






