
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.

Tuscan charm of villa - countryside
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

Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

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.

Belforti Tower
Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

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.
Popular amenities for Siena villa rentals
Private villa rentals

Villa with pool in Chianti Area

Luxury Villa on Chianti Wine Estate

Charming villa 15' walk to center stunning view

Valluccia 51

Terra Antica Suites & Villas – Cervognano

The Lazy Oak

Villa unesco heritage, Jacuzzi & garden. BB Daria

Fabulous 3Br Villa with 360° Views!
Luxury villa rentals

Agriturismo Podere Scaluccia Chianti, Florence 12 px

CHARMING VILLA IN CHIANTI

Poggio Novoli 6, Emma Villas

Podere on the Crete Senesi

Beautiful tuscan country house

Villa La Poggerina, private pool and amazing view

The Villa of the Spendereccia Brigade!

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

Stunning Tuscan Villa & Panoramic Infinity Pool

Villa San Martino 6-8 people

Casale La Querce-Tuscan Farmhouse with pool & view

Villa with pool in Siena

Romantic Villa with private pool and fabulous view

Romantic Villa with private pool - "Il Pollaio"

Tenuta Uzielli an elegant countryside villa

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 | G$33,674 GYD | G$28,236 GYD | G$37,229 GYD | G$25,098 GYD | G$37,857 GYD | G$71,949 GYD | G$61,910 GYD | G$62,328 GYD | G$46,432 GYD | G$43,086 GYD | G$49,779 GYD | G$55,217 GYD |
| 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 G$14,641 GYD 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
- Provence Vacation rentals
- Rome Vacation rentals
- Milan Vacation rentals
- Nice Vacation rentals
- Florence Vacation rentals
- Venice Vacation rentals
- Francavilla al Mare Vacation rentals
- Naples Vacation rentals
- Marseille Vacation rentals
- Italian Riviera Vacation rentals
- Cannes Vacation rentals
- Bologna Vacation rentals
- Family-friendly rentals Siena
- Serviced apartment rentals Siena
- Smoking-friendly rentals Siena
- Rentals with breakfast Siena
- Fitness-friendly rentals Siena
- Rentals with an EV charger Siena
- Cottage rentals Siena
- Rentals with a washer and dryer Siena
- Pet-friendly rentals Siena
- House rentals Siena
- Boutique hotels Siena
- Condo rentals Siena
- Rentals with a fireplace Siena
- Vacation home rentals Siena
- Rentals with outdoor seating Siena
- Bed and breakfasts Siena
- Apartment rentals Siena
- Rentals with a fire pit Siena
- Hotel rooms Siena
- Rentals with pools Siena
- Rentals with a hot tub Siena
- Rentals with a patio 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
- 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
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- The Boboli Gardens
- Spiagge bianche
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Mugello Circuit
- Spiaggia Marina di Cecina
- Palazzo Vecchio
- Things to do Siena
- Tours Siena
- Nature and outdoors Siena
- Sightseeing Siena
- Food and drink Siena
- Art and culture Siena
- Things to do Siena
- Food and drink Siena
- Nature and outdoors Siena
- Tours Siena
- Sports activities Siena
- Art and culture Siena
- Sightseeing Siena
- Things to do Tuscany
- Tours Tuscany
- Sports activities Tuscany
- Art and culture Tuscany
- Nature and outdoors Tuscany
- Wellness Tuscany
- Entertainment Tuscany
- Sightseeing Tuscany
- Food and drink Tuscany
- Things to do Italy
- Wellness Italy
- Nature and outdoors Italy
- Tours Italy
- Sightseeing Italy
- Entertainment Italy
- Food and drink Italy
- Sports activities Italy
- Art and culture Italy






