
Villa holiday 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

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.

A paradise in Montepulciano...
Villa Il Cubo is a full centralized air conditioned private house with large private swimming pool placed in the best garden spot for incredible views on the countryside around. Decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY!!!!!!

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 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.

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

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.
Popular amenities for Siena villa rentals
Private villa rentals

Country House Lo Spigo 4, Emma Villas

Villa with pool in Chianti Area

Country Charm & Jacuzzi

Tuscan villa in the heart of the Val d'Orcia

Romantic Villa with private pool - "Il Pollaio"

Podere on the Crete Senesi

Villa "The memory of time"

Villa with garden. The Cardinal's Garden.
Luxury villa rentals

Casale La Querce-Tuscan Farmhouse with pool & view

Valluccia 51

CHARMING VILLA IN CHIANTI

La Vignaccia (Farmhouse) - villa w/private pool

Villa of the 2 Olive Trees (Abbadia Isola)

Riecine Capanna 4

Villa Leopoldina, 6 pax, Private Pool

Dream House in Tuscany, with Amazing View and Pool
Villa rentals with a pool

Lovely Villa situated in nature

Ortaglia di Sotto Farm

La Bacaia

Tenuta Uzielli an elegant countryside villa

Villa Le Liscaie [Sienese Crete]

Villa with private pool in central Tuscany

Tuscany View - Villa Arianna

Detached villa with private pool
Destinations to explore
- Rentals with a fire pit Siena
- Farmstay rentals Siena
- Smoking-friendly rentals Siena
- Barn rentals Siena
- Family-friendly rentals Siena
- Castle rentals Siena
- Condo rentals Siena
- Rentals with a fireplace Siena
- Loft rentals Siena
- Hotel rooms Siena
- Rentals with outdoor seating Siena
- Rentals with pools Siena
- Apartment rentals Siena
- Tiny house rentals Siena
- Rentals with a patio Siena
- Rentals with an accessible height bed Siena
- Rentals with beach access Siena
- Boutique hotels Siena
- Rentals with a hot tub Siena
- Tent rentals Siena
- House rentals Siena
- Townhouse rentals Siena
- Rentals with an EV charger Siena
- Rentals with breakfast Siena
- Guesthouse rentals Siena
- Private suite rentals Siena
- Rentals with a sauna Siena
- Rentals with a balcony Siena
- Rentals with a home theatre Siena
- Serviced apartment rentals Siena
- Fitness-friendly rentals Siena
- Holiday home rentals Siena
- Rentals with a washing machine and dryer Siena
- Cottage rentals Siena
- Pet-friendly rentals Siena
- Waterfront rentals Siena
- Luxury rentals Siena
- Rentals with lake access Siena
- Nature eco lodge rentals Siena
- Bed and breakfasts Siena
- Villa rentals Tuscany
- Villa rentals Italy
- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Cala Violina
- Mercato Centrale
- Uffizi Gallery
- Fortezza da Basso
- Piazzale Michelangelo
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- Mugello Circuit
- Kite Beach Fiumara
- The Boboli Gardens
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Spiaggia Marina di Cecina
- Cala Di Forno
- Stadio Artemio Franchi
- Basilica di Santa Croce
- Things to do Siena
- Sightseeing Siena
- Art and culture Siena
- Nature and outdoors Siena
- Sports activities Siena
- Food and drink Siena
- Tours Siena
- Things to do Tuscany
- Wellness Tuscany
- Sports activities Tuscany
- Nature and outdoors Tuscany
- Entertainment Tuscany
- Art and culture Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Tours Tuscany
- Things to do Italy
- Food and drink Italy
- Art and culture Italy
- Wellness Italy
- Nature and outdoors Italy
- Sports activities Italy
- Tours Italy
- Sightseeing Italy
- Entertainment Italy




