
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.

Cottage in Val d'Orcia Tuscany, Jacuzzi & Hot Tub!
Welcome at Charming Cottage in Tuscan Villa! Immerse in the history of Montepulciano, Pienza, Cortona, Siena, Explore Val d'Orcia, natural hot pools and falls! Fully equipped kitchen, private patio for al fresco dining, magnificent bathroom with large Jacuzzi, and large bedroom with new top quality, Memory foam mattress. Thanks to thick walls, it's very cool in summer! We arrange Winery tours & tasting and cooking class. A/C, Free wifi, comfy sitting and sofas and Hot Tub with great view!

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 - 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.

A paradise in Montepulciano...
Villa Il Cubo has a large private park and swimming pool and marvellous views on the Tuscan countryside. It is fully air-conditioned and the decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point at a moderate extra contribution. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY. Exceptions are possible only if don't create unrentable gaps between one guest and the next.

San Giovanni in Poggio, Villa Meriggio 95 sqm
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

The Tower
Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.

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 villa rentals in Siena
Private villa rentals

Valluccia 51

The Lazy Oak

Montemarcoli

Beautiful Country House, near Siena with jacuzzi

Sestuccia

Villa Nannini Siena

Villa Cantucci

Tuscan Villa w/Pool -Minutes to Florence Center
Luxury villa rentals

Stunning Tuscan Villa & Panoramic Infinity Pool

Charming Chianti Villa | Garden & Panoramic Pool

Podere Scaluccia Chianti Agritourism, Florence

Villa in Montepulciano with a Pool

Villa with garden. The Cardinal's Garden.

[Le rondini in Tuscany] Exclusive View Pool Villa

Villa in Tuscany – private pool – sunsets over Cetona

Villa Isabella
Villa rentals with a pool

Tuscany Villa Mammi

Il Leccio - Casa la Mangiatoia (The Manger House)

Exclusive Farmhouse Pool & View of San Gimignano

Farmhouse in the Crete Senesi

Villa Tonacato - Charming Villa with private pool

Villa La Poggerina, private pool and amazing view

Private Villa in Chianti between Florence & Siena

The twigs
When is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £433 | £179 | £100 | £89 | £135 | £256 | £220 | £222 | £165 | £233 | £430 | £261 |
| 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 holiday rentals
Explore 30 holiday rentals in Siena

Nightly prices starting at
Siena holiday rentals start at £45 per night before taxes and fees

Verified guest reviews
Over 1,360 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
30 of Siena holiday rentals include wifi 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
- Family-friendly rentals Siena
- Hotel rooms Siena
- Rentals with a fireplace Siena
- Rentals with pools Siena
- Rentals with a washing machine and dryer Siena
- Rentals with a firepit Siena
- Fitness-friendly rentals Siena
- Pet-friendly rentals Siena
- Cottage rentals Siena
- Rentals with a patio Siena
- Apartment rentals Siena
- Rentals with outdoor seating Siena
- House rentals Siena
- Boutique hotels Siena
- Serviced apartment rentals Siena
- Rentals with a hot tub Siena
- Rentals with breakfast Siena
- Flat rentals Siena
- Rentals with an EV charger Siena
- Smoking-friendly rentals Siena
- Holiday home rentals Siena
- Bed and breakfasts Siena
- Villa rentals Siena
- Villa rentals Tuscany
- Villa rentals Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Stazione Santa Maria Novella
- Lake Trasimeno
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Cala Violina
- Mercato Centrale
- Fortezza da Basso
- Piazza della Repubblica
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Uffizi Gallery
- Del Chianti
- Mugello Circuit
- Piazzale Michelangelo
- Pitti Palace
- Palazzo Vecchio
- Spiagge Bianche
- Boboli's Garden
- Parco delle Cascine
- Gulf of Baratti
- Basilica of Santa Croce
- Piazza della Signoria
- Things to do Siena
- Food and drink Siena
- Tours Siena
- Art and culture Siena
- Nature and outdoors Siena
- Sightseeing Siena
- Things to do Siena
- Sightseeing Siena
- Sports activities Siena
- Nature and outdoors Siena
- Art and culture Siena
- Tours Siena
- Food and drink Siena
- Things to do Tuscany
- Sightseeing Tuscany
- Art and culture Tuscany
- Entertainment Tuscany
- Nature and outdoors Tuscany
- Tours Tuscany
- Sports activities Tuscany
- Food and drink Tuscany
- Things to do Italy
- Tours Italy
- Entertainment Italy
- Wellness Italy
- Nature and outdoors Italy
- Sightseeing Italy
- Sports activities Italy
- Food and drink Italy
- Art and culture Italy







