HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
check navigate-up navigate-left navigate-right expand
Book with Confidence Guarantee™
Comprehensive payment protection
Customer service available 24/7

Holidaymakers searching for holiday rentals in Siena Area also enquired about villas in Cortona, villas in Sansepolcro and villas in Arezzo

Make a holiday rental home, or villa in Siena Italy your home away from home

The Province of Siena is a hilly, landlocked province of Italy, situated in the middle of the Tuscany. The largest peak of Mount Amiata transforms from a ski resort to a lush mountain covered in thermal springs and exceptional walking. The whole area is lush in the summer, and it is often considered that the slower you move through Siena, the more you gain from the experience, which is why many people tour Siena by bicycle.

Things to do in Siena, Italy

Time seems to slow down in the Province of Siena, Italy. Nothing is rushed here, which has lead to the development of some fantastic local foods.

The mythical Abbey of San Galgano is one of the most magnificent monuments in the Province of Siena, Italy. The buildings and ruins are almost as impressive as the wealth of folklore and legends that surround them. It is certainly worth finding out a little more about the Abbey, as this is where the legendary sword in the stone is meant to have been. There are many preserved medieval towns in the region including San Gimignano, Monteriggioni, Montalcino, San Quirico d'Orcia, Pienza and Montepulciano.

As a rural region, Siena has many natural offerings for visitors. Bicycle and horse riding is very rewarding in Siena, and the hot springs of Petriolo near Val di Merse, let you indulge in a hot bath, surrounded by open woodland.

Siena restaurants are world-renowned. On offer are local delicacies including Cinta senese pork, minestraccia, and mushroom dishes.

Places to holiday from Siena, Italy

UNESCO declared the historic city of Siena a World Heritage site, and once you take a holiday rental in Siena, you will know why. If you turn down any street, it is likely that you will stumble across a treasure of some variety, a cobbled square, tiny church or historic building. The old part of the city is centred on the twelfth century Duomo Cathedral. The city of Siena also has some famed shopping, with small boutiques and fashion shops offering unique Italian wares. Siena also host the bi-annual Palio; a horse race which goes through the city. This happens on the 2nd July and the 16th of August.

Chianti is a beautiful rural area of Siena, famed for its delicious wine of the same name. It is a cycle-touring paradise, with rolling hills, vineyards, woods and isolated villages.

Val d'Elsa has a small but very attractive old town, housing two provincial museums, the Archaeological Museum and the Museum of Civic and Religious Art. The town sits above the river Elsa, and a holiday villa here is perfect for exploring both Siena and Florence.

The 6th century Lombard fortress at Val di Chiana is the best preserved in Italy. Val di Chiana is also famous for its unspoilt nature, thermal basins and thick woodland. Here you can relax, enjoying the thermal baths, quality food and natural richness of Tuscany.

Val d'Orcia is also on the UNESCO World Heritage list, as the natural beauty and world-famous images of chalk plains with few trees and fortified hilltop towns. It has been a centre of inspiration for many writers and artists, and you can not deny the beauty of the region and the views from your accommodation.

Weather in Siena, Italy

Siena enjoys hot summers peaking at over 30°C in the summer, but winters are cold, with January temperatures averaging around 2°C.

Flights to Siena, Italy

The Province of Siena has three international airports, Florence (FLR), Perugia (PEG) and Peretola (FLR). Cheap flights to Siena are often available from easyJet, Ryanair and British Airways.

Use filters to narrow your search results!

Siena Area Holiday Apartments & Villas (5,477)

  • 1 - 50 of 5,477
    • 3 BR
    • 3 BA
    • Sleeps 7
    7
      • 2 BR
      • 2 BA
      • Sleeps 5
      11
        • 2 BR
        • 2 BA
        • Sleeps 4
        49
          • 2 BR
          • 1 BA
          • Sleeps 5
          20
            • 1 BR
            • 1 BA
            • Sleeps 3
            17
              • 1 BR
              • 1 BA
              • Sleeps 3
              38
                • 2 BR
                • 2 BA
                • Sleeps 6
                1 Review
                  • 2 BR
                  • 1 BA
                  • Sleeps 4
                    • 1 BR
                    • 1 BA
                    • Sleeps 4
                    2 Reviews
                      • 3 BR
                      • 2 BA
                      • Separate Toilet
                      • Sleeps 8
                      12
                        • 1 BR
                        • 1 BA
                        • Sleeps 2
                        4
                          • 2 BR
                          • 2 BA
                          • Sleeps 6
                          12
                            £106
                            avg/night
                            • 2 BR
                            • 1 BA
                            • Sleeps 4
                            3
                              • 1 BR
                              • 1 BA
                              • Sleeps 4
                              18
                                • 1 BR
                                • 1 BA
                                • Sleeps 2
                                9
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 7
                                  17
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 4
                                    3
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 3
                                      11
                                        • Studio
                                        • 1 BA
                                        • Sleeps 4
                                        10
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 4
                                          3
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 2
                                            6
                                              • 2 BR
                                              • 3 BA
                                              • Sleeps 5
                                              31
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 3
                                                5
                                                  • 1 BR
                                                  • 2 BA
                                                  • Sleeps 2
                                                  19
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 4
                                                    1 Review
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 6
                                                      12
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 4
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 3
                                                          7
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                              • 2 BR
                                                              • 1 BA
                                                              • Separate Toilet
                                                              • Sleeps 6
                                                              5
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                2 Reviews
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  10
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 3
                                                                    2 Reviews
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      38
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 8
                                                                        39
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 4
                                                                          90
                                                                            • 3 BR
                                                                            • 3 BA
                                                                            • Sleeps 6
                                                                            61
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 2
                                                                              4
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 5
                                                                                4
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 2
                                                                                  17
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 3
                                                                                    5
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      4
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        20
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 2
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 5
                                                                                            1 Review
                                                                                              • 3 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 8
                                                                                                • 3 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 8
                                                                                                1 Review
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 4
                                                                                                  13
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 4
                                                                                                    6
                                                                                                    • 1 - 50 of 5,477
                                                                                                     

                                                                                                    Recent Reviews

                                                                                                    Perfect relaxing base to explore Chianti

                                                                                                    5 of 5
                                                                                                    Elisabetta and family were very warm hosts and the apartment was exactly what we were looking for. Having started our holiday in a remote cottage, the apartment offered a fantastic location to better explore the Chianti region. The property is close to a main road which offers short journeys to Poggibonsi, San Gimignano, Siena, Volterra and Firenze. We had forgotten about the noise from the road by the second day and found the apartment to offer a relaxing retreat on our lazy days. The apartment is spacious inside with all the required amenities and the outside space is excellent with space to eat and relax overlooking the large pool. Our hosts were hardly noticed and gave us the freedom and privacy that we hoped for. Everything was clean and well maintained (especially the large, light bathroom) and it was great to have a sheltered parking space to keep the car cool. We especially enjoyed our trips to San Gimignano for incredible gelato and wonderful meals out (Bel Soggiorno in particular). I'd highly recommend this property.
                                                                                                    • Review Submitted: 26-Jul-2016
                                                                                                    • Date of Stay: Jul 2016

                                                                                                    Il Prato - even better than a home from home!

                                                                                                    5 of 5
                                                                                                    This is our second time at Montecchio and again it was a total treat. We had our three small children in tow and they were accommodated for and loved the pool and large garden to run around in. The location is stunning and James and Penny deliver an amazingly high standard of service. The welcome hamper on arrival is more like a fully stocked fridge and store cupboard! The free wine every day is a treat and the finishes in the villa are all to a ridiculously high standard - Emma Bridgewater crockery! The housekeeper is on hand daily and there was nothing we wanted for. We love Montecchio and the surrounding area. The local towns are lovely and I could not recommend a week here more highly! Already recommended to friends and I have no doubt we will be back again.
                                                                                                    • Review Submitted: 20-Jul-2016
                                                                                                    • Date of Stay: Jul 2016

                                                                                                    4 weeks at L'Oliveto

                                                                                                    5 of 5
                                                                                                    We selected L'Oliveto at Club Montecchio because we wanted 3 bedrooms and baths and proximity to Siena and we were impressed with the positive reviews. We have stayed at other villas in Italy and Europe but never for four weeks. It is a beautiful sitting; the villa is beautiful and spotless; it has a massive pool which is cleaned frequently; the villa kitchen is equipped with everything you need; the town of Castelnuovo Berardenga is five minutes away with a lovely old town, restaurants, gym, grocery store, butcher, wineries, and lovely welcoming people. Even closer there are two small beautiful old villages (Villa a Sesta and San Gusme) with a number of wonderful restaurants and all the charm of Tuscany. What sets Club Montecchio apart, however, more than the endless wine, olive oil etc, is the concierge service and particularly the host James. There are so many day trips to towns, sites, wineries one could take how does one decide: email James and Rita. James will tell you which chef to hire, which winery to see, which restaurant to go to and Rita will make the reservations. We went to Florence, Pisa, Lucca, San Gimignano, Montepulciano, Cortona, Montelupo, Gubbio, Colle di Valle d'Elsa, Siena and so many other great towns all from our lovely home base with advise an email away. Rita and James even arranged for a fantastic Palio experience in Sienna. The concierge service saved us time, money and the stress of stumbling for the answers ourselves...invaluable! If you have the opportunity to visit Club Mintecchio do it!
                                                                                                    • Review Submitted: 15-Jul-2016
                                                                                                    • Date of Stay: Jun 2016