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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.

  • Showing 1-50 of 300+
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    Exceptional! 5.0/5
    (47 reviews)
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 8
    Apartment #1153926
    47
    Viewed 79 times in the last 48 hours
      Wonderful! 4.9/5
      (15 reviews)
      avg/night
      • 6 BR
      • 5 BA
      • Separate Toilets
      • Sleeps 14
      Villa #1617223
      15
      Viewed 95 times in the last 48 hours
        Exceptional! 5.0/5
        (53 reviews)
        avg/night
        • 2 BR
        • 2 BA
        • Sleeps 4
        House #6235319
        53
        Viewed 92 times in the last 48 hours
          Wonderful! 4.9/5
          (74 reviews)
          avg/night
          • 3 BR
          • 2 BA
          • Sleeps 6
          Chateau / Country House #436049vb
          74
          Viewed 69 times in the last 48 hours
            Exceptional! 5.0/5
            (26 reviews)
            avg/night
            • 4 BR
            • 3 BA
            • Sleeps 10
            Villa #6415307
            26
            Viewed 126 times in the last 48 hours
              Wonderful! 4.9/5
              (13 reviews)
              avg/night
              • 3 BR
              • 3 BA
              • Sleeps 7
              Barn #814311vb
              13
              Viewed 44 times in the last 48 hours
                Wonderful! 4.9/5
                (21 reviews)
                avg/night
                • 3 BR
                • 3 BA
                • Sleeps 6
                Villa #421433
                21
                Viewed 50 times in the last 48 hours
                  Exceptional! 5.0/5
                  (31 reviews)
                  avg/night
                  • 6 BR
                  • 7 BA
                  • Sleeps 12
                  Villa #1570885
                  31
                  Viewed 107 times in the last 48 hours
                    Wonderful! 4.9/5
                    (9 reviews)
                    avg/night
                    • 1 BR
                    • 1 BA
                    • Sleeps 4
                    Apartment #1627958
                    9
                    Viewed 27 times in the last 48 hours
                      Exceptional! 5.0/5
                      (24 reviews)
                      avg/night
                      • 2 BR
                      • 1 BA
                      • Sleeps 5
                      House #2196590
                      24
                      Viewed 26 times in the last 48 hours
                        avg/night
                        • 5 BR
                        • 5 BA
                        • Separate Toilet
                        • Sleeps 10
                        Villa #1097226
                        4
                        Viewed 106 times in the last 48 hours
                          Exceptional! 5.0/5
                          (8 reviews)
                          avg/night
                          • 1 BR
                          • 1 BA
                          • Sleeps 2
                          Chateau / Country House #6115214
                          8
                          Viewed 77 times in the last 48 hours
                            • 2 BR
                            • 2 BA
                            • Sleeps 5
                            House #824486vb
                            3
                            Viewed 57 times in the last 48 hours
                              Very Good! 4.0/5
                              (5 reviews)
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                              Cottage #696005vb
                              5
                              Viewed 86 times in the last 48 hours
                                Wonderful! 4.8/5
                                (18 reviews)
                                avg/night
                                • 3 BR
                                • 3 BA
                                • Sleeps 8
                                Villa #1729396
                                18
                                Viewed 68 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (12 reviews)
                                  avg/night
                                  • Studio
                                  • 1 BA
                                  • Sleeps 4
                                  Apartment #1768734
                                  12
                                  Viewed 75 times in the last 48 hours
                                    avg/night
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 6
                                    House #582787vb
                                    3
                                    Viewed 72 times in the last 48 hours
                                      Wonderful! 4.9/5
                                      (35 reviews)
                                      avg/night
                                      • 2 BR
                                      • 3 BA
                                      • Sleeps 5
                                      Villa #62257
                                      35
                                      Viewed 41 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (9 reviews)
                                        avg/night
                                        • 4 BR
                                        • 3 BA
                                        • Separate Toilet
                                        • Sleeps 6
                                        Villa #64607vb
                                        9
                                        Viewed 25 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (29 reviews)
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 4
                                          Cottage #8156600
                                          29
                                          Viewed 46 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (18 reviews)
                                            avg/night
                                            • 4 BR
                                            • 4 BA
                                            • Separate Toilet
                                            • Sleeps 10
                                            Multiple rentals Villa #1898892
                                            18
                                            Viewed 58 times in the last 48 hours
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Multiple rentals Apartment #6521915
                                              3
                                              Viewed 32 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (13 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 6
                                                Apartment #13190
                                                13
                                                Viewed 56 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (29 reviews)
                                                  avg/night
                                                  • 6 BR
                                                  • 6 BA
                                                  • Separate Toilet
                                                  • Sleeps 12
                                                  Villa #1636667
                                                  29
                                                  Viewed 37 times in the last 48 hours
                                                    Wonderful! 4.8/5
                                                    (23 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 3
                                                    Apartment #1803159
                                                    23
                                                    Viewed 63 times in the last 48 hours
                                                      Wonderful! 4.8/5
                                                      (10 reviews)
                                                      avg/night
                                                      • 5 BR
                                                      • 3 BA
                                                      • Sleeps 11
                                                      Castle #445224
                                                      10
                                                      Viewed 75 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (30 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 3 BA
                                                        • Separate Toilet
                                                        • Sleeps 7
                                                        Villa #709879vb
                                                        30
                                                        Viewed 74 times in the last 48 hours
                                                          Exceptional! 5.0/5
                                                          (9 reviews)
                                                          avg/night
                                                          • 5 BR
                                                          • 5 BA
                                                          • Sleeps 12
                                                          Villa #1812215
                                                          9
                                                          Viewed 44 times in the last 48 hours
                                                            Excellent! 4.7/5
                                                            (6 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            Apartment #1870265
                                                            6
                                                            Viewed 31 times in the last 48 hours
                                                              Excellent! 4.7/5
                                                              (9 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 12
                                                              Multiple rentals Villa #1980452
                                                              9
                                                              Viewed 80 times in the last 48 hours
                                                                Wonderful! 4.8/5
                                                                (20 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                House #6046194
                                                                20
                                                                Viewed 74 times in the last 48 hours
                                                                  Very Good! 4.0/5
                                                                  (5 reviews)
                                                                  avg/night
                                                                  • 8 BR
                                                                  • 4 BA
                                                                  • Sleeps 16
                                                                  Villa #1934854
                                                                  5
                                                                  Viewed 33 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (10 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    Apartment #1198165a
                                                                    10
                                                                    Viewed 36 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (30 reviews)
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 6
                                                                      Apartment #1494217
                                                                      30
                                                                      Viewed 44 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (133 reviews)
                                                                        avg/night
                                                                        • 8 BR
                                                                        • 8 BA
                                                                        • Separate Toilet
                                                                        • Sleeps 16
                                                                        Villa #388827
                                                                        133
                                                                        Viewed 77 times in the last 48 hours
                                                                          Exceptional! 5.0/5
                                                                          (32 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 3 BA
                                                                          • Sleeps 7
                                                                          Chateau / Country House #1225354
                                                                          32
                                                                          Viewed 18 times in the last 48 hours
                                                                            Excellent! 4.7/5
                                                                            (35 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            House #32221
                                                                            35
                                                                            Viewed 46 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (5 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 4
                                                                              Apartment #6066838
                                                                              5
                                                                              Viewed 33 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (66 reviews)
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 3
                                                                                Apartment #6132548
                                                                                66
                                                                                Viewed 23 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (30 reviews)
                                                                                  avg/night
                                                                                  • 5 BR
                                                                                  • 5 BA
                                                                                  • Sleeps 10
                                                                                  Villa #275267
                                                                                  30
                                                                                  Viewed 44 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (22 reviews)
                                                                                    avg/night
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 3
                                                                                    Apartment #435134
                                                                                    22
                                                                                    Viewed 27 times in the last 48 hours
                                                                                      Exceptional! 5.0/5
                                                                                      (14 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 3 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 4
                                                                                      Multiple rentals Chateau / Country House #1898892
                                                                                      14
                                                                                      Viewed 47 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (7 reviews)
                                                                                        avg/night
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 2
                                                                                        Multiple rentals Apartment #75284
                                                                                        7
                                                                                        Viewed 16 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (67 reviews)
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 5
                                                                                          House #6162521
                                                                                          67
                                                                                          Viewed 53 times in the last 48 hours
                                                                                            Wonderful! 4.8/5
                                                                                            (9 reviews)
                                                                                            avg/night
                                                                                            • 5 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 10
                                                                                            Villa #6256561
                                                                                            9
                                                                                            Viewed 61 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (23 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Apartment #6286989
                                                                                              23
                                                                                              Viewed 40 times in the last 48 hours
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                Villa #654136vb
                                                                                                4
                                                                                                Viewed 180 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (23 reviews)
                                                                                                  avg/night
                                                                                                  • 5 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 11
                                                                                                  House #6366466
                                                                                                  23
                                                                                                  Viewed 19 times in the last 48 hours
                                                                                                    Excellent! 4.7/5
                                                                                                    (13 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    Farmhouse #89525
                                                                                                    13
                                                                                                    Viewed 56 times in the last 48 hours
                                                                                                      Excellent! 4.4/5
                                                                                                      (8 reviews)
                                                                                                      avg/night
                                                                                                      • 4 BR
                                                                                                      • 4 BA
                                                                                                      • Sleeps 8
                                                                                                      Villa #1856404
                                                                                                      8
                                                                                                      Viewed 54 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Perfect fall stay

                                                                                                      5 of 5
                                                                                                      Nice and friendly owners and the cottage is located in a great location near Casole . Out the back windows there are rolling hills and when you walk out the front you have a lovely panoramic patio . Would most definitely recommend this accommodation.
                                                                                                      • Review Submitted: 20-Jan-2017
                                                                                                      • Date of Stay: Nov 2016

                                                                                                      UNFORGETTABLE!

                                                                                                      5 of 5
                                                                                                      This was a trip of a lifetime. The spectacular views, the rustic Barn, the food, the wine, the people, and of course Serena made it unforgettable. We hope to make the visit to Tuscany and The Barn a new Thanksgiving tradition. The property was exactly as described on the website and viewed in the pictures. It was very clean and well maintained. The house had everything you needed from pots and pans to umbrellas, espresso maker, tea kettle, spices even sporting equipment. There's even thyme and rosemary growing around the property. I highly recommend this property to anyone looking to make unforgettable memories with friends and family. Oh, one more plus, each bedroom has its own bathroom!
                                                                                                      • Review Submitted: 28-Nov-2016
                                                                                                      • Date of Stay: Nov 2016

                                                                                                      Wonderful villa in a beautiful setting

                                                                                                      4 of 5
                                                                                                      This is a beautiful villa, beautifully situated on a mountaintop with wonderful views of the Chianti region from every window of the villa. The villa works great for a multi-generational get-together, as it is divided into 3 separate apartments. The grounds of the villa are gorgeous and well-kept and the pool is well-maintained. A car is necessary for any outings, as the villa is quite remote and only accessed by dirt roads. There are no restaurants, shopping or other amenities within walking distance, so a vehicle is necessary to enjoy the wonderful Chianti area. We only have good things to say about the housekeeper/keyholder, who assisted us in many aspects. All in all the villa lived fully up to our expectations and more.
                                                                                                      • Review Submitted: 13-Oct-2016
                                                                                                      • Date of Stay: Sep 2016