Beginning of main content

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Holiday Rentals in Siena

See all Holiday Rentals in Siena
La Terrazza sul Campo

La Terrazza sul Campo

Via di Città 65, Siena
     
     
    4.8 out of 5 (89 reviews)

    Located in Siena Historical Center, this residence is steps from Museum of Torture, Piazza del Campo, and Siena Cathedral. University of Siena and Santa Maria ...

    La Terrazza sul CampoNZ$117

    La Terrazza sul CampoNZ$117
    Hotel Residence San Gregorio

    Hotel Residence San Gregorio

    Via Della Madonnina 4, Pienza
      3.0 out of 5.0
       
       
      4.4 out of 5 (25 reviews)

      Located in the heart of Pienza, this residence is within 6 mi (10 km) of Piazza Pio II, Palazzo Comunale, and Museo Diocesano. Palazzo Vescovile and Palazzo ...

      Hotel Residence San GregorioNZ$157

      Hotel Residence San GregorioNZ$157
      ApartHotel Anghel

      ApartHotel Anghel

      via Paolo Frajese 71, Siena
         
         
        3.9 out of 5 (168 reviews)

        Situated in a shopping district, this apartment building is within 6 mi (10 km) of Fontebranda, Siena Cathedral, and Piazza del Campo. University of Siena and ...

        ApartHotel AnghelNZ$90

        ApartHotel AnghelNZ$90
        Bosco della Spina

        Bosco della Spina

        via della Tinaia 13, Murlo
           
           
          4.7 out of 5 (81 reviews)

          Situated in a rural location, this residence is 0.1 mi (0.1 km) from Val di Merse and within 9 mi (15 km) of Museo della Mezzadria and Museum of Sacred Art in ...

          Palazzo Coli Bizzarrini

          Palazzo Coli Bizzarrini

          Piazza Antonio Gramsci 27, Siena
             
             
            4.5 out of 5 (82 reviews)

            Located in Siena Historical Center, this residence is steps from Stadio Artemio Franchi, Piazza Salimbeni, and Palazzo Salimbeni. Siena Cathedral and Piazza ...

            Palazzo Coli BizzarriniNZ$143

            Palazzo Coli BizzarriniNZ$143
            Villa Montarioso

            Villa Montarioso

            Via Montarioso 35, Monteriggioni
               
               
              4.2 out of 5 (84 reviews)

              Located in Val d'Elsa, this vacation home is within 6 mi (10 km) of Palasport Mens Sana, Santa Maria alle Scotte Polyclinic, and University of Siena. Piazza ...

              Villa MontariosoNZ$109

              Villa MontariosoNZ$109
              Camping Boschetto Di Piemma

              Camping Boschetto Di Piemma

              Localita' Santa Lucia 38C, San Gimignano
                3.0 out of 5.0
                 
                 
                3.7 out of 5 (3 reviews)

                Located in Val d'Elsa, this campground is within 6 mi (10 km) of Ornithological Museum, Museum San Gimignano 1300, and Historical Torture Museum. Archaeological ...

                Villa Il Borghetto

                Villa Il Borghetto

                Via Tufi no. 64, Siena
                   
                   
                  4.9 out of 5 (19 reviews)

                  Situated in Siena, this apartment building is within 6 mi (10 km) of Porta Tufi, Siena Cathedral, and Piazza del Campo. University of Siena and Orto Botanico ...

                  Villa Il BorghettoNZ$135

                  Villa Il BorghettoNZ$135
                  Camping Siena Colleverde

                  Camping Siena Colleverde

                  via Scacciapensieri 47, Siena
                    3.0 out of 5.0
                     
                     
                    4.0 out of 5 (100 reviews)

                    Situated in Siena, this campground is within 6 mi (10 km) of University for Foreigners of Siena, Santa Maria alle Scotte Polyclinic, and University of Siena. ...

                    Camping Siena ColleverdeNZ$45

                    Camping Siena ColleverdeNZ$45
                    Borgo delle More

                    Borgo delle More

                    Via di Montenero 18, Montepulciano
                       
                       
                      4.5 out of 5 (25 reviews)

                      Situated in a rural location, this apartment building is 0.1 mi (0.1 km) from Val di Chiana and within 6 mi (10 km) of Colonna del Marzocco and Palazzo Avignonesi. ...

                      Borgo delle MoreNZ$112

                      Borgo delle MoreNZ$112
                      Locanda Di San Martino

                      Locanda Di San Martino

                      Via San Martino 14, Siena
                         
                         
                        3.8 out of 5 (250 reviews)

                        Located in Siena Historical Center, this residence is within 6 mi (10 km) of Basilica di Santa Maria dei Servi, University of Siena, and Piazza del Campo. Siena ...

                        Locanda Di San MartinoNZ$76

                        Locanda Di San MartinoNZ$76
                        Antica Fonte Residenza di Siena

                        Antica Fonte Residenza di Siena

                        Strada Petriccio E Belriguardo 164, Siena
                          2.0 out of 5.0
                           
                           
                          4.5 out of 5 (11 reviews)

                          Situated in Siena, this residence is within 6 mi (10 km) of Siena Stadium, Santa Maria alle Scotte Polyclinic, and University of Siena. Siena Cathedral and Piazza ...

                          Antica Fonte Residenza di SienaNZ$114

                          Antica Fonte Residenza di SienaNZ$114
                          Fullino Nero

                          Fullino Nero

                          Strada del Petriccio e Belriguardo, Siena
                            2.0 out of 5.0
                             
                             
                            4.7 out of 5 (31 reviews)

                            Situated in a rural location, this aparthotel is within 6 mi (10 km) of Siena Stadium, Santa Maria alle Scotte Polyclinic, and University of Siena. Palasport ...

                            Fullino NeroNZ$105

                            Fullino NeroNZ$105
                            Villa Curina Resort

                            Villa Curina Resort

                            Località Curina, Castelnuovo Berardenga
                               
                               
                              4.9 out of 5 (22 reviews)

                              Situated in a rural location, this romantic residence is 8 mi (12.8 km) from Castle of Brolio and 12.4 mi (20 km) from Piazza del Campo. Siena Cathedral and ...

                              Numero 12 Hermes 9

                              Numero 12 Hermes 9

                              Vicolo del Macina, Siena
                                 
                                 
                                4.0 out of 5 (1 reviews)

                                Located in Siena Historical Center, this apartment building is steps from Casa di Santa Caterina, Siena Baptistry, and Teatro dei Rozzi. Siena Cathedral and ...

                                Appartamenti Bellarmino

                                Appartamenti Bellarmino

                                via di San Donato 10, Montepulciano
                                   
                                   
                                  4.7 out of 5 (33 reviews)

                                  Located in the heart of Montepulciano, this apartment building is steps from Val di Chiana, Dome of Montepulciano, and Consorzio del Vino Nobile di Montepulciano. ...

                                  Appartamenti BellarminoNZ$105

                                  Appartamenti BellarminoNZ$105
                                  Il Tosco

                                  Il Tosco

                                  Via del Poliziano 13, Montepulciano
                                     
                                     
                                    5.0 out of 5 (41 reviews)

                                    This family-friendly Montepulciano residence is located in the historical district, just steps from Val di Chiana and Torre del Pulcinella. Terme di Montepulciano ...

                                    Il ToscoNZ$330

                                    Il ToscoNZ$330
                                    Il Borgo di Terrensano

                                    Il Borgo di Terrensano

                                    Strada di Terrensano e Belcaro, 37, Siena
                                       
                                       
                                      4.7 out of 5 (3 reviews)

                                      Situated in a rural location, this residence is within 6 mi (10 km) of Porta Camollia, Siena Cathedral, and Piazza del Campo. Civic Museum and Palazzo Pubblico ...

                                      Palazzo Pacini

                                      Palazzo Pacini

                                      Via Gracco del Secco,14, Colle di Val d'Elsa
                                         
                                         
                                        4.9 out of 5 (37 reviews)

                                        Located in Val d'Elsa, this golf residence is within 6 mi (10 km) of Ranuccio Bianchi Bandinelli Archeological Museum, Colle di Val d'Elsa Cathedral, and Museo ...

                                        Palazzo PaciniNZ$154

                                        Palazzo PaciniNZ$154
                                        Podere il Pino

                                        Podere il Pino

                                        Localita Il Pino, n. 5, Poggibonsi
                                           
                                           
                                          4.8 out of 5 (6 reviews)

                                          Located in a rural location, this family-friendly apartment building is within 6 mi (10 km) of Church of San Lorenzo, Archeodromo di Poggibonsi, and Art in Color. ...

                                          Map

                                          You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Siena holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

                                          As much as you love your vacation rental, it’s always good to get out and explore to soak up Siena. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Siena. Seeing all the best attractions is bound to make you fall in love with Siena. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

                                          It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Siena short-term rentals, that won’t be hard to do.

                                          Other types of properties in Siena you may be interested in

                                          Hotel Athena

                                          Hotel Athena

                                          P Mascagni 55, Siena
                                            4.0 out of 5.0
                                             
                                             

                                            Hotel Athena is located within Siena's historic walls, near Piazza del Campo, Torre del Mangia, Palazzo Pubblico, Duomo, Museo dell'Opera Metropolitana, and ...

                                            Hotel AthenaNZ$114

                                            Hotel AthenaNZ$114
                                            Grand Hotel Continental Siena – Starhotels Collezione

                                            Grand Hotel Continental Siena – Starhotels Collezione

                                            Banchi Di Sopra 85, Siena
                                              5.0 out of 5.0
                                               
                                               

                                              Located in Siena Historical Center, this family-friendly Siena hotel is steps from Banca Monte dei Paschi di Siena, Piazza Salimbeni, and Palazzo Salimbeni. ...

                                              Grand Hotel Continental Siena – Starhotels CollezioneNZ$329

                                              Grand Hotel Continental Siena – Starhotels CollezioneNZ$329
                                              NH Siena

                                              NH Siena

                                              Piazza La Lizza 1, Siena
                                                4.0 out of 5.0
                                                 
                                                 

                                                Located in Siena Historical Center, this hotel is within 6 mi (10 km) of Stadio Artemio Franchi, Monte dei Paschi, and Santa Maria alle Scotte Polyclinic. University ...

                                                NH SienaNZ$111

                                                NH SienaNZ$111
                                                Rosewood Castiglion del Bosco

                                                Rosewood Castiglion del Bosco

                                                Localita Castiglion Del Bosco, Montalcino
                                                  5.0 out of 5.0
                                                   
                                                   

                                                  Located in a provincial park, this family-friendly hotel is within 9 mi (15 km) of Val di Merse, Museo della Mezzadria, and Museum of Sacred Art in Val d’Arbia. ...