Title: Siena Vacation Home Rentals from CA $133: Search Top Private Vacation Homes for Rent | Expedia.ca [Siena Travel Guide](https://expedia.ca/Siena.dx9821)[Hotels in Siena](https://expedia.ca/Siena-Hotels.d9821.Travel-Guide-Hotels)[Vacation Rentals in Siena](https://expedia.ca/Siena-Vacation-Rentals.d9821.Travel-Guide-VacationRentals)[Flights to Siena](https://expedia.ca/Cheap-Flights-To-Siena.d9821.Travel-Guide-Flights)[Things to do in Siena](https://expedia.ca/Things-To-Do-In-Siena.d9821.Travel-Guide-Activities)[Siena Car Rentals](https://expedia.ca/Car-Rentals-In-Siena.d9821.Car-Rental-Guide)[Siena Vacation Packages](https://expedia.ca/Siena.d9821.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/409000/409074-Siena.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Siena Vacation Rentals ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Siena Vacation Homes ![Property grounds](https://images.trvl-media.com/lodging/115000000/114190000/114180600/114180505/2419483e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114190000/114180600/114180505/d1a6db77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114190000/114180600/114180505/013b1ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/115000000/114190000/114180600/114180505/456c8609.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Tuscan-style apartment Suitable for families. Pets allowed Toscana 10/10 Exceptional (1) "Très bon emplacement par rapport à Sienne et maison spacieuse. Propriétaire agréable " CA $211 CA $266 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Siena-Hotels-Vrbo-Property.h114180505.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118770000/118760800/118760780/eae7e05b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/119000000/118770000/118760800/118760780/d008e9fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/119000000/118770000/118760800/118760780/6c75b5ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/119000000/118770000/118760800/118760780/473b9989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LOVE NEST SIENA YOUR LOVE NEST Toscana CA $162 CA $238 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Monteriggioni-Hotels-Vrbo-Property.h118760780.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/115000000/114250000/114245500/114245407/1665184f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/115000000/114250000/114245500/114245407/c3bcd9af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114250000/114245500/114245407/8a8a1809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114250000/114245500/114245407/76f44bf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC Radda in Chianti 8.0/10 Very good (1) "We spent a great family time at Adme’s house.The house has everything. Was very clean and well maintained . Will highly recommend." CA $995 CA $2,037 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-4-Bedroom-Stonehouse-With-Stunning-Pool-In-The-Chianti-Countryside-With-WiFi.h114245407.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/117000000/116730000/116729900/116729807/982e0e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116730000/116729900/116729807/e2c4506b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116730000/116729900/116729807/6fd9745a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116730000/116729900/116729807/0638ce9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment 'La Casa Di Nonna - Siena' with Private Terrace, Wi-Fi and Air Conditioning Camollia CA $301 CA $307 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Siena-Hotels-Apartment-La-Casa-Di-Nonna-Siena-With-Private-Terrace.h116729807.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/22000000/21800000/21793500/21793404/45405604.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21800000/21793500/21793404/79f76a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/22000000/21800000/21793500/21793404/3bcdc401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21800000/21793500/21793404/d84a7fa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### THE TOLOMEI - apartment in the heart of the main street Siena City Centre 8.0/10 Very good (4) "Excellent location, very nice apartment was just like the pictures. Painless check-in, we had a comfortable wonderful 3 days in Siena. The only negative was the drain in the master shower backs up, but there's a second bathroom so we just showered in there. Great place!" CA $180 CA $286 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Siena-Hotels-IL-TOLOMEI-Central-In-The-Middle-Of-Main-Street.h21793404.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/121000000/120630000/120621800/120621770/83d2cce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/121000000/120630000/120621800/120621770/b96a6461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120630000/120621800/120621770/9b0fa798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120630000/120621800/120621770/a2b817a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wave House 25 Siena City Centre CA $154 CA $206 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Siena-Hotels-Vrbo-Property.h120621770.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/3584552d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom, Kitchenette (Iris)](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/eb2dffec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/313690ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom, Kitchenette (Iris) | Private kitchen](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/a0c7f7fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo La Ferrozzola Castellina in Chianti 9.4/10 Exceptional (9) "Very nice agriturismo. " CA $186 CA $211 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Agriturismo-La-Ferrozzola.h42405029.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/39997d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/82776eb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Apartment, Garden View | Terrace/patio](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/164efada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/fd084814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Vacanze Le Case San Gimignano 9.0/10 Wonderful (8) "Situata in una posizione ideale per trascorrere un momento di relax accompagnati da una vista eccezionale. Davvero bella location." CA $129 CA $151 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/San-Gimignano-Hotels-Casa-Vacanze-Le-Case.h28401463.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/22000000/21140000/21136300/21136264/a26282ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon House, Kitchen, Hill View | Living area](https://images.trvl-media.com/lodging/22000000/21140000/21136300/21136264/e02bdbb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/22000000/21140000/21136300/21136264/007fccea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/22000000/21140000/21136300/21136264/85461a66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Zampugna Trequanda 9.2/10 Wonderful (5) "Beautiful and host is great!" CA $648 CA $717 total includes taxes & fees Oct 11 - Oct 12 [](https://www.expedia.ca/Trequanda-Hotels-Zampugna.h21136264.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/b5d9a4b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/ad4e5fad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/7ed60a74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/47f3dce1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Romantic farm in the Sienese hills Trequanda, Siena "Gemischt.Sehr gut: Zentrale Lage, viele Ausflugsmöglichkeiten (Siena, Cortona, Arezzo Pienza). Gepflegt, schöner Pool. Antonio ist die gute Seele des Hauses, freundlich, hilfsbereit und scheinbar immer fröhlich.Gut: Ausstattung des Hauses (wir haben im kleineren Poggiolino) gewohnt.Nicht gut: Zentrale Lage, direkt an einer wichtigen Regionalstraße. Also Ruhe in den Hügeln der Toskana hatten wir uns anders vorgestellt... Und:Im Schlafzimmer (UG) war es sehr warm (bei hohen Außentemperaturen).... CA $131 CA $284 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Trequanda-Hotels-Romantic-Farm-In-The-Sienese-Hills.h39866124.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/65000000/64180000/64173800/64173725/d2694dc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64180000/64173800/64173725/270-2f30764e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/65000000/64180000/64173800/64173725/2bbb35c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/65000000/64180000/64173800/64173725/1ee7a5de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort, relaxation and nature Monticiano 10/10 Exceptional (1) "Appartamento perfetto non manca nulla e proprietari accoglienti, e gentilissimi. Da tornare" CA $117 CA $165 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Monticiano-Hotels-Comodita.h64173725.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117990000/117985600/117985575/2a4b4895.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117990000/117985600/117985575/77d3ccf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117990000/117985600/117985575/c5e43f7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117990000/117985600/117985575/465c4e66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home 'La Casetta' with Private Terrace, Private Garden and Wi-Fi Volterra CA $107 CA $133 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Volterra-Hotels-Holiday-Home-La-Casetta-With-Private-Terrace.h117985575.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/a00997c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/35e78bb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/7e336ded.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/3c123570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti Monteaperti 10/10 Exceptional (2) "We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite" CA $233 CA $274 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Cosy-Double-Room-In-Pretty-Cottage-With-WiFi-And-AC-In-Enchanting-Monteaperti.h116957378.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69550000/69548900/69548805/3dabcf3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69550000/69548900/69548805/247b8232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69550000/69548900/69548805/0ff1b26b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/70000000/69550000/69548900/69548805/f9b59b9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Podere Belsogno-camera Lavanda Montalcino 10/10 Exceptional (4) "The stay was very pleasant, the room was very tidy and cosy. The view when waking up is breathtaking, as well as the whole place. Exactly as stated in the pictures. We were very welcomed by the host and you get a good breakfast. Would definitely come back again if I‘m in the area! Thank you very much for the stay!" CA $195 CA $227 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Montalcino-Hotels-Podere-Belsogno-Camera-Lavanda.h69548805.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19150000/19149100/19149003/4440a68e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/20000000/19150000/19149100/19149003/83ddb8ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/20000000/19150000/19149100/19149003/ff740e0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19150000/19149100/19149003/405b4867.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House with views of the Chianti impruneta 10/10 Exceptional (1) "Great place, quaint and spacious. Beautiful view and equipped with everything needed for a pleasant stay. " CA $110 CA $375 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Impruneta-Hotels-House-With-Views-Of-The-Chianti.h19149003.Hotel-Information) ![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/34638ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/acc5b1eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/6671f978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/6e6f272f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wonderful Tuscan farmhouse with large spaces and panoramic views impruneta 9.8/10 Exceptional (23) "If you are looking for a beautiful area close to but not in Florence this is the place for you! Rustic Tuscan farmhouse that is just lovely with beautiful views. Mattia is a wonderful host with great recommendations for visits and food. This is close to all that Tuscany has to offer, would definitely stay here again ." CA $122 CA $405 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Impruneta-Hotels-Beautiful-Tuscan-Farmhouse-With-Large-Spaces-And-Panoramic-Views.h39983368.Hotel-Information) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/d6cca00c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/901e36a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/05c4a567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/e1a1ee18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi Poggibonsi 10/10 Exceptional (2) "Pros: Tutto stupendo la casa la posizione è. La dolcezza della proprietaria" CA $146 CA $202 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Poggibonsi-Hotels-Holiday-Home-Piccolo-Angolo-Di-Tranquillita-With-Private-Garden-And-Wi-Fi.h112477726.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105090000/105089100/105089096/246e837e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/106000000/105090000/105089100/105089096/648e852d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/106000000/105090000/105089100/105089096/e8606c7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Books, computer monitors](https://images.trvl-media.com/lodging/106000000/105090000/105089100/105089096/2f33fa1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Domotic Suite at Villa Anna Buonconvento CA $117 CA $218 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Buonconvento-Hotels-Vrbo-Property.h105089096.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/69000000/68050000/68050000/68049942/3d55d541.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68050000/68050000/68049942/27c749dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68050000/68050000/68049942/11c868e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/69000000/68050000/68050000/68049942/d70cff47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Falco- Cignella Resort Tuscany Toscana 9.0/10 Wonderful (2) "Perfectly located in the center of the Heart of Tuscany. Great property with a clean and spacious interior. " CA $8,107 CA $9,193 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Trequanda-Hotels-Villa-Falco-Cignella-Resort-Tuscany.h68049942.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/727fddb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/d9e20b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/38560b1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/bbfe6d56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A LUXURY VILLA ON THE HILLS OF FLORENCE Impruneta CA $16,214 CA $18,098 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Impruneta-Hotels-A-Luxury-Villa-ON-THE-Hills-OF-Florence.h47026113.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-24&endDate=2025-10-25®ionId=9821&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSiena-Private-Vacation-Homes.d9821-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSiena-Private-Vacation-Homes.d9821-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Siena Hotel Reviews ![Hotel Executive](//images.trvl-media.com/lodging/1000000/10000/3600/3559/745fe44b_y.jpg) ### Hotel Executive 10/10 Excellent "Quiet and safe location. Easy parking. Room is modern and clean. Very friendly and helpful staff. Onsite restaurant with delicious food options. Also close to Siena old town" [](https://expedia.ca/Siena-Hotels-Hotel-Executive.h3559.Hotel-Information) ![Villa Ermellina Siena, a Tribute Portfolio Hotel](//images.trvl-media.com/lodging/1000000/80000/73300/73208/b5937afa_y.jpg) ### Villa Ermellina Siena, a Tribute Portfolio Hotel 10/10 Excellent "Very nice hotel and beautiful hotel. My only complaint is that the king bed I stayed in was very lumpy - I do mean very.. otherwise great place. Good size gym. Clean. Very friendly service." [](https://expedia.ca/Siena-Hotels-Hotel-Garden.h73208.Hotel-Information) ![Hotel Chiusarelli](//images.trvl-media.com/lodging/2000000/1120000/1110900/1110843/a501ded1_y.jpg) ### Hotel Chiusarelli 10/10 Excellent "A little older hotel but a clean sweet place. Staff are wonderful and they include a good breakfast. Great location and walkable to everything. " [](https://expedia.ca/Siena-Hotels-Hotel-Chiusarelli.h1110843.Hotel-Information) ![Hotel Italia](//images.trvl-media.com/lodging/1000000/1000000/997000/996973/7edddb53_y.jpg) ### Hotel Italia 10/10 Excellent "The service was really the highlight of our stay. Everyone was so friendly and helpful! Our room was perfect and we really loved the large bathroom and shower. Breakfast was good and the service there was very good as well. A very enjoyable stay!" [](https://expedia.ca/Siena-Hotels-Hotel-Italia.h996973.Hotel-Information) ![ Palazzo Ravizza](//images.trvl-media.com/lodging/2000000/1770000/1760200/1760168/9acb6317_y.jpg) ### Palazzo Ravizza 10/10 Excellent "What a unique and wonderful experience! This hotel is situated in the walled city and they helped us navigate in and out of the limited traffic zone. They also made a reservation for us at the most amazing little restaurant in Siena and just treated us spectacularly! Thank you for taking care of us for our short time with you!" [](https://expedia.ca/Siena-Hotels-Pensione-Palazzo-Ravizza.h1760168.Hotel-Information) ![Borgo Grondaie](//images.trvl-media.com/lodging/1000000/910000/905800/905710/58e23d32_y.jpg) ### Borgo Grondaie 10/10 Excellent "A hidden gem overlooking the city set in stunning grounds" [](https://expedia.ca/Siena-Hotels-Borgo-Grondaie.h905710.Hotel-Information) ![Villa Scacciapensieri Boutique Hotel](//images.trvl-media.com/lodging/3000000/2700000/2693500/2693499/b46a6593_y.jpg) ### Villa Scacciapensieri Boutique Hotel 10/10 Excellent "Beautiful grounds and main hotel area. Food was good as well. The room was nice, bed was comfortable." [](https://expedia.ca/Siena-Hotels-Villa-Scacciapensieri-Boutique-Hotel.h2693499.Hotel-Information) ![Hotel Certosa Di Maggiano](//images.trvl-media.com/lodging/1000000/530000/528500/528470/4c3dd1ab_y.jpg) ### Hotel Certosa Di Maggiano 10/10 Excellent "A wonderfully peaceful hotel in the middle of Tuscany. Amazing views. Great staff - friendly, professional and very helpful & accommodating. " [](https://expedia.ca/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information) ![Siena Vip](//images.trvl-media.com/lodging/17000000/16250000/16245600/16245550/4b41a72a_y.jpg) ### Siena Vip 10/10 Excellent "Our stay was great, included breakfast, able to walk up, yes, lots of uphill to the Cathedral. The Campo was a bit further past the Cathedral, easy downhill walk. The host greeted us as planned, our checkin was smooth. Check out was also easy.I had trouble getting a taxi back to the train station, a communication problem. The walk was not too bad, there are escalators and moving walkways." [](https://expedia.ca/Siena-Hotels-Siena-Vip.h16245550.Hotel-Information) ## Find out more about Siena ## Siena Vacation Homes information | Number of reviews | 35 | | --- | --- | | Accommodation | 124 Vacation Homes | | Lowest Price | CA $133 | | Highest Price | CA $18,098 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in San Rocco a Pilli](https://www.expedia.ca/4Star-San-Rocco-A-Pilli-Hotels.s40-0-d6285685.Travel-Guide-Filter-Hotels) - [Agostoli Hotels](https://www.expedia.ca/Agostoli-Hotels.d553248635975863234.Travel-Guide-Hotels) - [Lgbt Friendly Hotels in Bagnaia](https://www.expedia.ca/Bagnaia-Hotels-LGBT-Friendly-Hotel.0-0-d6046167-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Bossi Hotels](https://www.expedia.ca/Bossi-Hotels.d553248622858799636.Travel-Guide-Hotels) - [Lgbt Friendly Hotels in Casanova Pansarine](https://www.expedia.ca/Casanova-Pansarine-Hotels-LGBT-Friendly-Hotel.0-0-d6338184-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - 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