Title: Siena Vacation Home Rentals from CA $164: 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://images.trvl-media.com/place/9821/7379d030-252a-4e26-a469-e10785470ebc.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 In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for 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) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114190000/114180600/114180505/de5a02ac.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) ### Cozy Tuscan-style apartment Suitable for families. Pets allowed [](https://www.expedia.ca/Siena-Hotels-Cozy-Tuscan-Style-Apartment-Suitable-For-Families-Pets-Allowed.h114180505.Hotel-Information) Toscana 10/10 Exceptional (1) "Très bon emplacement par rapport à Sienne et maison spacieuse. Propriétaire agréable " ![France](https://a.travel-assets.com/egds/marks/flags/fr.svg) YVES A. CA $209 CA $264 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Siena-Hotels-Cozy-Tuscan-Style-Apartment-Suitable-For-Families-Pets-Allowed.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) ![Interior](https://images.trvl-media.com/lodging/119000000/118770000/118760800/118760780/e41ddf9a.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) ### LOVE NEST SIENA YOUR LOVE NEST [](https://www.expedia.ca/Monteriggioni-Hotels-Vrbo-Property.h118760780.Hotel-Information) Toscana CA $85 CA $209 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Monteriggioni-Hotels-Vrbo-Property.h118760780.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) ![Living area](https://images.trvl-media.com/lodging/22000000/21800000/21793500/21793404/42f20907.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) ### THE TOLOMEI - apartment in the heart of the main street [](https://www.expedia.ca/Siena-Hotels-IL-TOLOMEI-Central-In-The-Middle-Of-Main-Street.h21793404.Hotel-Information) Siena City Centre 8.4/10 Very good (5) "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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Serena F. CA $140 CA $240 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Siena-Hotels-IL-TOLOMEI-Central-In-The-Middle-Of-Main-Street.h21793404.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) | Private kitchen](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/a0c7f7fd.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) ![Balcony](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/56f95cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo La Ferrozzola [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Agriturismo-La-Ferrozzola.h42405029.Hotel-Information) Castellina in Chianti 9.4/10 Exceptional (9) "Very nice agriturismo. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ruth [](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) ![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) ![Apartment, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/028203d4.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) ### Casa Vacanze Le Case [](https://www.expedia.ca/San-Gimignano-Hotels-Casa-Vacanze-Le-Case.h28401463.Hotel-Information) San Gimignano 9.0/10 Wonderful (8) "Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10\. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jackie CA $144 CA $167 total includes taxes & fees Jan 28 - Jan 29, 2026 [](https://www.expedia.ca/San-Gimignano-Hotels-Casa-Vacanze-Le-Case.h28401463.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) ![Interior](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/38560b1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/8963b952.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 [](https://www.expedia.ca/Impruneta-Hotels-A-Luxury-Villa-ON-THE-Hills-OF-Florence.h47026113.Hotel-Information) Impruneta CA $16,094 CA $17,824 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Impruneta-Hotels-A-Luxury-Villa-ON-THE-Hills-OF-Florence.h47026113.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) ![Outdoor dining](https://images.trvl-media.com/lodging/65000000/64180000/64173800/64173725/02cc50e8.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) ![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) ### Comfort, relaxation and nature [](https://www.expedia.ca/Monticiano-Hotels-Comodita.h64173725.Hotel-Information) Monticiano 10/10 Exceptional (1) "Appartamento perfetto non manca nulla e proprietari accoglienti, e gentilissimi. Da tornare" ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Sandra V. CA $116 CA $164 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Monticiano-Hotels-Comodita.h64173725.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/f52ea845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, stovetop, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/a27ccb6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/2c97b1ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/77d8ad70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chianti Craft House Badia a Passignano [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Vrbo-Property.h83580374.Hotel-Information) Barberino Tavarnelle 9.8/10 Exceptional (9) "The house is beautiful and clean. The host is very welcoming and helpful. What more could one ask for! Thanks for having us. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elika M. CA $210 CA $305 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Vrbo-Property.h83580374.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) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/943e57af.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) ![Interior](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/05c4a567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi [](https://www.expedia.ca/Poggibonsi-Hotels-Holiday-Home-Piccolo-Angolo-Di-Tranquillita-With-Private-Garden-And-Wi-Fi.h112477726.Hotel-Information) Poggibonsi 10/10 Exceptional (2) "Pros: Tutto stupendo la casa la posizione è. La dolcezza della proprietaria" ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Anonymous traveller CA $141 CA $197 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Poggibonsi-Hotels-Holiday-Home-Piccolo-Angolo-Di-Tranquillita-With-Private-Garden-And-Wi-Fi.h112477726.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) ![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/47f3dce1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/62b86b12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Romantic farm in the Sienese hills [](https://www.expedia.ca/Trequanda-Hotels-Romantic-Farm-In-The-Sienese-Hills.h39866124.Hotel-Information) Trequanda, Siena 8.0/10 Very good (1) "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).... ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Heike K. CA $130 CA $277 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Trequanda-Hotels-Romantic-Farm-In-The-Sienese-Hills.h39866124.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69550000/69548900/69548805/0ff1b26b.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) ### Podere Belsogno-camera Lavanda [](https://www.expedia.ca/Montalcino-Hotels-Podere-Belsogno-Camera-Lavanda.h69548805.Hotel-Information) 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!" ![Austria](https://a.travel-assets.com/egds/marks/flags/at.svg) Johannes S. CA $193 CA $225 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Montalcino-Hotels-Podere-Belsogno-Camera-Lavanda.h69548805.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/118000000/117990000/117985600/117985575/812c14c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home 'La Casetta' with Private Terrace, Private Garden and Wi-Fi [](https://www.expedia.ca/Volterra-Hotels-Holiday-Home-La-Casetta-With-Private-Terrace.h117985575.Hotel-Information) Volterra CA $143 CA $169 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Volterra-Hotels-Holiday-Home-La-Casetta-With-Private-Terrace.h117985575.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/ec9bd8b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/a978fac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/30c3d6b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/cb24f428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Exclusive Stone Tower. [](https://www.expedia.ca/Murlo-Hotels-Exclusive-Tower-In-Stone.h40221427.Hotel-Information) Casciano 9.8/10 Exceptional (7) "The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael G. CA $129 CA $225 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Murlo-Hotels-Exclusive-Tower-In-Stone.h40221427.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) ![Interior](https://images.trvl-media.com/lodging/20000000/19150000/19149100/19149003/405b4867.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) ### House with views of the Chianti [](https://www.expedia.ca/Impruneta-Hotels-House-With-Views-Of-The-Chianti.h19149003.Hotel-Information) impruneta 10/10 Exceptional (2) "Great place, quaint and spacious. Beautiful view and equipped with everything needed for a pleasant stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Becky H. [](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) ![Dining](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/w2034h1365x14y0-0edee40d.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) ### Wonderful Tuscan farmhouse with large spaces and panoramic views [](https://www.expedia.ca/Impruneta-Hotels-Beautiful-Tuscan-Farmhouse-With-Large-Spaces-And-Panoramic-Views.h39983368.Hotel-Information) impruneta 9.6/10 Exceptional (25) "Loved the property and views,the owner was very helpful and informative would definitely come back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andy P. CA $298 CA $600 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Impruneta-Hotels-Beautiful-Tuscan-Farmhouse-With-Large-Spaces-And-Panoramic-Views.h39983368.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/34000000/33680000/33675900/33675891/w4029h2268x0y0-afe178cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33680000/33675900/33675891/4bcceb91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33680000/33675900/33675891/db850afc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/34000000/33680000/33675900/33675891/ba4a685f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Suite dei Ricordi - Apartment between Florence and Chianti [](https://www.expedia.ca/Impruneta-Hotels-La-Suite-Dei-Ricordi-Apartment-Between-Florence-And-Chianti.h33675891.Hotel-Information) Impruneta 10/10 Exceptional (1) "Carina abitazione ristrutturata tipica del centro di un paesino toscano di campagna (Impruneta a pochi chilometri da Firenze). Ottimi impianti e sistemi che rendono l'abitazione molto comoda ed attrezzata (un televisore piatto per stanza, condizionatore presente, cucina attrezzata, ecc. Parcheggi a pochi passi e gratuiti dalla sera alla mattina con negozietti a pochi passi. Massima disponibilità dei proprietari e tipica gentilezza toscana." ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Anonymous traveller CA $161 CA $238 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Impruneta-Hotels-La-Suite-Dei-Ricordi-Apartment-Between-Florence-And-Chianti.h33675891.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/36000000/35560000/35556300/35556207/9c1ff361.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/36000000/35560000/35556300/35556207/76c17147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/36000000/35560000/35556300/35556207/4c866191.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/36000000/35560000/35556300/35556207/b1f05fb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House with pool for 4 pax [](https://www.expedia.ca/Casole-DElsa-Hotels-House-With-Pool-For-4-Pax.h35556207.Hotel-Information) Casole d'Elsa 9.4/10 Exceptional (3) "Besser kann man es nicht haben. Den Pool hatten wir gefühlt immer für uns alleine. Die Lage der Unterkunft erlaubt es uns schnell in Siena und San Gimignano zu sein, auch die anderen Sehenswürdigkeiten in der Region waren schnell zu erreichen. In der Unterkunft war es sehr ruhig, ideal um sich zu erholen. Traumhaft schön. Wir kommen gerne wieder. Ciao Oli" ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Oliver E. CA $225 CA $439 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Casole-DElsa-Hotels-House-With-Pool-For-4-Pax.h35556207.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106010000/106004000/106003929/fdf431ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/107000000/106010000/106004000/106003929/19b592db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106010000/106004000/106003929/df47a6bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106010000/106004000/106003929/9d75a9e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi [](https://www.expedia.ca/Certaldo-Hotels-Holiday-Home-Sandra-House-With-Private-Garden-And-Wi-Fi.h106003929.Hotel-Information) Certaldo 10/10 Exceptional (1) "Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm." ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Anonymous traveller CA $177 CA $260 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Certaldo-Hotels-Holiday-Home-Sandra-House-With-Private-Garden-And-Wi-Fi.h106003929.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32650000/32642500/32642446/99362b4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/33000000/32650000/32642500/32642446/a9c07d80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32650000/32642500/32642446/7dba3345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/33000000/32650000/32642500/32642446/ba5e3c5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Dolce-Cuore-Luxe-Apartment-IN-Heart-OF-Tuscany.h32642446.Hotel-Information) San Donato CA $127 CA $370 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Dolce-Cuore-Luxe-Apartment-IN-Heart-OF-Tuscany.h32642446.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/70000000/69550000/69544700/69544621/4f91be71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/70000000/69550000/69544700/69544621/38b82591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69550000/69544700/69544621/2dbd5e66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69550000/69544700/69544621/8091895d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Podere Belsogno-camera Rosmarino [](https://www.expedia.ca/Montalcino-Hotels-Podere-Belsogno-Camera-Rosmarino.h69544621.Hotel-Information) Montalcino 9.0/10 Wonderful (4) "Owners live on property and were very helpful for our first visit to beautiful Montalcino in Tuscany. Spotless apartment. Walking to city center which is just lovely. Beautiful setting. We would return." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Larry V. CA $193 CA $225 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Montalcino-Hotels-Podere-Belsogno-Camera-Rosmarino.h69544621.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=2026-01-11&endDate=2026-01-12®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 Palazzetto Rosso](https://images.trvl-media.com/lodging/17000000/16290000/16288700/16288621/59460b3a_y.jpg) ### Hotel Palazzetto Rosso 10/10 Excellent "Excellent facilities and friendly, warm staff" [](https://expedia.ca/Siena-Hotels-Hotel-Palazzetto-Rosso.h16288621.Hotel-Information) ![Hotel Chiusarelli](https://images.trvl-media.com/lodging/2000000/1120000/1110900/1110843/a501ded1_y.jpg) ### Hotel Chiusarelli 10/10 Excellent "The room was spotlessly clean, the staff were welcoming and helpful, and the breakfast was delicious!" [](https://expedia.ca/Siena-Hotels-Hotel-Chiusarelli.h1110843.Hotel-Information) ![Hotel Italia](https://images.trvl-media.com/lodging/1000000/1000000/997000/996973/7edddb53_y.jpg) ### Hotel Italia 10/10 Excellent "Nice clean room. Close to train/bus station. Very good breakfast " [](https://expedia.ca/Siena-Hotels-Hotel-Italia.h996973.Hotel-Information) ![ Palazzo Ravizza](https://images.trvl-media.com/lodging/2000000/1770000/1760200/1760168/9acb6317_y.jpg) ### Palazzo Ravizza 10/10 Excellent "Having booked with another local hotel - The Athena - who were completely obnoxious and unhelpful regarding the parking. I stumbled across this gem. The staff were so helpful and accomplished \~ first class customer service." [](https://expedia.ca/Siena-Hotels-Pensione-Palazzo-Ravizza.h1760168.Hotel-Information) ![Relais La Corte Dei Cavalieri](https://images.trvl-media.com/lodging/16000000/15640000/15636900/15636837/c9a65eed_y.jpg) ### Relais La Corte Dei Cavalieri 10/10 Excellent "Awesome " [](https://expedia.ca/Siena-Hotels-Relais-La-Corte-Dei-Cavalieri.h15636837.Hotel-Information) ![Hotel Certosa Di Maggiano](https://images.trvl-media.com/lodging/1000000/530000/528500/528470/edea64a5_y.jpg) ### Hotel Certosa Di Maggiano 10/10 Excellent "The best in Siena." [](https://expedia.ca/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information) ![Hotel Athena](https://images.trvl-media.com/lodging/1000000/870000/866600/866580/ab5ee3fb_y.jpg) ### Hotel Athena 10/10 Excellent "Great location, very friendly staff" [](https://expedia.ca/Siena-Hotels-Hotel-Athena.h866580.Hotel-Information) ![Villa del Sole Siena](https://images.trvl-media.com/lodging/9000000/8680000/8674600/8674503/a259e0b9_y.jpg) ### Villa del Sole Siena 10/10 Excellent "Amazing rooms and service!!" [](https://expedia.ca/Siena-Hotels-Villa-Del-Sole-Siena.h8674503.Hotel-Information) ![Hotel Minerva](https://images.trvl-media.com/lodging/1000000/800000/800000/799995/bc9bd928_y.jpg) ### Hotel Minerva 10/10 Excellent "Helpful staff and overall vibe. " [](https://expedia.ca/Siena-Hotels-Hotel-Minerva.h799995.Hotel-Information) ## Find out more about Siena ## Siena Vacation Homes information | Number of reviews | 57 | | ----------------- | ------------------ | | Accommodation | 121 Vacation Homes | | Lowest Price | CA $164 | | Highest Price | CA $17,824 | ## 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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[Things to do in Monteriggioni ](https://www.expedia.ca/Things-To-Do-In-Monteriggioni.d5722.Travel-Guide-Activities) - [Things to do in Province of Siena ](https://www.expedia.ca/Things-To-Do-In-Province-Of-Siena.d6047850.Travel-Guide-Activities) - [Things to do in Quercegrossa ](https://www.expedia.ca/Things-To-Do-In-Quercegrossa.d6047905.Travel-Guide-Activities) - [Things to do in Sovicille ](https://www.expedia.ca/Things-To-Do-In-Sovicille.d602594.Travel-Guide-Activities) - [Book Vacation Homes in Siena on Expedia.it ](https://www.expedia.it/Siena-Case-Vacanze-Private.d9821-aaCaseVacanzePrivate.Guida-Viaggi-Alloggi)