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 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=VACATION_HOME&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) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114190000/114180600/114180505/de5a02ac.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 " ![France](https://a.travel-assets.com/egds/marks/flags/fr.svg) YVES A. CA $211 CA $266 total includes taxes & fees Oct 31 - Nov 1 [](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) ![Interior](https://images.trvl-media.com/lodging/119000000/118770000/118760800/118760780/e41ddf9a.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) ### LOVE NEST SIENA YOUR LOVE NEST Toscana CA $146 CA $223 total includes taxes & fees Oct 27 - Oct 28 [](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) ![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) ![Living area](https://images.trvl-media.com/lodging/22000000/21800000/21793500/21793404/42f20907.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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Serena F. CA $159 CA $263 total includes taxes & fees Nov 6 - Nov 7 [](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)](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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ruth 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/69000000/68050000/68050000/68049942/3d55d541.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) ![Interior](https://images.trvl-media.com/lodging/69000000/68050000/68050000/68049942/27c749dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68050000/68050000/68049942/6a211ee9.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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa C. CA $8,122 CA $9,091 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Trequanda-Hotels-Villa-Falco-Cignella-Resort-Tuscany.h68049942.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, 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) ![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) ### 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." ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Alex CA $127 CA $148 total includes taxes & fees Nov 7 - Nov 8 [](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) ![Outdoor banquet area](https://images.trvl-media.com/lodging/22000000/21140000/21136300/21136264/d0c26e60.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) ![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) ### Zampugna Trequanda 9.2/10 Wonderful (5) "Beautiful and host is great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) August CA $649 CA $719 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Trequanda-Hotels-Zampugna.h21136264.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) ![Lobby](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/bbfe6d56.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) ![Outdoor dining](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/d9e20b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A LUXURY VILLA ON THE HILLS OF FLORENCE Impruneta CA $16,245 CA $18,134 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Impruneta-Hotels-A-Luxury-Villa-ON-THE-Hills-OF-Florence.h47026113.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) ![Dining](https://images.trvl-media.com/lodging/118000000/117990000/117985600/117985575/398845f0.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) ### Holiday Home 'La Casetta' with Private Terrace, Private Garden and Wi-Fi Volterra CA $107 CA $133 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Volterra-Hotels-Holiday-Home-La-Casetta-With-Private-Terrace.h117985575.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) ![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) ![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) ![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 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 $134 CA $190 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Poggibonsi-Hotels-Holiday-Home-Piccolo-Angolo-Di-Tranquillita-With-Private-Garden-And-Wi-Fi.h112477726.Hotel-Information) ![TV, DVD player](https://images.trvl-media.com/lodging/69000000/68060000/68051700/68051629/fc2934d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68060000/68051700/68051629/269ff2c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/69000000/68060000/68051700/68051629/501031f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/69000000/68060000/68051700/68051629/b3b7fcb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Pesca - Cignella Resort Val D'orcia Toscana Toscana CA $8,122 CA $9,091 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Trequanda-Hotels-Vrbo-Property.h68051629.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) ![Property grounds](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/30c3d6b6.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) ![Interior](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/ff617fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Exclusive Stone Tower. Casciano 9.8/10 Exceptional (6) "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 $145 CA $244 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Murlo-Hotels-Exclusive-Tower-In-Stone.h40221427.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) ![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/40000000/39870000/39866200/39866124/7ed60a74.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) ### 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).... ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Heike K. CA $132 CA $284 total includes taxes & fees Oct 31 - Nov 1 [](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) ![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) ![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 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 $117 CA $166 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Monticiano-Hotels-Comodita.h64173725.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/cb3775a2.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) ![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 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. CA $110 CA $375 total includes taxes & fees Nov 2 - Nov 3 [](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) ![Dining](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/w2034h1365x14y0-0edee40d.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 (24) "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 $122 CA $400 total includes taxes & fees Nov 1 - Nov 2 [](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/84000000/83590000/83580400/83580374/f52ea845.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) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/de85b0c3.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) ### Chianti Craft House Badia a Passignano Barberino Tavarnelle 9.8/10 Exceptional (9) "Great food in the area. Beautiful church tour and a fantastic host for our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Craig & Conny M. CA $236 CA $336 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Vrbo-Property.h83580374.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35560000/35556300/35556207/52351e0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House with pool for 4 pax 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 $211 CA $430 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Casole-DElsa-Hotels-House-With-Pool-For-4-Pax.h35556207.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) ![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/70000000/69550000/69548900/69548805/fbd3a173.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) ![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 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 $195 CA $227 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Montalcino-Hotels-Podere-Belsogno-Camera-Lavanda.h69548805.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) ![Interior](https://images.trvl-media.com/lodging/33000000/32650000/32642500/32642446/3b201e90.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) ![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 San Donato CA $112 CA $354 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Dolce-Cuore-Luxe-Apartment-IN-Heart-OF-Tuscany.h32642446.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=2025-11-07&endDate=2025-11-08®ionId=9821&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&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 ![Villa del Sole Siena](//images.trvl-media.com/lodging/9000000/8680000/8674600/8674503/a259e0b9_y.jpg) ### Villa del Sole Siena 10/10 Excellent "Beautiful small hotel with an exceptional staff. " [](https://expedia.ca/Siena-Hotels-Villa-Del-Sole-Siena.h8674503.Hotel-Information) ![Hotel Athena](//images.trvl-media.com/lodging/1000000/870000/866600/866580/ab5ee3fb_y.jpg) ### Hotel Athena 10/10 Excellent "Excellent hotel with great service." [](https://expedia.ca/Siena-Hotels-Hotel-Athena.h866580.Hotel-Information) ![Piccolo Hotel Etruria](//images.trvl-media.com/lodging/19000000/18180000/18174100/18174068/e41ea97c_y.jpg) ### Piccolo Hotel Etruria 10/10 Excellent "Otima localização." [](https://expedia.ca/Siena-Hotels-Piccolo-Hotel-Etruria.h18174068.Hotel-Information) ![ Palazzo Ravizza](//images.trvl-media.com/lodging/2000000/1770000/1760200/1760168/9acb6317_y.jpg) ### Palazzo Ravizza 10/10 Excellent "Parking area is very safe. Staff very friendly and helpful. The property has a beautiful yard with stunning view." [](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 "This is a hidden Gem ! A reasonable rate with excellent staff and service. Easy walk to town center. Apartment was clean and comfortable.Great experience !" [](https://expedia.ca/Siena-Hotels-Borgo-Grondaie.h905710.Hotel-Information) ![Grand Hotel Continental Siena – Starhotels Collezione](//images.trvl-media.com/lodging/1000000/800000/796700/796662/8b42326b_y.jpg) ### Grand Hotel Continental Siena – Starhotels Collezione 10/10 Excellent "This is a 5+ star facility. Our room was outrageous with frescos and paintings on the walls and ceiling. The staff went out of their way to help us with our requests and provide a history of the property. Our room had 1.5 bathrooms and the breakfast had an excellent choice of items. " [](https://expedia.ca/Siena-Hotels-Grand-Hotel-Continental-Siena-Starhotels-Collezione.h796662.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 "Thank you for a nice stay! The woman at cafe making coffee was so sweet! " [](https://expedia.ca/Siena-Hotels-Villa-Scacciapensieri-Boutique-Hotel.h2693499.Hotel-Information) ![Hotel Italia](//images.trvl-media.com/lodging/1000000/1000000/997000/996973/7edddb53_y.jpg) ### Hotel Italia 10/10 Excellent "Very friendly and welcoming staff. Wonderful breakfast" [](https://expedia.ca/Siena-Hotels-Hotel-Italia.h996973.Hotel-Information) ![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) ## Find out more about Siena ## Siena Vacation Homes information | Number of reviews | 48 | | --- | --- | | Accommodation | 124 Vacation Homes | | Lowest Price | CA $133 | | Highest Price | CA $18,134 | ## 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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