Title: Siena Vacation Home Rentals from CA $166: 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) ![](https://images.trvl-media.com/place/9821/7379d030-252a-4e26-a469-e10785470ebc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 3 - Jul 5](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2026-07-03&endDate=2026-07-05&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 ![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) ![Interior](https://images.trvl-media.com/lodging/119000000/118770000/118760800/118760780/e41ddf9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118770000/118760800/118760780/ee5c01ed.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 $68 CA $188 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Monteriggioni-Hotels-Vrbo-Property.h118760780.Hotel-Information) ![TV, books](https://images.trvl-media.com/lodging/38000000/37020000/37012000/37011920/8cb3707e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/38000000/37020000/37012000/37011920/e6e2e691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/38000000/37020000/37012000/37011920/3bbdd967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/38000000/37020000/37012000/37011920/96956dcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming apartment in the Historic Center of Siena [](https://www.expedia.ca/Siena-Hotels-Charming-Apartment-In-The-Historic-Center-Of-Siena.h37011920.Hotel-Information) Siena City Centre 10/10 Exceptional (20 reviews) "Fantastic stay! So convenient too!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wesley C. CA $149 CA $275 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Siena-Hotels-Charming-Apartment-In-The-Historic-Center-Of-Siena.h37011920.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/22000000/21800000/21793500/21793404/5bec1a68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/22000000/21800000/21793500/21793404/9dbd798b.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 [](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 reviews) "I stayed for a month and found the apartment ti be very comfortable and si convenient for all that Siena has to offer." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Louise B. CA $163 CA $264 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Siena-Hotels-IL-TOLOMEI-Central-In-The-Middle-Of-Main-Street.h21793404.Hotel-Information) ![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) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114190000/114180600/114180505/de5a02ac.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/115000000/114190000/114180600/114180505/4e76a25b.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 review) "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 $236 CA $294 total includes taxes & fees Apr 7 - Apr 8 [](https://www.expedia.ca/Siena-Hotels-Cozy-Tuscan-Style-Apartment-Suitable-For-Families-Pets-Allowed.h114180505.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/29000000/28860000/28857600/28857589/20aa043f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/29000000/28860000/28857600/28857589/51f024c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/29000000/28860000/28857600/28857589/w1942h1294x0y2-ee23dc7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/29000000/28860000/28857600/28857589/w3888h2586x0y4-76f0f8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palazzo Bichi Ruspoli-Historical Res, near Campo Square and close to everything [](https://www.expedia.ca/Siena-Hotels-Palazzo-Bichi-Ruspoli-Historical-Res.h28857589.Hotel-Information) Siena City Centre 10/10 Exceptional (20 reviews) "Fantastic place,everything you could need is there, terrific position, host very quick to respond to messages. Just a fabulous stay." ![New Zealand](https://a.travel-assets.com/egds/marks/flags/nz.svg) Maggie M. CA $547 CA $715 total includes taxes & fees Apr 3 - Apr 4 [](https://www.expedia.ca/Siena-Hotels-Palazzo-Bichi-Ruspoli-Historical-Res.h28857589.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114490000/114488800/114488726/4fa84c04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114490000/114488800/114488726/ccd617eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/115000000/114490000/114488800/114488726/d34ca53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114490000/114488800/114488726/b0ed52b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Siena Countryside Stay [](https://www.expedia.ca/Montalcino-Hotels-Vrbo-Property.h114488726.Hotel-Information) Monterongriffoli CA $353 CA $490 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Montalcino-Hotels-Vrbo-Property.h114488726.Hotel-Information) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117790000/117789600/117789522/e22a1f8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117790000/117789600/117789522/1b1dee6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, bidet, towels, soap](https://images.trvl-media.com/lodging/118000000/117790000/117789600/117789522/893a4417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117790000/117789600/117789522/a132a77a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tuscan House Relax in the heart of the Tuscan countryside [](https://www.expedia.ca/Montespertoli-Hotels-Vrbo-Property.h117789522.Hotel-Information) Montespertoli CA $155 CA $188 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Montespertoli-Hotels-Vrbo-Property.h117789522.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/77d8ad70.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) ![Interior](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/f52ea845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/d91c6ec9.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 reviews) "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 $233 CA $331 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Vrbo-Property.h83580374.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/107000000/106550000/106548600/106548573/6a6edf2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106550000/106548600/106548573/ff10e0c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/107000000/106550000/106548600/106548573/aaeb9549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106550000/106548600/106548573/92c73dd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center [](https://www.expedia.ca/Montalcino-Hotels-Palazzo-Tamanti-Historic-4-Bedroom-Villa-In-Montalcino-Center.h106548573.Hotel-Information) Montalcino 10/10 Exceptional (2 reviews) "Absolutely the most stunning VRBO we have ever stayed at. Majestic In both stature and comfort. Every need anticipated and met. Communication with host and Valentina perfect. The standard of luxury located in a fairy tale setting! A must visit - we did not want to leave!! Cannot say enough about this special villa." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert K. CA $847 CA $1,481 total includes taxes & fees Mar 14 - Mar 15 [](https://www.expedia.ca/Montalcino-Hotels-Palazzo-Tamanti-Historic-4-Bedroom-Villa-In-Montalcino-Center.h106548573.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 | Living area](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/4734ab61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/260b4111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/29000000/28410000/28401500/28401463/4e7093c0.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 reviews) "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 $142 CA $165 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/San-Gimignano-Hotels-Casa-Vacanze-Le-Case.h28401463.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/22000000/21140000/21136300/21136264/63f9a000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/22000000/21140000/21136300/21136264/f06f717a.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 [](https://www.expedia.ca/Trequanda-Hotels-Zampugna.h21136264.Hotel-Information) Trequanda 9.2/10 Wonderful (5 reviews) "Beautiful and host is great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) August [](https://www.expedia.ca/Trequanda-Hotels-Zampugna.h21136264.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/df1d957c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/c2de7201.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/343d0b2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/80b09a28.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 reviews) "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) ![Interior](https://images.trvl-media.com/lodging/84000000/83360000/83354900/83354864/f910598d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/84000000/83360000/83354900/83354864/a7d5ba95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83360000/83354900/83354864/04a72517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83360000/83354900/83354864/b68fa7ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Casa-Vacanze-Chianti-Summer-With-Pool.h83354864.Hotel-Information) Gaiole in Chianti CA $724 CA $864 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Casa-Vacanze-Chianti-Summer-With-Pool.h83354864.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/126000000/125320000/125312900/125312869/579ecb81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125320000/125312900/125312869/d4153827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/126000000/125320000/125312900/125312869/f31f9c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/126000000/125320000/125312900/125312869/0bda44dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Lifi Cozy Tuscany House [](https://www.expedia.ca/Scandicci-Hotels-Cozy-Holiday-Home-With-Garden-In-Tuscany-San-Vincenzo-A-Torri.h125312869.Hotel-Information) San Vincenzo A Torri CA $247 CA $334 total includes taxes & fees Mar 21 - Mar 22 [](https://www.expedia.ca/Scandicci-Hotels-Cozy-Holiday-Home-With-Garden-In-Tuscany-San-Vincenzo-A-Torri.h125312869.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) ![Dining](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/602dd11a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/4b443108.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 review) "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 $127 CA $272 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Trequanda-Hotels-Romantic-Farm-In-The-Sienese-Hills.h39866124.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/f50de840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/48000000/47030000/47026200/47026113/95610811.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 $15,706 CA $17,138 total includes taxes & fees Mar 18 - Mar 19 [](https://www.expedia.ca/Impruneta-Hotels-A-Luxury-Villa-ON-THE-Hills-OF-Florence.h47026113.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69550000/69544400/69544397/cff65ca0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/70000000/69550000/69544400/69544397/72ce7109.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/70000000/69550000/69544400/69544397/8d2de3b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69550000/69544400/69544397/87505345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Podere Belsogno [](https://www.expedia.ca/Montalcino-Hotels-Podere-Belsogno.h69544397.Hotel-Information) Montalcino 10/10 Exceptional (1 review) "Charming and attentive hosts, stunning terrace with amazing views and a modern, attractive and well equipped rental that was a short walk to downtown Montalcino. We had a fabulous time and would go back again." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) David P. CA $550 CA $628 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Montalcino-Hotels-Podere-Belsogno.h69544397.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/102000000/101060000/101055400/101055376/d819075f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101060000/101055400/101055376/9c45c989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/102000000/101060000/101055400/101055376/8c19f886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101060000/101055400/101055376/526fbb44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning [](https://www.expedia.ca/Buonconvento-Hotels-Holiday-Home-La-Casa-Gialla-Di-Buonconvento-With-Wi-Fi-And-Air-Conditioning.h101055376.Hotel-Information) Buonconvento CA $216 CA $220 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Buonconvento-Hotels-Holiday-Home-La-Casa-Gialla-Di-Buonconvento-With-Wi-Fi-And-Air-Conditioning.h101055376.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/93000000/92320000/92310500/92310484/f8b8a4a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92320000/92310500/92310484/55477a6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92320000/92310500/92310484/0e7012b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92320000/92310500/92310484/w2534h1690x0y0-6dfa4245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The little Magician's secret corner [](https://www.expedia.ca/Sinalunga-Hotels-The-Little-Magicians-Secret-Corner.h92310484.Hotel-Information) Sinalunga CA $188 CA $295 total includes taxes & fees Mar 14 - Mar 15 [](https://www.expedia.ca/Sinalunga-Hotels-The-Little-Magicians-Secret-Corner.h92310484.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/c7076070.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/28000000/27470000/27461900/27461842/1d63c974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/72d49276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/bea6b45a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns. [](https://www.expedia.ca/Monteriggioni-Hotels-Pleasant-Characteristic-Hayloft-That-Has-Been-Renovated-Into-Holiday-Apartment-In-A-Part-Of-The-Chianti-That-Is-Ideal-For-Visiting-The-Most-Important-Towns.h27461842.Hotel-Information) Monteriggioni 10/10 Exceptional (12 reviews) "Monteriggioni is the perfect location between Siena, San Gimignani, and roads to Chianti. The hosts Marcela, Enzo, and Alessandro really made us feel at home and comfortable. The property is beautiful, quiet, with unforgettable sunsets! Time at the pool is refreshing and relaxing, with beautiful views of the surrounding countryside. The authentic Italian kitchen was perfect for creating your own breakfasts and dinners. The bathrooms with showers have all you need, and the beds are really... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel D. CA $352 CA $507 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Monteriggioni-Hotels-Pleasant-Characteristic-Hayloft-That-Has-Been-Renovated-Into-Holiday-Apartment-In-A-Part-Of-The-Chianti-That-Is-Ideal-For-Visiting-The-Most-Important-Towns.h27461842.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=2026-03-27&endDate=2026-03-28®ionId=9821&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_9821) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Siena%2C+Tuscany%2C+Italy®ionId=9821&latLong=43.31836%2C11.331622&adults=2&startDate=2026-06-11&d1=2026-06-11&endDate=2026-06-14&d2=2026-06-14&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Siena%2C+Tuscany%2C+Italy®ionId=9821&latLong=43.31836%2C11.331622&adults=2&startDate=2026-06-11&d1=2026-06-11&endDate=2026-06-14&d2=2026-06-14&lodging=APARTMENT) Villas [](https://www.expedia.ca/Hotel-Search?destination=Siena%2C+Tuscany%2C+Italy®ionId=9821&latLong=43.31836%2C11.331622&adults=2&startDate=2026-06-11&d1=2026-06-11&endDate=2026-06-14&d2=2026-06-14&lodging=VILLA) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Siena%2C+Tuscany%2C+Italy®ionId=9821&latLong=43.31836%2C11.331622&adults=2&startDate=2026-06-11&d1=2026-06-11&endDate=2026-06-14&d2=2026-06-14&lodging=VACATION_HOME) Residences [](https://www.expedia.ca/Hotel-Search?destination=Siena%2C+Tuscany%2C+Italy®ionId=9821&latLong=43.31836%2C11.331622&adults=2&startDate=2026-06-11&d1=2026-06-11&endDate=2026-06-14&d2=2026-06-14&lodging=RESIDENCE) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Siena%2C+Tuscany%2C+Italy®ionId=9821&latLong=43.31836%2C11.331622&adults=2&startDate=2026-06-11&d1=2026-06-11&endDate=2026-06-14&d2=2026-06-14&lodging=COTTAGE) Condos [](https://www.expedia.ca/Hotel-Search?destination=Siena%2C+Tuscany%2C+Italy®ionId=9821&latLong=43.31836%2C11.331622&adults=2&startDate=2026-06-11&d1=2026-06-11&endDate=2026-06-14&d2=2026-06-14&lodging=CONDO) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Siena%2C+Tuscany%2C+Italy®ionId=9821&latLong=43.31836%2C11.331622&adults=2&startDate=2026-06-11&d1=2026-06-11&endDate=2026-06-14&d2=2026-06-14&lodging=CHALET) ![](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 Certosa Di Maggiano](https://images.trvl-media.com/lodging/1000000/530000/528500/528470/edea64a5_y.jpg) ### Hotel Certosa Di Maggiano 10/10 Excellent "Absolutely fantastic stay. Photos don’t do it justice. Amazing food, and had a very fun time at the cocktail bar with Ricardo!" [](https://expedia.ca/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information) ![NH Siena](https://images.trvl-media.com/lodging/1000000/20000/15800/15716/w3840h2562x0y0-25695984_y.jpg) ### NH Siena 10/10 Excellent "I didn't use it. I only stayed one night." [](https://expedia.ca/Siena-Hotels-NH-Siena.h15716.Hotel-Information) ![Hotel Italia](https://images.trvl-media.com/lodging/1000000/1000000/997000/996973/e3da527a_y.jpg) ### Hotel Italia 10/10 Excellent "Very close to the bus and train station, lovely staff, clean room but a bit too warm even in February and no water kettle in the room, which was a bit surprising. " [](https://expedia.ca/Siena-Hotels-Hotel-Italia.h996973.Hotel-Information) ![ Palazzo Ravizza](https://images.trvl-media.com/lodging/2000000/1770000/1760200/1760168/5eddd92b_y.jpg) ### Palazzo Ravizza 10/10 Excellent "Beautiful, quiet and clean. Nice break from the bustle of Florence. Location is on the other side of the transition stop so get an uber if you have a lot luggage, otherwise it’s about a 35 minute walk if yo have a backpack. Because it’s on the other side, the hotel has a lovely garden with a view of the countryside. Breakfast was included and nice, including the well made cappuccino. " [](https://expedia.ca/Siena-Hotels-Pensione-Palazzo-Ravizza.h1760168.Hotel-Information) ![Hotel Athena](https://images.trvl-media.com/lodging/1000000/870000/866600/866580/e92eb5d8_y.jpg) ### Hotel Athena 10/10 Excellent "Excellent repeat stay. Top-notch staff, beautiful views and rooms, excellent breakfast and on-site dinner restaurant." [](https://expedia.ca/Siena-Hotels-Hotel-Athena.h866580.Hotel-Information) ![Hotel Santa Caterina](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540753/6057be8a_y.jpg) ### Hotel Santa Caterina 10/10 Excellent "Very beautiful hotel by the city wall,friendly staff and a good breakfast." [](https://expedia.ca/Siena-Hotels-Hotel-Santa-Caterina.h2540753.Hotel-Information) ![Hotel Minerva](https://images.trvl-media.com/lodging/1000000/800000/800000/799995/bc9bd928_y.jpg) ### Hotel Minerva 8/10 Good "Property was clean a tidy, was a little dated but still nice, view over Siena from the terrace was stunning. Staff were helpful and friendly giving us a map and guide of places of interest in the town. Included breakfast had great options and car park was convenient and safe." [](https://expedia.ca/Siena-Hotels-Hotel-Minerva.h799995.Hotel-Information) ![Cannon d'Oro](https://images.trvl-media.com/lodging/3000000/2530000/2525800/2525757/bda17ddf_y.jpg) ### Cannon d'Oro 10/10 Excellent "Lovely staff, very spacious room, and everything was spotless. Location ideal." [](https://expedia.ca/Siena-Hotels-Cannon-DOro.h2525757.Hotel-Information) ![Grand Hotel Continental Siena – Starhotels Collezione](https://images.trvl-media.com/lodging/1000000/800000/796700/796662/38b0d782_y.jpg) ### Grand Hotel Continental Siena – Starhotels Collezione 10/10 Excellent "The best hotel in siena for sure, thank you! " [](https://expedia.ca/Siena-Hotels-Grand-Hotel-Continental-Siena-Starhotels-Collezione.h796662.Hotel-Information) ## Find out more about Siena ## Siena Vacation Homes information | Number of reviews | 93 | | ----------------- | ------------------ | | Accommodation | 123 Vacation Homes | | Lowest Price | CA $166 | | Highest Price | CA $17,138 | ## 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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[Condo Rentals in Monsanto ](https://www.expedia.ca/Monsanto-Condos.d553248622859260555-aaCondos.Travel-Guide-Accommodation) - [Resorts in Monsanto ](https://www.expedia.ca/Monsanto-Resort-Hotels.d553248622859260555-aaResortHotels.Travel-Guide-Accommodation) - [Montarioso Hotels ](https://www.expedia.ca/Montarioso-Monteriggioni-Hotels.0-n553248635976008416-0.Travel-Guide-Filter-Hotels) - [Montecchio Hotels ](https://www.expedia.ca/Montecchio-Hotels.d6361508.Travel-Guide-Hotels) - [Hotels near Monteriggioni Badesse Station ](https://www.expedia.ca/Monteriggioni-Badesse-Station-Hotels.d6287325.Travel-Guide-Hotels) - [Hotel Wedding Venues Hotels in Monteriggioni ](https://www.expedia.ca/Monteriggioni-Hotels-Wedding-Hotels.0-0-d5722-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Monteriggioni Hotels ](https://www.expedia.ca/Monteriggioni-Hotels.d5722.Travel-Guide-Hotels) - [Monteroni d'Arbia Hotels ](https://www.expedia.ca/Monteroni-DArbia-Hotels.d6053877.Travel-Guide-Hotels) - [Monti di Sotto Hotels ](https://www.expedia.ca/Monti-Di-Sotto-Hotels.d6285679.Travel-Guide-Hotels) - [B&B in Murlo ](https://www.expedia.ca/Murlo-Bed-And-Breakfast.d6046740-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Farmstay in Orgia ](https://www.expedia.ca/Orgia-Agritourism.d6361512-aaAgritourism.Travel-Guide-Accommodation) - [Hotels near Palazzo Pubblico ](https://www.expedia.ca/Palazzo-Pubblico-Hotels.0-l6077946-0.Travel-Guide-Filter-Hotels) - [Pianella Hotels ](https://www.expedia.ca/Pianella-Hotels.d6285681.Travel-Guide-Hotels) - [Hotels near Piazza del Campo ](https://www.expedia.ca/Piazza-Del-Campo-Hotels.0-l6077950-0.Travel-Guide-Filter-Hotels) - [Castles in Poggibonsi ](https://www.expedia.ca/Poggibonsi-Castles.d4964-aaCastles.Travel-Guide-Accommodation) - [Ponte a Tressa Hotels ](https://www.expedia.ca/Ponte-A-Tressa-Hotels.d553248635149842909.Travel-Guide-Hotels) - [Quercegrossa Hotels ](https://www.expedia.ca/Quercegrossa-Hotels.d6047905.Travel-Guide-Hotels) - [Radi Hotels ](https://www.expedia.ca/Radi-Hotels.d6342138.Travel-Guide-Hotels) - [San Giovanni A Cerreto Hotels ](https://www.expedia.ca/San-Giovanni-A-Cerreto-Hotels.d553248622859516344.Travel-Guide-Hotels) - 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[Sovicille Hotels ](https://www.expedia.ca/Sovicille-Hotels.d602594.Travel-Guide-Hotels) - [Taverne d'Arbia Hotels ](https://www.expedia.ca/Taverne-DArbia-Hotels.d3000388927.Travel-Guide-Hotels) - [Vagliagli Hotels ](https://www.expedia.ca/Vagliagli-Hotels.d6047102.Travel-Guide-Hotels) - [Aparthotels in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Apart-Hotels.d6047917-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Bed-And-Breakfast.d6047917-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Chalets.d6047917-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Guest-Houses.d6047917-aaGuestHouses.Travel-Guide-Accommodation) - [Hostels in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Hostels.d6047917-aaHostels.Travel-Guide-Accommodation) - [Inns in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Inns.d6047917-aaInns.Travel-Guide-Accommodation) - 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[Visit Monteriggioni ](https://www.expedia.ca/Monteriggioni.dx5722) - [Visit Monteroni d'Arbia ](https://www.expedia.ca/Monteroni-DArbia.dx6053877) - [Province of Siena Vacations ](https://www.expedia.ca/Province-Of-Siena.d6047850.Destination-Travel-Guides) - [Visit Province of Siena ](https://www.expedia.ca/Province-Of-Siena.dx6047850) - [Visit San Giovanni A Cerreto ](https://www.expedia.ca/San-Giovanni-A-Cerreto.dx553248622859516344) - [Visit San Rocco a Pilli ](https://www.expedia.ca/San-Rocco-A-Pilli.dx6285685) - [Visit Siena City Centre ](https://www.expedia.ca/Siena-Siena-City-Centre.dx553248633938945205) - [Visit Siena Historical Center ](https://www.expedia.ca/Siena-Siena-Historical-Center.dx6285925) - [Visit Ville di Corsano ](https://www.expedia.ca/Ville-Di-Corsano.dx6361513) - [Car rental Monteriggioni ](https://www.expedia.ca/Car-Rentals-In-Monteriggioni.d5722.Car-Rental-Guide) - [Province of Siena Vacation Rentals ](https://www.expedia.ca/Destinations-In-Province-Of-Siena.d6047850.Vacation-Rental-Destinations) - [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)