Title: Siena Villas from CA $228 | 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) # Search Siena Villa Rentals from CA $228 - ![](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 [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [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 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Siena villas ![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/9dbd198e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/09f4ffea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/e1923c96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/59636b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Vico dʼArbia [](https://www.expedia.ca/Siena-Hotels-Villa-Capannina-With-Private-Pool.h123292182.Hotel-Information) CA $1,536 CA $1,695 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Siena-Hotels-Villa-Capannina-With-Private-Pool.h123292182.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/7dec8a2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/2e9c5263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/717cdd46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/e3bba8c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Vico dʼArbia [](https://www.expedia.ca/Siena-Hotels-Villa-Torre-Among-The-Hills-Of-Siena.h123292187.Hotel-Information) CA $2,185 CA $2,344 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Siena-Hotels-Villa-Torre-Among-The-Hills-Of-Siena.h123292187.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/798e008d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/1b99bc10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/1b3afdb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/571a61ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Vico dʼArbia [](https://www.expedia.ca/Siena-Hotels-Villa-Capanna-A-Window-Onto-Tuscany.h123292181.Hotel-Information) CA $2,185 CA $2,344 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Siena-Hotels-Villa-Capanna-A-Window-Onto-Tuscany.h123292181.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/94000000/93700000/93697500/93697424/7d69769f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/94000000/93700000/93697500/93697424/e03b4424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/94000000/93700000/93697500/93697424/2775c3c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93700000/93697500/93697424/w1276h853x4y0-c7c68e65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Montalcino [](https://www.expedia.ca/Montalcino-Hotels-VILLA-BRUNELLO-Twelve-Bedroom-Villa.h93697424.Hotel-Information) CA $9,580 CA $10,385 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Montalcino-Hotels-VILLA-BRUNELLO-Twelve-Bedroom-Villa.h93697424.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/d6476b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/a8ccbf55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/8099b959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/ff9693c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Sinalunga [](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information) 10/10 Exceptional (59) "Amazing property! Could not recommend more." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Annika P. CA $196 CA $228 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/06c0aef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/2598e840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/8e90470c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/e78584cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Siena [](https://www.expedia.ca/Buonconvento-Hotels-VILLA-CHIGI-Seven-Bedroom-Villa.h48711007.Hotel-Information) CA $9,633 CA $9,633 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Buonconvento-Hotels-VILLA-CHIGI-Seven-Bedroom-Villa.h48711007.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/28000000/27130000/27125200/27125149/d88438f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/28000000/27130000/27125200/27125149/b9fc2e11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27130000/27125200/27125149/96286a6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![](https://images.trvl-media.com/lodging/28000000/27130000/27125200/27125149/w745h499x12y7-5d6f59fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in siena [](https://www.expedia.ca/Chiusdino-Hotels-Panoramica-Casa-Con-Piscina-Privata.h27125149.Hotel-Information) 7.0/10 Good (10) "We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany.... ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Olivier B. CA $130 CA $240 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Chiusdino-Hotels-Panoramica-Casa-Con-Piscina-Privata.h27125149.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34190000/34180100/34180027/b294561e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34190000/34180100/34180027/7857356e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/35000000/34190000/34180100/34180027/56b29ef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34190000/34180100/34180027/675c208b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Montalcino [](https://www.expedia.ca/Montalcino-Hotels-Antico-Brunello.h34180027.Hotel-Information) CA $10,626 CA $11,705 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Montalcino-Hotels-Antico-Brunello.h34180027.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/dcfa042c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/782eb623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/52aa6660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/25aedd65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Gaiole in Chianti [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-CHIANTIGAIO-Fourteen-Bedroom-Villa.h33066451.Hotel-Information) CA $9,580 CA $10,385 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-CHIANTIGAIO-Fourteen-Bedroom-Villa.h33066451.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/1e6c21a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, table tennis](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/fb904e73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/9fd29a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, table tennis](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/c326d5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Montespertoli [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Milani-With-Shared-Pool.h78165677.Hotel-Information) 10/10 Exceptional (1) "The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott M. CA $2,463 CA $2,467 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Milani-With-Shared-Pool.h78165677.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/w2189h1640x4y5-0fbf58c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/51bd2610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/09a8ec09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/517571bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Montespertoli [](https://www.expedia.ca/Montespertoli-Hotels-Luxury.h32584249.Hotel-Information) 10/10 Exceptional (12) "Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elise D. CA $2,013 CA $2,306 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Montespertoli-Hotels-Luxury.h32584249.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/c92c20b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/4b9923b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/b48487ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/76c1c946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Colle Val D'Elsa [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-VILLA-ALTAMIRA-Eighteen-Bedroom-Villa.h122488659.Hotel-Information) CA $18,998 CA $18,998 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-VILLA-ALTAMIRA-Eighteen-Bedroom-Villa.h122488659.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96140000/96139500/96139408/87710dcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/97000000/96140000/96139500/96139408/80e6ed4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/97000000/96140000/96139500/96139408/3a8f67a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96140000/96139500/96139408/6d16baa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in San Gimignano [](https://www.expedia.ca/San-Gimignano-Hotels-Villa-Arnilu-With-Private-Pool-Wi-Fi.h96139408.Hotel-Information) CA $7,477 CA $8,074 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/San-Gimignano-Hotels-Villa-Arnilu-With-Private-Pool-Wi-Fi.h96139408.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/b8286297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/4a362287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/513cbcf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/b2bb8dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Radda in Chianti [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Villa-La-Petrosa-With-Private-Pool.h99430681.Hotel-Information) 10/10 Exceptional (1) "Pros: Świetna lokalizacja i przyjemne otoczenie domu. Dom położony na wzniesieniu z którego roztaczał się piękny widok. Cons: Osoba opiekująca się domem nie mówiła po angielsku co utrudniało komunikację. Nie byliśmy świadomi że dom podzielony jest na 2 części góra i piwnica w której były dodatkowe 3 pokoje. Uszkodzona pralka która nie dopierała pranych ubrań - brudna woda z zanieczyszczeniami które dodatkowo brudziły ubrania." ![Poland](https://a.travel-assets.com/egds/marks/flags/pl.svg) Anonymous traveller CA $1,806 CA $2,835 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Villa-La-Petrosa-With-Private-Pool.h99430681.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/06053989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/37bf79c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/682c69f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/08415ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Montespertoli [](https://www.expedia.ca/Montespertoli-Hotels-Luxury-Villa-With-Swimmingpool-In-Chianti-Sleeps-22-Large-Groups.h31539094.Hotel-Information) 10/10 Exceptional (38) "Excellent in every way. Highly recommend" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ed M. CA $2,093 CA $2,397 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Montespertoli-Hotels-Luxury-Villa-With-Swimmingpool-In-Chianti-Sleeps-22-Large-Groups.h31539094.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/7f0bb06d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/633059fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/7c521815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/57059e13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Toscana [](https://www.expedia.ca/Bagno-A-Ripoli-Hotels-Villa-Dei-Pavoni-Luxury-Villa-On-Top-Of-Hills-In-Florence.h110132299.Hotel-Information) 10/10 Exceptional (1) "The host was amazing! The property was beautiful. All was seamless! All of our needs were met. Highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leopard I. CA $2,869 CA $3,278 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Bagno-A-Ripoli-Hotels-Villa-Dei-Pavoni-Luxury-Villa-On-Top-Of-Hills-In-Florence.h110132299.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/81953563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/656217ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/ae2c6602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/a822b4f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Gaiole in Chianti [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Villa-Erbolino-With-Private-Garden.h83207211.Hotel-Information) 10/10 Exceptional (7) "Country location but easy access to a great local winery/restaurant and the town of Gaiole." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) russ h. CA $887 CA $925 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Villa-Erbolino-With-Private-Garden.h83207211.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/w1920h1279x0y1-a132bf6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/bc5dd1c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/09d64836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![9 bedrooms, free WiFi](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/0a5c24e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Castellina in Chianti [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-VILLA-IL-PRINCIPE-Nine-Bedroom-Villa.h76771413.Hotel-Information) CA $7,568 CA $8,373 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-VILLA-IL-PRINCIPE-Nine-Bedroom-Villa.h76771413.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/38e5a789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h854x2y0-790f85bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h863x2y0-ddee714e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h857x2y0-a94584e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Impruneta [](https://www.expedia.ca/Impruneta-Hotels-Vrbo-Property.h108275238.Hotel-Information) 10/10 Exceptional (3) "Pictures do not do it justice, this house and location is absolutely beautiful. Very comfortable beds, clean house, beauty views, nice fireplace.owner goes above and beyond to make you feel welcome. She had her local wine, cooked us a delishes breakfast, and also brought her olive oil to do tasting. We will definitely be back, i thank you for an amazing experience and a beautiful house." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lidija M. CA $553 CA $728 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Impruneta-Hotels-Vrbo-Property.h108275238.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76770000/76763300/76763252/09e999d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76770000/76763300/76763252/a9ba220a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76770000/76763300/76763252/4d84a43c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76770000/76763300/76763252/1fa7877a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Roccastrada GR [](https://www.expedia.ca/Roccastrada-Hotels-Pet-Friendly-Finca-Olivos-With-Mountain-View.h76763252.Hotel-Information) CA $1,842 CA $1,946 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Roccastrada-Hotels-Pet-Friendly-Finca-Olivos-With-Mountain-View.h76763252.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=2025-12-25&endDate=2025-12-26®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-Villas.d9821-aaVillas.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSiena-Villas.d9821-aaVillas.Travel-Guide-Accommodation) ## Top Siena Hotel Reviews ![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) ![Hotel Athena](https://images.trvl-media.com/lodging/1000000/870000/866600/866580/ab5ee3fb_y.jpg) ### Hotel Athena 10/10 Excellent "Excellent hotel, very helpful staff, highly recommended " [](https://expedia.ca/Siena-Hotels-Hotel-Athena.h866580.Hotel-Information) ![Hotel Italia](https://images.trvl-media.com/lodging/1000000/1000000/997000/996973/7edddb53_y.jpg) ### Hotel Italia 10/10 Excellent "This was a short stay for us in Siena. A great hotel. Friendly staff and the best bargain best breakfast we have had in Italy. Highly recommended" [](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 "Ideal in every way." [](https://expedia.ca/Siena-Hotels-Pensione-Palazzo-Ravizza.h1760168.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 "La habitación muy amplia, teníamos armario vestidor, sala, habitación amplia y un gran baño. Excelente la atención del personal. El lugar mágico maravilloso de epoca" [](https://expedia.ca/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information) ![Hotel Palazzetto Rosso](https://images.trvl-media.com/lodging/17000000/16290000/16288700/16288621/59460b3a_y.jpg) ### Hotel Palazzetto Rosso 10/10 Excellent "Amazing" [](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 very clean and the bathroom was nice. The staff was very helpful especially because we had personal issues to deal with and places we had to get to for resolution. They helped us navigate several things that we could not have done on our own. We are grateful! " [](https://expedia.ca/Siena-Hotels-Hotel-Chiusarelli.h1110843.Hotel-Information) ![Villa Scacciapensieri Boutique Hotel](https://images.trvl-media.com/lodging/3000000/2700000/2693500/2693499/b46a6593_y.jpg) ### Villa Scacciapensieri Boutique Hotel 10/10 Excellent "The villa was wonderful and absolutely beautiful. My friends and I absolutely loved our stay here. " [](https://expedia.ca/Siena-Hotels-Villa-Scacciapensieri-Boutique-Hotel.h2693499.Hotel-Information) ## Find out more about Siena ## Siena Villas information | Number of reviews | 97 | | ----------------- | ---------- | | Accommodation | 87 Villas | | Lowest Price | CA $228 | | Highest Price | CA $11,705 | ## Frequently asked questions ### How much do villas in Siena cost? ### How many villas are there in Siena? ### Why book your villa in Siena with Expedia? ### How can I find cheap villas in Siena? ### What is there to do near my villa in Siena? ## 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) - 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[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) - [Resorts in Val d'Elsa ](https://www.expedia.ca/Val-DElsa-Resort-Hotels.d6047917-aaResortHotels.Travel-Guide-Accommodation) - [Villa Parigini Hotels ](https://www.expedia.ca/Villa-Parigini-Hotels.d553248622847106390.Travel-Guide-Hotels) - [Resorts in Villa ](https://www.expedia.ca/Villa-Resort-Hotels.d553248635118822693-aaResortHotels.Travel-Guide-Accommodation) - [Ville di Corsano Hotels ](https://www.expedia.ca/Ville-Di-Corsano-Hotels.d6361513.Travel-Guide-Hotels) - [Volte Basse Hotels ](https://www.expedia.ca/Volte-Basse-Hotels.d3000416925.Travel-Guide-Hotels) - [Flights to Province of Siena ](https://www.expedia.ca/Destinations-In-Province-Of-Siena.d6047850.Flight-Destinations) - [Flights from Taverne d'Arbia ](https://www.expedia.ca/lp/flights/3000388927/flights-from-taverne-darbia) - [Flights from Val di Pugna ](https://www.expedia.ca/lp/flights/553248635149838501/flights-from-val-di-pugna) - [Flights from London (LHR) to Siena (SAY) ](https://www.expedia.ca/lp/flights/lhr/say/london-to-siena) - [Flights from Ottawa (YOW) to Siena (SAY) ](https://www.expedia.ca/lp/flights/yow/say/ottawa-to-siena) - [Flights from Québec (YQB) to Siena (SAY) ](https://www.expedia.ca/lp/flights/yqb/say/quebec-to-siena) - [Flights from Montreal (YUL) to Siena (SAY) ](https://www.expedia.ca/lp/flights/yul/say/montreal-to-siena) - [Flights from Vancouver (YVR) to Siena (SAY) ](https://www.expedia.ca/lp/flights/yvr/say/vancouver-to-siena) - [Flights from Calgary (YYC) to Siena (SAY) ](https://www.expedia.ca/lp/flights/yyc/say/calgary-to-siena) - [Flights from Toronto (YYZ) to Siena (SAY) ](https://www.expedia.ca/lp/flights/yyz/say/toronto-to-siena) - [Visit Badesse ](https://www.expedia.ca/Badesse.dx553248635118858455) - [Fortezza Medicea ](https://www.expedia.ca/Fortezza-Medicea-Siena-Historical-Center.d6287282.Vacation-Attraction) - [Visit Le Tolfe ](https://www.expedia.ca/Le-Tolfe.dx553248622897701422) - [Monteriggioni Castle ](https://www.expedia.ca/Monteriggioni-Castle-Monteriggioni.d6258231.Vacation-Attraction) - [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 Villas in Siena on Expedia.it ](https://www.expedia.it/Siena-Ville.d9821-aaVille.Guida-Viaggi-Alloggi)