Title: Siena Villas from CA $229 | 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 $229 - ![](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 [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 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) In three months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Siena villas ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/7a221817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/4793210d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/21b4c6c1.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) ### Villa Capannina with Private Pool, Wi-Fi and Air Conditioning [](https://www.expedia.ca/Siena-Hotels-Villa-Capannina-With-Private-Pool.h123292182.Hotel-Information) Vico dʼArbia CA $1,542 CA $1,703 total includes taxes & fees Dec 15 - Dec 16 [](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/ff90371f.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) ![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/19cb3d46.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 Torre Among the Hills of Siena [](https://www.expedia.ca/Siena-Hotels-Villa-Torre-Among-The-Hills-Of-Siena.h123292187.Hotel-Information) Vico dʼArbia CA $2,194 CA $2,354 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Siena-Hotels-Villa-Torre-Among-The-Hills-Of-Siena.h123292187.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/5adc06ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/b1163ba5.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) ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/d02fb280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Capanna: A Window onto Tuscany [](https://www.expedia.ca/Siena-Hotels-Villa-Capanna-A-Window-Onto-Tuscany.h123292181.Hotel-Information) Vico dʼArbia CA $2,194 CA $2,354 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Siena-Hotels-Villa-Capanna-A-Window-Onto-Tuscany.h123292181.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/94000000/93700000/93697500/93697424/251b3fca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/94000000/93700000/93697500/93697424/613e9801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24 [](https://www.expedia.ca/Montalcino-Hotels-VILLA-BRUNELLO-Twelve-Bedroom-Villa.h93697424.Hotel-Information) Montalcino [](https://www.expedia.ca/Montalcino-Hotels-VILLA-BRUNELLO-Twelve-Bedroom-Villa.h93697424.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/c2fdac3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, internet](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/2513fe04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/bbe8b3b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/9be37908.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### VILLA CHIGI - Seven Bedroom Villa, Sleeps 14 [](https://www.expedia.ca/Buonconvento-Hotels-VILLA-CHIGI-Seven-Bedroom-Villa.h48711007.Hotel-Information) Siena [](https://www.expedia.ca/Buonconvento-Hotels-VILLA-CHIGI-Seven-Bedroom-Villa.h48711007.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/6112d62c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/23903394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/28509faf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/afb73a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-CHIANTIGAIO-Fourteen-Bedroom-Villa.h33066451.Hotel-Information) Gaiole in Chianti [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-CHIANTIGAIO-Fourteen-Bedroom-Villa.h33066451.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/6a82a5cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/f6eed317.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) ![Interior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/8099b959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Il Poggio dell'Eremita [](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information) Sinalunga 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 $229 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.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) ![Apartment | Living room](https://images.trvl-media.com/lodging/35000000/34190000/34180100/34180027/80c82a53.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) ![Apartment | Living room](https://images.trvl-media.com/lodging/35000000/34190000/34180100/34180027/12277fe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Antico Brunello [](https://www.expedia.ca/Montalcino-Hotels-Antico-Brunello.h34180027.Hotel-Information) Montalcino CA $10,671 CA $11,754 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Montalcino-Hotels-Antico-Brunello.h34180027.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) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27130000/27125200/27125149/6b4bd921.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/28000000/27130000/27125200/27125149/31ed4590.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) ### panoramica casa con piscina privata [](https://www.expedia.ca/Chiusdino-Hotels-Panoramica-Casa-Con-Piscina-Privata.h27125149.Hotel-Information) siena 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 $131 CA $241 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Chiusdino-Hotels-Panoramica-Casa-Con-Piscina-Privata.h27125149.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/4cf121c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/ceef78fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/645be43d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/19fa198c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36 [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-VILLA-ALTAMIRA-Eighteen-Bedroom-Villa.h122488659.Hotel-Information) Colle Val D'Elsa [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-VILLA-ALTAMIRA-Eighteen-Bedroom-Villa.h122488659.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/dd7d2145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/944b728f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, table tennis](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/1b501725.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Milani with Shared Pool, Private Terrace & Wi-Fi [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Milani-With-Shared-Pool.h78165677.Hotel-Information) Montespertoli 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 $2,474 CA $2,477 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Milani-With-Shared-Pool.h78165677.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/5d1ad91c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/c44dc7fb.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) ![Interior](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/03ae69bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 'La Petrosa' with Private Pool, Private Garden and Balcony [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Villa-La-Petrosa-With-Private-Pool.h99430681.Hotel-Information) Radda in Chianti 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 $1,814 CA $2,847 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Villa-La-Petrosa-With-Private-Pool.h99430681.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) ![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/111000000/110140000/110132300/110132299/360bcf7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/63f2ab21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Dei Pavoni - Luxury Villa on top of hills in Florence [](https://www.expedia.ca/Bagno-A-Ripoli-Hotels-Villa-Dei-Pavoni-Luxury-Villa-On-Top-Of-Hills-In-Florence.h110132299.Hotel-Information) Toscana 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 $2,881 CA $3,292 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Bagno-A-Ripoli-Hotels-Villa-Dei-Pavoni-Luxury-Villa-On-Top-Of-Hills-In-Florence.h110132299.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/122000000/121060000/121054000/121053909/fed1b3ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/122000000/121060000/121054000/121053909/f0b3cc4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121060000/121054000/121053909/03709886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/122000000/121060000/121054000/121053909/79895cbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi and Air Conditioning [](https://www.expedia.ca/Murlo-Hotels-Villa-La-Casa-Nel-Bosco-Antiche-Dimore-With-Shared-Pool.h121053909.Hotel-Information) Siena CA $239 CA $243 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Murlo-Hotels-Villa-La-Casa-Nel-Bosco-Antiche-Dimore-With-Shared-Pool.h121053909.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96140000/96139500/96139408/6d16baa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![8 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96140000/96139500/96139408/de29df70.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) ![Pool](https://images.trvl-media.com/lodging/97000000/96140000/96139500/96139408/80e6ed4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa "Arnilù" with Private Pool & Wi-Fi [](https://www.expedia.ca/San-Gimignano-Hotels-Villa-Arnilu-With-Private-Pool-Wi-Fi.h96139408.Hotel-Information) San Gimignano CA $7,508 CA $8,108 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) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/f2af4ebd.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/84000000/83210000/83207300/83207211/41d8a81a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/0e2eec35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/61b3ffc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Villa-Erbolino-With-Private-Garden.h83207211.Hotel-Information) Gaiole in Chianti 10/10 Exceptional (8) "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 $891 CA $929 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Villa-Erbolino-With-Private-Garden.h83207211.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/60af890d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/ba66cbc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/f89f6ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/b543a4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning [](https://www.expedia.ca/Rignano-SullArno-Hotels-Villa-Il-Frassine-With-Private-Pool.h99787239.Hotel-Information) Rignano sull'Arno 7.0/10 Good (2) "We arrived after dark, tired from long overnight flight. We had no water pressure upstairs and no hot water anywhere. This was corrected the next day. One on-suite toilette would not flush properly and leaked at the grinder motor. A "tech" was called in. He informed us that he could not fix it, they would need to call someone else. When we continued to report the issue to the host, she informed us that the "tech" said it was working OK. The "tech" informed us that it was not but he could not fix... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Norman C. CA $2,524 CA $3,418 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Rignano-SullArno-Hotels-Villa-Il-Frassine-With-Private-Pool.h99787239.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/c3424e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/368811a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/ecc6720f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/8b48796e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Viniard Villa - Residence Le Rose in Chianti [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Viniard-Villa-Residence-Le-Rose-In-Chianti.h123669271.Hotel-Information) Castellina in Chianti CA $517 CA $1,058 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Viniard-Villa-Residence-Le-Rose-In-Chianti.h123669271.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76770000/76763300/76763252/ae26ba3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76770000/76763300/76763252/12f2ed0c.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) ![TV, fireplace](https://images.trvl-media.com/lodging/77000000/76770000/76763300/76763252/7bc5c5f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi [](https://www.expedia.ca/Roccastrada-Hotels-Pet-Friendly-Finca-Olivos-With-Mountain-View.h76763252.Hotel-Information) Roccastrada GR CA $1,849 CA $1,955 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Roccastrada-Hotels-Pet-Friendly-Finca-Olivos-With-Mountain-View.h76763252.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/9937dca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![9 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/e3cae5da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/87c073f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!! [](https://www.expedia.ca/Montespertoli-Hotels-Luxury.h32584249.Hotel-Information) Montespertoli 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 $2,021 CA $2,315 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Montespertoli-Hotels-Luxury.h32584249.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=2025-12-28&endDate=2025-12-29®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 | 75 | | ----------------- | ---------- | | Accommodation | 87 Villas | | Lowest Price | CA $229 | | Highest Price | CA $11,754 | ## 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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