Title: Cortona Vacation Home Rentals : Search Top Private Vacation Homes for Rent | Expedia.ca [Cortona Travel Guide](https://expedia.ca/Cortona.dx601360)[Hotels in Cortona](https://expedia.ca/Cortona-Hotels.d601360.Travel-Guide-Hotels)[Vacation Rentals in Cortona](https://expedia.ca/Cortona-Vacation-Rentals.d601360.Travel-Guide-VacationRentals)[Flights to Cortona](https://expedia.ca/Cheap-Flights-To-Cortona.d601360.Travel-Guide-Flights)[Things to do in Cortona](https://expedia.ca/Things-To-Do-In-Cortona.d601360.Travel-Guide-Activities)[Cortona Car Rentals](https://expedia.ca/Car-Rentals-In-Cortona.d601360.Car-Rental-Guide)[Cortona Vacation Packages](https://expedia.ca/Cortona.d601360.Destination-Travel-Guides) ![Cortona showing a city and farmland](https://images.trvl-media.com/place/601360/f4054673-52dd-4f97-8d57-389d1f349940.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cortona Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Cortona Vacation Homes ![Property grounds](https://images.trvl-media.com/lodging/93000000/92360000/92355700/92355622/0248fcc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92360000/92355700/92355622/20f3f653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92360000/92355700/92355622/35d33457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92360000/92355700/92355622/63933730.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cortona CA $114 CA $149 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Cortona-Hotels-Holiday-Home-With-Panoramic-Terrace-Ideal-For-Families-And-Couples.h92355622.Hotel-Information) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/40000000/39960000/39951800/39951786/0cf49d44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39960000/39951800/39951786/ae9cfe4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/40000000/39960000/39951800/39951786/dd03f600.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39960000/39951800/39951786/9baf88ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Fratticciola 10/10 Exceptional (1) "Host was extremely welcoming. Met us when we arrived and explained usage of all the amenities, including the clothes washer. Cottage was quintessential Rural Italian home. The hostess even provided us with some local wine and homemade biscotti. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy F. CA $146 CA $175 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Cortona-Hotels-House-In-The-Cortona-Countryside.h39951786.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/33000000/32640000/32632000/32631932/4c9dc305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32640000/32632000/32631932/ea734e62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, dishwasher, cookware/dishes/utensils](https://images.trvl-media.com/lodging/33000000/32640000/32632000/32631932/90-47ebfe31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, dishwasher, cookware/dishes/utensils](https://images.trvl-media.com/lodging/33000000/32640000/32632000/32631932/90-1ae59b4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Montecchio 9.0/10 Wonderful (2) "Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..." ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Monica S. CA $97 CA $127 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Cortona-Hotels-Montecchio-Di-Cortona.h32631932.Hotel-Information) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/90000000/89140000/89137900/89137839/e6444fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89140000/89137900/89137839/c583fb1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89140000/89137900/89137839/a1ed5b88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89140000/89137900/89137839/96faa0f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cortona 8.0/10 Very good (1) "Pros: Authentiek Toscaanse boerderij ( wij hadden de bovenste etage) met prachtige tuin en lekker zwembad met mooi uitzicht. De gastheer Angelo was top en de Toscaanse diners waren onvergetelijk. Bedankt dat ik mijn verjaardag zo heb mogen vieren. Hele mooie herinnering. Pizza’s bakken was ook een feest. Ook heel fijn dat er een airco was. Onze 4 puber jongens hebben zich prima vermaakt en leuk dat er nog andere gasten zijn uit andere appartementen die je dan ziet op hetToscaanse diner. Top... ![Netherlands](https://a.travel-assets.com/egds/marks/flags/nl.svg) Anonymous traveller CA $178 CA $185 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Cortona-Hotels-Apartment-La-Vecchia-Fornace-La-Terrazza-With-Shared-Pool-Wi-Fi.h89137839.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/69000000/68050000/68050000/68049942/3d55d541.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68050000/68050000/68049942/6a211ee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68050000/68050000/68049942/11c868e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68050000/68050000/68049942/27c749dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Toscana 9.0/10 Wonderful (2) "Perfectly located in the center of the Heart of Tuscany. Great property with a clean and spacious interior. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa C. CA $8,117 CA $9,109 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Trequanda-Hotels-Villa-Falco-Cignella-Resort-Tuscany.h68049942.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/19000000/18980000/18976700/18976608/f746b6f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18976700/18976608/e9d49b89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books](https://images.trvl-media.com/lodging/19000000/18980000/18976700/18976608/fc018cfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books](https://images.trvl-media.com/lodging/19000000/18980000/18976700/18976608/ddcd9ce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in CASTIGLIONE D'ORCIA 9.4/10 Exceptional (9) "Stayed here during the Tuscany Trail and was perfect for 4 of us. Centre of town and a great restaurant recommendation too! " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Graham S. CA $234 CA $278 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Castiglione-DOrcia-Hotels-Independent-House-In-The-Historic-Center.h18976608.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/b5d9a4b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/ad4e5fad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/40000000/39870000/39866200/39866124/7ed60a74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Vacation Home in Trequanda, Siena "Gemischt.Sehr gut: Zentrale Lage, viele Ausflugsmöglichkeiten (Siena, Cortona, Arezzo Pienza). Gepflegt, schöner Pool. Antonio ist die gute Seele des Hauses, freundlich, hilfsbereit und scheinbar immer fröhlich.Gut: Ausstattung des Hauses (wir haben im kleineren Poggiolino) gewohnt.Nicht gut: Zentrale Lage, direkt an einer wichtigen Regionalstraße. Also Ruhe in den Hügeln der Toskana hatten wir uns anders vorgestellt... Und:Im Schlafzimmer (UG) war es sehr warm (bei hohen Außentemperaturen).... ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Heike K. CA $132 CA $279 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Trequanda-Hotels-Romantic-Farm-In-The-Sienese-Hills.h39866124.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/20000000/19990000/19986400/19986371/373c757f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/20000000/19990000/19986400/19986371/35c81468.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19990000/19986400/19986371/934c21df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/20000000/19990000/19986400/19986371/05f902c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Castiglione del Lago 8.0/10 Very good (4) "El hotel no alcanzó el agua caliente y no se pudo bañar parte de la familia no contaba con suficientes amenidades " ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) RAUL [](https://www.expedia.ca/Castiglione-Del-Lago-Hotels-Poggio-Del-Sole.h19986371.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/85000000/84520000/84515400/84515383/6a2b762c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/85000000/84520000/84515400/84515383/f6f7b43b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/85000000/84520000/84515400/84515383/905084fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/85000000/84520000/84515400/84515383/bfe877c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in CHIANCIANO 10/10 Exceptional (3) "Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rob C. CA $351 CA $477 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Chianciano-Terme-Hotels-MONTEPULCIANO-A-DUE-PASSI-DALLA-VAL-DORCIA.h84515383.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119030000/119022000/119021969/c72cccfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Loft, Garden View | Living area](https://images.trvl-media.com/lodging/120000000/119030000/119022000/119021969/dc731c17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119030000/119022000/119021969/47a931e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Loft, Garden View | Terrace/patio](https://images.trvl-media.com/lodging/120000000/119030000/119022000/119021969/debc9a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Casamaggiore CA $110 CA $121 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Castiglione-Del-Lago-Hotels-Casa-Di-Cristina.h119021969.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92020000/92018400/92018366/0459e4ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92020000/92018400/92018366/e00d1488.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92020000/92018400/92018366/d8fc72da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92020000/92018400/92018366/8c44b07b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Arezzo CA $132 CA $180 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Arezzo-Hotels-Dolce-Casa-2-Summary.h92018366.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/98000000/97080000/97072500/97072488/5e0bf0da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97080000/97072500/97072488/90daa8d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/98000000/97080000/97072500/97072488/65910cba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/98000000/97080000/97072500/97072488/7812a5c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Castel Rigone 10/10 Exceptional (3) "The only thing this place could have that it doesn't is an infinity pool! We loved it here. It was a last minute booking and the host was super helpful. STUNNING views from the patio, and the lake is a short drive down the hill. Also, a very cool little town with restaurants just a two minute drive.Our favorite stays in Italy we're in these little remote towns. Soooo nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adam H. CA $143 CA $179 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Passignano-Sul-Trasimeno-Hotels-Vrbo-Property.h97072488.Hotel-Information) ![TV, DVD player](https://images.trvl-media.com/lodging/69000000/68060000/68051700/68051629/fc2934d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/69000000/68060000/68051700/68051629/501031f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68060000/68051700/68051629/269ff2c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68060000/68051700/68051629/28d9ff3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Toscana CA $8,117 CA $9,109 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Trequanda-Hotels-Vrbo-Property.h68051629.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/103000000/102660000/102651200/102651128/68e32b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/103000000/102660000/102651200/102651128/d2961175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![10 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102660000/102651200/102651128/c265586f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102660000/102651200/102651128/c7047ee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in perugia 10/10 Exceptional (1) "Pros: Great hosts, who were super helpful and responsive. Beautiful house and gardens. Cons: Nothing - it was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $3,761 CA $4,009 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Perugia-Hotels-Holiday-Home-Palazzetto-Bovini-With-Wi-Fi-And-Private-Pool.h102651128.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/8477e2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/9ee300f7.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/37000000/36370000/36364900/36364803/5d93306f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/a8b308d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Monticchiello 10/10 Exceptional (8) "An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! " ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Dan CA $154 CA $187 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Pienza-Hotels-Il-Focolare-Superior-Apartment-In-Monticchiello.h36364803.Hotel-Information) ![Comfort Apartment, 3 Bedrooms | View from property](https://images.trvl-media.com/lodging/110000000/109340000/109332900/109332831/13a35e4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Apartment, 3 Bedrooms | Pool](https://images.trvl-media.com/lodging/110000000/109340000/109332900/109332831/ca9a6ada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Apartment, 3 Bedrooms | Reception](https://images.trvl-media.com/lodging/110000000/109340000/109332900/109332831/c0f945f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Apartment, 3 Bedrooms | Exterior](https://images.trvl-media.com/lodging/110000000/109340000/109332900/109332831/97c318ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Città di Castello CA $406 CA $447 total includes taxes & fees Nov 28 - Nov 29 [](https://www.expedia.ca/Citta-Di-Castello-Hotels-Rustic-Holiday-Home-In-Citta-Di-Castello-With-Swimming-Pool.h109332831.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/107000000/106820000/106819800/106819737/313fd19a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/107000000/106820000/106819800/106819737/22bd898a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/107000000/106820000/106819800/106819737/78a1bea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106820000/106819800/106819737/65902230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Asciano 10/10 Exceptional (1) "Une très belle location dans l'environnement magique de la campagne toscane, Paolo est très accueillant , seul bémol la proximité de la route." ![France](https://a.travel-assets.com/egds/marks/flags/fr.svg) Joël P. CA $244 CA $263 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Asciano-Hotels-Vrbo-Property.h106819737.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/92000000/91790000/91782300/91782207/2e5fc023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/92000000/91790000/91782300/91782207/3d8fec8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91790000/91782300/91782207/708c8021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91790000/91782300/91782207/3bc34b88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in montalcino CA $244 CA $547 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/Montalcino-Hotels-Agritourism-In-Val-Dorcia.h91782207.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105090000/105089100/105089096/246e837e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/106000000/105090000/105089100/105089096/648e852d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Books, computer monitors](https://images.trvl-media.com/lodging/106000000/105090000/105089100/105089096/2f33fa1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/106000000/105090000/105089100/105089096/e8606c7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Buonconvento CA $117 CA $218 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Buonconvento-Hotels-Vrbo-Property.h105089096.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92320000/92310500/92310484/b3cec1c8.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) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92320000/92310500/92310484/w1168h870x1y0-a0f6f633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92320000/92310500/92310484/548b6835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Sinalunga CA $195 CA $304 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Sinalunga-Hotels-The-Little-Magicians-Secret-Corner.h92310484.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=2025-12-06&endDate=2025-12-07®ionId=601360&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_601360) ![](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%2FCortona-Private-Vacation-Homes.d601360-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCortona-Private-Vacation-Homes.d601360-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Cortona Hotel Reviews ![Hotel Villa Marsili](https://images.trvl-media.com/lodging/1000000/930000/922700/922648/c5455b25_y.jpg) ### Hotel Villa Marsili 10/10 Excellent "Most comfortable room and bed beds that we stayed in the whole time we were in Italy! Also, the breakfast was 10 out of 10! Much better than the five star hotel that we stayed at in Rome and Florence. " [](https://expedia.ca/Cortona-Hotels-Hotel-Villa-Marsili.h922648.Hotel-Information) ![Hotel Italia](https://images.trvl-media.com/lodging/2000000/1670000/1664000/1663916/22c9fd1e_y.jpg) ### Hotel Italia 10/10 Excellent "The personnel were warm and accommodating. The breakfast was amazing! The views were wonderful!" [](https://expedia.ca/Cortona-Hotels-Hotel-Italia.h1663916.Hotel-Information) ![Villa di Piazzano - Small Luxury Hotel of the World](https://images.trvl-media.com/lodging/1000000/980000/972000/971985/473f66a9_y.jpg) ### Villa di Piazzano - Small Luxury Hotel of the World 10/10 Excellent "Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly " [](https://expedia.ca/Cortona-Hotels-Villa-Di-Piazzano-Small-Luxury-Hotel-Of-The-World.h971985.Hotel-Information) ![Monastero di Cortona Hotel & Spa](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/cea3a0e9_y.jpg) ### Monastero di Cortona Hotel & Spa 10/10 Excellent "What a unique place. Near the top of the hill. Staff service and amenities were all great. Not an easy place to drive to. The taxis drive-in backwards the last eighth of a mile." [](https://expedia.ca/Cortona-Hotels-Monastero-Di-Cortona-Hotel-Spa.h23264410.Hotel-Information) ![Il Falconiere - Relais e Chateaux](https://images.trvl-media.com/lodging/1000000/530000/528500/528472/2334a48c_y.jpg) ### Il Falconiere - Relais e Chateaux 10/10 Excellent "What an incredible stay at Il Falconiere! Exceptional service and unforgettable experiences — from Silvia Baracchi’s amazing cooking class to an unbelievable dinner at the Michelin-starred restaurant. Breakfast in the glass room overlooking the Tuscan hills was pure magic. We loved wandering through Cortona — charming streets, fantastic restaurants, and surprisingly great shopping. Already dreaming of our next visit! " [](https://expedia.ca/Cortona-Hotels-Relais-Il-Falconiere.h528472.Hotel-Information) ![B&B Piccolo Hotel](https://images.trvl-media.com/lodging/13000000/12240000/12234700/12234603/ab339a34_y.jpg) ### B&B Piccolo Hotel 10/10 Excellent "We were able to drive up to the door and leave our car with staff. Staff was amazing. Breakfast had many options and always replenished. It is right off the main piazza. Would stay again for sure!" [](https://expedia.ca/Cortona-Hotels-BB-Piccolo-Hotel.h12234603.Hotel-Information) ![Hotel San Luca](https://images.trvl-media.com/lodging/3000000/2700000/2691400/2691302/5cf5bba0_y.jpg) ### Hotel San Luca 10/10 Excellent "great view, very clean, friendly staff" [](https://expedia.ca/Cortona-Hotels-Hotel-San-Luca.h2691302.Hotel-Information) ![Locanda agli Amici](https://images.trvl-media.com/lodging/91000000/90310000/90300600/90300548/5a958be8_y.jpg) ### Locanda agli Amici 10/10 Excellent "Very clean and beautiful room. Amazing views! Breakfast and staff were the best!" [](https://expedia.ca/Cortona-Hotels-Locanda-Agli-Amici.h90300548.Hotel-Information) ![Luxury Cortona view hilltop Villa](https://images.trvl-media.com/lodging/29000000/28850000/28840500/28840420/73d0cc6c_y.jpg) ### Luxury Cortona view hilltop Villa 10/10 Excellent "Beautiful villa of your dreams on a hillside near Cortona. Everything was exactly as described and the villa is very large. We had 4 couples each in the 4 master bedrooms which are huge and very nicely separated. Be aware the road up to the villa is very challenging! This is not walking distance or walkable to anything but within 10-15 minutes to Cortona. Not a problem for us at all. Very quiet, very beautiful, fantastic location to explore Tuscany and Umbria. Very large kitchen! We had the team there prepare us all a dinner one night and it was one of our favorite meals of the entire trip." [](https://expedia.ca/Cortona-Hotels-Luxury-Cortona-View-Hilltop-Villa.h28840420.Hotel-Information) ## Find out more about Cortona ## Cortona Vacation Homes information | Number of reviews | | | --- | --- | | Accommodation | Vacation Homes | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Acquaviva Hotels](https://www.expedia.ca/Acquaviva-Hotels.d6047638.Travel-Guide-Hotels) - [Farmstay in Arezzo](https://www.expedia.ca/Arezzo-Agritourism.d11306-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Arezzo](https://www.expedia.ca/Arezzo-Apart-Hotels.d11306-aaApartHotels.Travel-Guide-Accommodation) - [Apartments in Arezzo](https://www.expedia.ca/Arezzo-Apartments.d11306-aaApartments.Travel-Guide-Accommodation) - [B&B in Arezzo](https://www.expedia.ca/Arezzo-Bed-And-Breakfast.d11306-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Castles in Arezzo](https://www.expedia.ca/Arezzo-Castles.d11306-aaCastles.Travel-Guide-Accommodation) - 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