Title: Ossaia Vacation Packages & Trips 2026 from CA $1,998 | Expedia.ca [Ossaia Travel Guide](https://expedia.ca/Ossaia.dx6361235)[Hotels in Ossaia](https://expedia.ca/Ossaia-Hotels.d6361235.Travel-Guide-Hotels)[Vacation Rentals in Ossaia](https://expedia.ca/Ossaia-Vacation-Rentals.d6361235.Travel-Guide-VacationRentals)[Ossaia Car Rentals](https://expedia.ca/Car-Rentals-In-Ossaia.d6361235.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Ossaia Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your Ossaia Vacation Say farewell to the stress of planning and hello to a Ossaia vacation package. With the finer details organized before you go, you can focus on discovering this city, starting with Contrada Castello, which is good for dining, views and culture. A trip to Ossaia is a great opportunity to take in the sights. Check out well-known attractions like [Villa Bramasole](https://www.expedia.ca/Villa-Bramasole-Cortona.d553248635931712561.Vacation-Attraction), [Piazza della Repubblica](https://www.expedia.ca/Piazza-Della-Repubblica-Cortona-Old-Town.d6102854.Vacation-Attraction) and [Cathedral of Cortona](https://www.expedia.ca/Cathedral-Of-Cortona-Cortona-Old-Town.d6102846.Vacation-Attraction). Expedia has what you need to escape your routine. Tailor your vacation to Ossaia to suit your travel style, whatever that may be! ## Top Ossaia Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Hotel Duomo Firenze](https://images.trvl-media.com/lodging/3000000/2550000/2541700/2541603/89ed1f8e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Duomo Firenze Historic Centre of Florence CA $1,998 per person May 11 - May 16 found 1 day ago Roundtrip flight included Toronto (YYZ) to Florence (FLR) 9.2/10 Wonderful! (1,002 reviews) The hotel is so central any long walk can be accompanied by an afternoon trip back to the hotel. The staff are lovely and genuinely helpful and welcoming. Small family hotel with a big heart. Reviewed on Mar 30, 2026 ![Villa Cora](https://images.trvl-media.com/lodging/1000000/30000/22600/22579/01d144a6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Villa Cora Oltrarno CA $5,092 per person May 13 - May 19 found 13 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Florence (FLR) 9.8/10 Exceptional! (472 reviews) Amazing service and staff. Wow! Reviewed on Feb 21, 2026 ![The Moon Boutique Hotel & Spa](https://images.trvl-media.com/lodging/23000000/22260000/22255000/22254976/a69619e4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Moon Boutique Hotel & Spa Historic Centre of Florence CA $2,542 per person May 6 - May 11 found 3 hours ago Roundtrip flight included Ottawa (YOW) to Florence (FLR) 9.6/10 Exceptional! (512 reviews) Very nice - modern and clean hotel with great breakfast and very helpful staff. just outside the hotel there is a tram line and mini bus stand to commute the different parts of town. The only negative part was smaller room size but all other positive features of the hotel and staff overcomes this minor deficiency. Reviewed on Mar 30, 2026 ![Eurostars Florence Boutique](https://images.trvl-media.com/lodging/2000000/1170000/1167000/1166901/88283612_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars Florence Boutique Historic Centre of Florence CA $2,484 per person May 13 - May 19 found 13 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Florence (FLR) 8.6/10 Excellent! (483 reviews) The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants. Reviewed on Dec 13, 2025 ![Bernini Palace](https://images.trvl-media.com/lodging/1000000/20000/14000/13999/c71352fb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bernini Palace Historic Centre of Florence CA $4,166 per person Jun 24 - Jun 29 found 1 day ago Roundtrip flight included Ottawa (YOW) to Florence (FLR) 9.8/10 Exceptional! (1,010 reviews) The location and staff were great. Highly recommend. Reviewed on Mar 29, 2026 ## Ready to book your vacation to Ossaia? Choose your dates ## Ossaia Hotel Deals ![Villa di Piazzano - Small Luxury Hotel of the World](https://images.trvl-media.com/lodging/1000000/980000/972000/971985/c358cc6c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Villa di Piazzano - Small Luxury Hotel of the World Localita Piazzano, C.P. 6 Cortona AR CA $812 CA $906 total Apr 17 - Apr 18 includes taxes & fees 9.8/10 Exceptional! (228 reviews) Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly Reviewed on Nov 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=17%2F04%2F2026&endDate=18%2F04%2F2026&selected=971985&PinnedHotelID=971985&HadPinnedHotel=true®ionId=6361235) ![Monastero di Cortona Hotel & Spa](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/b2055c17_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Monastero di Cortona Hotel & Spa Via del Salvatore Cortona AR Fully refundableReserve now, pay when you stay CA $488 CA $549 total Apr 19 - Apr 20 includes taxes & fees [](https://expedia.ca/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=23264410&PinnedHotelID=23264410&HadPinnedHotel=true®ionId=6361235) ![Hotel Minerva](https://images.trvl-media.com/lodging/2000000/1190000/1183500/1183404/27963802_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Minerva Via Fiorentina, 4 Arezzo AR Fully refundableReserve now, pay when you stay CA $127 CA $149 total Apr 19 - Apr 20 includes taxes & fees 8.8/10 Excellent! (566 reviews) Great hitel with free parking,staff very helpful and clean rooms. Goodselection at breakfast. Reviewed on Mar 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=1183404&PinnedHotelID=1183404&HadPinnedHotel=true®ionId=6361235) [See all 5,099 properties in Ossaia](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=01%2F04%2F2026&endDate=02%2F04%2F2026®ionId=6361235) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### What to do in Ossaia ![3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch](https://mediaim.expedia.com/localexpert/47282553/e14b5a73-0ff4-428f-a567-234540a94e59.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch CA $124 per adult **98%** of travellers recommend [](https://expedia.ca/things-to-do/from-rome-bagnoregio-orvieto-day-trip-with-tuscany-wine-tasting-lunch.a47282553.activity-details) ![Oil museum and oil mill in Tuscany: tour and tasting](https://mediaim.expedia.com/localexpert/47137603/cba72fc6-87d4-4e36-971f-bc6dc0d28c6e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Oil museum and oil mill in Tuscany: tour and tasting CA $31 per adult [](https://expedia.ca/things-to-do/oil-museum-and-oil-mill-in-tuscany-tour-and-tasting.a47137603.activity-details) ![Montepulciano Wine Tasting in the Tuscan Countryside](https://mediaim.expedia.com/localexpert/50286653/77c79a76-70f1-4375-9739-0f0f71d7da02.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Montepulciano Wine Tasting in the Tuscan Countryside CA $39 per adult [](https://expedia.ca/things-to-do/montepulciano-wine-tasting-in-the-tuscan-countryside.a50286653.activity-details) [See all activities in Ossaia](https://expedia.ca/things-to-do/search?rid=6361235) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app