Title: Book the Best Hotels with POOL in Cortona in 2026 | 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) # Find Hotels with a Pool in Cortona - ![](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 availability on Cortona Hotels with a Pool Tonight [Dec 1 - Dec 2](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2025-12-01&endDate=2025-12-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 2 - Dec 3](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2025-12-02&endDate=2025-12-03&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2025-12-05&endDate=2025-12-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cortona Hotels with a Pool ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690302/5ae043c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690302/7ab23519.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690302/ae059bf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690302/db9065b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Locanda del Molino Cortona 9.6/10 Exceptional (33) "Great place to stay." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Christopher CA $118 CA $143 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Cortona-Hotels-Locanda-Del-Molino.h2690302.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/45000000/44720000/44719300/44719208/d29f2d69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Espresso maker, coffee/tea maker, highchair, toaster oven](https://images.trvl-media.com/lodging/45000000/44720000/44719300/44719208/001d410e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/45000000/44720000/44719300/44719208/8ed87f17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/45000000/44720000/44719300/44719208/18b7177f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country House Podere Casorbica Cortona 10/10 Exceptional (1) "Great place. Beautiful area " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristie [](https://www.expedia.ca/Cortona-Hotels-Country-House-Podere-Casorbica.h44719208.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/91000000/90310000/90300600/90300548/9905347b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/91000000/90310000/90300600/90300548/5a958be8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Camera Deluxe vista valle](https://images.trvl-media.com/lodging/91000000/90310000/90300600/90300548/49af1003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/91000000/90310000/90300600/90300548/1d2957ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Locanda agli Amici Cortona 9.8/10 Exceptional (34) "Amazing breakfast and first class service. Host was very attentive to details, the property is beautiful. Location is great, walking distance to a working monastery and to the town of Cortona. A peaceful spot and very safe. Beds were comfortable and the room was well appointed." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Tara [](https://www.expedia.ca/Cortona-Hotels-Locanda-Agli-Amici.h90300548.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/101000000/100780000/100776500/100776429/55c67d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, Patio](https://images.trvl-media.com/lodging/101000000/100780000/100776500/100776429/15fd01c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100780000/100776500/100776429/3fa1a54f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/101000000/100780000/100776500/100776429/5c55daf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cortona Resort Spa Cortona 7.0/10 Good (2) "Needs lotion in the guest rooms and towels. The staff was wonderful. So was the food. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Candice CA $246 CA $276 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Cortona-Hotels-Cortona-Resort-Spa.h100776429.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/1000000/920000/915500/915401/fc8cca77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/920000/915500/915401/6590bf1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/1000000/920000/915500/915401/19ce9ce1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Suite](https://images.trvl-media.com/lodging/1000000/920000/915500/915401/475d9752.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais La Corte dei Papi Cortona 9.6/10 Exceptional (64) "Beautiful with an amazing restaurant. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Frithjof CA $371 CA $421 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Cortona-Hotels-Relais-La-Corte-Dei-Papi.h915401.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/14000000/13420000/13416600/13416580/b9880d35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Villa, 2 Bedrooms](https://images.trvl-media.com/lodging/14000000/13420000/13416600/13416580/ef958304.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/14000000/13420000/13416600/13416580/ddfa0258.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/14000000/13420000/13416600/13416580/a14c9852.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo Villa Augusto Cortona 9.6/10 Exceptional (4) "Augusto was a great host. We appreciated the recommendations of local attractions in the area. The deluxe villa was very clean, quiet, and nicely decorated. We really enjoyed the garden that is on the property. By far our best stay in Tuscany." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristian CA $206 CA $235 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Cortona-Hotels-Agriturismo-Villa-Augusto.h13416580.Hotel-Information) ![Sauna, hot tub, steam room, massages](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/cea3a0e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/025dd887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/b2055c17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/0411b3d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monastero di Cortona Hotel & Spa Cortona Old Town 10/10 Exceptional (254) "Excellent hotel Staff very knowledgeable and friendly Loved everything about our stay and will return. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Florence and Robert CA $413 CA $468 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Cortona-Hotels-Monastero-Di-Cortona-Hotel-Spa.h23264410.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/90000000/89140000/89137900/89137842/9f5e957a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89140000/89137900/89137842/abf9035c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89140000/89137900/89137842/cf46db9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89140000/89137900/89137842/fce45a9b_edited_7837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi Cortona 9.0/10 Wonderful (2) "Pros: Il camino è stato come tornare bambini.Atmosfera Natalizia e tanto di più. Cons: Il Bidè non funzionava." ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Anonymous traveller [](https://www.expedia.ca/Cortona-Hotels-Apartment-La-Vecchia-Fornace-La-Casina-With-Shared-Pool-Wi-Fi.h89137842.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/40000000/39140000/39138300/39138214/67fbceef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39140000/39138300/39138214/17368504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39140000/39138300/39138214/144c6347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39140000/39138300/39138214/a4f15486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34 Cortona CA $8,681 CA $8,681 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Cortona-Hotels-VILLA-CORTONESE-Fifteen-Bedroom-Resort.h39138214.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/90000000/89730000/89722500/89722442/3cc98a7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/90000000/89730000/89722500/89722442/72547092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89730000/89722500/89722442/899cfb48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89730000/89722500/89722442/476340ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo 'Cuiano La Loggetta' with Shared Pool, Garden and Wi-Fi Cortona 10/10 Exceptional (1) "Lieu très agréable en pleine nature,en retrait des grandes villes" ![France](https://a.travel-assets.com/egds/marks/flags/fr.svg) Jacques N. CA $292 CA $300 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Cortona-Hotels-Farmhouse-Agriturismo-Cuiano-La-Loggetta-With-Shared-Pool.h89722442.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=2025-12-15&endDate=2025-12-16®ionId=601360&adults=2&amenities=POOL&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=AFFINITY_BF_PROMO_601360) ## Top Cortona Hotel Reviews ![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) ![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) ![Relais Villa Baldelli](https://images.trvl-media.com/lodging/1000000/930000/921400/921392/971bb732_y.jpg) ### Relais Villa Baldelli 10/10 Excellent "Beautiful place. Fantastic staff and breakfast. Close to Corrona, Assisi Arezzo. And a great cooking class. You will be glad you stayed here. " [](https://expedia.ca/Cortona-Hotels-Relais-Villa-Baldelli.h921392.Hotel-Information) ![Locanda del Molino](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690302/5ae043c7_y.jpg) ### Locanda del Molino 10/10 Excellent "Great place to stay." [](https://expedia.ca/Cortona-Hotels-Locanda-Del-Molino.h2690302.Hotel-Information) ## Frequently asked questions ### What's it like visiting Cortona? > If spending time by the pool is your idea of the perfect getaway, you may want to check out Cortona, which has 54 places to stay with pools. While you're visiting, you can explore sights such as Piazza della Repubblica and Giuseppe Garibaldi Memorial, and then relax poolside at one of the accommodations in Cortona that guests like for their pools. ### What are some accommodations with pools in Cortona? > [Monastero di Cortona Hotel & Spa](https://www.expedia.ca/Cortona-Hotels-Monastero-Di-Cortona-Hotel-Spa.h23264410.Hotel-Information): Features a full-service spa, an indoor pool, and a sauna. [Locanda del Molino](https://www.expedia.ca/Cortona-Hotels-Locanda-Del-Molino.h2690302.Hotel-Information): Offers a snack bar/deli, a seasonal outdoor pool, and daily. [Beautiful Tuscan farmhouse in the countryside with swimming pool](https://www.expedia.ca/Cortona-Hotels-Beautiful-Tuscan-Farmhouse-In-The-Countryside-With-Swimming-Pool.h32393078.Hotel-Information): Provides sun loungers, a pool, and kitchens. [Rustic Farmhouse for 8+2 person with Private Swimming Pool](https://www.expedia.ca/Cortona-Hotels-Rustic-Farmhouse-For-10-Person-With-Private-Swimming-Pool.h39406475.Hotel-Information): Features sun loungers, a pool, and complimentary wireless internet access. [VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34](https://www.expedia.ca/Cortona-Hotels-VILLA-CORTONESE-Fifteen-Bedroom-Resort.h39138214.Hotel-Information): Offers kitchens, a communal pool, and televisions. ### How many pool hotels will I find in Cortona? > Expedia's 54 hotels in Cortona give you a great choice for your poolside getaway. ### What is there to see and do in Cortona? > Spend some time experiencing the great outdoors at Val di Chiana. During your stay, check out sights such as Piazza della Repubblica, Giuseppe Garibaldi Memorial, and Villa Bramasole. ### When is the best time to book a hotel with a pool in Cortona? > You may want to think about a place to stay that has an outdoor pool if you plan to visit Cortona in the warmest months of August, July, or June when the average temp is 71°F. Lodging offering an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temperature is 42°F. ### What's the best way to travel around Cortona? > Knowing the transportation options in Cortona can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, hop aboard a train at Camucia-Cortona Station or Terontola-Cortona Station. 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