Portole Vacation Packages
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Your Portole Vacation
Lock in a Portole vacation package and get set to experience the best of this lively city. Think about staying in the neighborhood of Contrada Castello, which is great for dining, views and culture. Make your trip to Portole even more enjoyable by including some sightseeing. Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona are among the popular attractions worth exploring. Stop dreaming and start doing. Browse the wide range of options on Expedia today and put your Portole vacation plans into motion!
Top Portole Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Aurum Uffizi
Historic Centre of Florence
Price was CA $3,022, price is now CA $1,668 per person
CA $1,668
per person
May 22 - May 27
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
You have a lot of restaurants in a short walking distance. You have a famous sandwich shop you must try. Train station not too far. The hotel is very small. The staff is the best part
Reviewed on Apr 17, 2026
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
Price was CA $5,057, price is now CA $3,496 per person
CA $3,496
per person
Jun 5 - Jun 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
8.8/10 Excellent! (981 reviews)
The hotel was amazing. The location was fantastic for our short city break and the staff on reception could not have been more helpful. Our room was clean and the beds were so comfortable. We got great nights sleeps as it was so quiet. Would highly recommend.
Reviewed on Apr 19, 2026
Aurum Firenze
Historic Centre of Florence
Price was CA $2,525, price is now CA $1,749 per person
CA $1,749
per person
Jul 13 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Room was clean and the ac worked well. Large opening window to the street was nice. Great location to the train station and main attractions. Breakfast was poor. Very few items. Poor quality items and kept running out. Beautiful breakfast area - could easily be the best part of stay with a little effort.
Reviewed on Apr 20, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
Price was CA $2,918, price is now CA $2,054 per person
CA $2,054
per person
May 31 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (519 reviews)
Nice hotel close to the centre. Good breakfast and spa
Reviewed on Apr 18, 2026
L'Andana
Price was CA $3,783, price is now CA $2,668 per person
CA $2,668
per person
May 22 - May 27
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (86 reviews)
What an amazing place I hope to get back here next year again everybody was super nice. Property was super nice. It is quite relaxing. Great food apparently a great wine as well but I don’t drink. I highly recommend anybody to go.
Reviewed on Jul 5, 2025
Portole Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
The price is CA $992 per night from May 10 to May 11
CA $992
CA $1,104 total
May 10 - May 11
includes taxes & fees
9.8/10 Exceptional! (230 reviews)
This property is sublime. The details in the restoration, the history, the amenities all first class. The staff was amazing in making you feel comfortable and at home at the villa. Extremely peaceful.
Reviewed on Apr 19, 2026
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
The price is CA $546 per night from May 3 to May 4
CA $546
CA $611 total
May 3 - May 4
includes taxes & fees
9.4/10 Exceptional! (128 reviews)
Absolutely an amazing stay. Very charming and well kept. Essentially a resort with a palatial feel. Loved walking the grounds and relaxing. Excellent restaurant, breakfast was included. The setting is quiet and beautiful. Will book again.
Reviewed on Apr 13, 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
The price is CA $425 per night from Apr 29 to Apr 30
CA $425
CA $480 total
Apr 29 - Apr 30
includes taxes & fees
10/10 Exceptional! (265 reviews)
Heaven.
Reviewed on Apr 18, 2026
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.
What to do in Portole
Oil museum and oil mill in Tuscany: tour and tasting
CA $32
per adult
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
CA $193
per adult
98% of travellers recommend
Montepulciano Wine Tasting in the Tuscan Countryside
CA $41
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
