Italy Vacation Deals

Once among the most powerful regions in the world, Italy is now one of its most charming.

From the ancient Roman Colosseum to the Renaissance art of Florence, the sparkling Amalfi coastline and romantic Venice Canals, Italy and its people have long celebrated la dolce vita, the sweet life. What could be sweeter than a romantic honeymoon or special holiday spent with loved ones amid the historic cities, extraordinary countryside and scenic lake districts of this beautiful country.

EXCLUSIVE $150 OFF Europe Vacations at Hilton

Book from 06/22/26 to 08/30/26, travel from 06/22/26 to 03/31/27

Interior of the the Pantheon, Rome, Italy
Interior of the the Pantheon, Rome, Italy
Filters
All Vacation Deals
Europe
Italy

Choose Your Italy Vacation Deals

We've found hotels for you based on your selection.
Book now
hotel icon
airplane icon
Anglo American Hotel Florence, Curio Collection by Hilton
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$150 OFF Europe Vacations at Hilton

map-full icon

Ognissanti

Book from 06/22/26 to 08/02/26, travel from 06/22/26 to 03/31/27

  • check-small icon

    EXCLUSIVE $150 OFF

Book this deal View hotel arrow-right icon
Main
Main
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Consecutive stays at multiple participating hotels apply toward room night minimum. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Hilton Lake Como
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$150 OFF Europe Vacations at Hilton

map-full icon

Como

Book from 06/22/26 to 08/02/26, travel from 06/22/26 to 03/31/27

  • check-small icon

    EXCLUSIVE $150 OFF

Book this deal View hotel arrow-right icon
Terrace
Terrace
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Consecutive stays at multiple participating hotels apply toward room night minimum. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Hilton Milan
star-full icon
star-full icon
star-full icon
star-half icon
star-empty icon

$150 OFF Europe Vacations at Hilton

map-full icon

Milan Central Station

Book from 06/22/26 to 08/02/26, travel from 06/22/26 to 03/31/27

  • check-small icon

    EXCLUSIVE $150 OFF

Book this deal View hotel arrow-right icon
Property
Property
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Consecutive stays at multiple participating hotels apply toward room night minimum. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Hilton Sorrento Palace
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$150 OFF Europe Vacations at Hilton

map-full icon

Sorrento

Book from 06/22/26 to 08/02/26, travel from 06/22/26 to 03/31/27

  • check-small icon

    EXCLUSIVE $150 OFF

Book this deal View hotel arrow-right icon
Property View
Property View
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Consecutive stays at multiple participating hotels apply toward room night minimum. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Palazzo Caracciolo Naples
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$150 OFF Europe Vacations at Hilton

map-full icon

Naples Historic Center

Book from 06/22/26 to 08/02/26, travel from 06/22/26 to 03/31/27

  • check-small icon

    EXCLUSIVE $150 OFF

Book this deal View hotel arrow-right icon
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Consecutive stays at multiple participating hotels apply toward room night minimum. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
De Bonart Naples, Curio Collection by Hilton
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

$150 OFF Europe Vacations at Hilton

map-full icon

Napoli/Capodichino, Italy

Book from 06/22/26 to 08/02/26, travel from 06/22/26 to 03/31/27

  • check-small icon

    EXCLUSIVE $150 OFF

Book this deal View hotel arrow-right icon
Exterior
Exterior
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Consecutive stays at multiple participating hotels apply toward room night minimum. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Cosmopolita Rome Colosseum, Tapestry Collection by Hilton
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$150 OFF Europe Vacations at Hilton

map-full icon

Roman Forum

Book from 06/22/26 to 08/02/26, travel from 06/22/26 to 03/31/27

  • check-small icon

    EXCLUSIVE $150 OFF

Book this deal View hotel arrow-right icon
Exterior
Exterior
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Consecutive stays at multiple participating hotels apply toward room night minimum. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
DoubleTree by Hilton Rome Monti
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$150 OFF Europe Vacations at Hilton

map-full icon

Rome Termini

Book from 06/22/26 to 08/02/26, travel from 06/22/26 to 03/31/27

  • check-small icon

    EXCLUSIVE $150 OFF

Book this deal View hotel arrow-right icon
Exterior
Exterior
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Consecutive stays at multiple participating hotels apply toward room night minimum. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Aleph Rome Hotel, Curio Collection by Hilton
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

$150 OFF Europe Vacations at Hilton

map-full icon

Via Veneto

Book from 06/22/26 to 08/02/26, travel from 06/22/26 to 03/31/27

  • check-small icon

    EXCLUSIVE $150 OFF

Book this deal View hotel arrow-right icon
Property
Property
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Consecutive stays at multiple participating hotels apply toward room night minimum. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Rome Cavalieri, Waldorf Astoria Hotels & Resorts
star-full icon
star-full icon
star-full icon
star-full icon
star-full icon

$150 OFF Europe Vacations at Hilton

map-full icon

Montemario

Book from 06/22/26 to 08/02/26, travel from 06/22/26 to 03/31/27

  • check-small icon

    EXCLUSIVE $150 OFF

Book this deal View hotel arrow-right icon
Property
Property
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Consecutive stays at multiple participating hotels apply toward room night minimum. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Spring House Hotel Rome Vatican, Tapestry Collection by Hilton
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$150 OFF Europe Vacations at Hilton

map-full icon

Vatican City

Book from 06/22/26 to 08/02/26, travel from 06/22/26 to 03/31/27

  • check-small icon

    EXCLUSIVE $150 OFF

Book this deal View hotel arrow-right icon
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Consecutive stays at multiple participating hotels apply toward room night minimum. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Hilton Rome Airport Hotel
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$150 OFF Europe Vacations at Hilton

map-full icon

Rome Leonardo da Vinci, Italy

Book from 06/22/26 to 08/02/26, travel from 06/22/26 to 03/31/27

  • check-small icon

    EXCLUSIVE $150 OFF

Book this deal View hotel arrow-right icon
Property
Property
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Consecutive stays at multiple participating hotels apply toward room night minimum. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.

You will be transferred to our traditional site.

We are currently working on enhancements to this part of our website. A new version will be available soon. Don’t worry – switching over will not interrupt your booking.

Welcome to the all-new Pleasant Holidays booking experience !

You can now plan your next vacation with our exciting new booking engine. Some advanced features are still being developed, and selecting these options may require you to return to our traditional booking experience. Don’t worry – switching over will not interrupt your booking.

We've updated your online experience to make sure you can get your dream vacation. Since our makeover is still in progress, you may experience shifts from our traditional booking experience to our new one.

Are you a travel agent ? We are also working on a new digital experience specifically for travel professionals and we can’t wait for you to see it. Until then, please continue to use the traditional experience here: Pleasantagent.com.

You are a travel agent? Go to Pleasantagent.com. and enjoy the optimized experience for travel professionals.

support icon

Contact us

support icon

Any questions ?

Our travel advisors will be happy to help!

Call 1-800-742-9244
email icon
net.support@pleasant.net

Copied!
info icon

Are you sure you want to
delete this file?

Once deleted, you’ll need to
upload a new agreement form.