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Featured Deals
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Property OUTRIGGER Reef Waikiki Beach Resort
$150 OFF per booking. For travel through 12/15/26.
ME London
SAVE up to $400. For travel through 09/30/26.
Property View Grand Wailea Maui, A Waldorf Astoria Resort
$150 OFF per booking. For travel through 12/15/26.
Property Aston at Papakea Resort, Maui
$150 OFF per booking. For travel through 12/15/26
Caribbean Antigua AdobeStock Caribbean Exclusive
$300 OFF per booking on 5+ nights. For travel through 12/15/26.
InterContinental Osaka
Michelin-starred restaurant + SAVE up to $400. For travel through 09/30/26.
Outdoor Pool Phaea Cretan Malia, a member of Design Hotels
Daily breakfast + SAVE up to $400. For travel through 09/30/26.
Pool Ocean Key Resort, Key West
$50 resort credit + daily breakfast for two. Book by 02/09/26 for travel through 12/31/26.
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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.
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