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Portland Early Booking Deals

Best Vacations from Portland

Vacation Deals to Amazing Resorts

Portland, if you like to plan ahead with an early bird deal, look no further! You'll find the perfect hotel stay in the Caribbean, Mexico and Central America below. Want to make it a package with air included? Pick your ideal dates and shop using our booking box on this page.

CANCUN  ▪  RIVIERA MAYA  ▪  PUNTA CANA  ▪  JAMAICA  ▪  LOS CABOS  ▪  PUERTO VALLARTA  ▪  COSTA RICA  ▪  ANTIGUA

Punta Cana

  • Save Up to 35%

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$119*: 5/1-7/31

$199*: Now-4/30

Costa Rica

  • 4th Night Free††

BREAKFAST PLAN RESORT STAYS

Per Night From:

$125*: Now-6/30

$145*: 7/1-7/31

Riviera Maya

  • Up to $1460 in Resort Coupons††

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$155*: 5/1-7/31

$189*: Now-4/30

Puerto Vallarta

  • Up to 35% Off
  • Up to $600 Resort Credit††

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$165*: 5/1-7/31

$215*: Now-4/30

Antigua

  • Up to $600 Resort Credit††
  • Up to 28% Off

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$185*: 6/1-7/31

$209*: Now-5/31

Los Cabos

  • Up to 49% Off
  • $100 Instant Savings for 4-5Nt Stays††
  • $200 Instant Savings for 6Nt+ Stays††

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$219*: 5/1-7/31

$225*: Now-4/30

Jamaica

  • Up to 60% Off
  • Up to $778 in Resort Coupons††

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$239*: Now-5/31

$275*: 6/1-7/31

Cancun

  • Up to 62% Off

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$239*: 5/1-7/31

$375*: Now-4/30

Trip Protection & Insurance

Traveling within three days? Our Travel Advisors can make it happen! Call 1-800-309-4717 to book.
††Restrictions apply. Call for details. *$119 price is based on the nightly rate at Catalonia Bavaro Beach Golf & Casino Resort on May 26. Prices reflect hotels that feature breakfast plans and all-inclusive plans. Advertised prices available for bookings made electronically through your travel agent or on vacationexpress.com; small service fee of $10 applies when booking through Vacation Express Call Center. Hotel-only prices include hotel and hotel taxes and are per person per night, based on double occupancy for minimum 3-night stays. Above offers are only valid for new bookings and are not valid for groups. Air can be added for an additional charge to hotel-only offers. For full terms and conditions, hotel information and description of all services, please refer to vacationexpress.com or call for details. Some upgrades are subject to availability upon check-in. Packages are limited and subject to change without prior notice. Some hotels in the Cancun, Riviera Maya, Isla Mujeres and Cozumel areas of Mexico charge an environment fee of approximately $1.21 per room, per night. Hotels in Antigua charge a Tourism Guest Levy of $5 USD per person, per night. Fees are subject to change without notice and are payable at the hotel. Book by 3/20/26. Not responsible for errors or omissions. Registered Florida Seller of Travel no. St 38441. State of California Seller of Travel Certificate of Registration #2107538-40.

Cancun Logo Riviera Maya Logo Los Cabos Logo Vallarta Nayarit Logo Dominican Republic Logo Jamaica Logo Costa Rica Logo Antigua Barbuda Logo

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