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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  ▪  COZUMEL  ▪  LOS CABOS  ▪  PUERTO VALLARTA  ▪  COSTA RICA  ▪  SAINT LUCIA

Puerto Vallarta

  • $600 Resort Credit for 5Nt+ Stays††

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$125*: 1/4-2/28

Riviera Maya

  • Up to 40% Off

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$149*: 1/4-2/28

Cozumel

  • Save Up to 45%

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$159*: 1/4-2/28

Punta Cana

  • Exclusive Sale
  • Stay at 1, Play at 3 Resorts

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$159*: 1/4-2/28

Los Cabos

  • Up to 2 Kids Stay Free
  • $200 Krystal Coupons††

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$165*: 1/4-2/28

Costa Rica

  • Up to $150 Instant Savings††

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$169*: 1/4-2/28

Cancun

  • Up to 45% Off

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$179*: 1/4-2/28

Jamaica

  • Save Up to 40%
  • Up to $500 Resort Credit††

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$185*: 1/4-2/28

Saint Lucia

  • Kids Stay, Play & Eat Free
  • Up to $600 Resort Credit††

ALL-INCLUSIVE RESORT STAYS

Per Night From:

$339*: 1/4-2/28

Trip Protection & Insurance

Traveling within three days? Our Travel Advisors can make it happen! Call 1-800-309-4717 to book.
Kid's hotel offer based on one child per full paying guest and offered on select departures only; qualifying ages and maximum number of kids vary by resort and does not apply to airfare, transfers & booking fees. ††Restrictions apply. Call for details. *$125 price is based on the nightly rate at Grand Palladium Vallarta Resort & Spa on January 26. 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 Saint Lucia charge a Country Sustainability Fee of $6 USD per person, per night. Fees are subject to change without notice and are payable at the hotel. Book by 10/31/25. 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 Cozumel Logo Los Cabos Logo Vallarta Nayarit Logo Dominican Republic Logo Jamaica Logo Costa Rica Logo St. Lucia Logo
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