The Real Deal: Round-trip airfare to Maui on United Airlines and three nights at the 59-room Kaanapali Ocean Inn, from $585 per person—including all taxes and fees.
When: Monday departures through Dec. 7, 2009; other travel dates may be available through Dec. 15 at a possibly higher cost.
Gateways: San Francisco. Additional gateways, including Chicago, Denver, Houston, L.A., Miami, New York City, Phoenix, and Seattle, are available at higher rates.
The fine print: Round-trip air-hotel transfers start at $116 per person. There are no fuel surcharges, and all taxes and fees are included. Based on double occupancy; single supplement is $708. Read these guidelines before you book any Real Deal.
Book by: No deadline; based on availability.
Contact: Pleasant Holidays, 800/742-9244, pleasantholidays.com.
Why it's a deal: According to a recent search on Kayak, the lowest round-trip fare in mid-October between San Francisco and Maui is $487 with taxes (American). For an additional $98, the Pleasant Holidays package covers airfare as well as three nights' accommodations and all taxes and fees.
More: Optional activities include a visit to the Maui Ocean Center ($25 per person), a walk to waterfalls ($78 per person), a day tour of Haleakala National Park ($94 per person), or a waterfalls and rain forest hike in Hana ($156 per person).
Add nights at the Kaanapali Ocean Inn for an extra $85 per room per night. If you book a five-night vacation package, you can get $100 off a Hertz car rental; five-day package rates vary depending on departure city, hotel, and number of children and adults traveling.