Big Island, Hawaii Vacation Packages and Specials

For new bookings only. Now - 12/14/17. Prices are USD, based on double occupancy and includes all applicable taxes. Based on availability at time of booking and subject to change without notice. Restrictions & blackout dates may apply. Does not include resort fees payable in Hawaii. Not combinable with other specials or promotions. Inquire about air-inclusive packages with Hawaiian, Delta, Alaska, or other airlines with your travel agent.

Terms & Conditions : Offer valid on new bookings only of seven nights minimum in destination (may split stay between multiple properties, subject to hotel minimum night stays). Any prices shown are based on double occupancy except if expressly noted otherwise. Purchase of Classic Vacations’ Change & Cancellation Waiver required to qualify for the Take Off to Tahiti instant Classic credit. One Classic credit per booking, while supplies last. The 2-for-1 tour offer is valid only on the Half- Day Bora Bora Discovery or the Full-Day Bora Bora Tour, and requires a minimum of two passengers to qualify. All terms and conditions for the instant Classic credit also apply to the additional $100 credit for West Coast and Canadian departures, valid from the following airports: FAT, SNA, SAN, LAX, BUR, SFO, SJC, PDX, SEA, PSP, YVR, YYC, YEG, YYZ, YUL, YQB, YBA, YHZ, YYJ, YQR, YWG, YOW. Offers are subject to availability at time of booking and may be changed or discontinued at any time without notice. Blackout dates, minimum night stays, minimum stay requirements on air, seasonal surcharges, resort fees (if any), and other restrictions may also apply. Booking and travel dates may vary by property. Subject to hotel minimum night stays. Other promotions and departure dates available which may result in a different rate and/or hotel inclusions. Customer is responsible for hotel taxes and fees on free night offers. All prices shown are in USD. Not valid for Group Travel. Classic Vacations CST #2079429-20.

Terms & Conditions : Offer valid on new bookings only of seven nights minimum in destination (may split stay between multiple properties, subject to hotel minimum night stays). Any prices shown are based on double occupancy except if expressly noted otherwise. Purchase of Classic Vacations’ Change & Cancellation Waiver required to qualify for the Take Off to Tahiti instant Classic credit. One Classic credit per booking, while supplies last. The 2-for-1 tour offer is valid only on the Half- Day Bora Bora Discovery or the Full-Day Bora Bora Tour, and requires a minimum of two passengers to qualify. All terms and conditions for the instant Classic credit also apply to the additional $100 credit for West Coast and Canadian departures, valid from the following airports: FAT, SNA, SAN, LAX, BUR, SFO, SJC, PDX, SEA, PSP, YVR, YYC, YEG, YYZ, YUL, YQB, YBA, YHZ, YYJ, YQR, YWG, YOW. Offers are subject to availability at time of booking and may be changed or discontinued at any time without notice. Blackout dates, minimum night stays, minimum stay requirements on air, seasonal surcharges, resort fees (if any), and other restrictions may also apply. Booking and travel dates may vary by property. Subject to hotel minimum night stays. Other promotions and departure dates available which may result in a different rate and/or hotel inclusions. Customer is responsible for hotel taxes and fees on free night offers. All prices shown are in USD. Not valid for Group Travel. Classic Vacations CST #2079429-20.

Terms & Conditions : Offer valid on new bookings only of seven nights minimum in destination (may split stay between multiple properties, subject to hotel minimum night stays). Any prices shown are based on double occupancy except if expressly noted otherwise. Purchase of Classic Vacations’ Change & Cancellation Waiver required to qualify for the Take Off to Tahiti instant Classic credit. One Classic credit per booking, while supplies last. The 2-for-1 tour offer is valid only on the Half- Day Bora Bora Discovery or the Full-Day Bora Bora Tour, and requires a minimum of two passengers to qualify. All terms and conditions for the instant Classic credit also apply to the additional $100 credit for West Coast and Canadian departures, valid from the following airports: FAT, SNA, SAN, LAX, BUR, SFO, SJC, PDX, SEA, PSP, YVR, YYC, YEG, YYZ, YUL, YQB, YBA, YHZ, YYJ, YQR, YWG, YOW. Offers are subject to availability at time of booking and may be changed or discontinued at any time without notice. Blackout dates, minimum night stays, minimum stay requirements on air, seasonal surcharges, resort fees (if any), and other restrictions may also apply. Booking and travel dates may vary by property. Subject to hotel minimum night stays. Other promotions and departure dates available which may result in a different rate and/or hotel inclusions. Customer is responsible for hotel taxes and fees on free night offers. All prices shown are in USD. Not valid for Group Travel. Classic Vacations CST #2079429-20.

Package must include Hotel and Flight OR Hotel and Car to be valid. Offers valid on new bookings only. Prices shown are per-person, land only based upon double occupancy, except if expressly noted otherwise. Offers are subject to availability at time of booking and may be changed or discontinued at any time without notice. Blackout dates, minimum night stays, minimum stay requirements on air, seasonal surcharges, resort fees (if any), and other restrictions may also apply. Individual offers may require purchase of Travel Smart Plan or travel waiver. Offers are not valid for Group Travel. Some booking and travel dates may vary. Other promotions and departure dates available which may result in a different rate and/or hotel inclusion. Customer is responsible for hotel taxes and fees on the free night offers, where applicable. For those properties where Classic Vacations has access to dynamic pricing rates, those rates will likely fluctuate from time to time based on market conditions and other factors beyond Classic Vacations control. Classic Vacations CST# 2079429-20.

Rates are based on round-trip air travel from San Jose (SJC) to Oahu; Oakland (OAK) to Maui and Kauai; Portland (PDX) to the Island of Hawaii and are subject to airline and/or resort availability. Rates quoted are per person, based on double occupancy. Advertised vacation rate(s) valid for select travel 8/28/17 for The Westin Nanea Ocean Villas and 8/21/17 for all other properties.

Unless otherwise indicated: rates quoted are per person, based on double occupancy and are for the lowest accommodation category. Gratuities, transfers and excursions are additional. Advertised rates are subject to additional taxes and surcharges, however, such amounts, if collected by Pleasant Holidays, are included in land-only and air-inclusive advertised rates. Daily resort or facility fees payable directly to the hotel at check-out may apply; such fee amounts are excluded from advertised rates and will be advised at the time of booking. Rates may not be available on all travel dates. Airline tickets may be non-refundable. Additional restrictions may apply, including, but not limited to, baggage charges for first and/or second checked bag, advance purchase requirements, and blackout dates. Itinerary changes/cancellations are subject to Pleasant Holidays-imposed fees from $25 (for Canada or contiguous U.S. travel) or from $50 (for all other travel) per person, in addition to any applicable airline or other supplier-imposed change/cancellation penalties, plus applicable fare differentials (certain changes involve pre-notification deadlines). Airline fees and policies may vary; contact Pleasant Holidays for information. For baggage fees and other details, see www.iflybags.com. Rates involving roundtrip air transportation from other gateways may differ. Rates, terms, conditions, availability, itinerary, government taxes, surcharges, deposit, payment and cancellation terms and policies are subject to change without notice. Cruise rates capacity controlled.

Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply.

BOGO Activity Offer: Valid on new bookings made 5/1 - 6/4/17 for travel 5/1 - 12/15/7 Minimum 3-night hotel accommodations at participating property and roundtrip airfare required. When traveler purchases one activity for his/her Hawaii vacation through Pleasant Activities, he/she will receive a second activity of equal or lesser value free of charge for that same vacation. Maximum value of complimentary activity is $500. At time of booking, a voucher will be generated for the BOGO activity offer; the voucher can then be redeemed by the traveler or his/her travel agent by calling 1-888-229-7770. When traveler purchases the identified activity for his/her Hawaii vacation through Pleasant Holidays, he/she will receive a second identified activity free of charge for that same vacation. Fees and surcharges are excluded and must be paid for both tours. Limit of one complimentary activity per booking. Certain restrictions apply.

Not responsible for errors or omissions.

HAWAI‘I AIR CREDIT: Valid on new bookings of at least five (5) consecutive nights at a participating property on Maui, Kaua‘i, or Hawai‘i Island; or of at least four (4) consecutive nights on O‘ahu and Lanai. The credit can vary and increase with length of stay. Each credit is per room booked, not per traveler. Combinable with select Classic Hawai‘i promotional offers. Valid for bookings made 5/15/17 - 6/30/17 for travel through 12/15/17. Additional restrictions and blackout dates may apply. Offers are subject to availability at time of booking and may be changed or discontinued at any time without notice. Offers valid on new bookings only. Prices shown are per person, land only based upon double occupancy, except if expressly noted otherwise. Blackout dates, minimum night stays, minimum stay requirements on air, seasonal surcharges, resort fees (if any), and other restrictions may also apply. Offers are not valid for Group Travel. Some booking and travel dates may vary. Other promotions and departure dates available which may result in a different rate and/or hotel inclusion. Customer is responsible for hotel taxes and fees on the free night offers, where applicable. For those properties where Classic Vacations has access to dynamic pricing rates, those rates will likely fluctuate from time to time based on market conditions and other factors beyond Classic Vacations’ control. All prices shown are in USD. Not valid for Group Travel.

FREE ALAMO ECONOMY CAR RENTAL: Valid on new bookings of at least three (3) consecutive nights at any Classic Hawai‘i property. Booking window 5/15/17 - 6/30/17 for travel through 12/15/17. May be combined with select Classic Hawai‘i promotional offers and requires the purchase of the Classic’s travel waiver. Free Alamo economy car valid for 5-7 nights only. For upgraded car categories and/or stays longer than 7 nights, a 5-7 night economy car credit will be applied. One (1) free economy car or equivalent credit per booking.

HAWAI‘I AIR CREDIT: Valid on new bookings of at least five (5) consecutive nights at a participating property on Maui, Kaua‘i, or Hawai‘i Island; or of at least four (4) consecutive nights on O‘ahu and Lanai. The credit can vary and increase with length of stay. Each credit is per room booked, not per traveler. Combinable with select Classic Hawai‘i promotional offers. Valid for bookings made 5/15/17 - 6/30/17 for travel through 12/15/17. Additional restrictions and blackout dates may apply. Offers are subject to availability at time of booking and may be changed or discontinued at any time without notice. Offers valid on new bookings only. Prices shown are per person, land only based upon double occupancy, except if expressly noted otherwise. Blackout dates, minimum night stays, minimum stay requirements on air, seasonal surcharges, resort fees (if any), and other restrictions may also apply. Offers are not valid for Group Travel. Some booking and travel dates may vary. Other promotions and departure dates available which may result in a different rate and/or hotel inclusion. Customer is responsible for hotel taxes and fees on the free night offers, where applicable. For those properties where Classic Vacations has access to dynamic pricing rates, those rates will likely fluctuate from time to time based on market conditions and other factors beyond Classic Vacations’ control. All prices shown are in USD. Not valid for Group Travel.

FREE ALAMO ECONOMY CAR RENTAL: Valid on new bookings of at least three (3) consecutive nights at any Classic Hawai‘i property. Booking window 5/15/17 - 6/30/17 for travel through 12/15/17. May be combined with select Classic Hawai‘i promotional offers and requires the purchase of the Classic’s travel waiver. Free Alamo economy car valid for 5-7 nights only. For upgraded car categories and/or stays longer than 7 nights, a 5-7 night economy car credit will be applied. One (1) free economy car or equivalent credit per booking.

HAWAI‘I AIR CREDIT: Valid on new bookings of at least five (5) consecutive nights at a participating property on Maui, Kaua‘i, or Hawai‘i Island; or of at least four (4) consecutive nights on O‘ahu and Lanai. The credit can vary and increase with length of stay. Each credit is per room booked, not per traveler. Combinable with select Classic Hawai‘i promotional offers. Valid for bookings made 5/15/17 - 6/30/17 for travel through 12/15/17. Additional restrictions and blackout dates may apply. Offers are subject to availability at time of booking and may be changed or discontinued at any time without notice. Offers valid on new bookings only. Prices shown are per person, land only based upon double occupancy, except if expressly noted otherwise. Blackout dates, minimum night stays, minimum stay requirements on air, seasonal surcharges, resort fees (if any), and other restrictions may also apply. Offers are not valid for Group Travel. Some booking and travel dates may vary. Other promotions and departure dates available which may result in a different rate and/or hotel inclusion. Customer is responsible for hotel taxes and fees on the free night offers, where applicable. For those properties where Classic Vacations has access to dynamic pricing rates, those rates will likely fluctuate from time to time based on market conditions and other factors beyond Classic Vacations’ control. All prices shown are in USD. Not valid for Group Travel.

FREE ALAMO ECONOMY CAR RENTAL: Valid on new bookings of at least three (3) consecutive nights at any Classic Hawai‘i property. Booking window 5/15/17 - 6/30/17 for travel through 12/15/17. May be combined with select Classic Hawai‘i promotional offers and requires the purchase of the Classic’s travel waiver. Free Alamo economy car valid for 5-7 nights only. For upgraded car categories and/or stays longer than 7 nights, a 5-7 night economy car credit will be applied. One (1) free economy car or equivalent credit per booking.

HAWAI‘I AIR CREDIT: Valid on new bookings of at least five (5) consecutive nights at a participating property on Maui, Kaua‘i, or Hawai‘i Island; or of at least four (4) consecutive nights on O‘ahu and Lanai. The credit can vary and increase with length of stay. Each credit is per room booked, not per traveler. Combinable with select Classic Hawai‘i promotional offers. Valid for bookings made 5/15/17 - 6/30/17 for travel through 12/15/17. Additional restrictions and blackout dates may apply. Offers are subject to availability at time of booking and may be changed or discontinued at any time without notice. Offers valid on new bookings only. Prices shown are per person, land only based upon double occupancy, except if expressly noted otherwise. Blackout dates, minimum night stays, minimum stay requirements on air, seasonal surcharges, resort fees (if any), and other restrictions may also apply. Offers are not valid for Group Travel. Some booking and travel dates may vary. Other promotions and departure dates available which may result in a different rate and/or hotel inclusion. Customer is responsible for hotel taxes and fees on the free night offers, where applicable. For those properties where Classic Vacations has access to dynamic pricing rates, those rates will likely fluctuate from time to time based on market conditions and other factors beyond Classic Vacations’ control. All prices shown are in USD. Not valid for Group Travel.

FREE ALAMO ECONOMY CAR RENTAL: Valid on new bookings of at least three (3) consecutive nights at any Classic Hawai‘i property. Booking window 5/15/17 - 6/30/17 for travel through 12/15/17. May be combined with select Classic Hawai‘i promotional offers and requires the purchase of the Classic’s travel waiver. Free Alamo economy car valid for 5-7 nights only. For upgraded car categories and/or stays longer than 7 nights, a 5-7 night economy car credit will be applied. One (1) free economy car or equivalent credit per booking.

HAWAI‘I AIR CREDIT: Valid on new bookings of at least five (5) consecutive nights at a participating property on Maui, Kaua‘i, or Hawai‘i Island; or of at least four (4) consecutive nights on O‘ahu and Lanai. The credit can vary and increase with length of stay. Each credit is per room booked, not per traveler. Combinable with select Classic Hawai‘i promotional offers. Valid for bookings made 5/15/17 - 6/30/17 for travel through 12/15/17. Additional restrictions and blackout dates may apply. Offers are subject to availability at time of booking and may be changed or discontinued at any time without notice. Offers valid on new bookings only. Prices shown are per person, land only based upon double occupancy, except if expressly noted otherwise. Blackout dates, minimum night stays, minimum stay requirements on air, seasonal surcharges, resort fees (if any), and other restrictions may also apply. Offers are not valid for Group Travel. Some booking and travel dates may vary. Other promotions and departure dates available which may result in a different rate and/or hotel inclusion. Customer is responsible for hotel taxes and fees on the free night offers, where applicable. For those properties where Classic Vacations has access to dynamic pricing rates, those rates will likely fluctuate from time to time based on market conditions and other factors beyond Classic Vacations’ control. All prices shown are in USD. Not valid for Group Travel.

FREE ALAMO ECONOMY CAR RENTAL: Valid on new bookings of at least three (3) consecutive nights at any Classic Hawai‘i property. Booking window 5/15/17 - 6/30/17 for travel through 12/15/17. May be combined with select Classic Hawai‘i promotional offers and requires the purchase of the Classic’s travel waiver. Free Alamo economy car valid for 5-7 nights only. For upgraded car categories and/or stays longer than 7 nights, a 5-7 night economy car credit will be applied. One (1) free economy car or equivalent credit per booking.

*Conditions Apply: For air-inclusive prices, additional fees for baggage may apply. Please contact your airline or refer to its website for detailed information regarding their checked baggage policies, or alternatively please visit our baggage policy page. Special promotions valid on new bookings only. Prices are per person, based on double occupancy accommodations. Tour and land packages only include round-trip midweek fares from select cities and do not include meals unless otherwise indicated. Savings reflect land prices only and vary by resort and travel dates. Availability is limited. Seats may not be available on all flights or tours. Rates and/or package prices on airfares, cruises and tours are subject to holiday blackouts, peak period surcharges, and cancellation charges may be applicable of up to the full price paid depending on the fare and/or package and when it is cancelled. U.S. or international government imposed taxes and fees of up to $60 may apply on arrivals and departures depending on the itinerary chosen, and are payable to the appropriate airport authority. Some fares may be non-refundable, but may be exchanged for a fee of up to $200, plus any additional airfare costs due to difference in new airfares. Other restrictions may apply and vary by resort and airline carrier. Contact GOGO Vacations for further details. GOGO Vacations does not assume responsibility for any errors or omissions in the content of the offers displayed.

Rates are based on roundtrip air travel to/from Oakland (OAK) for Kauai and Maui and San Jose (SJC) for Oahu and the Island of Hawaii and are per person, based on double occupancy. Advertised vacation rate(s) valid for departures 9/18/17.
Hawaii - Double Car Rental Upgrade Offer: Valid on new bookings made 6/5 - 7/9/17 for travel 6/5 - 12/15/17 Minimum 5-night hotel accommodations at participating property required. Age restrictions apply for car rental. Upgrade is from Midsize to Convertible, Jeep, Luxury or SUV.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions.

Rates are based on roundtrip air travel to/from Oakland (OAK) for Kauai and Maui and San Jose (SJC) for Oahu and the Island of Hawaii and are per person, based on double occupancy. Advertised vacation rate(s) valid for departures 9/18/17.
Hawaii - Double Car Rental Upgrade Offer: Valid on new bookings made 6/5 - 7/9/17 for travel 6/5 - 12/15/17 Minimum 5-night hotel accommodations at participating property required. Age restrictions apply for car rental. Upgrade is from Midsize to Convertible, Jeep, Luxury or SUV.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions.

Rates are based on roundtrip air travel to/from Oakland (OAK) for Kauai and Maui and San Jose (SJC) for Oahu and the Island of Hawaii and are per person, based on double occupancy. Advertised vacation rate(s) valid for departures 9/18/17.
Hawaii - Double Car Rental Upgrade Offer: Valid on new bookings made 6/5 - 7/9/17 for travel 6/5 - 12/15/17 Minimum 5-night hotel accommodations at participating property required. Age restrictions apply for car rental. Upgrade is from Midsize to Convertible, Jeep, Luxury or SUV.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions.

Rates are based on roundtrip air travel to/from Oakland (OAK) for Kauai and Maui and San Jose (SJC) for Oahu and the Island of Hawaii and are per person, based on double occupancy. Advertised vacation rate(s) valid for departures 9/18/17.
Hawaii - Double Car Rental Upgrade Offer: Valid on new bookings made 6/5 - 7/9/17 for travel 6/5 - 12/15/17 Minimum 5-night hotel accommodations at participating property required. Age restrictions apply for car rental. Upgrade is from Midsize to Convertible, Jeep, Luxury or SUV.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions.

*Requirements: Packages must be booked at least one day prior to departure. Prices include government taxes and fees, but do not include baggage fees See details.

Price is per person based on single occupancy. Prices are subject to change based on party size, inventory availability and departure period.