Maui Beach, Lanai in background

Maui Vacation Packages

 from $635
 
Maui consistently lands atop travel-magazine reader polls as one of the world's best, most romantic islands. Why? How about a wealth of glorious beaches, luxe resorts, gourmet cuisine, fantastic luaus, and world-class windsurfing, whale watching, snorkeling, diving and hiking? Maui is known as the 'Valley Island' because of its two large extinct volcanoes divided by a tropical central valley. It's the second-largest of the Hawaiian islands and the most developed of the Neighbor Islands. Its windsurfing and surf spots are some of the best in the world.
 

The BEST offers in the Islands

  • Book by 8/26/18
All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more

Maui

  • Lahaina, Maui Our 2.5-Star classification designates those properties offering comfortable accommodations with standard amenities. Guests can expect dependable services in a clean and comfortable environment. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Set on the ocean's edge in Lahaina Town along historic Front Street, this condo resort features spacious accommodations and a wealth of activities at your doorstep.

    • Studio Mountain View Premier
    • FREE Wi-Fi

    3 nights with flight from $630+

    San Francisco, California (SFO) departures, valid for travel 09/24/18

  • Kaanapali Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This deluxe condominium resort combines the comfort and convenience of a condominium with hotel-caliber services.

    • Studio with Kitchen
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $679+

    San Francisco, California (SFO) departures, valid for travel 09/24/18

  • Wailea, Maui Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    This serene all-suite hotel in beautiful Wailea offers expansive accommodations and a host of amenities.

    • Studio King
    • Complimentary daily breakfast
    • Connecting rooms available upon request
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE

    3 nights with flight from $787+

    San Francisco, California (SFO) departures, valid for travel 09/24/18

  • Kaanapali Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    Set at the foot of Black Rock, affording spectacular views, this hotel honors its legendary location and Hawaiian heritage.

    • Resort View
    • Reduced rates
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $819+

    San Francisco, California (SFO) departures, valid for travel 09/24/18

  • Kaanapali Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Commanding a spectacular stretch of Kaanapali Beach, this magnificent resort offers a family-friendly getaway.

    • Mountain View
    • Daily breakfast buffet for two
    • 15% spa discount
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $837+

    San Francisco, California (SFO) departures, valid for travel 09/24/18

  • Kaanapali Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Set on 26 pristine oceanfront acres, this resort offers a unique blend of resort and villa-style living.

    • Studio Island View
    • Reduced rates
    • Connecting rooms available upon request
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $962+

    San Francisco, California (SFO) departures, valid for travel 09/24/18

  • Kaanapali Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Located on North Ka’anapali Beach, this new resort features spacious one, two and three-bedroom villas with luxurious amenities accommodating up to 8 adults.

    • Resort View One Bedroom Villa
    • 3 Breakfast buffet vouchers per stay
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1027+

    San Francisco, California (SFO) departures, valid for travel 09/24/18

  • Wailea, Maui Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This magnificent resort on 22 oceanfront acres on Maui's sunny side has been transformed to embrace the beauty of its natural surroundings.

    • Garden View
    • Includes a double upgrade to Premium Ocean View
    • Connecting rooms available upon request
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1032+

    San Francisco, California (SFO) departures, valid for travel 10/01/18

  • Wailea, Maui Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    Situated on 40 acres of tropical gardens, and opening onto Maui's beautiful Wailea Beach, this resort offers elegant accommodations and a breathtaking ambiance.

    • Run of House
    • Daily continental breakfast in Cafe Kula or Grand Dining Room for ages 18 & older
    • 15% off spa services
    • Complimentary lei greeting and welcome drink
    • FREE Wi-Fi
    • Kids 17 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1119+

    San Francisco, California (SFO) departures, valid for travel 01/28/19

  • Wailea, Maui Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    Maui's only all-suite and villa luxury oceanfront resort features elegant accommodations with sophisticated amenities in the upscale Wailea resort area.

    • Deluxe Ocean View King
    • Reduced rates
    • Complimentary lei greeting and welcome drink
    • Connecting rooms available upon request
    • Kids 18 & younger stay FREE
    • Ask about Honeymoon amenities

    3 nights with flight from $1327+

    San Francisco, California (SFO) departures, valid for travel 10/01/18

Central America - EXCLUSIVE $100 OFF per booking offer: Valid on new bookings made 8/20 - 10/14/18 for select travel 8/20/18 - 6/30/19. Minimum 3-night stay at a participating hotel, resort or guided vacation and roundtrip airfare required. Discount is per booking, taken at time of booking and reflected in rates shown. All offers subject to change or cancellation without notice.
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. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]