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Travel Advisor: Diane Dewing ECC
(863) 884-7086
Richman, O'Hare & Associates - Dream Vacations
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Slider Pleasant Holidays

Pleasant Holidays offers curated vacation experiences to some of the world’s most sought-after destinations, including Hawaii, Mexico, the Caribbean, and Europe. Whether you're dreaming of a tropical beach escape, a cultural European adventure, or a family getaway, Pleasant Holidays has the perfect trip tailored to your needs.

Choose from a wide variety of options to match your style and budget. Your next unforgettable adventure with Pleasant Holidays is waiting.

Start planning today and create memories that will last a lifetime!

  • ‘Alohilani Resort Waikiki Beach

    Honolulu, Hawaii (Oahu)
    Family Friendly
    Call for Special Pricing (863) 884-7086

    Offers & More

      • WTH Exclusive: Receive Up to $150 Vacation Credit
      • Hot Deals: $175 Air Credit and a $175 Hertz Car Credit
      • Pleasant Holidays Exclusive: Reduced rate and a $25 Daily Resort Credit Per Room With Select Room Categories
      • Kids 17 & Under Free in Room
      • Across from Waikiki Beach
      • Near the Honolulu Zoo, Waikiki Aquarium and Waikiki Shell Amphitheater
      • Historical Iolani Palace and Polynesian Cultural Center Nearby
  • Aston Kaanapali Shores

    Lahaina, Hawaii (Maui)
    Family Friendly
    Call for Special Pricing (863) 884-7086

    Offers & More

      • WTH Exclusive: Receive Up to $150 Vacation Credit
      • Hot Deals: $175 Air Credit and a $175 Hertz Car Credit
      • Pleasant Holidays Exlusive: Complimentary Daily Breakfast For Two with Select Room Categories
      • Kids 17 & Under Free in Room
      • Beachfront Location
      • Hula Lessons, Pickleball Court, Lei Making
      • Golf Nearby
  • Beaches Turks & Caicos Resort Villages and Spa

    Turks and Caicos Islands
    All-Inclusive Family-Friendly
    Call for Special Pricing (863) 884-7086

    Offers & More

      • WTH Exclusive: Receive Up to $150 Vacation Credit
      • Hot Deals: $200 OFF Vacation Package
      • Pirates Island Waterpark Includes Lazy River, Surf Simulator, Waterslides
      • Water & Resort Activities
      • Beachfront
  • JOIA Aruba by Iberostar

    Aruba
    Family Friendly
    Call for Special Pricing (863) 884-7086

    Offers

      • WTH Exclusive: Receive Up to $150 Vacation Credit
      • Hot Deals: $200 OFF Vacation Package
      • Receive up to $800 resort credit
      • Beachfront Hotel Located Along the Shores of Eagle Beach
      • Spacious Rooms with Modern Amenities
      • Options for Water Sports, Golfing, and a Casino Also Lie in Close Proximity to the Hotel
  • Moon Palace Jamaica

    Ocho Rios, Jamaica
    All-Inclusive Family-Friendly
    Call for Special Pricing (863) 884-7086

    Offers & More

      • WTH Exclusive: Receive Up to $150 Vacation Credit
      • Hot Deals: $200 OFF Vacation Package
      • A Powder-Sand Paradise in Ocho Rios
      • 5 Pools & FlowRider® Double Wave Simulater
      • Children's Program & Spa Services
  • Riu Palace Aquarelle

    Montego Bay, Jamaica
    All-Inclusive Family-Friendly
    Call for Special Pricing (863) 884-7086

    Offers & More

      • WTH Exclusive: Receive Up to $150 Vacation Credit
      • Hot Deals: $200 OFF Vacation Package
      • Receive up to $788 in resort coupons
      • 4 Pools and Splash Water World Water Park
      • Beachfront and Beach Services
      • Live Entertainment & Water Activities
  • The Royal at Atlantis

    Bahamas
    Family Friendly
    Call for Special Pricing (863) 884-7086

    Offers

      • WTH Exclusive: Receive Up to $150 Vacation Credit
      • Hot Deals: $200 OFF Vacation Package
      • Save up to 30%
      • The Royal is the icon of Atlantis, featuring the awe-inspiring mythology of the Lost City of Atlantis risen from the sea.
      • Intimate proximity to the world’s largest open-air marine habitat situated at its center and the famed Atlantis casino by its side.
  • The Twin Fin

    Honolulu, Hawaii (Oahu)
    Family Friendly
    Call for Special Pricing (863) 884-7086

    Offers & More

      • WTH Exclusive: Receive Up to $150 Vacation Credit
      • Hot Deals: $175 Air Credit and a $175 Hertz Car Credit
      • Pleasant Holidays Exclusive: Includes a Guaranteed Room Upgrade from Partial Ocean View to Ocean View.
      • Kids 17 & Under Free in Room
      • Across from Waikiki Beach
      • Near Kapiolani Park and the Honolulu Zoo
      • Putting Green, Tennis Court, Snorkeling
  • Waikoloa Beach Marriott Resort & Spa

    Waikoloa, Hawaii (Big Island)
    Family Friendly
    Call for Special Pricing (863) 884-7086

    Offers & More

      • WTH Exclusive: Receive Up to $150 Vacation Credit
      • Hot Deals: $175 Air Credit and a $175 Hertz Car Credit
      • Pleasant Holidays Exclusive: Includes Daily Continental Breakfast For Up to Two Guests at Hawaii Calls Restaurant and 10% Off Mandara Spa Services with Select Room Categories
      • Kids 17 & Under Free in Room
      • 3 Pools, Including a Sand-Bottom Keiki Pool and Infinity Pool
      • Cultural Activities
      • Golf, Hiking, and More!
  • Wailea Beach Resort - Marriott, Maui

    Wailea, Hawaii (Maui)
    Family-Friendly
    Call for Special Pricing (863) 884-7086

    Offers & More

      • WTH Exclusive: Receive Up to $150 Vacation Credit
      • Hot Deals: $175 Air Credit and a $175 Hertz Car Credit
      • Pleasant Holidays Exclusive: Includes Daily Continental Breakfast For Up to Two Guests at Starbucks or Whale's Tale and Waived Extra Person Charge for 3rd and 4th Guests.
      • Kids 17 & Under Free in Room
      • In the Heart of Wailea Near Shopping and 3 Championship Golf Course
      • Enjoy Spectactular Sunsets
      • Relax at 5 Pools Across & Enjoy Live Entertainment, Snorkeling & More!