Orlando Florida

Florida Vacation Packages

 
There’s no mistaking why this is called the Sunshine State. Its subtropical and tropical climate offers plenty of warm days year round, perfect for exploring the many attractions of one of America’s favorite playgrounds. Enjoy hundreds of miles of whitesand beaches, the warm waters of the Gulf of Mexico, and a generous share of Orlando's world-famous amusement parks enticing kids of all ages to come and play. The Sunshine State offers family-friendly vacation fun year-round. Bordered by open water on almost every side, there's a beach destination to suit any taste, from the quiet stretches of the southwestern coast to the sizzling nightlife of Miami. Of course, Florida is also home to some of the world's most famous theme parks, and a visit to Orlando guarantees a good time, with rides, shows and colorful characters everywhere you turn.
 

Up to $100 OFF per booking

  • $100 OFF stays of 5 nights or longer
  • $75 OFF on stays of 4 nights
  • $50 OFF on stays of 2-3 nights
  • Book by 4/14/19 for travel through 7/29/19
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
  • The Diplomat Beach Resort - Curio Collection by Hilton
    The Diplomat Beach Resort - Curio Collection by Hilton
    Hollywood Beach, Florida 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 high-rise resort on Hollywood Beach offers a refreshing getaway with endless opportunities to relax and unwind.

    • Intracoastal
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    2 nights with flight from $440+

    Denver, Colorado (DEN) departures, valid for travel 05/06/19 - 05/09/19
    See Details
  • Casa Marina, A Waldorf Astoria Resort
    Casa Marina, A Waldorf Astoria Resort
    Key West 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.

    Nestled along the southern edge of Key West, this resort overlooks more than 1,100 feet of beach reserved exclusively for hotel guests.
    • Guest
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Kids 17 & younger stay FREE

    2 nights with flight from $478+

    Denver, Colorado (DEN) departures, valid for travel 05/06/19 - 05/09/19
    See Details
  • Sheraton Sand Key Resort
    Sheraton Sand Key Resort
    Clearwater Beach 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 tranquil resort is located on one of America's top rated beaches.

    • King
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Kids 17 & younger stay FREE

    2 nights with flight from $577+

    Denver, Colorado (DEN) departures, valid for travel 05/06/19 - 05/09/19
    See Details
  • The Diplomat Beach Resort - Curio Collection by Hilton
    The Diplomat Beach Resort - Curio Collection by Hilton
    Hollywood Beach, Florida 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 high-rise resort on Hollywood Beach offers a refreshing getaway with endless opportunities to relax and unwind.

    • Intracoastal
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    3 nights with flight from $604+

    Boston, MA (BOS) departures, valid for travel 05/06/19 - 05/09/19
    See Details
  • Sheraton Sand Key Resort
    Sheraton Sand Key Resort
    Clearwater Beach 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 tranquil resort is located on one of America's top rated beaches.

    • King
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Kids 17 & younger stay FREE

    3 nights with flight from $651+

    Houston, Texas (IAH) departures, valid for travel 05/06/19 - 05/09/19
    See Details
  • Casa Marina, A Waldorf Astoria Resort
    Casa Marina, A Waldorf Astoria Resort
    Key West 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.

    Nestled along the southern edge of Key West, this resort overlooks more than 1,100 feet of beach reserved exclusively for hotel guests.
    • Guest
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Kids 17 & younger stay FREE

    3 nights with flight from $662+

    Boston, MA (BOS) departures, valid for travel 05/06/19 - 05/09/19
    See Details
  • The Confidante - By Hyatt
    The Confidante - By Hyatt
    Miami Beach, Florida 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.

    Featuring gorgeous ocean views and a beach-chic setting, this Miami hotel is the ideal place to explore Little Havana, Wynwood, and the Design District.
    • Standard
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    3 nights with flight from $689+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 05/06/19
    See Details
  • JW Marriott Marco Island Beach Resort
    JW Marriott Marco Island Beach Resort
    Marco Island, Florida 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.

    Situated on three miles of pristine beachfront property this resort offers an exhilarating retreat from the ordinary.

    • Tropical Resort View
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    3 nights with flight from $733+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 05/27/19 - 05/30/19
    See Details
  • The Ritz-Carlton, Naples
    The Ritz-Carlton, Naples
    Vanderbilt Beach 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.

    From celebratory sunsets, Ritz Kids® programs, world-class golf, luxury spa experiences and Club Level amenities, this is more than a beachfront hotel. It is an unforgettable family vacation in the making.
    • Coastal View Double
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    2 nights with flight from $1118+

    San Diego, California (SAN) departures, valid for travel 05/06/19 - 05/09/19
    See Details
  • The Ritz-Carlton, Naples
    The Ritz-Carlton, Naples
    Vanderbilt Beach 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.

    From celebratory sunsets, Ritz Kids® programs, world-class golf, luxury spa experiences and Club Level amenities, this is more than a beachfront hotel. It is an unforgettable family vacation in the making.
    • Coastal View Double
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    3 nights with flight from $1443+

    Boston, MA (BOS) departures, valid for travel 05/06/19 - 05/09/19
    See Details
US Cities and Canada - EXCLUSIVE up to $100 OFF per booking offer: Valid on new bookings made 2/25 - 4/14/19 for travel 2/25 - 7/29/19. Minimum 3-night hotel accommodations at participating hotel and roundtrip air required. Savings is $50 off stays of 2-3 nights, $75 off stays of 4 nights and $100 off stays of 5 nights or longer. Savings is per booking, taken at time of booking and reflected in rates shown. Certain restrictions apply.
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.]