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 at Marriott Hotels & Resorts

  • $100 OFF on stays of 5 nights or longer
  • $75 OFF on stays of 4 nights
  • $50 OFF on stays of 2-3 nights
  • Book by 12/23/18 for travel through 4/29/19
All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more
  • Orlando World Center Marriott
    Orlando World Center Marriott
    Universal 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.

    A vacation paradise, this resort offers a multitude of activities and comfortable, family-friendly accommodations.
    • Resort View
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    3 nights with flight from $411+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 02/18/19
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  • Walt Disney World Dolphin
    Walt Disney World Dolphin
    Disney 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 landmark hotel's tropical landscaping and tranquil waterways offer a magical retreat.

    • Run of House
    • 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 $600+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 02/25/19
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  • Walt Disney World Swan
    Walt Disney World Swan
    Disney 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.

    The perfect gateway to Central Florida's theme parks, this resort offers magical surroundings and luxurious amenities.

    • Run of House.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 $622+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 02/25/19
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  • The Westin Cape Coral Resort at Marina Village
    The Westin Cape Coral Resort at Marina Village
    Ft Myers, 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 beautiful resort offers breathtaking views of the Gulf of Mexico, Caloosahatchee River and Tarpon Point Marina.
    • Traditional Double
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    3 nights with flight from $649+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 02/25/19
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  • 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

    3 nights with flight from $716+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 03/11/19
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  • W Fort Lauderdale
    W Fort Lauderdale
    Ft Lauderdale, 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.

    South Florida's hottest locale, this beachfront resort is the hidden playground of the stars.

    • Wonderful Queen
    • 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 $804+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 02/25/19
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  • Marriott Stanton South Beach
    Marriott Stanton South Beach
    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.

    Set on the trendiest corner of Ocean Drive, this chic, contemporary hotel features an enviable beachfront setting.
    • City View - King
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    3 nights with flight from $840+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 02/25/19
    See Details
  • Marriott Key Largo Bay Beach Resort
    Marriott Key Largo Bay Beach Resort
    Key Largo 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.

    Panoramic views of a tropical waterfront paradise overlooking the Gulf of Mexico sets the back drop of pure relaxation on the beach.

    • Guest
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • FREE Wi-Fi

    3 nights with flight from $989+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 02/25/19
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  • 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
    • Kids 17 & younger stay FREE

    3 nights with flight from $1171+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 03/18/19
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  • W South Beach
    W South Beach
    South Beach, Florida 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 chic contemporary beachfront resort embraces Miami's lively and stylish vibe.

    • Wonderful
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Ask about Kids17 & younger stay FREE

    3 nights with flight from $1322+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 02/25/19
    See Details
US Cities and Canada - EXCLUSIVE up to $100 OFF per booking with Marriott Hotels & Resorts Offer: Valid on new bookings made 11/12 - 12/23/18 for travel 11/12/18 - 4/29/19. Minimum 2-night hotel accommodations at participating Marriott 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 rate 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.]