Orlando Florida

Florida Vacation Packages

 from $619
 
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 more
  • $75 OFF 4-night stays
  • $50 OFF 2- and 3-night stays
  • Book by 9/16/18 for travel through 12/31/18
All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more

Florida

  • Orlando, 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.

    An oasis of stylish comfort, this all-suite hotel is just a stone's throw from Orlando’s many theme parks and attractions.

    • 1 Bedroom Suite
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • FREE Wi-Fi
    • Kids 12 & younger stay FREE

    3 nights with flight from $243+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 09/08/18

  • 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
    • Reduced rate
    • Kids 9 & younger Stay and Eat Free

    3 nights with flight from $439+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 09/08/18

  • Captiva 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.

    Discover the magnificence of native Florida at this resort set amid a wildlife preserve bordering the Gulf of Mexico.

    • 1 Bedroom Villa
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Kids 16 & younger stay FREE

    3 nights with flight from $461+

    Boston, MA (BOS) departures, valid for travel 09/08/18

  • Bonita Springs, 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 eco-friendly resort is set on 26 acres overlooking breathtaking Estero Bay Aquatic Preserve.

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

    3 nights with flight from $505+

    Boston, MA (BOS) departures, valid for travel 09/08/18

  • 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.

    This impressive resort overlooking lively Miami Beach welcomes guests with a gracious, contemporary spirit.

    • Legendary Deluxe - King Bed
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Kids 11 & younger stay FREE

    3 nights with flight from $597+

    Boston, MA (BOS) departures, valid for travel 09/08/18

  • 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 $606+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 09/08/18

US Cities and Canada - EXCLUSIVE up to $100 OFF per booking offer: Valid on new bookings made 7/23 - 9/16/18 for travel 7/23 - 12/31/18. Savings is $50 per booking for stays of 2 - 3 nights, $75 per booking for stays of 4 nights and $100 per booking for stays of 5 nights or longer. Minimum 2-night stay at a participating resort required. Savings is per booking and taken at time of booking.
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.]