Palm Trees, 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. Book your Florida Vacation Package today.
Winter Savings
Up to 50% off, free nights, room upgrades and more
  • Book by 2/23/20 for travel through 9/28/20
 
FREE 3-Day Midsize Hertz Car Rental at ALL Florida Hotels and Resorts
  • Minimum 3-night vacation packages
  • Book by 2/23/20 for travel through 9/28/20
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
  • 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.

    Enjoy a distinctive vacation experience at this family-friendly resort featuring upscale accommodations and a water park.

    • King Guest
    • EXCLUSIVE FREE 3-Day mid-size car rental for all Florida hotels

    3 nights with flight from $574+

    Boston, MA (BOS) departures, valid for travel 04/01/20 - 04/04/20

  • Universal Studios, Orlando 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 FREE 3-Day mid-size car rental for all Florida hotels

    3 nights with flight from $674+

    Boston, MA (BOS) departures, valid for travel 04/01/20 - 04/04/20

  • Downtown Miami 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.

    Located at the intersection of downtown and the Miami Arts District, this resort offers gorgeous waterfront views.

    • King Guest
    • EXCLUSIVE FREE 3-Day mid-size car rental for all Florida hotels

    3 nights with flight from $711+

    Boston, MA (BOS) departures, valid for travel 04/01/20 - 04/04/20

  • 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 FREE 3-Day mid-size car rental for all Florida hotels
    • Exclusive Theme Park benefits

    3 nights with flight from $714+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 04/08/20 - 04/11/20

  • 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.

    Blending refined Mediterranean flair with the vibrancy of Miami Beach, this hotel offers impeccable service and style for an unforgettable vacation.

    • Ocean View King
    • EXCLUSIVE FREE 3-Day mid-size car rental for all Florida hotels

    3 nights with flight from $725+

    Boston, MA (BOS) departures, valid for travel 04/01/20 - 04/04/20

  • 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 FREE 3-Day mid-size car rental for all Florida hotels
    • Exclusive Theme Park benefits

    3 nights with flight from $815+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 04/08/20 - 04/11/20

  • 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 King
    • EXCLUSIVE FREE 3-Day mid-size car rental for all Florida hotels

    3 nights with flight from $827+

    Boston, MA (BOS) departures, valid for travel 04/01/20 - 04/04/20

  • 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.

    • ADA King Tub
    • EXCLUSIVE FREE 3-Day mid-size car rental for all Florida hotels

    3 nights with flight from $833+

    Boston, MA (BOS) departures, valid for travel 04/01/20 - 04/04/20

  • 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.

    • One Bedroom Villa
    • EXCLUSIVE FREE 3-Day mid-size car rental for all Florida hotels

    3 nights with flight from $915+

    Newark, New Jersey (EWR) departures, valid for travel 04/01/20 - 04/04/20

  • 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.

    Set on the island's only natural-sand beach, this intimate boutique-style resort in Key West offers gorgeous ocean views and plenty of outdoor activities.

    • Key West View
    • EXCLUSIVE FREE 3-Day mid-size car rental for all Florida hotels

    3 nights with flight from $1023+

    Boston, MA (BOS) departures, valid for travel 04/01/20 - 04/04/20

  • Ft Lauderdale, Florida 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 upscale retreat, set on 16 waterfront acres, is the perfect setting for a seaside getaway.

    • King Balcony
    • EXCLUSIVE FREE 3-Day mid-size car rental for all Florida hotels

    3 nights with flight from $1163+

    Boston, MA (BOS) departures, valid for travel 04/01/20 - 04/04/20

  • 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.

    • Non Water View King
    • EXCLUSIVE FREE 3-Day mid-size car rental for all Florida hotels

    3 nights with flight from $1527+

    Newark, New Jersey (EWR) departures, valid for travel 04/01/20 - 04/04/20

US Cities - Winter SAVINGS offers: Valid on new bookings made 01/13/2020 - 02/23/2020 for select travel 01/13/2020 - 09/28/2020. Offers vary by hotel and travel dates, and may be category-specific, require advance booking, be restricted to specific days of the week and/or require a minimum night stay. Booking and travel dates vary by hotel. Certain restrictions and blackout dates may apply. EXCLUSIVE 3-Day Mid-Size Hertz Car Rental offer: Valid on new bookings made 01/13/2020 - 02/23/2020 for select travel 01/13/2020 - 09/28/2020. Roundtrip airfare and minimum 3-night stay at any hotel or resort in Pleasant Holidays' Florida portfolio required. FREE mid-size Hertz car rental valid for a maximum of 3 days. Age restrictions may apply for car rental.
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.]