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.
 

Winter Savings
Up to 45% OFF, FREE nights, room upgrades and more

  • Book by 2/24/19 for travel through 9/30/19
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
  • Universal's Cabana Bay Beach Resort
    Universal's Cabana Bay Beach Resort
    Universal 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.

    Enjoy vibrant, retro style with rooms and suites with stellar recreation from a cool lazy river and pools to bowling and more.
    • Standard 2 Queens
    • Kids 17 & younger stay FREE

    3 nights with flight from $475+

    Pittsburgh, Pennsylvania (PIT) departures, valid for travel 03/04/19 - 03/07/19
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  • Pier Sixty-Six Hotel and Marina
    Pier Sixty-Six Hotel and Marina
    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 resort, a timeless jewel set along the IntraCoastal Waterway, is renowned for its dazzling waterfront views, fine cuisine and indulgent spa services.
    • Marina Guestroom - King
    • Complimentary shuttle service to/from the beach
    • FREE Wi-Fi

    3 nights with flight from $562+

    Pittsburgh, Pennsylvania (PIT) departures, valid for travel 03/04/19 - 03/07/19
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  • 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.
    • ADA King Shower

    3 nights with flight from $578+

    Pittsburgh, Pennsylvania (PIT) departures, valid for travel 03/04/19 - 03/07/19
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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 guaranteed room upgrade
    • Kids 17 & younger stay FREE
    • Reduced rates

    3 nights with flight from $634+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 03/18/19
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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 guaranteed room upgrade
    • Kids 17 & younger stay FREE
    • Reduced rates

    3 nights with flight from $670+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 03/18/19
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  • 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 Room - 1 King

    3 nights with flight from $876+

    Boston, MA (BOS) departures, valid for travel 03/04/19 - 03/07/19
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  • Marriott Palm Beach Singer Island Resort & Spa
    Marriott Palm Beach Singer Island Resort & Spa
    West Palm 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.

    Luxury meets leisure at this sleek, boutique-style oceanfront resort.

    • One Bedroom Resort View

    3 nights with flight from $980+

    Pittsburgh, Pennsylvania (PIT) departures, valid for travel 03/04/19 - 03/07/19
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  • Hyatt Centric Key West Resort and Spa
    Hyatt Centric Key West Resort and Spa
    Key West 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 waterfront resort offers incomparable luxury and is just minutes away from Old Town Key West.
    • One King Bed
    • Kids 17 & younger stay FREE

    3 nights with flight from $1112+

    Pittsburgh, Pennsylvania (PIT) departures, valid for travel 03/04/19 - 03/07/19
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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
    • Kids 17 & younger stay FREE

    3 nights with flight from $1240+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 04/01/19 - 04/04/19
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US Cities and Canada - Winter Savings Offers: Valid on new bookings made 1/7 - 2/24/19 for select travel 1/7 - 9/30/19. 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.
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.]