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.
 

EXCLUSIVE up to $100 OFF per booking

  • $100 OFF stays of 5 nights or longer
  • $75 OFF stays of 4 nights
  • $50 OFF stays of 2-3 nights
  • Book by 9/15/19 for travel through 12/31/19
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
  • Universal's Loews Sapphire Falls Resort
    Universal's Loews Sapphire Falls Resort
    Universal Studios, Orlando 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.

    Exclusive Theme Park Benefits. Universal's Loews Sapphire Falls Resort brings Caribbean-inspired relaxation and tropical elegance to Universal Orlando.

    • Standard Two Queens
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Complimentary daily Theme Park shuttle

    3 nights with flight from $445+

    Boston, MA (BOS) departures, valid for travel 10/28/19 - 10/31/19
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  • Hyatt Regency Clearwater Beach Resort and Spa
    Hyatt Regency Clearwater Beach Resort and Spa
    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 remarkable hotel, inspired by West Indies style, is set between the turquoise waters of the Gulf of Mexico and the Intracoastal Waterway.
    • Deluxe King
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    3 nights with flight from $454+

    Boston, MA (BOS) departures, valid for travel 10/28/19 - 10/31/19
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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 Two Doubles River View
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    3 nights with flight from $468+

    Denver, Colorado (DEN) departures, valid for travel 10/28/19 - 10/31/19
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  • Marriott Miami Biscayne Bay
    Marriott Miami Biscayne Bay
    Downtown Miami 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.

    Located at the intersection of downtown and the Miami Arts District, this resort offers gorgeous waterfront views.
    • King
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    3 nights with flight from $471+

    Houston, Texas (IAH) departures, valid for travel 10/28/19 - 10/31/19
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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

    3 nights with flight from $485+

    Boston, MA (BOS) departures, valid for travel 10/28/19 - 10/31/19
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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 Tub
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • 3rd night FREE

    3 nights with flight from $496+

    Houston, Texas (IAH) departures, valid for travel 10/28/19 - 10/31/19
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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
    • Reduced rates

    3 nights with flight from $499+

    Boston, MA (BOS) departures, valid for travel 10/28/19 - 10/31/19
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  • DoubleTree Resort by Hilton Hollywood Beach
    DoubleTree Resort by Hilton Hollywood Beach
    Hollywood Beach, 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 resort on the Intracoastal Waterway overlooking the Atlantic Ocean offers spacious and comfortable accommodations.
    • Run of House
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    3 nights with flight from $547+

    Houston, Texas (IAH) departures, valid for travel 10/28/19 - 10/31/19
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  • Pink Shell Beach Resort & Marina
    Pink Shell Beach Resort & Marina
    Ft. Myers 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.

    Situated on a sugar-white beach overlooking the Gulf of Mexico, this resort is the ideal choice for guests seeking adventure, relaxation and fun.

    • One Bedroom
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Daily breakfast included

    3 nights with flight from $654+

    Denver, Colorado (DEN) departures, valid for travel 10/28/19 - 10/31/19
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  • Sheraton Suites Key West
    Sheraton Suites Key West
    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 all-suite hotel offers a warm, welcoming island atmosphere just a stone's throw from Smathers Beach.

    • One Bedroom Garden View Suite King
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    3 nights with flight from $678+

    Houston, Texas (IAH) departures, valid for travel 10/28/19 - 10/31/19
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  • Eden Roc Miami Beach
    Eden Roc Miami 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.

    This impressive resort overlooking lively Miami Beach welcomes guests with a gracious, contemporary spirit.
    • Legendary Deluxe King
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Daily $25 resort credit per room

    3 nights with flight from $691+

    Houston, Texas (IAH) departures, valid for travel 10/28/19 - 10/31/19
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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.
    • ADA King Shower
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    3 nights with flight from $734+

    Houston, Texas (IAH) departures, valid for travel 10/28/19 - 10/31/19
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  • Fort Lauderdale Marriott Harbor Beach Resort & Spa
    Fort Lauderdale Marriott Harbor Beach Resort & Spa
    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.

    • Balcony King
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Reduced rates

    3 nights with flight from $814+

    Houston, Texas (IAH) departures, valid for travel 10/28/19 - 10/31/19
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  • 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.
    • King
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    3 nights with flight from $1035+

    Denver, Colorado (DEN) departures, valid for travel 10/28/19 - 10/31/19
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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.

    • Spectacular Studio Suite King Ocean View
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking

    3 nights with flight from $1038+

    Houston, Texas (IAH) departures, valid for travel 10/28/19 - 10/31/19
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US Cities and Canada - EXCLUSIVE up to $100 OFF per booking offer: Valid on new bookings made 7/22 - 9/15/19 for travel 7/22 - 12/31/19. Minimum 2-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.]