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.
 

FREE 3-Day Midsize Hertz Car Rental at ALL Arizona, California & Florida Hotels and Resorts

  • Book by 11/10/19 for travel through 3/30/20
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
  • Universal's Endless Summer Resort - Surfside Inn and Suites
    Universal's Endless Summer Resort - Surfside Inn and Suites
    Universal Studios, Orlando Our 3-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.

    Exclusive Theme Park Benefits. At Universal Orlando's first Value property, guests will enjoy the casual, free-spirited lifestyle of surf culture while enjoying an extra affordable Universal Orlando vacation.
    • Standard Two Queens
    • FREE 3-Day Mid-Size Hertz Car Rental
    • Exclusive Theme Park Benefits

    3 nights with flight from $280+

    Boston, MA (BOS) departures, valid for travel 12/02/19 - 12/05/19
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  • Sheraton Vistana Resort Villas Lake Buena Vista/Orlando
    Sheraton Vistana Resort Villas Lake Buena Vista/Orlando
    Universal Studios, Orlando 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 family-oriented resort is nestled in a lush tropical setting, just minutes from Walt Disney World® Theme Parks.
    • One Bedroom Villa
    • FREE 3-Day Mid-Size Hertz Car Rental

    3 nights with flight from $310+

    Boston, MA (BOS) departures, valid for travel 12/02/19 - 12/05/19
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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.

    • Traditional Two Doubles
    • FREE 3-Day Mid-Size Hertz Car Rental

    3 nights with flight from $460+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 12/16/19 - 12/19/19
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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
    • FREE 3-Day Mid-Size Hertz Car Rental

    3 nights with flight from $488+

    Houston, Texas (IAH) departures, valid for travel 12/02/19 - 12/05/19
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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.
    • King Deluxe
    • FREE 3-Day Mid-Size Hertz Car Rental

    3 nights with flight from $492+

    Houston, Texas (IAH) departures, valid for travel 12/02/19 - 12/05/19
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  • South Seas Island Resort
    South Seas Island Resort
    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
    • FREE 3-Day Mid-Size Hertz Car Rental

    3 nights with flight from $504+

    Boston, MA (BOS) departures, valid for travel 12/02/19 - 12/05/19
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  • Fort Lauderdale Marriott Pompano Beach Resort & Spa
    Fort Lauderdale Marriott Pompano Beach Resort & Spa
    Pompano 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.

    Memories of a vacation with a wide range of watersports and beach activities await at this award-winning hotel featuring accommodations with private balcony ocean views.
    • Two Queens
    • FREE 3-Day Mid-Size Hertz Car Rental

    3 nights with flight from $507+

    Newark, New Jersey (EWR) departures, valid for travel 12/02/19 - 12/05/19
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  • Hilton Cabana Miami Beach
    Hilton Cabana Miami Beach
    Miami 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.

    Escape to this beachfront hotel with direct access to the Atlantic Ocean and Intracoastal Waterway views, located on famed Collins Avenue and four miles to South Beach.

    • King
    • FREE 3-Day Mid-Size Hertz Car Rental

    3 nights with flight from $583+

    Newark, New Jersey (EWR) departures, valid for travel 12/02/19 - 12/05/19
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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
    • FREE 3-Day Mid-Size Hertz Car Rental

    3 nights with flight from $640+

    Boston, MA (BOS) departures, valid for travel 12/02/19 - 12/05/19
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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
    • FREE 3-Day Mid-Size Hertz Car Rental
    • Daily $25 resort credit per room

    3 nights with flight from $661+

    Newark, New Jersey (EWR) departures, valid for travel 12/02/19 - 12/05/19
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  • Hyatt Regency Sarasota
    Hyatt Regency Sarasota
    Lido 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 resort-style hotel in Sarasota is just minutes from the spectacular white-sand beaches of the Gulf of Mexico.

    • Balcony King
    • FREE 3-Day Mid-Size Hertz Car Rental

    3 nights with flight from $709+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 12/02/19 - 12/05/19
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  • The Resort at Longboat Key Club
    The Resort at Longboat Key Club
    Sarasota 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 magnificent resort features white sand beaches, world-class amenities and a wide array of delicious dining options.
    • Junior Suite Golf View
    • FREE 3-Day Mid-Size Hertz Car Rental

    3 nights with flight from $727+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 12/09/19 - 12/12/19
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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.

    • Non Water View Two Queens
    • FREE 3-Day Mid-Size Hertz Car Rental

    3 nights with flight from $761+

    Boston, MA (BOS) departures, valid for travel 12/02/19 - 12/05/19
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  • Marriott Palm Beach Singer Island Resort & Spa
    Marriott Palm Beach Singer Island Resort & Spa
    Singer Island 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
    • FREE 3-Day Mid-Size Hertz Car Rental
    • Reduced rates

    3 nights with flight from $844+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 12/02/19 - 12/05/19
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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.
    • One Bedroom Suite with Balcony
    • FREE 3-Day Mid-Size Hertz Car Rental

    3 nights with flight from $898+

    Newark, New Jersey (EWR) departures, valid for travel 12/02/19 - 12/05/19
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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.
    • King
    • FREE 3-Day Mid-Size Hertz Car Rental
    • Daily breakfast included

    3 nights with flight from $923+

    Newark, New Jersey (EWR) departures, valid for travel 12/02/19 - 12/05/19
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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.

    • Resort View Queen
    • FREE 3-Day Mid-Size Hertz Car Rental

    3 nights with flight from $984+

    Boston, MA (BOS) departures, valid for travel 12/02/19 - 12/05/19
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  • The Ritz-Carlton Sarasota
    The Ritz-Carlton Sarasota
    Sarasota-Bradenton, Florida 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.

    Experience the signature sunset celebration at this luxury waterfront resort. There's fun for the entire family with Ritz-Kids® activities, Beach Club and Golf Club access.

    • Resort View King
    • FREE 3-Day Mid-Size Hertz Car Rental

    3 nights with flight from $1180+

    Chicago O'Hare, Illinois (ORD) departures, valid for travel 12/02/19 - 12/05/19
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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 Bay View
    • FREE 3-Day Mid-Size Hertz Car Rental
    • Daily $25 resort credit per room

    3 nights with flight from $1190+

    Newark, New Jersey (EWR) departures, valid for travel 12/02/19 - 12/05/19
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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
    • FREE 3-Day Mid-Size Hertz Car Rental

    3 nights with flight from $1696+

    Oahu, Honolulu, HI (HNL) departures, valid for travel 12/02/19 - 12/05/19
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US Cities - EXCLUSIVE 3-Day Mid-Size Hertz Car Rental Offer: Valid on new bookings made 9/16 - 11/10/19 for travel 9/16/19 - 3/30/20. Roundtrip airfare and minimum 3-night stay at any hotel or resort in Pleasant Holidays’ Arizona, California or Florida portfolio. 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.]