SAVE $100 per booking on stays of 5 nights or longer
SAVE $75 per booking on stays of 4 nights
SAVE $50 per booking on stays of 2-3 nights
Book by 6/25/17 for travel through 10/31/17

All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more

Florida Vacation Packages

 from $479

ME Miami

 

Aura. Exclusive $50 OFF per booking. Stays of 5 nights or longer receive exclusive $100 OFF per booking. FREE Wi-Fi.

 

3 nights with air from $479

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Sanibel Sunset Beach Inn

 

Garden View. Exclusive $50 OFF per booking. Stays of 5 nights or longer receive exclusive $100 OFF per booking.

 

3 nights with air from $519

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South Seas Island Resort, Captiva

 

Harbourside Guest. Exclusive $75 OFF per booking. Stays of 5 nights or longer receive exclusive $100 OFF per booking. 4th night FREE. Kids 16 and younger stay FREE. Ask about 5th night FREE.

 

4 nights with air from $559

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The Confidante - By Hyatt

 

Standard. Exclusive $50 OFF per booking. Stays of 5 nights or longer receive exclusive $100 OFF per booking. Ask about kids stay FREE.

 

3 nights with air from $585

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Hilton Key Largo Resort

 

Canopy View King. Exclusive $50 OFF per booking. Stays of 5 nights or longer receive exclusive $100 OFF per booking. Kids 17 and younger stay FREE.

 

3 nights with air from $629

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Hyatt Centric Key West Resort and Spa

 

Deluxe King. Exclusive $50 OFF per booking. Stays of 5 nights or longer receive exclusive $100 OFF per booking. FREE Wi-Fi. Ask about kids stay FREE.

 

3 nights with air from $629

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Casa Marina, A Waldorf Astoria Resort

 

Guest Room. Exclusive $75 OFF per booking. Exclusive 4th night FREE. Stays of 5 nights or longer receive exclusive $100 OFF per booking. Kids 17 and younger stay FREE.

 

4 nights with air from $635

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Pink Shell Beach Resort and Marina, Ft. Myers

 

One-Bedroom. Exclusive $50 OFF per booking. Stays of 5 nights or longer receive exclusive $100 OFF per booking. Includes daily buffet breakfast for two. Includes one signature Pink Shell Beach tote, beach chairs and beach umbrellas.

 

3 nights with air from $665

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Rates are based on roundtrip air travel to/from Chicago (ORD) for Miami, Sanibel, Captiva, Key Largo, Key West and Ft. Myers, based on double occupancy. Advertised vacation rate(s) valid for departures 8/21/17 for Casa Marina, A Waldorf Astoria Resort and 8/22/17 for all other properties.
US Cities and Canada - SAVE up to $100 per booking: Valid on new bookings made 5/1 - 6/25/17 for travel 5/1 - 10/31/17. 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.]