Keys Season Deals
“No worries” is kind of our whole thing.
Filters
Flexibility Promise
Affordable Rates, Clean Rooms, and a Free Night Too!
Blue Fin Inn -Welcome to beautiful Islamorada and the Blue Fin Inn, where affordable accommodations, friendly service, and the laid-back charm of the Florida Keys...
Flexibility Promise
Another Day in Paradise
Hyatt Vacation Club/Beach House -Stay four nights, your fourth consecutive night is free. Pay now.
Flexibility Promise
Sip, Sail, & Save
Islamorada Luxe Charters -Enjoy 20% off any half-day charter or longer with Islamorada Luxe Charters, plus your choice of a complimentary charcuterie board or tropical fruit...
Flexibility Promise
Book early for late summer & fall discounts
Wild Dolphin Tours -Book early and receive 10% off all Snorkeling and Sandbar Charters.
Flexibility Promise
Keys Season Discount
Ibis Bay Beach Resort -Book 3 nights between August 1st, 2026 and October 31st, 2026 and get 25% off your stay. Offer not valid during holidays or special events. Offer only...
Flexibility Promise
Conchiglia Summer Weekly Program
Conchiglia Key West -Enjoy Conchiglia’s Summer Weekly Program in the heart of Key West, featuring special Italian dining experiences throughout the week: Monday Margarita...
Flexibility Promise
Stay 2 Nights, Get The 3rd Night Free
Banana Bay Resort Marathon -Limited-time offer! Make your next island escape last a little longer. At Banana Bay Resort & Marina, when you stay two nights, your third night is...
Flexibility Promise
Keys Season Special
Flamingo Lodge and Restaurant -Keys Season Special Stay between August and October and receive up to 20% off the nightly rate on lodge rooms. Blackout dates apply.
Flexibility Promise
Flexibility Promise
Stay More, Save More
Coconut Palm Inn -Make your Florida Keys escape last a little longer at Coconut Palm Inn & Marina. Book a weekday stay (Sunday–Thursday) between June 10 & October 31...
Flexibility Promise
Another Day in Paradise
Hyatt Vacation Club/Windward Pointe -Stay four nights, your fourth consecutive night is free. Pay now.
Flexibility Promise
Your Inns, Your Island.
Key West Historic Inns -Pick Your Perks*: pick 2 - Reduced GAF from $45 to $25 - Complimentary upgrade for VIP, including complimentary welcome amenity - Complimentary 1 hour...
Flexibility Promise
Old Florida Charm Starting at Just $75 a Night
Key Lantern -Welcome to the Key Lantern Motel, where friendly service, clean accommodations, and classic Old Florida charm make every stay enjoyable. Escape to...
Flexibility Promise
One Night Free--Stay 7, pay for 6 nights
Key Lantern -Welcome to Key Lantern Motel, where friendly service, clean and comfortable rooms, and classic Old Florida charm create a relaxing home away from home...
Flexibility Promise
Weekday Specials Starting at Just $75!
Blue Fin Inn -Escape to beautiful Islamorada without breaking the budget. Sunday through Thursday, enjoy rates from just $75 to $85 per night for one or two guests...
Flexibility Promise
One More Night of Islander Life - Third Night Free
Islander Resort -There’s a moment in every stay when you wish you had just one more day. One more morning by the water, one more afternoon in the sun, one more evening...
Flexibility Promise
FREE Sail Boats, Kayaks, Canoes, Paddleboards, Fishing/Snorkel Gear, Bicycles with Cottage Rental
Key Lime Sailing Club and Cottages -🌴 STAY. SAIL. PADDLE. EXPLORE. — IT’S ALL INCLUDED! ⛵ At Key Lime Sailing Club & Cottages, your cottage rental is more than just a place to stay
$250 Off per stay!
Oasis Beach House -Offering $250 off per weekly stay booked in this time period.
WOW Wednesdays, (Wine on Wednesdays)
Digiorgio's Cafe Largo -Beat the Clock with Veuve Cliquot. Glasses of Veuve priced by the hour, starting at 5pm Half-price bottles of wine - great way to try that bottle you...
August Sun or October Fun? Save $25 Either Way!
Yankee Freedom Dry Tortugas Ferry -Ready to tick a massive bucket-list adventure off your list without emptying your wallet? If you book your tropical escape aboard the Yankee Freedom...
26/27 Season Show Ticket Packages
Marathon Community Theatre & Cinema -Available July 1, 2026- June 30, 2027 Purchase a season membership and get 20% off 4 show or 3 show ticket package as well as membership perks.
Twisted Happy Hours
Twisted Shrimp -Happy Hour Special Join us from 4–6 PM and enjoy select seafood favorites at special prices, plus 2-for-1 beer and wine. Perfect for a quick bite...
Keys Season Special
Flamingo Lodge and Restaurant -During Keys Season take a 90 minute trip into the Backcountry of Everglades National Park! Venture up the Buttonwood Canal through Coot Bay and Tarpon...
Stay Longer, Save More
Havana Cabana -Extend your time in paradise and your savings. Enjoy 15% off stays of 3–4 nights or 20% off stays of 5 nights or more at Havana Cabana.
2026 Vacation Pass Booklet
Key West Attractions Association -The 2026 Key West Vacation Pass Coupon Book is your all-in-one savings guide to experiencing the best of Key West for less. Packed with exclusive...
Culinary Escape
Tranquility Bay Beachfront Resort -Enjoy tasty savings and experience authentic Florida Keys cuisine at Tranquility Bay Beachfront Resort. Receive $50 per night dining credit for use at...
Keys Season
Key West Historic Inns -Book 2 nights, get 3rd @ 50% off + $50 Visa Gift Card and $50 Resort Credit
THE BEST & ORIGINAL KEY WEST HAPPY HOUR
Half Shell Raw Bar -Since 1972 at Half Shell Raw Bar Gulfside at the Key West Bight Marina Join us 7 days a week from 4:30 PM – 6:30 PM 50% OFF all Starters 30% OFF...
Summer in the Keys
DoubleTree Resort by Hilton Grand Key - Key West -Slip away to DoubleTree Grand Key Resort Key West by Hilton and enjoy up to 20% off stays of 3 nights or more, plus complimentary daily parking. From...
Taste The Keys
Taste The Keys -Taste the Keys is a month-long culinary event held October 1–31 at participating restaurants throughout Key Largo and the Upper Florida Keys. Locals...
Discover Key Largo
Courtyard by Marriott Key Largo -Discover Key Largo, includes 20 percent off Sundries @ The Market coupon, Local Souvenir
