Keys Season Deals
“No worries” is kind of our whole thing.
Filters
Flexibility Promise
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 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
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
Another Day in Paradise
Hyatt Vacation Club/Beach House -Stay four nights, your fourth consecutive night is free. Pay now.
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
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
Florida Dream Drive
Baker's Cay Resort -Escape to Baker’s Cay Resort & Enjoy: 20% off best available rate $50 daily resort credit to use on waterfront dining, sunset cocktails, and island...
Flexibility Promise
Another Day in Paradise
Hyatt Vacation Club/Windward Pointe -Stay four nights, your fourth consecutive night is free. Pay now.
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
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
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
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
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
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
End of Summer Deal
No Worries Concierge -25% Off ALL Package Concierge Services from 8/1/26-10/1/26
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
Book early for late summer & fall discounts
Wild Dolphin Tours -Book early and receive 10% off all Snorkeling and Sandbar Charters.
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
Monroe County Locals: 25% Off Dining
Four Marlins -There’s never been a better excuse to dine by the ocean. Monroe County locals can enjoy 25% off their entire check at Four Marlins Oceanfront Dining...
🐟 Fish All Day, Save 30% ☀️
Freewheeler Vacations -From sunrise casts to sunset cruises, your Upper Keys escape just got even better. Book now and enjoy 30% off your stay with Freewheeler Vacations...
Escape to Margaritaville Beach House Key West
Margaritaville Beach House Key West -Keys Season means exclusive savings—enjoy up to 25% off your stay at Margaritaville Beach House Key West. Relax in laid-back island luxury just steps...
$10 Summer Savings
Conch Tour Train -See the best of Key West on the tour that has showcased the island since 1958. Save $10 on Adult Admission aboard the World Famous Conch Tour Train...
Sunset Happy Hour
Bayside Grille -Enjoy Happy Hour Food & Drink with Live Music at the Most Photographed Sunset in Key Largo
Fly Into Fantasy Fest — Direct from FLL to Key West
Tropic Ocean Airways -Skip the traffic and the long drive down the Keys. Tropic Ocean Airways is now offering scheduled seaplane service from Fort Lauderdale straight to...
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...
Sweet Summer Savings At Island Bay Resort!
Island Bay Resort -Save on your reservation between June 10th, 2026, and September 14th, 2026! Stay 2 nights, save 10% on your stay. Stay 3 nights, save 15% on your stay...
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.
Keys Season Discount at Divers Direct
Divers Direct - Key Largo -$30 off $150 or more at Divers Direct Key Largo or Key West CODE: KEYSSZN26
Keys Season Specials
Sea Haven Realty -Off Season Special: Enjoy up to 20% off select vacation rentals for stays between August 1 and October 31.
UP TO 30% OFF WEEKLY STAY SAVINGS
Sun Outdoors Key Largo -Make your long weekend getaway into a full vacation for seven nights or more and enjoy great savings (up to 30% off*) at our participating resorts. It...
20% Wild Bird Hospital and Guided Sanctuary Tours
Florida Keys Wild Bird Center -Visit the Florida Keys Wild Bird Center and use offer code KeysSeason during check out for 20% off a Staff-Guided Sanctuary Tour or Behind-the-Scenes...
Park & Stay
Hyatt Centric Key West Resort and Spa -Make your Key West getaway even more effortless. With this exclusive offer, enjoy complimentary standard self-parking for one vehicle each night of...
Hot Summer Special
Coco Plum Inn -Book a 3-night stay June 1 - September 30, 2026, and receive a fourth night free. This offer cannot be combined with any other specials or promotions...
