Keys Season Deals
“No worries” is kind of our whole thing.
Filters
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
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
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
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
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
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
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
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
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
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
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
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
Another Day in Paradise
Hyatt Vacation Club/Beach House -Stay four nights, your fourth consecutive night is free. Pay now.
Flexibility Promise
Another Day in Paradise
Hyatt Vacation Club/Windward Pointe -Stay four nights, your fourth consecutive night is free. Pay now.
Keys Season: Take Home Original Art
Key West Art Center & Gallery -"An Affordable Summer Collection at the Key West Art Center" Original Art within reach at $175.00, 10"X10" Original Paintings by 50+ Local Artists...
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...
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...
Happy hour
City Hall Cafe & Wine Bar -Half off all glasses of wine and all beers $10 happy hour menu from 3 PM to 6 PM every day
Perry Adventures
The Perry Hotel & Marina -Get up to 25% off our nightly rate at The Perry Hotel & Marina — and an exclusive consultation with our renown concierge, plus preferred pricing on...
Famous Martini & Meatball
Digiorgio's Cafe Largo -Sponsored with Grey Goose Vodka, experience a Grey Goose Martini with a homemade Meatball for only $10
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...
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...
Park & Play
Sun Outdoors Marathon -Enjoy more savings than you expect when you take advantage of our Park & Play Program. Just park your RV once, then leave it to come back and play as...
Rise and Shine
Marquesa Hotel -Drift away from reality to island time with a stay at the charming Marquesa Hotel nestled in Old Town. Enjoy daily breakfast for two in our award...
Countdown to Summer
The Islands of Islamorada -Whether it’s a relaxing getaway or an adventurous island vacation, our private villas provide the perfect home base for your summer memories. Secure...
Save a Sea Turtle, Sip Sustainably!
The Turtle Hospital -Make a splash for conservation! Join us for the Florida Keys Miles of Savings and help protect our oceans. Every paying adult admission to The Turtle...
30% off several waterfront rental homes and estates in Islamorada.
Island Villa Rental Properties -Take advantage of 30% savings on weekly and monthly stays and enjoy effortless living in Islamorada.
Unlimited use of paddle boards, kayaks, bicycles at no charge.
The Caribbean Resort -Free unlimited use of outdoor Watersport's, including fishing rods, paddle boards, bicycles, and kayaks.
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...
