Keys Season Deals
“No worries” is kind of our whole thing.
Filters
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 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
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
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
End of Summer Deal
No Worries Concierge -25% Off ALL Package Concierge Services from 8/1/26-10/1/26
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
Flexible Escape Offer
Hawks Cay Resort -Enjoy 25% off your stay plus a $50 nightly resort credit to put toward dining, spa treatments, or anything else that makes you forget your inbox...
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
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
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
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
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 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
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
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
Book early for late summer & fall discounts
Wild Dolphin Tours -Book early and receive 10% off all Snorkeling and Sandbar Charters.
UP TO 30% OFF WEEKLY STAY SAVINGS
Sun Outdoors Marathon -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...
$100 OFF
Bean Sportfishing -Enjoy $100 off all Charters with Capt. Bean in the Sportfishing Capital of Islamorada from July 1st until October 31st. Price includes bait, tackle...
Keys Season - Delivery Free
Provisions Ahead -It’s Keys Season! Book your Premium Pre-Arrival Grocery Delivery for anytime between August 15th and October 31st and we’ll waive our $59 Delivery Fee...
Dine & Unwind Special at Little Limon Rooftop
Little Limón -Elevate your evening at Little Limon Rooftop, where sweeping Atlantic Ocean views meet bold Asian‑fusion flavors and a vibrant raw bar in the heart of...
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...
Kids Eat Free at ReelCatch in Islamorada
ReelCatch -Make Tuesday nights a family favorite at ReelCatch, where great food and coastal vibes come together. Kids 12 and under eat FREE every Tuesday night...
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...
Endless Blue
Ocean Key Resort & Spa -Indulge in luxury accommodations and the very best oceanfront views on the island at the newly reimagined Ocean Key Resort & Spa. Start each morning...
Dive Together – 50% Off 2nd Diver
Southpoint Divers -Buy one afternoon reef dive, get your second dive 50% off. .
La Dolce Vita Happy Hour
Digiorgio's Cafe Largo -Experience a Taste of Italy at Key Largo's Premier Italian restaurant for Happy Hour. Key Largo's most extensive food items for Happy Hour with an...
VISIT FLORIDA KEYS
The Gardens Hotel & Cottages d'vine Wine Gallery -4th Night Free! Restrictions: Valid Sunday through Thursdays, New Reservations Only, Not Valid Oct 21 - 24, 2026
Hot Summer Special
Ambrosia Key West -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...
World‑Famous Tiki Bar Rum Runner Rendezvous
Tiki Bar at Three Waters Resort & Marina -Ease into island time at the world‑famous Tiki Bar, where tropical vibes, ocean breezes, and legendary cocktails set the scene. Available daily from 3...
Visit the Florida Keys without the FEES!
Courtyard by Marriott Key West Waterfront -NO RESORT FEES & NO PARKING FEES, Escape the crowds and experience Key West as it was meant to be—relaxed, tropical, and unforgettable. Courtyard by...
🐟 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...
