Long bridge stretches over turquoise ocean under a blue sky.

Keys Season Deals

“No worries” is kind of our whole thing.

From August 1 through October 31, The Florida Keys & Key West opens up in the best way with fewer crowds, real experiences and more ways to save. Book now and get great offers on the best of The Keys, all with the peace of mind that comes with our flexibility promise — free cancellation and storm protection. So you can plan with confidence, knowing you’re covered, in the event you need to make a change.

Flexibility Promise

Book early for late summer & fall discounts

Wild Dolphin Tours Jul 1, 2026 - Oct 31, 2026

Book early and receive 10% off all Snorkeling and Sandbar Charters.

Flexibility Promise

Monroe County Locals: 25% Off Dining

Four Marlins Aug 1, 2026 - Sep 30, 2026

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...

Flexibility Promise

FREE Sail Boats, Kayaks, Canoes, Paddleboards, Fishing/Snorkel Gear, Bicycles with Cottage Rental

Key Lime Sailing Club and Cottages Sep 3, 2026 - Oct 15, 2026

🌴 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

Old Florida Charm Starting at Just $75 a Night

Key Lantern Aug 9, 2026 - Dec 17, 2026

Welcome to the Key Lantern Motel, where friendly service, clean accommodations, and classic Old Florida charm make every stay enjoyable. Escape to...

Flexibility Promise

Sip, Sail, & Save

Islamorada Luxe Charters Aug 1, 2026 - Oct 31, 2026

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

Stay 2 Nights, Get The 3rd Night Free

Banana Bay Resort Marathon Jun 10, 2026 - Oct 31, 2026

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

Stay More, Save More

Coconut Palm Inn Aug 1, 2026 - Oct 31, 2026

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 May 4, 2026 - Oct 31, 2026

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 Jun 1, 2026 - Dec 31, 2026

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

Buy the Boat Sunset Cruise

Morning Star Sailing Charters Sep 3, 2026 - Oct 15, 2026

Sunset cruise for up to 6 guest $300 off

Flexibility Promise

Florida Dream Drive

Baker's Cay Resort Jul 1, 2026 - Sep 30, 2026

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 May 4, 2026 - Oct 31, 2026

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

Keys Season Special

Flamingo Lodge and Restaurant Aug 1, 2026 - Oct 31, 2026

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

Your Inns, Your Island.

Key West Historic Inns Aug 1, 2026 - Oct 31, 2026

Pick Your Perks*: pick 2 - Reduced GAF from $45 to $25 - Complimentary upgrade for VIP, including complimentary welcome amenity - Complimentary 1 hour...

Flexibility Promise

End of Summer Deal

No Worries Concierge Aug 1, 2026 - Oct 1, 2026

25% Off ALL Package Concierge Services from 8/1/26-10/1/26

Flexibility Promise

Another Day in Paradise

Hyatt Vacation Club/Beach House May 7, 2026 - Dec 31, 2026

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 Jun 1, 2026 - Dec 31, 2026

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 Aug 9, 2026 - Dec 17, 2026

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

Conchiglia Summer Weekly Program

Conchiglia Key West Sep 1, 2026 - Oct 15, 2026

Enjoy Conchiglia’s Summer Weekly Program in the heart of Key West, featuring special Italian dining experiences throughout the week: Monday Margarita...

Flexibility Promise