Top Islamorada Hotel Deals

Make the Most of Your Islamorada Stay

Cultural heart of the Keys

Islamorada stretches across 6 islands in the heart of the Florida Keys, where the Atlantic meets Florida Bay in waters that have earned this village its reputation as the Sportfishing Capital of the World. The Morada Way Arts & Cultural District anchors the social scene with monthly art walks, while landmarks like the History of Diving Museum and Theater of the Sea reveal the area's maritime heritage. Upper Matecumbe Key serves as the sophisticated center, home to Cheeca Lodge and premier waterfront dining at Chef Michael's and Pierre's, where hook-to-cook seafood defines the culinary experience.

Island-hopping experiences

Each island offers distinct character. Windley Key's Fossil Reef Geological State Park preserves Henry Flagler's railroad quarry, while boat-access-only Indian Key Historic State Park protects 1800s ruins from the wrecking industry era. Robbie's Marina provides the quintessential Keys moment of hand-feeding massive tarpon from the dock. The village's low-profile architecture and tropical aesthetic create an atmosphere notably more relaxed than Key West, appealing to travelers seeking nature-focused luxury over nightlife energy.

Strategic Keys location

Islamorada's position makes it an ideal base for exploring the wider Keys, with Key Largo's coral reefs 25 minutes north and Key West 90 minutes south. Miami International Airport lies 90 miles north, with shuttle services providing direct connections to the village's accommodations.

Frequently Asked Questions about Islamorada

Can I use my miles on Delta Stays to book hotels in Islamorada?

Yes, you can use your Delta miles for your hotel reservation in Islamorada, or you can opt for a miles-plus-cash combination to provide more booking options. When you log in to your Delta SkyMiles® account, you will also discover Member offers at select properties that could enhance your travel experience.

What is the benefit of booking my Islamorada hotel directly on Delta Stays?

As a SkyMiles Member, you will earn 2 miles per $1 spent on completed hotel stays and vacation rentals reserved through Delta Stays. Plus, you will receive access to Member promotions at select properties, along with the option to complete payment using miles, cash, or a combination. Simply sign in to your SkyMiles account or enter your SkyMiles number at checkout when paying with cash to ensure you earn your miles. Please allow up to 8 weeks after completing a stay for miles to appear in the SkyMiles account provided. Please also note that if you use miles to pay for any portion of your stay, you will not earn miles on that reservation, including any amount paid with cash.

Is it possible to change or cancel my hotel booking made through Delta Stays?

Cancellation policies differ depending on the property you choose. We suggest reviewing the cancellation policies displayed in the detailed information for each hotel before completing your reservation. You'll find that some rates are refundable, while others are non-refundable. Please note that if you make changes to or cancel your booking, this may affect the number of miles you earn and receive in your account.

Can I use my Delta SkyMiles® American Express® Card to book?

Your Delta SkyMiles® Gold, Platinum, or Reserve American Express® Card offers enhanced mileage earning potential along with a suite of benefits, including an annual statement credit up to $200 that can be utilized for prepaid accommodations when booking through Delta Cars and Stays. These offers are subject to specific terms and conditions. For an overview of all advantages associated with your card membership, please visit the Delta SkyMiles® American Express Credit Cards page where you can review complete benefit details.

Can I earn MQDs on Delta Stays hotel bookings?

From time to time, Delta Stays may present special opportunities for SkyMiles Members to earn Medallion® Qualification Dollars on their hotel and vacation rental bookings made through Delta Stays. We recommend accessing the Delta Stays MQD Offer page to view current MQDs promotions and examine their terms and conditions.

Do I need to have a Delta SkyMiles account to book hotels on Delta Stays?

No, Delta Stays is available to everyone for hotel bookings. However, by becoming a SkyMiles Member, you will unlock the ability to earn miles and access Member-only prices and offers. As a Member, you will earn 2 miles per $1 you spend on Delta Cars and Stays (excluding taxes and additional charges). Plus joining SkyMiles is free. Become a Member today by visiting the delta.com.

On Delta Stays, can I book a vacation rental?

Yes, beyond traditional hotels, Delta Stays provides an extensive collection of vacation rentals for your travel needs. Explore the variety of homes, condos, and unique accommodations powered by Vrbo on the Vacation Rentals page.

What hotels in Islamorada have high ratings?

In Islamorada, you’ll find 24 hotels to choose from when you book on Delta Stays. Chesapeake Beach Resort has a guest rating of 9.2 out of 10, and features a private beach and 2 outdoor pools. Another top-rated resort is Cheeca Lodge & Spa and guests enjoy its 3 outdoor pools. Amara Cay Resort has a rating of 8.8 including good ratings for the outdoor pool. The resort has a private beach and an ocean-view restaurant.

What is a good area in Islamorada to book for my trip?

Islamorada is home to a variety of fascinating neighborhoods that appeal to travelers and locals.

Matecumbe delivers authentic Keys living where you can snorkel crystalline waters at Anne's Beach, feed tarpon at Robbie's, and sip craft beer at Florida Keys Brewing Co. after exploring the Hurricane Monument and MoradaWay Arts District. Popular places to stay in the area include Cheeca Lodge & Spa and Amara Cay Resort.

What's a good time of year to visit Islamorada?

To experience Islamorada during great weather, consider a visit between December and April when temperatures are warm with sunny skies and low humidity. For off-peak prices and fewer crowds, consider visiting from late August through October when rates drop significantly, though you'll want to stay flexible and monitor hurricane forecasts.

What hotels in Islamorada are located closest to Anne's Beach?

Anne's Beach offers shallow, clear waters and a scenic boardwalk winding through mangroves. Visit during low tide for more beach space to explore the Florida Keys coastline. Cheeca Lodge & Spa is a popular hotel, which is just a short drive away. Islander Resort is another well-reviewed hotel and it is within a short drive.

What hotels in Islamorada are near Florida Keys Brewing Co.?

The Upper Keys' first microbrewery crafts island-inspired beers with Key lime and honey flavors. Sip seasonal brews in the art-filled taproom or lush beer garden with live music. Popular hotels include Cheeca Lodge & Spa which is steps away. Islander Resort is another well-reviewed hotel and it is also close by.

What hotels in Islamorada are located closest to Islamorada County Park?

This 40-acre waterfront retreat features a bayfront beach, marina, and scenic trails with exercise stations. Cool off in the community pool or explore the specialized dog parks. Cheeca Lodge & Spa is a popular hotel, which is just a short drive away. Another top hotel is Islander Resort and it is within a short drive.

What 4- and 5-star/luxury hotels can I find in Islamorada?

Islamorada offers many notable luxury hotels. At Cheeca Lodge & Spa, guests love the 3 outdoor pools. To explore luxury stays in other destinations, visit the Luxury Stays page.

*Terms and conditions:

Mileage Offer:

SkyMiles Members will earn two (2) miles per US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Opens in a new window on the base hotel rate for a completed hotel stay. Base hotel rate is the cost of the hotel room, before taxes and fees, charged at the time of booking or upon checkout. Taxes and fees, gratuities, room service other booking charges, or any bookings which are paid or reduced by miles, redemption vouchers or discount codes are excluded from mileage credit. For clarity, if miles are used as a form of payment (whether for all or a portion of the booking), no portion of the booking will be eligible to earn miles under this offer. Except with respect to the Hertz Mileage offer (listed below), SkyMiles Members will earn two (2) miles per eligible US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Cars on the base car rental rate for a completed car qualifying rental booking (“Qualifying Dollars”). A qualifying rental booking includes rentals at a participating location for one or more days at rates other than travel industry rates or discounts, wholesale of tour package rates or discounts, wholesale tour package rates, insurance/dealer replacement rates, corporate and government rates, group travel discounts, or rentals in conjunction with a frequent flyer car award, or other corporate agreements applicable to the respective car company. Calculation of the applicable standard mileage offer is listed below by car rental company. Qualifying Dollars include the base car rental rate, which is the cost of the car rental before taxes and fees, charged at the time of booking. Taxes, fees, other incidental charges, or other booking charges or any bookings which are paid or reduced by redemption vouchers or discount codes are excluded from mileage credit and are not included in the Qualifying Dollars.

This mileage offer does not apply to stays or car rentals booked through Delta Vacations or any cruises booked through Delta Cruises.

Standard mileage offer for car rentals booked at https://www.delta.com/Opens in a new window or https://carsandstays.delta.com/Opens in a new window:

Hertz Reservations:

• General SkyMiles Members earn 4 miles per Qualifying Dollar

• Silver Medallions earn 5 miles per Qualifying Dollar

• Gold Medallions earn 6 miles per Qualifying Dollar

• Platinum Medallions earn 7 miles per Qualifying Dollar

• Diamond Medallions earn 8 miles per Qualifying Dollar

Dollar and Thrifty Reservations:

• All SkyMiles Members earn 4 miles per Qualifying Dollar

Alamo, Enterprise, National, Avis, Budget, Payless and SIXT Reservations:

• All SkyMiles Members earn 2 miles per Qualifying Dollar