Your Islamorada vacation
From family vacations to last-minute romantic getaways, make Orbitz your first and only stop for Islamorada vacations. You can customize your trip with flights, hotels and activities to match your travel plans and tastes. Sweeten the pot with extra savings when you book your flight and hotel together.
Create your own Islamorada travel plans
Build your own Islamorada vacation itinerary. Choose a flight that matches your schedule and a hotel with the amenities you need. Book them together for extra discounts you won't find when booking separately.
Find Islamorada travel discounts
Be the first to know about exclusive offers and last-minute deals on Islamorada travel. Sign for our deals e-mail , or follow us on Twitter and Facebook for promo codes, discounts and more. Our global network of travel experts find big-time savings and travel deals just for you.
Get Islamorada travel support 24/7
Reach out to an Orbitz travel specialist for Islamorada vacation assistance. Our specialists are available around the clock at 1-800-504-3248. We can even help with last-minute Islamorada vacations.
Sign up for free Islamorada travel alerts
Make travel plans smoother with Orbitz Care Alerts. Receive real-time info about flight delays, weather and other events via phone, e-mail or text. Keep up to six other people in the loop with travel alerts, too.
Scope out your Islamorada vacation options and savings
With the Orbitz Matrix Display, you can view all your flight and hotel options quickly. Plus, you'll see what you can save on your travel packages when you book them together.
Islamorada Vacation Packages
Luxury guest rooms, fine dining, private-beach location in IslamoradaCheeca Lodge & Spa sits on 27 oceanfront acres of Upper Matecumbe Key in the village of Islamorada. It's located 78 miles from Miami International Airport and 80 miles from Key West. For 55 years,... More
Comfortable, kitchen-equipped rooms on private beach in IslamoradaDesigned with vintage 1950s flavor, the Islander Resort offers cottage-style rooms and suites in Islamorada. Located among the palm trees on more than 25 acres of oceanfront property, the resort boasts a... More
A full tropical experience with water-based sports and heated pool La Siesta Resort & Marina in Florida is on a natural, usually full beach, but there are plenty of activities to take advantage of within the hotel itself, from the poolside Cantina grill to the fully... More
84001 Overseas Highway Map
Marina and Florida Keys accommodations on a lively beachfront The Holiday Isle Resorts & Marina offers the classic Florida Keys experience of cocktails and marina life with great views across the ocean. With a busy beachfront, outdoor tiki bar and a thriving marina... More
84457 Old Overseas Highway Map
Winter Sale, Save 15% Off
Every one of our tropical standards and suites captures a breathtaking water view. Relax on your private balcony that overlooks either the magnificent Atlantic Ocean or Pelican Coves own sheltered marina. Additionally, our efficiencies include fully equipped kitchens.At... More
the key to hospitality...welcome to the Hampton Inn & Suites Islamorada. The Islamorada village of islands in the Florida Keys beckons fishermen, honeymooners and nature-lovers with its bountiful oceanic splendor, warm tropical nights, and ecological treasures. The... More
Ocean-view rooms and villas on Islamorada beachChesapeake Beach Resort rests on 6.5 acres of oceanfront beach and gardens, located in Islamorada, halfway between Miami and Key West. Newly remodeled, the resort offers state-of-the-art amenities and luxurious accommodations... More
Situated in the heart of Islamorada halfway between Miami and Key West The Moorings is an 18-acre property harboring 18 cottages and homes on what was once a coconut plantation. Ranging from one to three bedrooms each residence is self-sufficient with its own well... More
Cottages, suites and duplexes in a tropical setting on the Atlantic Ocean in Islamorada. Each one-bedroom unit comes with a king or queen bed, a fully equipped kitchen, living room with sofa bed and patio or balcony. Tastefully decorated with tropical style furniture. Two... More