Islamorada Vacations

Hotel options

Hotel stay must be within date range of Leave and Return.

Room 1
*Ages of children at time of trip (for pricing, discounts)


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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.

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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

Hotel only $159

1 Cheeca Lodge and Spa

5 stars
4.3 / 5 80 reviews

81801 Overseas Hwy Map

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

Hotel only $154

2 Pelican Cove Resort and Marina

4 stars
3.9 / 5 57 reviews

84457 Old Overseas Highway Map

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. At Pelican Cove, year-round sunshine assures plenty of outdoor... More

Hotel only $129

3 Postcard Inn Beach Resort & Marina at Holiday Isle

4 stars
3.7 / 5 100 reviews

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

Hotel only $129

4 La Siesta Resort and Marina

3 stars
3.7 / 5 24 reviews

80241 Overseas Hwy Map

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

Hotel only $509

5 The Moorings Village and Spa

3 stars
Not yet reviewed

123 Beach Road Map

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

Hotel only $159

6 Pines and Palms Resort

3 stars
4.3 / 5 15 reviews

80401 Old Highway Map

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

Hotel only $242

7 Amara Cay Resort

3 stars
3.3 / 5 9 reviews

80001 Overseas Highway Map

Anchored in the laid-back style and carefree atmosphere that make Islamorada the sport fishing capital of the world, the new Islamorada Resort introduces a new level of luxury to the Upper Keys. With hammocks dotting a sandy shoreline, palm trees surrounding a shimmering... More

Hotel only $209

8 Islander Bayside

3 stars
4.0 / 5 1 reviews

81450 Overseas Highway Map

Guests of Islander Bayside are welcome to enjoy the amenities of our sister property Islander Resort, located at mile marker 82.1 on the ocean side. Islander Resort has two pools, a Jacuzzi, 1100 feet of coral sand beach and an amazing restaurant called Blue Water Tiki... More

Hotel only $199

9 Islander Resort, a Guy Harvey Outpost

3 stars
3.8 / 5 71 reviews

82100 Overseas Highway Map

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

Hotel only $143

10 Chesapeake Resort

3 stars
3.5 / 5 33 reviews

83409 Overseas Highway Map

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

  • Promo Code Terms and Conditions

    Book a qualifying 4-night flight + hotel vacation package between January 1, 2014 12:00AM CST and June 30, 2015 11:59PM CST, for $1000 or more for travel between January 1, 2014 and September 30, 2015 via Orbitz and instantly receive $150 off the hotel portion of your booking through the use of the promotion code. Limit one discount per hotel room and one promotion code per booking. Discounts are not redeemable for cash for any reason. Promotion codes cannot be resold. Any attempt at fraud will be prosecuted to the fullest extent of the law. Void where prohibited, taxed or restricted. Orbitz reserves the right to change or limit the promotion in its sole discretion. Promo code not valid for Las Vegas, NV bookings.

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