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Islamorada Vacations

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

Room 1
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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.

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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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Scope out your Islamorada vacation options and savings
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Islamorada Vacation Packages

Hotel only $179

1 Cheeca Lodge and Spa

5 stars
4.2 / 5 64 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 $127

2 Islander Resort, a Guy Harvey Outpost

3 stars
3.8 / 5 64 reviews

82100 Overseas Highway Map

Save 15%

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 $129

3 Islamorada Resort

3 stars
3.3 / 5 9 reviews

80001 Overseas Highway Map

Stay 4 Nights Save 20%

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 $156

4 Islander Bayside

3 stars
Not yet reviewed

81450 Overseas Highway Map

Save 15% On Your Stay!

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 $169

5 Chesapeake Resort

3 stars
3.5 / 5 29 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

Hotel only $149

6 La Siesta Resort and Marina

3 stars
3.7 / 5 19 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 $149

7 Postcard Inn Beach Resort & Marina at Holiday Isle

4 stars
3.6 / 5 83 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 $109

8 Pelican Cove Resort and Marina

4 stars
3.7 / 5 43 reviews

84457 Old Overseas Highway Map

Stay 4 nights Save 20%

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 $399

9 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 $299

10 Casa Morada

3 stars
4.7 / 5 3 reviews

136 Madeira Road Map

Guests of Casa Morada enjoy the seclusion of a private tropical island but are only minutes away from some of the best dining and outdoor activities in the Florida Keys. More