A beach with white lounge chairs, a covered pavilion, and palm trees.

Find 5 Star Hotels in Islamorada, FL from $211

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Check availability on Islamorada 5 Star Hotels

Tonight
Sep 17 - Sep 18
Tomorrow
Sep 18 - Sep 19
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Islamorada 5-star hotels

Balcony
Premium bedding, in-room safe, desk, laptop workspace
Property grounds
Lobby

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
RAIBEL
$187 nightly
$211 total
Sep 30 - Oct 1
Total with taxes and fees
Cheeca Lodge & Spa
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Islamorada.
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

97000 Overseas Hwy Key Largo FL
$286 nightly
$322 total
Sep 28 - Sep 29
Total with taxes and fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
$206 nightly
$232 total
Sep 20 - Sep 21
Total with taxes and fees
Amara Cay Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

84001 Overseas Hwy Islamorada FL
$264 nightly
$297 total
Sep 24 - Sep 25
Total with taxes and fees
9/10 Wonderful! (272 reviews)
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Islamorada

The turquoise waters between the Keys offer world-class fishing that even beginners can enjoy with knowledgeable local guides. Spend mornings snorkeling coral reefs teeming with tropical fish, then unwind at waterfront restaurants where chefs cook your fresh catch.

See all hotels in Islamorada
A wooden pier extending into the sea with a gazebo at the end.

Top Islamorada Hotel Reviews

Find out more about Islamorada

There's nothing wrong with enjoying the finer things in life. Why not ask for complete opulence during your holiday to Islamorada? There's no reason to delay a getaway to Islamorada any longer. You'll join the multitudes of vacationers who have made Islamorada so fashionable in the last few seasons. Additionally, the hotels in this area receive high marks for customer service, so you know you'll be looked after during your getaway. You deserve an outstanding getaway. Reserve one of our 5-star hotels in Islamorada and indulge in the finer things in life for a while.

5-Star Hotels in Islamorada

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Spa treatments, delicious meals, and attentive guest service are all waiting for you. You're sure to find exactly the accommodation you need. We should also mention, the hotels in this area receive high marks for customer satisfaction, so you know you'll be looked after during your getaway. How do you want to relax? A body scrub that will leave you feeling outstanding? 24-hour room service, so you can order that filet mignon in the wee hours of the morning? A Swedish massage to help your cares fall away? Don't want to take our word for it? Then explore the 853 reviews various guests have left on Expedia and get to know these places.

You won't sleep and order room service the entire time, though. We've got you covered. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Islamorada are the perfect place to relax after an exciting day.

Your Getaway Starts Today

The results are in, and Islamorada 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. Don't put off your dream vacation any longer -- Expedia can help you land a great deal on accommodation. Pick out one of Expedia's Islamorada 5-star hotels today and relax in the lap of luxury at your convenience.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Islamorada?
How much you pay for a 5-star hotel in Islamorada can vary based on when you want to travel and how long you plan to stay, among several factors. Take advantage of our price per night filter and other search tools to score the best rate on a high-end getaway.
  • Search for the lowest price per night from $232
What makes a hotel 5 stars in Islamorada?
From gourmet restaurants and all-day fitness centers to pools and the finest bedding, the 5-star experience in Islamorada is all about relaxation and luxury. But it takes more than just upscale conveniences to receive a 5-star rating. Stays must also offer outstanding guest-centric services like beauty treatments, on-site dry cleaning and laundry and 24/7 room service.
Are there any 5-star all-inclusive resorts in Islamorada?
Find an upscale escape that includes your lodging, meals, bar and entertainment in Islamorada with our handy filters. Search for properties with a 5-star rating and select the "All inclusive" filter. Be sure to check what's included in the upfront price. That way, you'll be ready to maximize the many perks on offer when you get there.

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