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

Five Star Hotels in Islamorada

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Islamorada 5 Star Hotels

Tonight
20 Sept - 21 Sept
Tomorrow
21 Sept - 22 Sept
Next weekend
25 Sept - 27 Sept
In two weeks
2 Oct - 4 Oct

Our top choices for Islamorada 5-star hotels

Balcony
Poolside bar
Lobby
Premium bedding, in-room safe, desk, laptop workspace

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
RAIBEL
S$297
includes taxes & fees
21 Sept - 22 Sept
Cheeca Lodge & Spa
Save an average of 15% on thousands of hotels when you're signed in

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
S$411
30 Sept - 1 Oct
includes taxes & fees
8.6/10 Excellent! (1,186 reviews)
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
S$300
22 Sept - 23 Sept
includes taxes & 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
S$379
27 Sept - 28 Sept
includes taxes & fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Still don't see what you're looking for?
See all properties in Islamorada.
You can also use these popular filters to refine your search.
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 snorkelling coral reefs teeming with tropical fish, then unwind at waterfront restaurants where chefs cook your fresh catch.

See all hotels in Islamorada
A white two-story house with blue accents, surrounded by palm trees and a sandy area.

Top Islamorada Hotel Reviews

Find out more about Islamorada

Stay in Luxury: 5 Star Hotels in Islamorada

There's nothing wrong with enjoying the finer things in life. Indulge your every desire on your upcoming leisure time. Treat yourself with a stay in a 5-star hotel during your Islamorada trip. You'll join the multitudes of holidaymakers who have made Islamorada so fashionable recently. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. 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

You'll have a wonderful time at one of these 5-star hotels. Exceptional customer care, luxurious bedding, and deeply relaxing spa offerings are waiting for you. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready for a wonderful adventure. What kind of amenities will make your stay a wonderful one? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A body scrub that will leave you feeling refreshed and alive? Butler services? Whatever it is your heart desires, you're bound to find it here. Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs. 

But you aren't going to spend your entire holiday in your room, of course. You're in luck. 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 waiting for you to relax after an exciting day.

Make Your Escape

The results are in, and Islamorada 5-star hotels are the place to be when you book your next holiday. If you've been dreaming about a holiday set here, then go ahead and book it. It's time to plan your next great escape -- this is a great time to find 5-star hotel deals in Islamorada! Choose one of our Islamorada 5-star hotels today and soothe yourself in luxe surroundings at your convenience.

Expedia India is rated 4 stars by Feefo based on 1038 reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Islamorada?
There are many different pricing options for 5-star hotels in Islamorada on Expedia. How much you'll pay will depend on when you travel, trip length and other factors. Compare available accommodation for your desired dates and use our pricing and other filters to lock in the ideal high-end stay.
  • Search for the lowest price per night from S$300
What makes a hotel 5 stars in Islamorada?
In Islamorada, a hotel must offer a certain amount of high-end amenities to earn 5 stars. These may include on-site gyms, spas and saunas, gourmet restaurants, luxury bathroom products, premium bedding and more. What also sets 5-star hotels apart is their superior service. You can look forward to things like nightly turn-down services, in-room massages and concierge services. Some may also offer additional touches like welcome gifts.
Are there any 5-star all-inclusive resorts in Islamorada?
Find a luxurious escape that includes your room, meals, activities and entertainment in Islamorada with the help of Expedia's filters. Search for properties with a 5-star rating and select the "All inclusive" filter. Be sure to check what's included in the price. That way, you'll be ready to maximize all the perks on offer as soon as you arrive.

Explore a world of travel with Expedia