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

5 Star Hotels in Islamorada, Florida

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Check availability on Islamorada 5 Star Hotels

Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Islamorada 5-star hotels

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.
A spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.
A tropical resort with a swimming pool, palm trees, and a waterfall.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
RAIBEL
€255
includes taxes & fees
13 Oct - 14 Oct
Cheeca Lodge & Spa
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.
A gated entrance to a resort with palm trees and a clear sky.
A pool area with clear blue water, white lounge chairs, and palm trees.

2. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
€582
includes taxes & fees
7 Oct - 8 Oct
The Islands of Islamorada
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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
€328
18 Oct - 19 Oct
includes taxes & fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
€219
18 Oct - 19 Oct
includes taxes & fees
8.8/10 Excellent! (1,324 reviews)
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
€281
19 Oct - 20 Oct
includes taxes & fees
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 snorkelling coral reefs teeming with tropical fish, then unwind at waterfront restaurants where chefs cook your fresh catch.

See all hotels in Islamorada
An aerial view of a coastal town with a marina, surrounded by clear blue waters and green islands.

Top Islamorada Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Staff is very helpful, rooms are clean, and there is a lot to do on the property!"
Morgan 2-night trip
Posted 4 hours ago
Cheeca Lodge & Spa

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 €219
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.