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

Best Luxury Hotels in Islamorada

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Check availability on Islamorada Luxury Hotels

Tonight
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Islamorada luxury hotels

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
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.
A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
  • Experience seaside opulence with private beach access, three outdoor pools, and oceanfront dining at this beachfront Matecumbe resort.
RM608
RM982 total
includes taxes & fees
4 Oct - 5 Oct
Cheeca Lodge & Spa
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A gated entrance to a resort with palm trees and a clear sky.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.
A resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.

2. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
RM2,130
RM2,664 total
includes taxes & fees
13 Oct - 14 Oct
The Islands of Islamorada
An aerial view of a resort with a large pool, palm trees, and a beach.
A beach with clear water, a wooden pier, and lounge chairs under a tree.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.

3. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
  • Beachfront luxury awaits at this Key Largo resort with spa treatments and ocean views.
RM1,073
RM1,432 total
includes taxes & fees
15 Oct - 16 Oct
Playa Largo Resort & Spa, Autograph Collection
A dining area with tables set for two, overlooking a beach with palm trees and a sunset view.
A spacious living room with large windows, comfortable seating, and decorative plants.
A poolside area with blue chairs and a thatched-roof structure.
A spacious bar area with high ceilings and large windows, offering views of the ocean.

4. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
RM894
RM1,168 total
includes taxes & fees
4 Oct - 5 Oct
Reefhouse Resort & Marina
View all properties

Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Great place"
Juan 4-night trip
Posted 1 day ago
Chesapeake Beach Resort
Islander Resort

Islander Resort

10/10 Excellent
"It great amenities but pools are small."
Jaily 2-night trip
Posted 2 days ago
Islander Resort
Amara Cay Resort

Amara Cay Resort

8/10 Good
"This resort was absolutely beautiful!! The pool was amazing, a resort style pool. The resort had its own private beach area and a dock. Had plenty of seating everywhere, many cool sitting areas around the property. The only negative thing I could say is that the staff didn’t pick up trash and towels around the pool which seemed odd and it was off season so it wasn’t busy. It’s such a beautiful resort that I would think that would be a priority to keep it clean. Another cool thing is that they have a water taxi and shuttle to their 2 sister resorts which you can utilize all of those amenities as well. They also included bike rentals, paddle boards and kayaking on site which is convenient. You can also bring your private boat there and leave it at the dock for a fee. I would absolutely stay there again!"
Melissa 1-night trip
Posted 3 days ago
Amara Cay Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

10/10 Excellent
"Ya’ll just need a microwave."
Nathalee 3-night trip
Posted 3 days ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Casa Morada

Casa Morada

10/10 Excellent
"always a favorite!"
robert 2-night trip
Posted 6 days ago
Casa Morada
Drop Anchor

Drop Anchor

10/10 Excellent
"Exceeded all my expectations, definitely going back. Highly recommend"
Payman 3-night trip
Posted 7 days ago
Drop Anchor

Frequently asked questions

Are you looking for a luxury hotel for your stay in Islamorada?
During your visit, you might want to enjoy the ocean views and sunsets which Islamorada is known for.
What's the best luxury place to stay in Islamorada?
Cheeca Lodge & Spa is a luxury resort with a private beach and 3 restaurants, and it's a popular choice for Expedia travellers looking for an elegant place to stay. Another upscale choice for your holiday is The Islands of Islamorada.
When can I expect good weather in Islamorada?
Planning for the weather is an important factor for making your trip to Islamorada a success, especially when you're splurging. The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 22°C. Average annual precipitation for Islamorada is 1122 mm.
What's there to see and do in Islamorada?
Experience all that Islamorada has to offer when you visit Bud n' Mary's Dive Center, Robbie's of Islamorada and Anne's Beach. If you have a bit of extra time while you're in the area, you might want to check out Fiesta Key and Everglades National Park.

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