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

Luxury Hotels in Islamorada, Florida

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Check availability on Islamorada Luxury Hotels

Tonight
Aug 15 - Aug 16
Tomorrow
Aug 16 - Aug 17
Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30

Our top choices for Islamorada luxury hotels

1. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
P22,084
P28,668 total
includes taxes & fees
Sep 13 - Sep 14
The Islands of Islamorada

2. Islander Resort

Islander Resort
Matecumbe
  • Beachfront luxury awaits at Florida Keys haven with private shores, poolside bars, and lavish lanai rooms.
P14,232
P20,152 total
includes taxes & fees
Sep 13 - Sep 14
Islander Resort

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
  • Seaside elegance awaits at this Islamorada resort with 3 pools, diverse dining, and a marina.
P12,732
P18,818 total
includes taxes & fees
Sep 7 - Sep 8
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
  • Beach luxury reimagined at Key Largo resort with private sands, refreshing pools, and coastal dining.
P14,538
P19,737 total
includes taxes & fees
Aug 24 - Aug 25
Baker's Cay Resort Key Largo, Curio Collection by Hilton

5. 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.
P9,156
P14,794 total
includes taxes & fees
Aug 18 - Aug 19
Cheeca Lodge & Spa

6. 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.
P14,661
P19,876 total
includes taxes & fees
Aug 31 - Sep 1
Playa Largo Resort & Spa, Autograph Collection

7. Amara Cay Resort

Amara Cay Resort
Matecumbe
  • Florida Keys resort offers private beach paradise with upscale rooms, coastal activities, and luxurious relaxation.
P10,311
P16,086 total
includes taxes & fees
Aug 18 - Aug 19
Amara Cay Resort

8. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
P9,482
P15,154 total
includes taxes & fees
Aug 18 - Aug 19
La Siesta Resort & Villas

9. Villas At Hawks Cay Resort

Villas At Hawks Cay Resort
Marathon
  • Indulge in oceanfront splendor at this Florida Keys resort with 5 pools, private beach, and full-service spa treatments.
P47,542
P57,282 total
includes taxes & fees
Sep 13 - Sep 14
Villas At Hawks Cay Resort

10. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
P13,435
P17,568 total
includes taxes & fees
Aug 16 - Aug 17
Reefhouse Resort & Marina
View all properties

Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"10/10 recommend! We will be back again! We love coming here and bringing the boat. Staff is great and properly/rooms are so clean."
Matthew 6-night trip
Posted 3 hours ago
Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Always a good time!"
Laura 2-night trip
Posted 20 hours ago
Amara Cay Resort
Drop Anchor

Drop Anchor

10/10 Excellent
"We were only there two nights so we didn’t have much interaction with the staff, but it was well kept and convenient for our needs as a family."
Katharine 2-night trip
Posted 1 day ago
Drop Anchor
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

10/10 Excellent
"Stayed in build 7 and it had a great view restaurant was good the bars where nice and most of all I booked a fishing trip with Whiskey Throttle guide service and Sean put me on a dinosaur of a tarpon and boy was it a beast. If the fishing is slow grab Whiskey Throttle for a great water adventures."
Gary 1-night trip
Posted 1 day ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Casa Morada

Casa Morada

10/10 Excellent
"It's a beautiful property! A hidden treasure in Islamorada : )"
Ira 2-night trip
Posted 5 days ago
Casa Morada
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

10/10 Excellent
"Wow! I stayed there for a week and I really felt like I was in my little slice of heaven! The resort is decorated beautifully. The room definitely has the Florida keys vibe and the staff were so awesome. I would have loved to stay there forever. I can't wait to go back!!!"
Kevin 7-night trip
Posted 11 days ago
Coconut Cove Resort and Marina

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 travelers looking for an elegant place to stay.
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 temp of 83°F, while the coldest months are January and February with an average of 72°F. Average annual precipitation for Islamorada is 44 inches.
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, Islamorada County Park, and Founders Park. If you have a bit of extra time while you're in the area, you might want to check out Robbie's of Islamorada and Anne's Beach.

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