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
Sep 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Islamorada luxury hotels

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 pool area with clear blue water, white lounge chairs, and palm trees.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.

1. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
P29,833
P37,607 total
includes taxes & fees
Oct 1 - Oct 2
The Islands of Islamorada
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A bar area with a wooden counter, bar stools, and potted plants.
A wooden pier leading to a beach with palm trees and a row of beach huts.
A paved pathway leading to a beach with palm trees and a view of the ocean.

2. Islander Resort

Islander Resort
Matecumbe
  • Beachfront luxury awaits at Florida Keys haven with private shores, poolside bars, and lavish lanai rooms.
P17,911
P24,726 total
includes taxes & fees
Oct 27 - Oct 28
Islander Resort
A wooden deck with a view of the ocean and a palm tree.
A spacious dining area with high ceilings, wicker furniture, and large windows.
A coconut drink with a straw, a cherry, and a slice of fruit on a table by a pool with a waterfall and palm trees in the background.
A spacious interior with a high ceiling, large windows, and a central chandelier.

3. 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.
P17,386
P23,007 total
includes taxes & fees
Oct 12 - Oct 13
Baker's Cay Resort Key Largo, Curio Collection by Hilton
An aerial view of a resort with a large pool, palm trees, and a beach.
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.
A beachside patio with lounge chairs, a table, and a view of the ocean.

4. 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.
P16,449
P21,953 total
includes taxes & fees
Oct 13 - Oct 14
Playa Largo Resort & Spa, Autograph Collection
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A beach with palm trees, a clear blue sky, and a calm sea.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.
A coastal resort with a beach, a swimming pool, and multiple buildings.

5. 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.
P13,459
P19,716 total
includes taxes & fees
Oct 18 - Oct 19
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.
A beach with palm trees, a dock, and lounge chairs.
A resort pool with palm trees, beach chairs, and umbrellas.
An aerial view of a resort with a swimming pool, palm trees, and a dock.

6. Amara Cay Resort

Amara Cay Resort
Matecumbe
  • Florida Keys resort offers private beach paradise with upscale rooms, coastal activities, and luxurious relaxation.
P9,668
P15,450 total
includes taxes & fees
Oct 18 - Oct 19
Amara Cay Resort
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 hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.

7. 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.
P9,319
P15,058 total
includes taxes & fees
Oct 4 - Oct 5
Cheeca Lodge & Spa
A resort pool with palm trees and lounge chairs, surrounded by a beachfront.
A resort with a large pool surrounded by lounge chairs, a beach area, and a building with multiple floors.
An aerial view of a resort island with a large building, a swimming pool, and a boat docked nearby.
A modern living room with a sofa, chairs, a dining table, a TV, and a view of the ocean.

8. 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.
P23,704
P30,537 total
includes taxes & fees
Oct 1 - Oct 2
Villas At Hawks Cay Resort
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 beach with thatched umbrellas, palm trees, and blue lounge chairs.
A spacious bar area with high ceilings and large windows, offering views of the ocean.

9. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
P12,454
P16,514 total
includes taxes & fees
Oct 1 - Oct 2
Reefhouse Resort & Marina
A wooden deck with a pool and chairs overlooking a beach with palm trees.
A bar area with stools, a counter, and hanging lanterns.
A hotel room with a sofa, a desk, a chair, a TV, and a balcony with curtains.
A pool area with palm trees and a view of the ocean.

10. Grassy Flats Resort & Beach Club

Grassy Flats Resort & Beach Club
Marathon
P12,600
P17,178 total
includes taxes & fees
Oct 31 - Nov 1
Grassy Flats Resort & Beach Club
View all properties

Top Islamorada Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"All the place is amazing but the rooms needs a little be of work to upgrade, and the beach was not as we imagined"
Daniel 3-night trip
Posted 12 hours ago
Cheeca Lodge & Spa
Islander Resort

Islander Resort

10/10 Excellent
"Amazing place would definitely recommend"
Steven 2-night trip
Posted 1 day 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 2 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 2 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 5 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 6 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 travelers looking for an elegant place to stay. Another upscale choice for your trip 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 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, 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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